Aiming for a Rising Tide, Carole Wacey, Women Creating Change
Carole Wacey is the President of the long-standing Women’s City Club — recently rebranded as Women Creating Change— a nonprofit, non-partisan, activist organization dedicated to advancing the rights of women to shape the future of New York City. Carole’s career has spanned several sectors and created many opportunities for her to reinvent the wheel. She gets the non-profit world like no other.
You can listen to this on iTunes here.
Media as a Vehicle for Storyteller, LinYee Yuan, Mold Magazine, Podcast #105
LinYee Yuan is a design journalist as well as the editor and founder of MOLD magazine. Inspired by the UN’s distressing news of the world’s ability to feel itself in the future, LinYee created MOLD to inspire designers to improve food systems through creative, human-centric solutions. LinYee and I had tons to talk about from design to food to motherhood.
You can listen to this on iTunes here.
Designing a New Kind of Coverage, Ashley Hunter, HM Risk Group, Podcast #104
Ashley M. Hunter is the president of HM Risk Group, an international insurance, reinsurance and risk management brokerage that specializes in reproductive health coverage. Ashley has had an inspiring career of going from studying violin to becoming a major player in reinventing the landscape of medical insurance coverage for the reproductive technology industry.
You can listen to it on iTunes here.
Returning to the Art Galleries, Mary Leigh Cherry, Podcast #103
Mary Leigh Cherry is the Director of the newly opened Tonya Bonakdar Gallery in Los Angeles. Her long career as a gallery owner, curator, and collector has made her a prolific figure in the art world on both coasts. Our conversation made for an episode that will be highly valuable to anyone involved or interested in the art world.
You can listen to this on iTunes here.
Growing Cannabis E-Commerce, Anna Duckworth & Kate Miller, Miss Grass, Podcast #102
Kate Miller and Anna Duckworth are the Co-Founders behind Miss Grass, a content-driven cannabis marketplace gearing up to make a leap into becoming a nation-wide brand focused on conscious consumerism around cannabis products and companies. Kate and Anna had a great story to share about how they met, tucked their heads down for six months, and then launched into success.
You can listen to this on iTunes here.
I Can Build This Better, Sara Hicks, Reaction Commerce, Podcast #101
Sara Hicks is the Co-Founder and CEO of Reaction Commerce an online platform that powers the back end of commerce businesses big and small with customizable, open source code. Sara talks with me about her ‘aha’ moment of inspiration and the major moves that her company is taking today.
You can listen to this on iTunes here.
Battling Systems of Oppression, Robin Steinberg, The Bail Project, Podcast #100
Our 100th episode is one that the Positively Gotham Gal team is incredibly proud of — thank you to all you listeners for getting us here!
This episode features Robin Steinberg, an American lawyer, social justice advocate, and leader in the field of holistic public defense. Steinberg is the CEO of The Bail Project, a national organization modeled after The Bronx Freedom Fund, which she co-founded with her husband David Feige in 2007. Robin sat down with me to talk about the incredible work she’s doing to reform the social justice system in America, and what’s inspired her to do this kind of work for the last thirty years plus.
We need more Robin’s. You can find out more about The Bail Project at bailproject.org.
You can listen to this weeks podcast here.
What’s Your Why? Anna Barber, TechStars LA, Podcast#99
Anna Barber is the Managing Director of TechStars LA, where she acts as an investor, advisor, connector and coach for founders. Anna has had a long and successful career that spans several sectors, and her perspective of what she’s accomplished and how she feels about her work now is an interesting listen for anyone at any stage of their career. She is way ahead of her time on how she has approached her career.
You can listen to this on iTunes here.
Finance Made Simple, Tina Hay, Napkin Finance, Podcast #98
Tina Hay is the Founder and CEO of Napkin Finance, a multi-media company focused on creating content around learning and understanding finance. Tina and I chatted about her goals of creating palatable content, and the exciting directions her company is about to take
You can listen to the podcast on iTunes here.
Sheer Will and Self-Confidence, Jesse Genet, Lumi, Podcast #97
Jesse Genet is the Co-Founder and CEO of Lumi, a company that creates packaging solutions for modern supply chain teams. Jesse has a killer story of taking leap-of-faith after leap-of-faith from an early age, straight on into her latest venture, without a single break for self-doubt in between.
You can listen to it on iTunes here.
Getting Innovative with Content Creation, Kristina Budelis and Lisbeth Kaufman, Kitsplit, Podcast #96
Kristina Budelis and Lisbeth Kaufman are the Co-Founders of Kitsplit an online rental house that lets content creators further cash in on the gig economy by renting out their gear to peers in their community. Lisbeth and Kristina share their story of meeting at ITP to starting their company in the middle of graduate school. Major inspiration for anyone out there with an idea they’re eager to launch.
You can listen to this on iTunes here.
A Lifetime of Learning and Reinvention, Minnie Ingersoll, TenOneTen Ventures, Podcast#95
Minnie Ingersoll is the newest Investor at TenOneTen Ventures, a Venture Capital firm investing in early-stage tech startups. Minnie previously co-founded a startup, and now finds herself thriving on the other side of the venture table. She is proof positive that starting over with your career at age 40 can be majorly rewarding
You can listen to the podcast on iTunes here
From Hedge Funds to Founder, Lindsey Johnson, Weezie Towels, Podcast #94
Lindsey Johnson is the Co-Founder and CEO of Weezie Towels. This week Lindsey and I sat down to talk about her transition from hedge funds to become a startup founder herself — and the big plans she has in mind for her companies future.
You can listen to this on Itunes here.
Relationships in Brand Building, Catherine & Chloe Zadeh, Podcast #93
Catherine and Chloe Zadeh are the mother and daughter team behind ZADEH, a brand created from Catherine’s modern jewelry designs for men and women. Catherine got her start making jewelry at the 92nd Street Y of all places, and today she’s one of New York’s hottest designers. With her daughter Chloe now at the helm of the family business, the team has set their sights on creating an empire.
You can listen to this on iTunes here.
You Don’t Need a Recipe, Alison Cayne, Haven’s Kitchen
Alison Cayne is the Founder of Haven’s Kitchen, a cooking school and event space in New York City. Alison’s journey is so inspiring — in this episode she gave me the story behind her return to grad school after having five children, and how she rose above her own lack of self-confidence to become a powerhouse entrepreneur. Alison’s story is proof that like the best cooking, you don’t need a recipe for success.
You can listen to the podcast on iTunes here.
Empowering with Education, Lauren Bille & Ashley Spivak, Cycles + Sex, Podcast#91
Lauren Bille & Ashley Spivak are the Co-Founders of Cycles + Sex, a women’s health initiative that started out as an
You can also listen to the podcast on iTunes here.
Do You Want to Be a Best, or a Favorite? Linda Derschang, The Derschang Group, Podcast #90
Linda Derschang is the founder and CEO of The Derschang Group, a mix of restaurants, cafes, and bars in Seattle, Washington. Linda joined me to talk about the journey from opening a punk clothing store in Denver to the massive group of bars and restaurants in Seattle today
You can listen to the podcast on iTunes here.
Imagining the Well Woman, Carolyn Witte, Ask Tia
Carolyn Witte is the Co-Founder and CEO of
You can listen to this on iTunes here
Once You Feel Empowered, You Can Do Anything, Podcast#88, Patti Russo
Patti Russo is the Executive Director of the Women’s Campaign School at Yale — an intensive program designed to train women to run for office and manage political campaigns. Patti’s story is inspiring. Certainly something we might need in the midst of the political turmoil. Patti also has a lot of insights to share that go beyond just politics.
You can listen to this on iTunes here.
Just Keep Going, Abigail Stone, Otherland, Podcast # 87
Here’s our first episode of 2019.
Abigail Stone is the founder and CEO of Otherland, a new candle company focused on self-care, great scents, and art-inspired style. Abigail sat down with me to talk about her journey from a career as an art buyer for Ralph Lauren, to starting over in business school, and the success she’s found since.
You can listen to it on iTunes here.
Chasing the Idea Moment, Susannah Vila, Flip, Podcast #86
Susannah Vila is the Co-Founder and CEO of Flip — an online service that helps renters get out of their leases, and helps subletters find new apartments. Susannah cut her teeth in the world of political NGO’s before realizing that her real passion was entrepreneurship, and her first order of business was tackling a problem she’d been dealing with for years
You can listen to this on Itunes here.
The Power of the Network: Mackenzie Barth & Sarah Adler, Podcast #85
Spoon University Mackenzie Barth and Sarah Adler are the Co-Founders of Spoon University, an online food magazine that they started in their college dorm rooms eventually being acquired by a major media company. Kenzie and Sarah sat down with me this week to share the story of their unprecedented success.
You can listen to this on iTunes here
Knowing That You Are the Expert, Melanie Elturk, Haute Hijab, Podcast #84
Melanie Elturk is Co-founder, CEO, and Chief Designer at Haute Hijab — an online retail brand that as Melanie says, “makes the world’s best hijabs for the world’s most powerful women”. Melanie went from a stable career in a law firm to diving headfirst into her growing e-commerce empire, and she doesn’t hold back about what a daunting move that was to make.
You can listen to the podcast on Itunes here.
Breaking Ground in the Construction Business, Sarah Carter & Ally Varady, CV Partners, Podcast #83
Sarah Carter and Ally Varady are the founders of CV-Partners, a project management firm that specializes in taking construction projects from concept to completion, and all the endless details in between.
You can listen to this on Itunes here.
Calculated Learning and Trusting Your Gut – Connie Wong & Susan Zheng, Planted , Podcast#8
Connie Wong and Susan Zheng are the founding partners of Planted, a match-making service for job-seekers, and companies in search of entry-level talent. Connie and Susan both know all about the difficulties in making the decision to switch career paths and potentially break out on your own — this team took an interesting path of calculated learning through employment, before really digging into their own business venture.
You can listen to it on iTunes here.
Dining and Relationships, Shari Bayer, Bayer Public Relations, Podcast #81
Shari Bayer is the founder and president of Bayer Public Relations, a full-service public relations, consulting and marketing agency in NYC that specializes in restaurants and other food-based companies. Shari had a long path to starting her own PR firm, but all the dots connected perfectly to get Shari where she is today.
You can listen to this on iTunes here.
Rethinking Energy – Robyn Beavers, Blueprint Power, Podcast #80
Robyn Beavers is the Co-Founder and CEO of Blueprint Power a real estate and energy tech company that turns buildings into urban power plants. Robyn had a real ‘aha’ moment when she came up for the idea for Blueprint, and her journey towards entrepreneurship is one not to miss.
You can listen to this on iTunes here.
The Best Way to Raise Money is to Sell Product, Eliza Blank, The Sill, Podcast #79
Eliza Blank is the founder and CEO of The Sill an e-commerce platform including two brick and mortar stores in NYC designed to bring home gardening back into the mainstream. Eliza and I sat down and talked about how she took The Sill from idea to business with a mission.
You can listen to this on iTunes here.
Building a Business out of Giving Back – Deborah Koenigsberger, Hearts of Gold, Podcast#78
Deborah Koenigsberger is the owner and stylist of brick-and-mortar boutique Noir et Blanc, and Founder of the non-profit organization Hearts of Gold. Deborah is a powerhouse and a real advocate for women and children in need. We sat down this week to talk about the work she does through Hearts of Gold, and how her venture got started.
You can listen to this on iTunes here.
Focused on Financial Savvy, Shannon McLay, Financial Gym, Podcast #77
Shannon McLay is the Founder & President of Financial Gym, a company that provides personal training for your finances, regardless of what’s in your bank account. Shannon told me all about her start as a floor trader for big banks where she was often referred to as “the decoration,” and how she powered through that glass ceiling, built strong networks, and transitioned into fundraising and starting her own business
You can listen to the podcast on Itunes here
It’s All About Endurance Training – Nadia Boujarwah, Dia&Co, Podcast#76
Nadia Boujarwah is the Co-Founder and CEO of Dia&Co a shopping and styling resource for plus-sized fashion. Nadia and I talked about how she took her career from investment banking analyst to starting her own business, and all the hurdles in between.
You can listen to this on iTunes here.
Becoming a Resource for Artists, Keri Putnam, Sundance Institute, Podcast #75
Keri Putnam is the Executive Director of Sundance Institute. The Sundance Institute is a non-profit that puts on an incredible film festival but also serves to support, champion, and promote independent artists in film, theater, and ever-expanding new mediums. Keri and I discussed everything from how she started her career to what representation means for her and the future of organizations like Sundance.
You can listen to it here on iTunes.
Balancing Problem Solving While Celebrating Success, Kate Bradley Chernis, Podcast #74
Kate Bradley Chernis is the Co-Founder & CEO of Try Lately — a marketing and advertising service that streamlines content creation for everyone from the top marketing companies to the individual blogger. Kate and I talked about what led to her starting Lately after a successful career in broadcasting and advertising, and what it means to balance your strengths and weaknesses in an effective way in order to keep moving your business forward. Great lessons for entrepreneurs at any stage of the game.
You can listen to the podcast on iTunes here.
Investing in Women, BBG Ventures, Podcast#73
Episode 73: Investing in Women – Susan Lyne & Nisha Dua, BBG Ventures – Part 2 of 2 Susan Lyne and Nisha Dua are the Founding Partners of BBG – Built By Girls – Ventures, A Venture Capital firm that focuses on women founders and women-led startups. Their story truly defies what comes to mind when you think of VC’s. In this two-part episode, Susan, Nisha, and I had so much to talk about. From the unconventional way that their partnership began to incredible advice about raising money and common mistakes too many entrepreneurs make. Tons of great tips for anyone on how to get out there and crush it like a girl.
You can listen to this episode here on iTunes.
Built By Girls, Focusing on Women, Susan Lyne and Nisha Dua, Podcast#72
Susan Lyne and Nisha Dua are the Founding Partners of BBG – Built By Girls – Ventures, A Venture Capital firm that focuses on women founders and women-led startups. Their story truly defies what comes to mind when you think of VC’s. In this two-part episode, Susan, Nisha, and I had so much to talk about. From the unconventional way that their partnership began to incredible advice about raising money and common mistakes too many entrepreneurs make. Tons of great tips for anyone on how to get out there and crush it like a girl. Stay tuned for next week when we dive into Susan & Nisha’s own battles with raising capital and how they pushed through it.
You can listen to this on Itunes here.
This week for Motivate Monday we’re celebrating the record number of women running for office in the upcoming midterms, and revisiting Episode 30: Get Focused On Your Mission, featuring former NYC mayoral candidate and current CEO of Women In Need, Christine Quinn.
You can listen to the podcast on iTunes here.
Episode 70: Giving a Local Brand National Reach – Pam Wasserstein, New York Magazine
Pam Wasserstein is the CEO of New York Media, leading the premium content company on an ambitious expansion in several areas, including video, branded content, live events and e-commerce, while growing audience and revenue at core brands New York Magazine, nymag.com, Vulture, the Cut, Daily Intelligencer, Grub Street, Select All and the Strategist. Before becoming the CEO, Wasserstein served as co-chair and head of strategy. Pam and I talked about what took her from working as a lawyer to being the top dog of a media empire.
Here is the link in iTunes.
This week’s Motivate Monday is a for-sure favorite episode of mine: Episode 10, Your First Step Needs to Be Your Best Step, with Karen Cahn, founder of iFundWomen. If you haven’t listened to this episode recently, it’s definitely worth a re-visit — my conversation with Karen is full of great tips for fundraising and attracting investors.
You can listen to it here on iTunes.
A Stiletto-strapped Business – Amanda Curtis & Gemma Sole, Nineteenth Amendment, Podcast #69
Amanda Curtis and Gemma Sole are the co-founders of Nineteenth Amendment, a direct-to-designer fashion house for clothing and accessories that are more personal, beautiful, and responsible than anything off the rack. The co-founders were named as Forbes 30 Under 30 for retail/e-commerce and Apparel Magazine’s 30 Under 30. I sat down with the duo to talk about the inspiration for their venture, and what helped them pave the way to their brand’s success.
You can listen to it on Itunes here.
Motivate Mondays, Episode 19: A Brand is an Ideology – Linda Ong
This week’s Motivate Monday features Episode 19: A Brand is an Ideology with Linda Ong of Civic Entertainment Group. It’s one of my favorite episodes that happens to be loaded with useful ideas and concepts about branding. This one’s overdue for a re-listen if you’ve been thinking about branding or marketing shifts in your own entrepreneurial ventures — and you can’t go wrong with Linda’s wildly inspiring story.
You can listen to it on iTunes here
Every Woman Has A Story, Christina Asquith, The Fuller Project, Podcast #68
Christina Asquith, the founder of The Fuller Project, is an award-winning journalist for over 14 years, writing for The New York Times, The Economist, The Christian Science Monitor, The Guardian and was a staff writer at The Philadelphia Inquirer. Her book, “Sisters in War: Love, Survival and Family in the New Iraq” is based on the 18 months she lived in and reported from Baghdad, Iraq. Christina and I sat down to talk about her very impressive career, and how she managed to carve a space for women’s stories long before it was a trending topic.
Follow the Fuller Project on Twitter.
Here is the podcast on iTunes.
With the season in full swing, I’m out of the city and enjoying my summer slow down out east in the Hamptons. My change in locale got me thinking about a particular Long Island entrepreneur who we featured on Episode 41: Putting in the Time to Build Traction with Carissa Waechter of Carissa’s Bakery. Not only is Carissa’s product just delicious, I love how fearlessly patient Carissa was when it came to finding the right partners to expand her business. Definitely worth a re-listen for anyone in the middle of putting together a deal.
Episode 67: The Art of Stamina – Tanja Hollander, Are You Really My Friend?
Tanja Hollander is an artist who works with photography, video, social media and data to understand cultural and visual relationships. Her largest and most noteworthy project to date, ‘Are you really my friend?’ debuted in its entirety as an exhibition, short documentary, and book for a year at MASS MoCA in 2017. Tanja and I talked about the enormous undertaking that this project became and how she’s found the stamina to keep making work.
I really enjoyed listening to this before posting today.
Here is the link on iTunes
Summer’s Motivate Monday
This week’s Motivate Monday is Episode 4: Just Build with Nancy Lublin of CrisisTextLine. In light of recent high-profile losses to suicide, and the report published by The Center For Disease Control and Prevention on the shocking increase in national suicide rates, it seemed like an opportune moment to revisit CrisisTextLine, and the incredibly creative way that Nancy’s keeping her non-profit -and at-risk-teens – alive.
Nothing Based on Fear, Larissa Thompson, Sarah Bryden-Brown, ONDA, Podcast #66
Larissa Thompson and Sarah Bryden-Brown are two of three powerhouse women behind ONDA — an online retail and brick-and-mortar store that serves as the go-to authority on natural beauty in the marketplace. I sat down with Larissa and Sarah this week to talk about how they met, and what’s made their venture such a success.
iTunes link is right here.
Summer’s Motivate Mondays
Every summer we slow things down and release new episodes of Positively Gotham Gal bi-weekly. This year I’ll be using those Mondays in-between to revisit some of my favorite, worth a re-listen episodes from the 65 (can’t believe that number!) we’ve done so far. Sort of like a Throwback Thursday, but Gotham Gal style.
This week’s Motivate Monday is Episode 56: No Brands Were Built Overnight with Ariel Kaye of Parachute Home. Ariel just opened her first east coast brick and mortar location in Soho (129 Grand Street) which makes for a perfect reason to revisit Ariel’s episode which is full of insights and strategies for launching a modern-day retail company.
You can hear the podcast on Itunes right here.
Leading with What You Love, Sharon Kazan Harris, Rarecat Wines, Podcast#65
While spending many years working in executive positions in publishing, advertising, technology, and a tech investing, Sharon Kazan Harris’s dream of working in the wine industry was ever present. Today, she is the sole owner and Director of Winemaking for RARECAT Wines. Sharon shared with me everything from how she fell in love with wine, to how she uses one passion project to fuel another: her mission to empower women across the USA & beyond.
Here is the link to iTunes.
Branding In Unexpected Places, Archie Gottesman, Jewbelong, Podcast #64
If you’ve never heard of Archie Gottesman but have lived in or visited New York – you are familiar with her work. For 20 years, she was the voice behind Manhattan Mini Storage’s iconic, hilarious billboard and subway ads. Now she’s applying her prolific branding acumen to something desperately in need of a marketing re-boot- Judaism. Jewbelong aims to reconnect disengaged Jews with fresh and fun ideas for living your best Jewish life.
Here is it on iTunes
Producing is Problem Solving, Peggy Rajski, Podcast #63
Peggy Rajski is an Academy Award-winning filmmaker who’s produced over a dozen feature films, directed an Oscar-winning short, and garnered more than 40 major award nominations along the way. Her directorial debut TREVOR, a poignant comedy about a musical-theater-obsessed 13-year-old boy whose world is turned upside down when word spreads at school that he’s gay led to the creation of The Trevor Project, a pioneering nonprofit organization she founded that is the country’s leading provider of life-saving services for LGBTQ youth. Peggy had some great insights to share about how she carved a space for herself in the competitive indie film marketplace.
Here is the link in iTunes
Your Business is the Journey, Loren Brill, Sweet Loren’s, Podcast #62
This week on the podcast we have Loren Brill, Founder & CEO of Sweet Loren’s, a cookie dough company founded on the promise of irresistible taste and natural, better-for-you ingredients. Beating cancer at a young age, Loren made it her mission to eliminate processed foods from her diet and live life to the fullest. Loren and I sat down to talk about the challenges of building a brand, breaking into the commercial food space, and some of the incredible lessons she’s learned along the way.
Here is the link in Itunes.
Trailblazing the Restaurant Scene Clare de Boer, Jess Shadbolt, Annie Shi, KING, Podcast #61
Clare de Boer, Jess Shadbolt, and Annie Shi are the three entrepreneurs behind King, an amazing restaurant here in the West Village of NYC, on King Street. The trio sat down with me this week to talk about how they met, what inspired them and paved the way for their amazing and ambitious restaurant venture, and how they plan to support the next generation of women restaurateurs.
Here is the link to iTunes.
Working in Regenerative Technology, Stacy Flynn, Evrnu, Podcast #60
You can also listen to the podcast on iTunes here.
Stacy Flynn is the co-founder and CEO of Evrnu – a textile company that recycles discarded cotton garments to create premium, renewable fibers that are tackling the rampant pollution and labor exploitation issues in the current fast-fashion market. She is actively reinventing the textile and apparel business model to preserve the future of apparel. Stacy and I talked about everything from polyester to LED light bulbs and the lessons learned in between.
Part 2 of Christina Tosi, Relentless Pursuit, # 59
You may know Christina Tosi from the judges’ panel of MasterChef and MasterChef junior, but she’s also a savvy businesswoman whose relentless passion for baking took her all the way from assembling triple layer cheesecakes in high school to opening her very own bakery with David Chang called Milk Bar Bakery. This week, Christina and I dissected what it took to launch Milk Bar, and how she went about building her business into the empire it is today.
Here is Part 1 if you missed it last week.
Relentless Pursuit, Christina Tosi, Milk Bar Bakery, Podcast #58
Role Models Podcast
This is the last Monday posting podcasts where I am the guest. We will be back to our regularly scheduled program next Monday.
I really enjoyed this podcast. David Noel, who lives in Berlin, is someone I met years ago and is a big part of the tech world spending many years at Soundcloud. Worth listening to his conversations with inspiring women on his Role Model podcasts
Angel Investing with Patrick O’Shaughnessy
I am posting some of my favorite podcasts where I sat on the other side of the table until I make my way back to NYC to meet with some more memorable female entrepreneurs.
Patrick’s podcast is called the Investors Field Guide. Definitely worth listening to others that he has done.
You can listen to the podcast here.
There Are No Shortcuts, Courtney Gould, SmartyPants Vitamins, Podcast#57
Courtney Nichols Gould is the Co-Founder/Co-CEO of SmartyPants Vitamins, the leading maker of premium comprehensive supplements, committed to bringing more health to more people every day. Courtney got her start working as an apprentice to the board of directors at GM, and went on to work as the COO for numerous tech and web startup companies before embarking on her own entrepreneurial venture. Courtney and I talked about a ton of great topics, listen carefully if you’re interested in a crash course in CPG companies and raising capital the smart way.
No Brands Were Built Overnight, Ariel Kaye, Parachute, Episode 55
Ariel Kaye is the Founder and CEO of Parachute Home, a retail business with the mission of supplying consumers with the best sheets, bedding, and home essentials on the market, as well as inspiring a community around sleep, wellness and creating a comfortable home. Ariel and I discussed how her background in branding and advertising really informed her ability to thoughtfully and methodically build her business from one sheet to entire home goods and lifestyle brand.
I always say, well Ariel, first she did sheets, then she did sheets. Then she did sheets and then she brought a towel.
And I think that’s the key to your success. But why sheets?
So lots of reasons why sheets. But you know for me I think it was I was a super consumer so shopping a lot in the home space helping friends and family decorate their homes found myself at this like time in life where I was ready to do something different and saw this opportunity within the home space in general. But as I looked more and did more digging within the category I realized that your bedroom and the sheets that you sleep in are just such an important part of your life. You spent a third of your life in bed, sleep impacts everything and sheets historically have been this product that you buy off the shelf because it’s in front of you because you’re desperate because the current sheets you have have holes in them and are disgusting and you go into a big box retailer and you just buy something because it’s there. And it’s been this completely undifferentiated experience that has been also confusing and frustrating
And not connected to a brand.
And not connected to a brand. So zero brand loyalty at all and you know.
And licensing crap.
And it’s all the same. And so it’s all packaged the same it’s all stacked the same and there just really is no emotional connection. But yet this is a product that you like I said, use a third of your life and it really does have an impact. So I felt like there was this huge opportunity to kind of converge this wellness thinking and this emotional connection that you could have with the brain that I think consumers were yearning for and longing for with brands and actually just choosing for it’s like I don’t need to spend money with brands that don’t mean anything to me that aren’t valuable that aren’t adding some sort of you know education or whatever it is.
So many like you know a lifestyle brand starting sheets but let’s go backwards. Yeah. So where’d you grow up?
And you’re still in the L.A. area. And were you always sort of interested in you know how your bedroom looked and all that kind of stuff when you were a kid?
Not as much when I was a kid. But definitely once I left the house and especially once I had my first apartment there was a real sense of pride. When I moved into my first apartment. I love hosting so I love having people over and cooking dinner and just having my friends around all the time. So I found myself really taking a lot of effort and really you know spending time decorating and refreshing and just you know and wanting to show that all.
Well yeah, cuz you live in it. I mean it makes sense to me actually when I was a kid and I worked three jobs from the time I was 15 years old. And the first thing I do with my money is I renovated my entire bedroom and I like painted the stripes on the wall I was like I totally owned it, I was way into it.
Yeah, and it was just so fun. And you know I was living in New York at the time and had this like first apartment and I just I cared a lot and that was really fun.
So you left L.A. to basically go to New York to go to school.
I went to NYU and then I went to grad school and I worked a number of different jobs and all sorts of industries and was kind of confused for many years in terms of what I wanted to do.
Did you go directly into grad school?
No I worked in PR. I worked as a publicist for a few years and before that I actually thought I was gonna go to law school. But after a few years found myself just kinda at a crossroads. I had had two PR jobs and an advertising job in the course of two and a half years. But nothing was sticking.
So you really didn’t enjoy it.
No I wasn’t. It wasn’t really satisfying. Like the both sides of my brain in a way that I was hoping it my job would.
And so into the wild and you went to grad school?
Yeah and then I found myself just sort of desperate for something different and realized that I could buy myself some time by getting more education and figuring out in your brain. Yeah. And actually it was in grad school that I started this home design blog. Just something to do because I was so into my home and at that point I had moved into an even better apartment in New York that was really big and just unusual for all intensive purposes. Yeah it was huge and just I had this massive bedroom and this huge living room and it really became the party hangout place for my friends and so I started doing a lot of renovation projects and then I started having friends ask me for their design input and helping them design places and so I had this blog that was sort of a scrapbook. Also this is like WAY before blogs were cool I mean I was like 2007 that I started my blog and so I just started.
Which is a long time ago so I. Was we’re now 2018 and I started my blog 15 years ago. So yeah I mean that was really early stuff.
I could have been a Blogger But I you know.
I think you did all right.
But yeah I had this blog and it was like it was a scrapbook It was fun. It was just I like but I had had this passion for home that I sort of realized in a different way through the blog and then found a job after grad school and advertising which I actually really loved for many years and feel like it’s been a huge part of the way that I’ve built parachute.
Because of what you’ve learn when you were in advertising. Interesting enough is people that you graduated with in graduate school. Well isn’t it Karen.
Oh yeah. Well Karen I was an undergrad. Yeah. Those are both undergrad. But yes that is true.
I mean that’s pretty amazing. Those are two other women that are also entrepreneurial. So that’s pretty amazing.
And like almost all of my close friends from high school all have their own companies too. We are like all a group of founders which has been also a huge support. And just like you know it’s really nice to be friends with people that you grew up with who also get what.
Well you’re going through the same shit. What It’s like to build a company.
Exactly and you can be like really you know go out to dinner and just commiserate or celebrate you know. But understand the highs and lows and everything in between. So that’s fun.
That’s interesting now when you were in advertising you know what kind of products did you work on. What were you doing. Were you doing product. Were you doing.
I was on the strategic side of Creative’s so I doing a lot of consumer behavior research both qual and quant and I was working I worked on American Express for a long time so with that it was I was working on everything from card products to membership rewards. But really there was like underlying like luxury consumer piece. And also I was like the token millennial and the token person that was like could tap into you know being the advocate for the millennial shopper and so I was that person that was you know they were trying to appeal to that audience. And like you know the emerging affluent you know mid 20s late early 30s consumer who was going to be getting an American Express card. So that was a big part of what they did. And then I worked on another bunch of other brands from time to time like Burger King and Comcast which is always fun. And Panasonic. I mean there was there was a ton of stuff. And actually my favorite thing to do is work on new business pitches because those were like mini startup projects we like got really deep and learned all about new areas and did some prototyping for different products. But I was also really connected to the New York startup scene during those times and I was sent to South by Southwest every year so it was really like.
You’re watching it from afar but you weren’t in it.
I was watching from far and wishing that I was in it. And so when so when I decided that it was time to kind of think about what was next I knew that I wanted to make the jump to something that was more entrepreneurial and definitely be in a just a quicker paced environment because being on an ad agency with a thousand people the New York office and working for huge mega brands. There’s so much red tape and just things don’t move fast and you don’t get to see the fruits of your labor in a way that you definitely do when you’re building something.
So when you decided you know I mean because like anyone can have the entrepreneurial spirit. But it’s about having a good idea. Those are two separate things. And I think there’s actually I find it comical how they teach entrepreneurship in business school. But at the end of the day you don’t have an idea right. You can’t be an entrepreneur. Or you can but it might not go anywhere. And so when did you. Did you make the leap and start this prior to quitting ad agency or you just said Screw this I’m I’m closing shop and moving my apartment I’m moving to LA.
I was it was the end of 2012 when like literally the last few days of the year when the idea for parachute really came into mind and I had you know I’m meeting with a friend in New York.
And was just singing in your head?
It was just like this is an idea. I mean what was going on though. Also at the same time was that direct to consumer businesses were just really starting to gain momentum right away. Warby Parker was really out picking up speed and I was just like wait a second. Like this makes sense and I really thought critically about it because I knew it wasn’t going to make sense for every category or for every product line.
Although we’re trying to make it.
Everyone is trying to make that happen. But just like in reality there are reasons why certain categories work direct to consumer and other ones don’t like don’t need to be or they’re just there’s too many other brands and there’s already brand loyalty and so I realize that a lot of the characteristics of what I believed would make a successful direct to consumer business were in. Like I saw that in the home space. So first part of the year liked it all throughout January. I was still working but was spending a lot of time working also on this idea. So like building a pitch deck and talking to anyone and everyone I knew that had worked in home textiles I was doing a lot of product research buying all the products that I could find in New York sampling just like seeing what was out there and trying to understand if this was actually a feasible idea. And then by mid February I was like This is it I’m taking the plunge I’m doing it which was like completely premature and you know.
Yes and no.
Yes and No. I mean it all it all worked out in the end but what I really wanted to do was. Well I wanted to move back. I knew I was going move back to L.A. to start this. But I also I wanted to know how these products were made because I’m not a textile designer by trade and you know I knew what I liked and I knew the aesthetic and I had this idea for a product assortment and a lot of that you know never changed. Like I really from the beginning and from those early inception moments like it’s the idea for parachute and how we’ve evolved was already there but I needed to understand like what it actually took to make a sheet.
Well that’s interesting because you know you see a lot of these new I mean I’ve seen all the decks you’ve seen a lot of the companies of people that you know are graduating from grad school. They’ve decided we’re going to be in the world of making gym clothes. And nobody has ever designed a pair of shorts in their entire life. Yeah you know. Or. And that is such a personal thing to like style and clothing. I mean very different than sheets. Yes it’s a very very different business. And I see them all the time or like we’re going to start a company making this. But we’ve never you know we’re going to make a company in agriculture we’ve never spent any time in agriculture but we really feel that there should be this in the agriculture world.
Yes. Yes. And you could argue that I was there at the beginning. I mean sheets are.
But everyone uses a sheet.
Everyone uses a sheet there are standard sizes you’re not designing for a body type although at this point now that we have robes we sort of are. But that’s a different product anyway. It’s not like clothes at all in reality but so I just needed to understand and so there was only so much that you know the Internet at that point could teach me about how to manufacture these products so I I found myself calling then like getting in touch with a number of different factories throughout Europe and for me it was always about Europe because I knew that building a brand required building trust and I knew that quality was going to be so inherent in that.
It’s very different over there. I mean I just came back randomly enough from Paris doing the design of a house and those products. They’re not here. You literally cannot find those products here. And it’s really strange but you know they look at home is in a very very different way.
Yeah. And to me it was really important that I was able to tell a story about what we were doing and who we were working with and.
Well you learned it from your Ad days.
Yeah exactly. Like I knew that there had to be a compelling narrative and this is like really interesting story behind that we could tell and that would be intriguing and inspiring for people so I went directly to Portugal and Italy because that’s where this heritage is and that’s like where the best sheets in the world have been made and found a lot of family owned factories that have been doing this for over 100 years passed down from generation to generation and just like these people are actual craftsmen like they’re actual artisans and that word also gets thrown out a ton you know in ways that aren’t really actually accurate but these are like people that know this craft. And they understand.
I mean you look at the Gucci family or like you know. There’s so many different families Missoni family. I mean these are years that are Zenga I mean all of it.
They’re really and you know they care so much it’s not just about they care about the product. They care about the land and they care about it. They breathe it. So I mean they like wear a three piece suit to the factory every day. I mean it’s just such a different culture. Yeah it’s just like appreciation for the finer things. And so you know for me it was about understanding if I could afford to buy these products and if we could sell them you know.
At the price that makes sense.
Well you got rid of the middleman right there.
Right. And you know and actually design a collection that made sense and so I brought like a huge suitcase full of all the samples of all the things that I liked and sat down and it was such an eye opening experience. I mean what people a lot of people don’t know and we’ve actually shot a lot of videos now at our factories. But you know you need so much space to make a sheet. Like it the machines are huge huge like football field size, airplane hangers. And there’s many of them like. It starts at this thread and it goes throughout this like crazy process so many people touch the product. It’s so detail oriented and it just blew my mind. I mean it’s like all the excitement that I felt leading up to that but yeah they’re making it out of a thread. And even fiber before that. It’s just it’s beyond. And so I came back from that trip just like I’m completely consumed and ready to hit the ground running but also had no idea where to begin. Which was fun and confusing sometimes sad and sometimes exciting. All of the emotions but I really like realized that you know this could be something big and it was something that I felt so passionate about. And just it was like Game on. Like this is it it’s time.
And so what was the first move i mean parachute which is a great name and how did you come up with that?
It’s inspired by the movement of the fabric when you make the bed so that billowing sheet as it as it falls down when you shake it. But really I mean we had some bad names before.
Yeah like that’s a tough part of the process.
It’s really part of the process. And then you have to build a brand around it. So really it did in many ways in many ways the name makes sense but doesn’t make sense into any product because you have to just build a brand around it.
Yeah I mean if you think about all these iconic brands it’s like so random what their name but now it’s like of course that’s just synonymous with whatever.
And so when you raise money in the beginning -I don’t remember did you have a product or not.
Yeah I raised money. I had launched. Well I got a little bit of money from being in launchpad and that basically went in one day and then out directly to the manufacturer the next to buy our first batch of inventory. Like the entire check. Every single penny of it was like oh cool I’ve got money in this bank account. There it goes. Yeah and then the product came in and then I launched in January of 2014 and was able to raise that seed round. I believe it was around March that it happened. So I launched- had a few months of data. You know I was like.
Well it’s funny because I mean and my thesis has changed so much and just even in terms of, although I still think that the one thing I’ve done really well is invest in super scrappy people that are survivors. But I remember when you know Karen said you have to meet my friend Ariel she’s doing this company called parachute and you need to talk to her and I was like what is it exactly? And the minute she told me I was like oh my god that makes so much sense. It’s just so smart. I mean no one has done that.
Yeah. I mean we were first to market and obviously this space has gotten way more crowded and like all of a sudden there’s a ton of mattress companies and there’s a whole bunch of things. But you know there had never really been a true brand. And for me coming from a brand background like that really like I mean I said it was a huge aha moment like wait a second I can do what I love to do which build build a new brand and a category that really needs one and that consumers would appreciate.
Something you care about. And so but it’s interesting what you just said is to build a brand. I think that one thing that you’ve done in a lot of these brands are not doing is they’re they’re building jello shots. It’s not that they’re not building a brand but they’re not giving. I like to look behind the curtain and say how much are you paying for customer acquisition yet. How often is this customer coming back. How loyal says customer. You know and you know what you’ve done is you’ve been very methodical building a very solid foundation and being insanely scrappy about the amount of money you spend you know from building out your office to. We can talk about you know why you made the decision to do brick and mortar as well as an online business which I think was a really smart there. But you’ve always been very methodical and bought thinking about how you build that foundation.
Ariel: It’s always been super important to me I think also because I started this business at a time where I was already watching businesses kind of skyrocket to success and then sadly crash and burn. I mean I think we’re funding capital yeah with tons of capital and I really saw that as a cautionary tale I mean for me it’s always been you know we spent the past four years actually building the engine. Like to now transition into you know building something that’s much bigger, but from day one it’s always been about you know real business metrics. I think so many people focus on these top line revenue numbers. You know it’s like you’re going acquire the customer at any cost and it can be really detrimental you know and you can also- I mean we look at loyalty from the first time you see the brand and how we communicate. You’re really in the business of building emotional connections not transactions. And I think that’s a big difference in terms of what our strategy is in a a lot of people do. It’s like kind of smart. And you know for us what we see so often is that people you know you pay for. You incentivize your customers with you know 30 percent off or 20 dollars back on your first purchase and then you pay them to give you a good review and then you pay them to do this. You pay them to do that you pay that and it’s just you know it’s building this experience that isn’t authentic and it’s you know cutting a lot of corners and doing things that just in money pissing into the wind. The valuation getting you know ridiculously overpriced.
Joanne: I totally agree. So when was it you know did you always have in the back of your mind that the, or did you see it. I mean certainly we saw it with Warby Parker but you know- you have this direct to consumer business you’re growing it online. I’ve always been a fan of 80 percent online 20 percent brick and mortar. When was your like- ok, We need to open a store and now is the time.
Well I think you know we always I always knew from the beginning that people like people historically have 90 percent of purchases made online. And when you look at all of them they still are yeah.
Joanne: Grocery’s 97 percent.
Ariel: You look at the incumbents it’s like you know any of the big big players you know between 75 percent 85 percent of their of their sales are happening off line and they’ve got hundreds of stores some have thousands of stores and you know they’re also mostly furniture brands at their core that also sell sheets. But you know I think what I saw was that people respond in a different way when they touch and feel the product. And you’re never going to be able to replicate that online although we try many ways with video and just images and bringing the products to life.
Joanne: At one point used to be able to get swatches.
Ariel: You can still request them secretly and we’ll send them to you for free we just don’t. It’s like became too big of a deal. It’s a major deal yeah. It’s just is too much money. It’s a lot of labor to a lot of labor and we couldn’t automate that at just rush you cannot
Joanne: you can actually there are companies that can do for you and you can still be there.
Ariel: They serve a purpose for a specific customer we’re happy to you know give them the swatches that they need. But in general it felt like a lot go into the bedside drawer and it just wasn’t worth it. But you know the response that we were getting from people that were seeing the products putting it between their hands was just like Whoa these are so good. And I really are.
Joanne: Yeah and there they are.
Ariel: But you know I look at stores as a way to build you know a future things that’s obviously revenue you driving which is great but for us it’s like putting a stake in the sand and really having presence and this awareness play in this community driving opportunity for us because we’d look at our stores not just as again transactional you know locations they We host events we have pop and we do a lot of stuff within communities and so there really a way for us to bring the brand to life and drive this lifestyle brand and also create beautiful spaces. I mean I think what we do also that so differently than traditional retailers is like our stores are between 450 and 800 square feet. Or I guess right now. Well yeah that’s where we’re tracking and that’s what we’re doing. And so they’re small. We don’t have beds on the floor like it’s we’ve got pillows and we’ve got all the fabrics you can see everything and see the colors together and the way that the fabrics look when they’re paired next to each other but it’s really like going into the living room. And people I want to buy the chairs and the tables everything.
Joanne: Yeah and you can continue to partner with companies that make sense to come in for like a couple weeks and to go to the store.
Ariel: Yeah it’s just really fun. It brings into life I mean and there’s also people like we want to be where our customers are and we are 100 percent aware that there are people that prefer to shop online and so we also want to be able to serve those customers and we get a lot of people that come into the store that like I’ve been following you guys forever. I’m so excited to see the product in person and then they’re ready to shop and then they shop online. And it’s you know it’s easy
Joanne: Right because they know what they want.
Joanne: But then you know you added more so you added these gorgeous towels that are amazing. Yes. And you know longtime I thin into towels and into robes now and children’s.
So you know that sort of happened quicker because you know you already built what you’re going to be able to do.
Yep. So we launched we waited two years before we launched a towel and then we just launched one towel and we gave that like some breathing room and listened to customers and made sure that the product was working within our assortment and it was and then we launched robes and those were just like this huge success for us and then great. Yeah I’m obsessed with our robes. But then a year after we first launched our first towel collection we introduced shower curtains and bath mats and tub mats and so then we had this like full bath assortment. And that was really exciting because it actually gave us a chance to- It gave us an opportunity to really market those products as a collection and actually do so profitably which like you mentioned is really important from a customer acquisition cost and so we were able to acquire customers through bath in a more meaningful way.
Joanne: so you’re in intimate areas
Ariel: Yeah we like, we’re in intimate areas of the home and like we like to be. We like to think about all these places where you’re like we’re comfort can be enhanced and be the brand that does enhance it right.
Joanne: And nobody’s really doing that in the children’s space you know
Ariel: Yeah, I mean our collection with the baby and toddler and all that stuff is was completely by demand I mean our customers were you know wanted our products. We don’t use any toxic chemicals or synthetic finishes in our products for adults.
Joanne: Right. Larger people.
Ariel: And so they were like why can’t we just get the mini like we like. It’s really actually hard to find great quality products and also the aesthetic. You know we like don’t want these bright colors always in our nurseries we want them to really relaxing. So we took a lot of cues from our customers there and we’re expanding that collection quite a bit actually in the next few months so it’s pretty amazing.
Joanne: And so where are you brick and mortar at this point?
Ariel: So we’ve got two stores today. We’re got one in Venice and one in Portland Oregon and we’ve got a few more coming in the next few months.
Joanne: So can you talk about where they’re going to be more opening in New York.
Ariel: Right. So on Crosby and Graham- we are also really excited to be able to host events it’s a slightly larger store and we’re making sure that we can host dinners in there and which is great.
Joanne: You did the right thing there too. It’s like – you waited until you found the right location.
Ariel: Absolutely. And we looked for a long time. It was really hard to find a great location. It’s so weird because there’s a lot available but it just wasn’t the right fit for us. But we did a pop up actually last December in New York and that was really fun, in that area. And it was you know it was great to just tell people like hey we’re coming and get that response and and just and just you know test what it would look like. But that should open in April and I’m super excited about that store. And then we’re opening one in Silverlake.
Joanne: Interesting. Fantastic. That makes a lot of sense
Ariel: We’re going to do a second in L.A. since this is our hometown we want to make sure that we’re covered here
Joanne: And Silver Lake, Venice, is like a different city.
Ariel: It is. And I mean we look at where our customers live it’s largely those are like two main hubs for us so and there’s so much stuff happening downtown in Echo Park and all of those areas so it feels like a great place because we like again we’re like we’re very much a product that people need. So as you’re moving you know we want to be around an area where we’re going to be as really fun. It’s got a lot of great neighbors and it’s great to be around.
Joanne: That’s fantastic. Any other cities?
Ariel: We’re hoping for San Francisco this year and potentially Dallas and Chicago. But we’re still very early in those stages but we want to be in five. We want the five new stores this year and could be quite a bit more next year.
Joanne: That makes sense. I mean those locations make a lot of sense.
Ariel: Yes so we look at it two ways it’s like we want to be where customers are and then there’s also areas where we under inducts a bit and we want to be like we want to have a presence so we can grow the customer base. But you know it’s fun in Venice and in Portland we get you know the locals and the people that live here. But we also get a lot of tourists coming by and people that are in town and have heard about us and just want to see the products in person. And so we again we want to be where our customers are and definitely major metropolitan areas is where we’ll start. But you know I see a world by like 2020 where you know 25 stores
Joanne: Which is amazing and how about in terms of product do you see you know you’re you know you’re in children you’re in full on bath. You know do you see other products.
Ariel: So we have tabletop right now too. We’ve got some table linens and napkins and placemats and that kind of stuff and that’s been really fun because it’s like the most communal
Joanne: And they’re beautiful I ordered, I saw them they came up and I want to try this out.
Ariel: They’re fun and we like we design them so that they could be machine washed easily and you know they don’t need to be ironed and very casual feel. Yeah exactly. Goes with the brand. Exactly like your everyday linens. I’m really trying to use more cloth napkins instead of paper towels. Personally it’s a goal. So you know it’s good to have them around and then. We’re like starting to think about rugs as a potential new category they’ll be like ways away.
We’re very early right thinking and trying to develop her point of view but I think for us what we what we try to do is like really understand our point of view what we want to be in this category. How are the products that we can. What are the products we want to introduce first. I mean we’ve got a ton of new stuff happening in bedding and bath and table and baby actually all this year. So we’ve got about 45 new styles coming out
Joanne: which is huge.
Yeah that’s, it’s great.
Joanne: Yeah. All right well thank you so much for coming. I love your Parachute. Of course I’m an investor. In all full disclosure. But you know it’s been really fun watching your journey and it’s really you know it’s been interesting watching your journey and being involved in the journey as I see so many different consumer brands and I and I’m a big believer not only in the brand but how you have built the business in a very thoughtful methodical scrappy way. Not just by pouring a bunch of money into something and thinking it’s going to stick on the wall and I think that it’s one of the things that we keep talking about on this podcast which is it’s not easy and it’s not a quick fix.
It’s definitely not a sprint it’s a marathon.
It is a marathon now for sure.
Ariel: And it’s also I mean no brands were built overnight. So I think that’s like what I keep telling myself what our team talks about. I mean there there are reasons why brands take time and cutting corners just never never works out
Joanne: It never works out now. And you know I mean in 2020 when you’ll look back you’ll be having completely different conversations.
Ariel: I’m looking forward to that. But I love them. I’m willing to wait a bit. So all I know there is let’s take that slow but yeah I know it’s really exciting. I’m really excited about the brand and how things are growing and it’s going be a big year for us. That’s great.
Joanne: Well thank you for coming.
Ariel: Thank you for having us.
Making A Business out of Making Connections, Dana Astrow, ARC, Episode 55
Dana Astrow has been influencing the landscape of creativity in the brand marketing and advertising/film production community since her early beginnings in the industry. Since launching ARC, Dana has successfully and nearly single-handedly filled a definitive niche as a creative recruiter who connects the makers behind some of the most effective top-level content being produced today. Dana and I sat down for some real talk about how she’s had to make not one, or two, but three big leaps in her career — definitely some relatable content for anyone who’s balanced motherhood and career, started a business, left a partnership, the list goes on.
Joanne: I’m Joanne Wilson, and this is Positively Gotham Bound. Small meaningful conversations with women entrepreneurs about their approach to life, business, and everything in between.
Dana Astrow has been influencing the landscape of creative in the brand marketing in advertising film production community since her early beginnings in the industry. Since ARC, A-R-C, Dana has successfully and nearly single-handedly filled a definitive niche as a creative recruiter who can next to makers behind some of the most effective top level content being produced today. Dana and I sat down for some real talk about how she’s had to make not one or two, but three big leaps in her career – definitely some reliable stuff for anyone who’s balanced motherhood and career, started a business, left a partnership, and the list goes on.
Dana, you’ve been an entrepreneur since I met you. I know you don’t think of yourself as an entrepreneur, but you are an entrepreneur because you have your own company.
Joanne: Yeah, and you have forged on your own. You have great reputation and made an impact on a variety of companies in helping young upcoming directors find their way into the advertising world. Not only here’s a deal for you, but really helping their nurture their careers. But you started out in advertising?
Dana: I started out repping directors, working exclusively for a particular production company, and then they would have a roster of talent and then go out. My clients at the time would be all the advertising agencies, mostly producers, copywriters, art directors, creative directors, and pitching the talent to the advertising agency. I worked on staff for production companies, I don’t know, probably for seven years. Then branched out on my own, went into business with Peter Ziegler. Then he and I split up, and we each had our own talent agencies.
Joanne: Which is interesting, but let’s go back. You grew up in Queens and then your parents decided in high school that you should move to Los Angeles, and they ruined your life.
Dana: Pretty much.
Joanne: That’s a pretty major thing though…
Dana: It was.
Joanne: To up and move someone in high school…
Dana: It was insane.
Joanne: And particularly…
Dana: Did you hear that, mom and dad?
Joanne: Yeah. I mean, living in a city that you’re completely … You can get around, do whatever you want for everything, and then they move you to Los Angeles. Whole new people, whole new weather, and you have to drive.
Dana: Yeah. I have to say, when you’re 14 it wouldn’t matter where you’re moving, it’s great as we know…
Joanne: It’s one of the worst experiences ever. You’ll be starting from the eighth grade.
Dana: Ninth isn’t so pretty either, so I had …. It was just a crazy time. Living in Los Angeles, it was 1979, 1980 was insane. It was like the book/movie Less Than Zero.
Joanne: It was a crazy time.
Dana: It was a crazy time.
Joanne: But then you went back to the east coast to go to school.
Dana: Went to BU.
Joanne: Then you went directly…
Dana: Majored in advertising/marketing.
Joanne: Then you went to New York. Then you landed a job and worked in the ad agency. Did you always work for an ad agency?
Dana: I was working for a production company. My first job answered phones, receptionist. My then boss at the time asked me what I wanted to do, I thought everybody comes in here and says I want to be a producer. I’m just going to tell him, I want to do what he does. He was the salesman of the repping part of directors. He took a shining to me, it was done. I was like, okay. Then I got promoted. Prior to, in high school, I was salesperson in clothing stores, and different things. I had to do some things…
Joanne: And you have great people skills, so that was the perfect thing for you.
Joanne: Yeah, I can’t imagine you’d want to be director. It doesn’t seem part of your DNA.
Joanne: Not at all. What was it after being for seven years that you’re okay, I’m going to go off and do this by myself?
Dana: The last couple years, I worked on staff at a production company as their in-house sales rep. I started to bring in talent to the company. I was saying, I’m capable of more than just hey come work with us kind of a thing. I wanted to be recognized, so they then promoted me to executive producer, but did a little bait and switch and put me in another company of theirs at the time which was Bedford Falls. It’s was Ed Zwick, Marshall Herskovitz, Peter Horton, and all those guys wanted to direct television commercials. They brought me in there to help build up the talent side of what the company would be.
One of the directors I had a relationship with did follow me in there, but it was so hard. Although they were at the top of their game, they were never available. It was very hard to convince the advertising community to look at feature, or even television directors, as full-time players in who they were going up against. I did that for a year and then I just realized. Peter, a former colleague of mine, was always knocking on my door saying we should do something together. Let’s open our own independent repping company. Finally, I think I was worn down enough by then, and I was like done.
Joanne: You were done, because you were out of there, and you knew that.
Dana: I was like, I can’t be beholden to this criteria anymore. I want to choose the talent or the companies that…
Joanne: That you want to work with.
Joanne: Which is one of the greatest things about your industry, is that you your own company, you represent these people. By representing these people, you get to work with people you really like.
Dana: Yes. To even take it one step further from pivoting out of that model of being an independent rep, where I represented a different production company, music companies, a whole slew of different types of companies. Now in recruiting, my relationships are just literally, we have thousands of clients and thousands of candidates versus this is my roster of who I work with, so just one step further…
Joanne: Taking it to another level. But what was interesting, you worked with Peter for how long, how many years?
Dana: We were partners for four years.
Joanne: I always thought that you carried the show over there.
Dana: It’s funny you say that, because I always look back on that and think… I love him as a person so much, but he was in the thick of…
Dana: … insanity with newborn children, a lot going on in his life personally. Of the dynamic of our personalities, it just became too taxing on me.
Joanne: It’s like you were very … Everything was in order, everything was buttoned up, and he was all over the place.
Dana: I was a little bit of a livewire at that time. He had temper problem.
Joanne: I’m sure probably does still.
Dana: It’s in check. Again, I think between his temper… Here he is two little babies, starting his own business – although we were doing really well, we had a great run – I think… It’s funny, I look back on that a lot because I adore him….
Joanne: That’s where you started your own.
Dana: And, by the way, he’s wildly successful. He’s done incredibly well without me. But our…
Joanne: The dynamic didn’t work.
Dana: I would say it’s timing.
Joanne: Yeah, he’s definitely a livewire hustler.
Dana: Yeah. He was dialing for dollars. I’d be on one phone call for an hour, and he was dialing 55…
Joanne: Yeah, he had a different thing.
Dana: Totally different approach.
Joanne: When you finally made that decision, this is not going to work out. That’s a lot, it takes a lot because you were in a company, you realized your value was tremendous. You were like wait a second, I’m running my own company in a company, so why should I be in a company? I might as well run my own company at a company. Then you were running your own company in a partnership, and then you’re like what am I doing here, for what?
Dana: I think a couple things: A, I was pregnant towards the end and kept thinking to myself how am I going to have a baby when I have this baby? There was so much managing of him at that particular time – no disrespect because I do love him. Mindy, ePop was one of our big clients, was like I’m not going to talk to him anymore.
Joanne: That would be the big one.
Dana: That became the lynchpin or excuse for me to say this can’t go on anymore.
Joanne: That was hard. I remember that, that was really hard. That takes a lot of strength to be able to say we’re going to get divorced from this little marriage here.
Dana: It was not fun.
Joanne: It was not fun and not pretty. Then you went on your own and had a child, and another child, and then you moved to Los Angeles.
Dana: That’s right, I came back to the place I hated.
Joanne: You came back to the place you hated, but it made sense.
Joanne: I think it was one of the better decisions you guys made. It’s been great for you guys in terms of both your life and also your careers.
Joanne: How far along were you in New York in building that business before you came here?
Dana: I was with Peter for four years, then I had Astrow Girl for four years, and then we moved here in 2004. I, for about 18 months, two years, was a stay at home mom.
Joanne: That’s right, and you were just trying to figure it out.
Joanne: Let’s talk about how the industry has changed, because I think that was one of the reasons too, even when you were staying at home and trying to figure out what’s next, is the industry is changing in regards to… Now, there is actually much more fluidity in regards to you’re only in advertising director, or you only do movies, or you only do TV. Now, there’s people in tech world who want these people to maybe do projects for them.
Dana: Right, there’s so many brands, even agencies, so many businesses that want to create content. Some of them have set up their own content studios internally. Some will still outsource it, but client in general, I think has become so much more sophisticated about content creation. Not to mention, content creation just doesn’t look like a 30 second television commercial, it’s a webisode. Who are the people that are on YouTube? Not blogger.
Joanne: Yeah, the YouTubers.
Dana: Everyone is making content all the time, and companies/clients are using all this content for their advertisements. It’s not just formulated systems. Yeah, the business has change dramatically. There is crossover, yet at the same time I still need a commercial director, or music video director. I’m using really dated terms now. I need a documentary star. I think that the platform is so much bigger. What’s happened is, someone said this a few times I always borrow their line, everyone is everyone else’s lane.
Joanne: That’s a great line.
Dana: Right. There is no sense what’s happening in the business where I can do that too, I can work 25… The other word I love is producer editor, so it’s predator. Everyone is shooting their own content, editing, creating, doing the visual effects, and trying to be all things to all people.
Joanne: You can because there’s so much more access to the…
Dana: The channels to where you’re sending your information.
Joanne: Exactly, or even the physical hard goods that you use in order to create these things. It’s not like you have these big huge things you have to rent anymore. You can play around with anything, which is pretty amazing.
Joanne: So, you were home for 18 months, a lot of women- listen, I think that is one of the hardest challenges for women that are interested in working and want to be engaged intelligently, but still want to have the balance to be home and be there for their children. You really in many ways I think created the absolute perfect opportunity for yourself. Because you’re not beholden to anyone. I mean, I’ve been with you when you’ve been having conversations in the car, or wherever it is you need to have them in order to move the business forward.
Dana: Right. No, I definitely do my job from anywhere, wearing anything, at any time of the day, there is no…
Joanne: It’s like, what’s that ad where the girl was in her pajamas with the slippers? She was at home doing work as an advertising .
Dana: It was great. And yeah, absolutely. I think I wanted to back to work. It was a hard transition to go from having your career in an office, people, and things like that in New York, then we moved to LA I was like oh hi, I’m in the witness protection program. When I was putting the girls to school saying Solomon was so much easier than Astrow. I’m not even Astrow any more, now I’m Solomon. Who’s that? I felt very lost. Again after 18 months, two years, I was like I’ve got to do something. I don’t know what it’s going to be, and just started contacting people in our industry. I felt like I was a handyman for a good year, where it’d be like hey, can you help me change the light bulb? I was like sure and put myself out there in that capacity to consult.
I started out at first working with another independent rep that was in New York, she just wanted some business advice. I’m not a coach, but I was like I will talk to you an hour every week and give you my idea… Then I realized from that conversation, she was like what I really want is for you to help connect me to other companies that need my business. I was like, oh okay. Then I started reaching out to various production company clients for her, connected them and set up a different pay structure. Then those clients, those production companies were like hey, if you’re helping her, maybe you can help us find talent. I was like okay, let me try that now. Created a model and different price points for those matchmaking services, which then turned into I need a head of production, I need an executive producer, blah, blah, blah.
Joanne: Right. Really, it’s an evolution of what your business has become. What’s interesting, and it all goes down to one of the things you’re really great at, I think that it’s a skill that people don’t talk about, which is being a connector, and being a huge Rolodex, just always networking. You have done that in your industry that have allowed you in many ways to take what you did at the very beginning, and those dots have connected. Now, you’ve got the ability to not only just yes, I can get you a documentary person, but if you have a hole in your industry and need to hire someone full-time I might be able to find that person for you too.
Dana: Right. I do think a lot about even your personality. I’m so much happier when everyone else is having a good time at a party. I don’t care that much about my… I’m so much happier if you like that friend over there, that’s how I am.
Joanne: It works for you.
Dana: The best thing in the world is it’s the candidate or client, particular candidate when some’s been out of work, they’ve found their dream job – I can hardly say we’re solely responsible for that – but you’ve made that change in someone’s career or life.
Joanne: It’s huge. You look at LinkedIn, which is such an interesting platform, which has changed the head hunting world. But at the end of the day, it’s still is those connections and you’re still going to say, is these the right people, who you know and what you know. I think I play head hunter all day long in a different form but is the same thing which I think is so powerful.
Dana: So much of it is the person’s… I mean, there’s the person…
Joanne: There’s the skill set, hands down. You’re going to be like I’ve never been an art director before, but I’m a nice person.
Dana: The person has to have the talent or the skill set, but then it’s really the culture fit.
Joanne: Which is so important.
Dana: That’s where I think the head hunting, recruiting, or the matchmaking whatever you want to call it, that’s where it really comes into place.
Joanne: Yes. People talk about that more in companies now than they ever did before, the importance of culture fit. Even today, we’re seeing that companies are giving women and family members more time to take off to whatever it may be, because they have to. They say it has to do with, because the unemployment is so low. Whatever it is, and what it takes, I don’t really care. But I think that that is one of the things we’ve both done, which I think is incredible, is that we’ve managed our own lives and been able to be at home or be on vacations or go to the kids’ basketball games or whatever it is, and still make a name for ourselves and create our own success even with a 3:00 basketball game.
Dana: Yeah, I’d be checking text message every two seconds.
Joanne: But it works.
Dana: It’s so funny, as you were saying that. You’re right, we’re so fortunate to have been able to create these worlds to move in and out of, to be available to kids, family, or whatever, and also work hard and full-time. You never feel at peace with any of it, you just don’t. I remember you saying that to me early on about you’re never going to feel … You’re damned if you do and damned if you don’t. It’s just you never feel like I’ve got it mastered, there’s no mastering of it, you just have to go with feeling bad that your kids are knocking on your office door and outside making faces at you, you’re putting your hand up like shut up I’m on a call. Then you’re getting text or phone calls while you’re supposed to be at your kids’ doctor appointment, or basketball game. Trying to shut that down, but your brain is like someone is trying to get in touch with me.
Joanne: Because there’s no structure.
Joanne: You’re never going to feel like I’m mastered this, there is no mastering. I think it’s probably in general in life for people…
Dana: Yeah, I think that’s true. I think particular for women than it is for men. For sure, men get a little… I think that’s changed dramatically too, but it’s like I got to go to work, that’s what I do, work. I’ll be home at dinner. That’s how it is, and the next moment it’s over. Your job is never over.
Dana: It’s completely fluid.
Joanne: How do you see the industry changing? You have your finger on the pulse of entire creative industry in Los Angeles in regard to be it creating content, be it creating ads, movies, or what have you. What is the biggest change you’ve seen over the past couple years and thinking this is where this is going?
Dana: This is where it’s changed. Without making it just about us, but what I think the biggest change we seen is the directorial talent piece where 50% of our model was making exclusive placements for a director to go to a particular production company. Because of what we’re talking about, so many different kinds of content is being made at so many different price points, that model seems to be shrinking. There needs to be a bigger platform which we’re trying to work on particularly for directors where they can have a freelance life as well as maybe an exclusive life. But they can be called upon for so many different projects.
To make a long story short, I think that model, that exclusive I only live at this one place, and I only work here, is broken. There has to be more availability and more ways to …
Joanne: To talk fluid.
Dana: Yeah, more fluid.
Joanne: Everyone is almost a freelance person?
Dana: Kind of.
Joanne: Yeah, which is an interesting way to look at your industry. How about in terms of females?
Dana: I will say it’s still the one-percenters. In any business when you look at even feature films, the action hero movies where you’ve got this top tier directors that are always going to make … Like a Steven Spielberg movie or Ridley Scott movie – then there’s everybody else, like we saw at Sundance. There kind of filmmakers may be once every five years are making a movie because it’s so hard. Those filmmakers need to find other places to make money and to create content. And there was a time when that was like, you know, Dayton Faris, Val, that was Little Miss Sunshine. Those guys can kill it in commercials, but even that’s changing too. There’s not enough of those super high end commercial work being made anymore like the franchises. There’s the franchises of the films or there’s everybody else.
Joanne: That’s interesting. Alice Prager who we actually own a couple pieces of, who’s an artist. She has made a couple advertisements. She did Gucci recently. She also did something else for someone else. Her work is very, very specific, the minute you see it. I think she did it, I want to say for J. Crew or Nordstrom’s or something like that.
Dana: I was reading about who’s she’s with.
Joanne: Her stuff is beautiful. It fascinates me what’s she’s done. She’s an artist by training, actually I don’t even think she’s by training, but her work as been…
Dana: Well, she’s a fine artist, she’s been in that world…
Joanne: She’s been in photography, then she started making movies, mix media and through that mix media that are pieces of art, you call that.
Dana: Think about those brands, those are super high end.
Joanne: Super high-end brands.
Dana: That kind of talent … She defines them.
Joanne: She totally defines them. The minute you see it, I’m like oh Alice Prager must have done this.
Dana: Remember LV purses? They were, Steven Sprouse did a Louis Vuitton bag.
Joanne: Oh, totally.
Dana: All the bags that were artist generated…All those super high-end designers want to associate with…
Dana: … whatever is the coolest artist, happening person on the planet right now.
Joanne: For sure, because that’s what they have to do. Have you seen the industry change dramatically for women over the past 5 to 10 years?
Dana: Sadly. I wish I could say otherwise. I think someone had just hung up with a woman who was part of designing our website her name is Isabelle Albuquerque. She’s so unbelievably talented, crazy talented. She’s like, I think this “Me Too” thing is going to be amazing for women in our industry. You’re going to find out. I will say that every production company that comes to us will be like, if you have any female directors send them our way. We do, and sadly there aren’t that many of them, and they don’t make the cut for the production companies. There’s not enough, or they’re inaccessible…
Joanne: They’re not making conscious decisions to hire these women.
Dana: They’ll say that. Even in the jobs, there’s a certain… I can always feel the bias coming in about I want someone that, let’s say it’s an executive producer hired, this is all lifestyle job for them. I’m like, what do you mean by that? They won’t say they don’t have kids. They won’t say I don’t want a woman. But it’s okay if we’re talking about a man with a family, but it becomes something different if we’re talking about a woman with a family in terms of when they want the lifer type, or the lifestyle persons that can travel. I was like, if they’re doing a great job, what difference will any of that stuff mean. You can just feel a wall go up.
Joanne: What’s interesting is, is that the generation that I know of people in their 30’s or early 40’s and have young children, the man is just involved as the woman. Those companies are not really looking at how people are running their partnerships in their lives.
Dana: Yeah, for sure. I think this is very generational. The decision makers are still thinking old school, and not who gives a crap. If this person is a Rockstar ….
Joanne: They’re a Rockstar. Have you ever thought about going and spending time on some of these crazy YouTube videos and reaching out to some of these new interesting people that are shooting things? That you’re like, hey, maybe I can help you make a reel, I think you’re interesting, or you’re past that?
Dana: I’m past that.
Joanne: You have people that work for you now.
Dana: I could do that. We don’t even have the bandwidth. They actually come to us. This new platform that we are going to present to brands directly and content creators, it’s all for freelance directors. We already have probably 100 directors …
Joanne: Putting stuff on your website?
Dana: Yeah, we’re still in the building stages of it. We can reach out to and say; would you like to be part of this? It’s a subscription-based platform, as it will be for brands, agencies, and in-house agencies, and even anybody that …. The client that needs to create context so that contents can find each other. Again, it’s subscription based, it’s not now it’s transactional, you pay us this much money for that placement. You can work with that person 87 times.
Joanne: You’re creating a very interesting database. For many ways the LinkedIn of your industry, or a marketplace for your industry.
Dana: Yeah, that’s …
Joanne: But having you at the top gives the prominence because you know the talent, and you also have proven yourself as a leader in the industry.
Dana: Right. We know what you’re looking for. The search engine will be fantastic. We’re going through all the steps to figure out what are the most important things that people need, where it’s going to fall apart, where it’s going to work and schedule being one of them. A lot of the filmmakers come to us, maybe at some point too we will have somebody scouring the marketplace. Again, not that we’re the only people, but we do have a big influx of filmmakers that will be like, will you help me. We’ll say to them right now, here’s what we’re doing. Are you interested? They’d be like, I’m so interested in that, keep me in mind when you launch.
Joanne: I love the subscription model for so many reasons. One is, is that even though it’s not the best analogy but if you look at the first dibs, or artsy. The concept was, when you make a transaction on our platform, we will make some of the money. Here’s what happens, no one stays on the platform, they just go off the platform. They had to change the model, the model being is if you have your stuff up here you pay us monthly in order to keep your stuff there.
Dana: Because you could go to that person without us.
Joanne: Right, one on one. If you are charging an artist one price, because some of these YouTubers are younger and they can’t afford it, but then you’re charging the agencies a completely different price point, so they have access to thousands of everybody….
Dana: A different kind of access, and they can choose to post, where freelance projects, which is hopefully what will end up happening. Again, they can decide to be private and not…
Joanne: To the world.
Dana: … to look and see whatever they want, or they can open it up and be content, anybody can contact us too, then sort through. Again, the idea is that if it’s curated like an Etsy or with a certain kind of flavor. Hopefully, because we’ve all been doing this for a long time, we understand what the flavor of our audience is looking for.
Joanne: Right, that’s pretty cool. That will be the place to go. What’s the website going to be called?
Dana: Jerry Solomon, invented the name, invented the concept for that matter too. He was like, you got to figure out what to do with all these people. It’s going to be called Unaffiliated.
Joanne: I love that. Do you have your URL yet, unaffiliated.com?
Dana: I don’t know if it’s a .com, but we bought all…
Joanne: Three dots, yeah.
Joanne: Yeah, in California. That’s very cool.
Dana: .TV or who knows what.
Joanne: Right. Of course, you bought them all. If you’re a young filmmaker out there…
Dana: Or a seasoned filmmaker.
Joanne: That’s right, or more seasoned, put your thing…. Why wouldn’t you?
Dana: That again is why a lot of this came about, is because my age category we are dealing with a lot of these seasoned filmmakers that have already been to three or four different production companies.
Joanne: They have done that.
Dana: Yeah, it doesn’t make sense anymore to sit in this exclusive relationship if there’s no work coming in. Why not put yourself out there and figure out how to have another tool in your tool bag?
Joanne: Completely. It really is huge. You have seen the downfall of these small individual houses that have: we’re responsible for eight directors and …
Dana: Each have bills, $5 million a year.
Joanne: That’s just how it works.
Dana: And now that industry is over.
Joanne: Yeah, so this is one of the new paradigms, what you’ve been building.
Dana: I always think about the medical industry, where these private practices with super high-end doctors that are charging blah, blah, because those insurance companies and just the way our healthcare has become. They’re getting eaten up by Cedars Sinai or.., and they buy the practices and bundle them, and create a different platform. It’s definitely eaten into the way a doctor can make money, unless they are an executive in that plan. It’s not that dissimilar.
Joanne: No, it isn’t that dissimilar. Yeah, I think what you’re doing is… What is great is, it’s great for the agencies, but it’s really great for the artists.
Dana: Yeah, for the content makers -it gives them exposure, and hopefully a way around….
Joanne: Because they’re all entrepreneurs.
Dana: Yeah, for them too. Oh, that project is cool I’m going to see if I can… whatever, be it all natural. But I can put myself out there for that and 25 other things if I want to. I’m not locked into one particular space completely.
Joanne: Then you have to add the calendar, they each get their calendar.
Dana: That parts going to be well, we we’re like – . You can’t sign on unless your calendar has been updated, in my head that’s what I’m thinking.
Joanne: Totally, that’s a 2.0.
Dana: Communication in the calendar, we’re done, we’re sunk.
Joanne: No, there has to be a calendar for quantitative.
Dana: There is, but even just the updating of the calendar.
Joanne: Yeah, it’s important.
Dana: Because often what happens just in regular production, is so and so available? They’re bidding on other stuff, but yes, they are available at this moment, for that week.
Joanne: But this afternoon they’re not.
Dana: Pretty much.
Dana: So, being able to figure out a way so that’s managed, where you’re not bait and switching people, which you can’t because you really want that job… If you’re a content maker, you want that job.
Joanne: You’re going to make it work.
Joanne: The one that’s good. All right. Thank you for coming today. And in all transparency, Dana is my sister-in-law.
Joanne: It’s also being on the sidelines and watching your career over the last 20 years. 20 years?
Dana: Jerry and I were married 20 years this year, so I’ve know you 20 some.
Joanne: 20 years, wow.
Dana: That’s so weird. I think of that sometimes, I’m like, how did that happen?
Joanne: How did that happen? I know because we’re only 24.
Dana: Exactly, yeah.
Joanne: Anyway, thank you.
Dana: Your welcome. This was awesome.
Joanne: This was good.
Embracing the Unknown, Jessica Koslow, SQIRL, Podcast #54
Jessica Koslow is the owner and chef of SQIRL, one of L.A.’s most popular cafes that has led to a cookbook, a jam company, a pop-up venture in New York City, and soon enough, a much-anticipated second location on L.A.’s West Side. Jessica and I sat down and talked a lot about a question that comes up for many entrepreneurs: ‘how do you make that big leap out of security, and into starting your business?
Here is the transcript below.
Joanne: I’m Joanne Wilson and this is Positively Gotham Gal. Small, meaningful conversations with women entrepreneurs about their approach to life, business, and everything in between.
Joanna: Jessica Koslow is the owner, visionary, and chef and everything else behind Sqirl, one of LA’s most popular cafes that started with the jam company and led to a cookbook and they’ve had a pop-up venture in New York City and soon enough a much anticipated second location on LA’s Westside. Jessica and I sat down and talked a lot about a question that comes up for many entrepreneurs, how do you make that big leap out of security into starting your own business? So, you came on the scene with a jelly. You know? Out of nowhere.
Jessica: It’s true, it’s true.
Joanne: I mean, it is true. It’s like, “a jelly?”
Jessica: It’s really humbling to say that, too. You know?
Joanna: I mean, it’s pretty amazing. You know?
Joanna: And then like everyone is like Sqirl, Sqirl, Sqirl. Have you been to Sqirl? You know? Have you seen the lines at Sqirl? It’s just like, who is this girl? But let’s go back, back. Where did you grow up?
Jessica: I grew up here. I grew up in Southern California, in Long Beach, California and I grew up figure skating since the age of 5.
Joanne: So, did you like ‘I, Tonya?’
Jessica: I loved ‘I Tonya.’ I was like did they superimpose Margot Robbie’s face on to Tonya’s body? Probably. Or someone else’s body? But it also brought me back to that point in time.
Joanne: And figure skating in Southern California?
Jessica: So, actually some of the best figure skaters in the world or in the United States are from Southern California.
Joanne: Who knew? Okay.
Jessica: Because this is a place that you do it because it’s a sport and you want to win not because it’s a pastime. So, if you’re into figure skating, you’re into it because your deep in.
Joanne: Okay. And how long do you keep that going for?
Jessica: I was skating until I was in college. I was on the US team for 4 years.
Jessica: And I never really understood what food was during that time. It was for fuel, it wasn’t to explore.
Joanne: So, it was a very different passion.
Joanne: Yeah, it kept you going. Just as a complete sidebar, being in something that is a very structured female-oriented sport that you were in oh, not that there’s not men in figure skating, have you of course been watching this whole gymnastics thing that’s rolled out?
Jessica: You mean with the doctor?
Joanne: How crazy?
Jessica: How sad?
Joanne: Beyond sad and all the people that were held accountable and did nothing about it.
Jessica: Yeah. I mean, what’s also interesting is West figure skating we never had a doctor. There was never, again, because I was on the US team, there were I mean there were hoops that we had to go to but there was never like a specific physician. Maybe it’s different now but I can’t even imagine in our sport but in gymnastics to have that happen is appalling and sad and I have been watching it.
Joanne: Yeah, yeah. Well, he got…
Jessica: Did he get life in… I mean, he’s never…
Joanne: 175 years.
Jessica: Yeah, he’s never seeing the light of day.
Joanne: No, ever again. He doesn’t deserve to see the light of day.
Joanne: He actually deserves worse than that.
Jessica: Yeah. He does. But I feel that Judicial System frowns upon death these days so, you know, but I’m sure the rest of his life in prison is pretty much like death.
Joanne: Yeah, I think that’s actually a better way than death.
Joanne: So, go back, so, figure skating all the way through High School?
Jessica: Yeah, all the way through High School, some of college.
Joanne: And where do you go to college?
Jessica: I went to undergraduate in Brandeis in Massachusetts.
Joanne: In Massachusetts, right.
Jessica: So, I moved across country.
Joanne: Much colder there.
Jessica: Very, very cold and I was skating there as well and then stopped and once I finally stopped, I started…
Joanne: And why did you stop?
Jessica: Well, I think two things. One is that I did a sport that no longer exists in the world. It’s called school figures and they’re intricate Figure 8 patterns in the ice and I won nationals and I won the last us competition in the world at the time. I think they’ve kind of brought it back to life but it’s really more of a pastime now. So, that was like 2000 and once that ended that focus had to be put into something else and that was food.
Joanne: And were you contemplating your plan be at that point or had that been in the works somehow at all?
Jessica: No, you know, when you’re like 20, plan B is plan A. You know?
Joanne: Right, right. It’s just an evolution.
Jessica: And I still think I’m going through that, wow, have I really thought about a plan B? Now, I really need to think about plan B and plan C. What does that look like? But, yeah, maybe I’m still 20 inside.
Joanne: I think we all are to be perfectly honest with you.
Joanne: As someone who is much older than you…So, skating ended…
Jessica: And I met a friend in Massachusetts who owns a cranberry farm and we would go out to Carver Mass and see the bog and pick…
Joanne: Very Massachusetts.
Jessica: So Massachusetts. But it was really this, it was a beautiful moment of seeing what I could do or explore outside the world of what I thought was my future and I always, also my mom is a single mother, she’s a physician, and she always was very strongly in favor of higher education and so, because of that, that was really a plan B. That was, the back end was look, as much as your figure skating, your schooling is just as important if not more so. So, get in there and get to cracking.
Joanne: Nice Jewish mother.
Jessica: Yes, nice Jewish mother.
Joanne: Exactly. And so was your mom a cook? Was she into cooking?
Jessica: No, it was like the opposite my mom. My mom like burned steaks and potatoes are really overly salted and, you know, the thing that she’s really great at tapioca pudding from box.
Joanne: Okay. It works.
Jessica: Cornbeef that came out of a bag but everything else was like, keep it away.
Joanne: That’s hilarious. And so, you saw these cranberries…
Jessica: Yeah and it’s not so much that. The cranberries might be a metaphor for the change of my life. You know? And starting to really dig into food systems and exploring what food was for me.
Joanne: And is that how you went about it in terms of educating yourself? You know, what is food? How is it helping?
Jessica: Mhmm and also just what does it mean to be food from Massachusetts? What does it mean to be food from California? As I kept coming back here to go to school, or after Massachusetts I moved to D.C. and then to Atlanta and, you know, I went a number of places in the United States.
Joanne: And did you work in restaurants along the way?
Jessica: Yeah, I did. After grad school, I was in grad school in D.C. and I moved to Atlanta and…
Joanne: And what was your grad school?
Jessica: It was media theory. I went to Georgetown and I did media theory.
Joanne: And climbed steps.
Jessica: Yeah, I climbed a lot of steps. Yeah. I felt really out of place in D. C. because it’s so political.
Joanne: It’s a weird place.
Joanne: I mean, I grew up outside D. C.
Jessica: I see.
Joanne: So, then you left?
Jessica: I left Georgetown and moved to Atlanta and once I got to Atlanta I said, I’m out, like I have been kind of under the mom thumb, kind of doing the path that I thought I was supposed to take…
Joanne: If you were going to be in the food world?
Jessica: Well, if I was going to be an academic.
Joanne: Okay. So, you went after the Academia originally?
Jessica: Yeah and then afterwards I started cooking in kitchens and my mom was like, I put you through higher education, I’m giving her an accent she really doesn’t have by the way, but, you know, like the mom, I’ve given my life to put you through schooling and this is how you are repaying me? Your $10 an hour job working as a pastry cook? And I couldn’t have been happier.
Joanne: At the end of the day that is what mothers want. I just want you kids to be happy.
Jessica: Right, right. But, I don’t know, my mom wants to show me around.
Jessica: Now she can.
Joanne: Now she can.
Jessica: Now she can. Now, the whole thing was, you know, I believed in you the whole way, and I’m like you kind of, maybe. But underneath it all, I think she’s just worried.
Jessica: She was worried about, look, this is a path of unknown, this is a challenging future for you. What is your next step? How are you going to make this climb from being a $10 an hour pastry cook to maybe having something that is your own? And I felt like I needed to be honest and let those things evolve. I needed to figure out how to develop the idea and what was really passionate for me and turn that into a tangible thing.
Joanne: Was your mother entrepreneurial?
Jessica: I mean, she’s a dermatologist. She has two offices. I would say so, yeah.
Joanne: Yeah, 100% and your father? Do you have a relationship with him?
Jessica: I don’t have a relationship with him and I would say he’s probably not entrepreneurial.
Jessica: I’m more interested in his family. His parents had grocery stores in Richmond, Virginia called Koslow’s and they also, my grandfather was the head of Rich Foods. So, he did all of the canning and packaging and they always said don’t get into this business.
Joanne: Well, you know, there’s so many people in the Chinese food business that are the second generation of Chinese food restaurant owners that have been told the same thing.
Joanne: I mean, usually what you see is what you end up being.
Jessica: And what’s so funny is it almost skips a generation because these kids, my father and my aunt, they see how hard my grandparents worked and how maybe they weren’t home all the time or that struggle of just the operations and so they’re like, I’m out, I’m not, that is definitely not my path. I’m like, wait a minute, that’s beautiful.
Joanne: Right. That looks great.
Joanne: That looks phenomenal. So, was L. A. in the forecast? Or just, you know, you threw out a dart and that’s where you ended up?
Jessica: It was New York next and New York was, I got scared. I left food and I got a job at Fox as a digital producer and worked on every American Idol and So You Think You Can Dance and 24 and it was just something totally else. I don’t know how this landed on my plate. My background in academics and a little luck landed me at News Corp. So, I got my job transferred out to L. A. after a couple years in New York and the job kept me here where I was working in the offices here and then I started cooking again at night. So, I was baking at night for this place called The Village Bakery and I was doing their midnight shift from midnight to 8 a.m., go home and sleep a couple hours, and then I would end up at the Fox lot.
Jessica: Yeah. And that was obviously not going to work forever.
Joanne: But you obviously had this insane passion for cooking or you wouldn’t have beaten the hell out of your body like that.
Jessica: Yeah and I also think that there is, I know how many people are dealing with this, this moment okay I’m in a role that pays me really well, I have benefits, maybe I have health care, but this isn’t what I want to do or I know there’s something more for me.
Joanne: Oh, yes.
Jessica: I know so many of these, I mean, I have so many friends in this boat who are like, how do you make that leap out of security?
Joanne: It’s hard.
Jessica: It is hard.
Joanne: It’s hard to dive into that, you know, into the pool head-first. It also, I see people who are like I paid off my student debts and I’m just going to go and do what it is I’m passionate about for a while. And, you know, this whole concept of, you know, 50 is the new 30 or 40 is the new 20 …
Joanne: I mean, it’s bullshit.
Joanne: Because at the end of the day we are still at that age and there’s a point where you start to have a mortgage, you get married, you start to have children, and, you know, you can’t afford to just, you know, not pay the rent.
Joanne: Or put food on the table.
Joanne: And so, there is a point where I think that we become more creative and there’s more opportunities and, you know, you get up every day, you should love what you do.
Jessica: Yeah and that was a moment where, once I left Fox, I paid, even when I started Sqirl and I started the jam company, I paid myself $500 a month for about a year-and-a-half. I had saved enough money that, I at least wanted to give myself a salary to make myself feel bad I was worthwhile, that I was taking that leap into this thing.
Joanne: That’s great advice, by the way.
Jessica: Yeah, I think so. You should feel valued by yourself. Even if it’s $500.
Joanne: It doesn’t make any difference, it’s I’m getting paid for my value. I completely agree.
Joanne: Because, you know, sometimes founders spend years and don’t make a penny.
Jessica: Or they just put it all back in the company and even today I still, all the checks that come in, even if they are for me or an appearance or something I’m doing, it all goes into Sqirl. I own it 100%.
Jessica: I don’t have any investors there and yet I see it somehow. You know?
Jessica: I think giving yourself a value when you go, when you start is really important to keep your morale up about what you’re doing.
Joanne: I totally agree, I think that’s amazing.
Joanne: So, here you were working basically 20 hours a day and sleeping four, maybe.
Jessica: There was definitely some like, is that a rainbow?
Joanne: And so, at what point did you say, Okay, when I walk in this week on Friday, I’m resigning and here’s where I’m going?
Jessica: Well, it was actually the other way around where I was let go and the reason why…
Joanne: Well, that actually makes life easier.
Jessica: It made it but, that was, it was also this time where it was 2010 and it was the height of the recession and Fox had gone through three layoffs and they were like going through their fourth and so it was basically the entire office shuttered afterwards. I have a friend that just left her post at New York Magazine and I’m like, good for you that you just made that decision to leave.
Joanne: Yeah, golden handcuffs are tough.
Jessica: They are tough.
Joanne: They are tough.
Jessica: So, having them sawed-off was really the best thing that happened to me.
Joanne: I had the same experience. I was fired and then it was like I’m never returning to that industry.
Jessica: Look at me now.
Joanne: Yeah, I was like I’m never going back.
Joanne: Because it sent me in a completely different trajectory. So, Fox Did you a solid.
Jessica: They did me a solid and what’s so funny is, my manager, she loved me and I love her. I knew that this was a decision that was based around here financial cuts and even today like they’ll be something that happens on Facebook and she’ll be like I’m so proud of you. You know?
Joanne: That’s great.
Jessica: You know that it was the right thing.
Joanne: Right, it had to get done.
Jessica: It had to.
Joanne: So, where were you? You were laid off.
Jessica: I was laid off and I was just like, all right, well, thanks for making a decision and I’m just going to go cook. So, I cooked, I moved to Australia, I started, I was staging in Australia at a place called Dench, and then I came back.
Joanne: Okay. And where is that? Is it in Sydney? Melbourne?
Jessica: Melbourne, yeah.
Joanne: I mean, it’s interesting, I mean, that you say Australia because your food is very reminiscent of Australian food.
Jessica: We get that, we have so many Aussies that come in…
Joanne: That doesn’t surprise me and we were down there years ago but there’s something about your food that is very clean and healthy and interesting to flavor palates that, to me, remind me of Australia.
Jessica: You know, to the States, daytime eating wasn’t really a thing. You know? We were kind of stuck in the same like hollandaise pancakes, french toast but when I got to Australia, I was like, wow, everyone’s really about like vibrant all day eating and hangs. I was like, this is a different scenario than in the States. It was in the back of my mind as all right there’s so many parallels to California whether it’s the light, the produce, some of the produce.
Joanne: The sky.
Jessica: The sky, the sun. It did impact how, I was like, wow, there’s all of these places, like the local, where’s the local here? And at the time, when I opened, well, I opened the cafe in 2012.
Jessica: The local didn’t really exist. It was a corporate coffee shop called Intelligentsia in Silverlake.
Joanne: Right. And also Silver Lake was just starting to become a mecca for new living.
Jessica: It’s true. I mean, I dug a hole from Greenpoint where I was living and I popped up in Silverlake.
Joanne: So, you opened up, you found this place which is the tiniest little spot.
Jessica: I know. It is.
Joanne: And you also didn’t make it that you’re going to have this full on restaurant with tons of people to sit. It was sit on the corner, sit out on the bench. If you’re lucky you can grab three or four stools that are available here.
Jessica: Yeah, it’s true.
Joanne: And you come in and get your food and you hang out with, you know, out on the streets.
Jessica: Yeah, it was, it’s 800 square feet inside. It’s probably 1000 square feet all in. I found it on Craigslist. it was $10,000 to buy out the business and it was $2,500 a month for rent and I…
Joanne: Which is amazing.
Jessica: It’s amazing and also terrifying.
Jessica: How can I afford this, you know? I was just making jams at the time and in my head I was saying, look, I’m 7 minutes from my home to work. That is a quality of life that is hard to find in Los Angeles, to find a place that’s close to home that you can live your life and be in the restaurant industry is pretty pretty rare.
Jessica: So, I’m going to take it. And at first, I, my first accountant said look, by the end of the year you’re going to be done. You’re not going to make it.
Joanne: How uplifting.
Jessica: How uplifting. I know. Maybe it wasn’t like that, maybe I’m giving her like the dark, like that dark…
Joanne: Accounting side to her?
Jessica: Yeah, yeah. But it was definitely a moment of, okay, doing this beautiful product of jam is not enough. As many classes as I taught, as many relationships that I went over within my community of farmers and chefs, it wasn’t enough.
Jessica: And so, at that point in 2012, I knew that I needed to figure out how to evolve and I also think a scary thing or an interesting thing is that having the jar allows you to hide behind your product. like, I didn’t have to be on Yelp, I didn’t have to be out in the open and talking to people, having people walk through the door and give you an automatic judgement. I mean, that is what everyone does these days and you have to be ready to be a 4 or 3 or 2 star. You know?
Joanne: Yeah. But you also did something else a lot of women don’t do and they should do, is you didn’t call it by your name. Because you can’t…
Jessica: You call me by your name, I’ll call you by mine.
Joanne: Exactly because you called it Sqirl and you can sell Sqirl. Like the woman behind Tate’s, the cookies, her story is she originally was called her name and she had these terrible investors and they completely hosed her but she had the building and the whole thing crumbled, no pun intended, and she came back and she put the name Tate’s and she said it was literally just a complete game changer for my mind because my name wasn’t on that door anymore.
Joanne: It was Tate’s. It was like this company, it was mine but it was this different kind of an umbrella.
Jessica: Yeah. I think there’s something powerful about figuring out why you why you name something, what you do.
Joanne: How did you come up with Sqirl?
Jessica: Sqirl is, squirreling things away is an old-time preserving term and it’s a girl who’s squirreling.
Jessica: So, the spelling is a little off other. The other backstory is that my…
Joanne: Which is the ingenious, by the way.
Jessica: Yeah, yeah because then, you know, you get a lot of jokes, I love squirrel, is there a squirrel in here. You’re like, oh, God, I can’t. But it does take it away from the animal and kind of puts it into an action.
Jessica: And that was good when for the cafe as something that is preserving California produce and fermenting California produce and being a part of this community. It feels like the right name for the cafe.
Joanne: And so you went from the jams, you open the cafe, and how soon did you become profitable?
Jessica: The cafe became profitable by May of 2013. So, when I opened the cafe, I had a partner. The guys who have go get ’em tiger were doing the coffee in the front and then they left in May and I took over the entire thing.
Joanne: And boom.
Jessica: And boom. Yeah and I think they’re, now they have a number of places and they’re profitable as well but we needed each other to kind of get our ideas about who we are, what we wanted behind us.
Jessica: And, actually, it was a really great, I think it’s hard to have a partner in a space like that…
Joanne: I think it’s very hard.
Jessica: Because there’s so many different ideas about like how to operate, especially how to be welcoming to people, like your idea of front of house service might be very different than someone who only has done like cafe culture. So, as someone who worked in fine dining, I know and respect and expect a certain level of service versus kind of what I was getting when it was this co-thing but it was a very beautiful time of growth that even like the customers who are still coming in like they revel in that moment. You know?
Joanne: I’m sure.
Joanne: Yeah, I think that for anyone being in the space with multiple partners is very, very difficult and we’re going to see more of that because, you know…
Jessica: And it’s something that I just, that’s why I’ve turned down any kind of like Grand Central Market or, it’s just, it’s hard.
Joanne: It is very hard and, you know, the retail brick-and-mortar space is becoming much more difficult to draw in a customer and so how do you become something that is concept oriented that is curated with a variety of brands versus one so that people are continuing to come.
Joanne: You know? Food always draws, right? People have got to eat.
Joanne: People don’t have to shop.
Jessica: It’s true. Although, man, I went to Juicy today. I got like two side salads and I love Travis and I think his food is really clean and classic and I know where it comes from and it’s one of the very few restaurants that I go to in Los Angeles because I trust it. But it was $15 for like these two scoops of side salad. I was like, this is also a challenge, is how do we feed people in the future at a price that brings people in?
Joanne: Well, you know, we can look at, which is the one, is it Local, that they charge different prices in Beverly Hills than they charge in, you know, East L.A.?
Jessica: Oh, really?
Joanne: Yeah. It’s a fast dine, you know, like fast-casual.
Jessica: I don’t know what that is.
Joanne: And I love that.
Jessica: I love that, too. That’s great.
Joanne: Because that speaks to my social side which is, you know, we know…
Jessica: Know your clientele.
Joanne: Right, know your clientele and understand if your rent is going to be $1,000 in East L.A. and $5,000 a month in Beverly Hills then you can serve the same product but the prices should be accordingly to the audience so that everybody can have healthy food. You know?
Joanne: It’s just an interesting thought box.
Jessica: I like that.
Jessica: I want to know what that place is because I don’t know, I’m like I need to go there tomorrow.
Joanne: I’ll look it up and I’ll remember. It’s great and I remember reading about it. they just raised money and I reached out to him because I had written about him and he emailed me and said thank you so much. I said, listen, I love what you’re doing, I mean to me that’s a brand-new paradigm.
Jessica: That’s great.
Joanne: And I think it’s really intelligent.
Joanne: And then they’re raising money but he’s out of my price range but I said, you know, I only wish you success because to me that is, that makes us more of a community build as, you know, I had our kids in the school.
Jessica: Because people in East L.A. can also afford to eat it.
Jessica: And they can experience what people in Beverly Hills are eating.
Joanne: And they can experience healthy, good food.
Joanne: You know, I think that’s really important. So, Sqirl’s now been open for…
Jessica: I mean, Sqirl started in 2011 in March.
Jessica: So, we’re coming up on 7 years.
Joanne: Seven years and in between you wrote a cookbook.
Jessica: I did, yeah, and I have another one coming out next year.
Joanne: And you sell your products, your consumer products, your jams to, I mean, I’ve seen them all over the place.
Joanne: So, you have really two separate businesses.
Jessica: Yeah, I do.
Joanne: Are you making all the jams here still?
Jessica: We do.
Joanne: That’s great.
Jessica: We still make them all so we control that product from start to finish. I think it would be interesting to have a smaller line that we co-pack that’s for hotels and restaurants.
Joanne: Right. But you need to…
Jessica: Well, that’s different.
Joanne: That’s a different story, right. So, a different level and a different business.
Jessica: And that’s what’s so, people are always like why don’t you do the small jars? And you’re like, it’s another layer.
Joanne: Yeah, it is another layer.
Jessica: You know? And every layer takes a little time.
Joanne: And every layer needs people that are attentive to it 24/7.
Jessica: Yeah. That’s true.
Joanne: So, you can’t just have the same people do the same thing.
Joanne: You need to bring in another person to oversee that or it ends up not what you want it to be.
Joanne: So, that’s a whole thing too.
Jessica: So, recently we’ve taken over the entire building…
Jessica: At Sqirl so instead of just having 800 square feet we have 5000 now.
Joanne: Which is a huge difference.
Jessica: Which is a huge difference but that…
Joanne: I’ll have to go back down and take a look.
Jessica: Yeah, but that’s why, and I don’t know if the last time you were there I had the next door space?
Joanne: You were talking to me that you were about to literally sign that week on the next door space.
Jessica: Wow. Well, it’s been a while since you’ve been over.
Jessica: Because that’s been, but now we’re doing Sqirl Away.
Joanne: That’s great.
Jessica: So next to Sqirl is Sqirl Away which is more of like a convenience, take out, everything is pretty done. But, you know, we’ve taken, we’ve gone, we started small with what we could afford and since then we’ve evolved and it’s kind of been amazing to see that evolution of what Sqirl is.
Joanne: Which is amazing and what’s really amazing is you still own 100% of your business.
Jessica: It’s true.
Joanne: And I think when we spoke you were also talking to a variety of people that wanted to partner with you.
Jessica: For the next product. And I think also because of Sqirl Away, at the time I didn’t have enough finances to build out Sqirl Away, the second iteration, but now since I’ve waited a couple of years and gained the entire lower level of the building, I’m good.
Joanne: You’re good, that’s great.
Joanne: And there will be more.
Jessica: So, time, if you’ve got time then it’s on your side.
Joanne: I think that most people don’t think about that.
Joanne: Right? I mean, I’ve known so many founders that five or six years in, you know, all of the sudden boom and these things don’t happen overnight and when you own them by yourself and you take time to build the platform oh, which you’ve done, you know, going to the next level certainly is difficult but because you own it you have a very different conversation with people that want to be involved with you.
Jessica: So, I have a lot of friends who are also incredible female entrepreneurs and they, male entrepreneurs as well, and every start January they do kind of a lay of the land for their year plan and or five year plan and that’s something like I don’t do. I have this idea about where I want to go but I don’t do that component of the work and I wonder maybe this would have happened a lot sooner if I had taken the, you know, would of could of.
Joanne: Yeah but here you are.
Joanne: You know? You’ve got a wonderful, profitable business. You’re looking to grow, you know, in a new area in L.A. and, you know, you have jams on shelves, you have a cookbook, you’re in magazines, and anyone that’s in the food world knows who you are and knows what you’ve done with that restaurant, and in many ways what you’ve done is what a lot of people that you talked about earlier that aren’t happy in their business life and really want to do something and, you know, the romantic vision is to do what you’ve done.
Jessica: Yeah. Also, my industry, people tend to push, I have to open something else, I have to open, what’s my next thing, what’s my next thing.
Joanne: Yes, they do and that’s a big mistake.
Jessica: And it is a big mistake. I have, there are a lot of people that I really love and I’m like, man, you moved so fast can you find that next location and, you know, why are you, like, fish sandwiches on the pier? Really? You can do better.
Joanne: Well, that’s interesting because I think that in the end most of them end up dying because out of that and the amount of people that are coming to talk to me about their businesses, we’re like, wait a second, your profitable, building a nice business, why are you raising money exactly because this isn’t a billion-dollar idea, you know, maybe it’s a 5 or a 10 or a 50 million dollar idea. So, why don’t you just grow it because no one else is doing what you are doing? And they’re just like, oh, people have said that. It’s like you don’t want to deal with an investor if you don’t have to. Anyway, thank you so much for coming on our show today.
Jessica: Thank you.
Joanne: I mean, it’s really amazing what you’ve done and it all started with the jam.
Jessica: The jelly.
Joanne: The jelly, all right.
Jessica: Thanks for having me.
Joanne: Our thanks to Jessica for joining us on the podcast this today. You can check out Sqirl by visiting them in Silverlake or going to their website at sqirlla.com and, by the way, it is sqirlla .com.
Stop Apologizing for Being Women , Lizzie Francis & Kara Weber, Podcast #53
Lizzie Francis and Kara Weber are the Founding duo behind Brilliant Ventures. Their serial entrepreneurial credentials, amplified by a network of go-to-market experts with skin in the game, and a second proprietary network of the most accomplished, amazing and connected women in LA, make for the perfect set of assets to this investment firm. Lizzie and Kara really attribute their success to their fantastic partnership. They told me all about how they met, and what prompted them to quit their jobs and ‘stop apologizing for being women.’
For those who want, here is a transcript of the podcast.
Joanne: I’m Joanne Wilson, and this is Positively Gotham Gal. Small meaningful conversations with women entrepreneurs about their approach to life, business, and everything in between.
Lizzie Francis and Kara Webber are the founding duo behind Brilliant Ventures. Their serial entrepreneurial credentials amplified by a network of go to market experts with skin in the game, and a second proprietary network of the most accomplished amazing and connected women in LA. I have to say, many times I refer to them as the mayors of the tech world in Los Angeles. Lizzie and Kara really attribute their success to their fantastic partnership, and they told me all about how they met and what prompted them to quit their jobs and stop apologizing for being women.
Lizzie: We are talking about….
Lizzie: We’re talking about serial killers, right?
Joanne: Correct. So Brilliant Ventures, which by the way is a brilliant name. I always refer to the two of you as the female mayors of the LA tech world. It’s come full circle in regards to entrepreneurs, and then going out and raising capital that is investing in women, which is awesome. I’ve known you, Kara, since the mid-90’s.
Kara: Yeah, I think so.
Joanne: Wow, that’s kind of crazy. Lizzie, I just got to know you. I want to go back in time, how you came to be and what your history is. Let’s start with you, you’re from the Los Angeles area?
Lizzie: My mother was born and raised here actually and ended up on the east coast just after World War II because she was in internment camp. But my mom was born in City of Angels Hospital, 1940. I have come full circle by coming back to Los Angeles, but no I was born and raised in Washington D.C. I’m a west coaster who has come back from the east coast to her west coast roots.
Joanne: Did you go to college in that area, or did you leave Washington?
Lizzie: No, I went to upstate New York. Kara and I both chose incredibly cold locations for our college experience. I went to Cornell University.
Joanne: You went to Cornell?
Joanne: Then what did you do after Cornell?
Lizzie: I decided I really liked the cold, so I went straight to Chicago.
Joanne: Which is so cold.
Lizzie: It is so cold. I was actually part of that first internet wave, which was before the first crash, that worked in investment research for a company called Zacks Investment Research. We did the first round of lead generation, because that first cohort of people who were trading online, we would sell those leads to brokers. Traditional broke restaurants, which was really interesting conversation to have back in 99-2000 with people who didn’t understand that the internet was going to actually disrupt the entire financial services sector.
Joanne: Right, or the whole world for that matter. Yeah.
Lizzie: From there, ended up parlaying that into a great startup in LA called Lower My Bills, which I ended up selling to Experian, which also did leads in the consumer space, and at the time was the largest online advertiser. That’s where Kara and I collided in LA, because we were both recent transplants to Los Angeles through a mutual friend, my closest friend from childhood and one of Kara’s best and closest friends when she moved to Los Angeles. We, at the time, were these two weirdos who were in the tech space.
Joanne: You were in the financial tech space.
Joanne: I mean, totally unsexy, but at least you were warm. You went to school in, where was it?
Kara: I went to Williams.
Joanne: Williams, right.
Kara: Williamstown, Massachusetts, with beautiful Berkshires.
Joanne: Beautiful town.
Kara: Gorgeous town. I ended up living there for nine years.
Joanne: That’s right.
Kara: Because I started my first company there with college classmates and one of our professors. We built the company in Williamstown, or as my friend Bill Peabody who really was the founder of it said, we were doing something.
Joanne: It was…?
Kara: Tripod. He said, we were doing something. I’m not sure we were building a company, but we were….
Joanne: I remember talking to you out there thinking, what are you doing? Why are you living there?
Kara: I’m so grateful that I did, that was a magical time in my life. It was my first moments out of college, I was from suburban Pittsburgh. Anything that wasn’t suburban Pittsburgh was exciting to me, because I was a grown up, I was an adult. The same way any young person in college, or maybe right out of college, has that experience. I feel incredibly grateful, not only that the first company I …
Joanne: It was a success itself.
Kara: We sold it in February 98. We got to ride it for two years.
Joanne: You did.
Joanne: We can point to a handful of companies that succeeded, and that would mean succeed equals exit, and Tripod was one of them.
Kara: For sure. During that time, I met this cute actor who lived in New York, since I started commuting back and forth from the Berkshires to New York which was my life for a long time. Moved to New York to be with the cute actor, he had just done this pilot for this show, something about Sex in the City. I had no idea what it was, I thought it was some dirty HBO show. He couldn’t leave New York, he sure didn’t want to move to the Berkshires. I ended up moving to New York, did my … I always love talking to people in the digital space about what they did between 2001-2004.
Joanne: Because a lot of people from the original, which you both were in, went home and never ever came back.
Kare: Or went to business school. I mean, the stories are always amazing.
Joanne: Or went to large companies and started their own businesses that had never needed funding. They were just entrepreneurial, never came back, or a lot moved to LA.
Kara: A lot moved to LA. That’s what we did, because that same year 2001, not only was the internet exploding and not in the good way.
Kara: Imploding, thank you. People with science degrees probably would have said imploding. Both the Writer’s Guild and Actors Guild were threatening to strike that year. The internet had imploded, and my actor husband… There was no production, production had been shut down.
Joanne: That’s right, I remember that.
Kara: What should we do? Let’s go to LA for a year or two.
Joanne: And here you are?
Kara: I fell in love with LA so quickly and so powerfully, and I’ve thought about it, Lizzie and I have talked about it a lot over the years. The women I met here in LA were very different from the women I had known in New York.
Lizzie: Listen, I have spent now, this is my fourth winter here, and I reconnected with people I didn’t realize were here, but I’ve met a lot of really new interesting women. It’s a very different relationship in different people. It really is than my New York friends.
Kara: Yes, it’s completely different. My experience was that every one of the women that I quickly was drawn to and befriended was an entrepreneur in one form or another. Whether it was our mutual friend Kristen, who introduced us who’s a writer, and learning the realities of being a writer or actor or director and how you are…. You’re running a business. You are your business in a way when you work in that field. I can go through a long list, but then meeting Lizzie and literally feeling like there was one other green alien in the city and I found her. I had found the other green alien in the city.
Joanne: When you guys met, you just became friends, hung and talked? Or did you start talking about we’ve actually have had this experience together separate, but this tech experience, and maybe we should figure out what we should do together?
Kara: Do you think we would raise more money for our next fund if….? How should we answer that to raise the most money?
Lizzie: We never talked about anything but the future of technology, ever. Sadly, no. Because of the fact we were the only two people we knew who had the same past and were actually continuing to ride through that first terrible down market, which had upsides and implosion in other ways. We did really counsel each other about where we saw things moving and changing.
Joanne: Right, because you all believed.
Lizzie: We believed.
Kara: We all believed. We all just knew that everything was overvalued, and the mortgage industry sort of got in the way.
Kara: I remember when I got here, and everybody said, why don’t you go be an assistant at one of the agencies or studio with a director? I was like I just sold a company. What are you talking….? No, I’m not doing it. I remember meeting with a, LA had very, very few digital head-hunters at the time, still has a shockingly small number of established ones, but meeting with one of them at the time who said, oh, the internet. You want an internet job? He said, that didn’t work out, that’s over. I remember very clearly in that moment thinking, it hasn’t begun. It’s not over. I’m sorry, what are you talking about. I didn’t even know it, Gil Elbaz and Eva Ho, and everybody were off in the building creating AdSense and really changing the world and the future of the internet in that way. It was a very different time, but we connected, and I think it has been a core of the success of our partnership, which any partnership is always a gamble. Ours has been, really for me and I know you would say the same, really magical in how fantastic it’s been to partner together and be working together.
Joanne: You guys connect really well.
Kara: We connect really well, and I think we didn’t start talking about tech, but about who we are in our lives. Right after I met you, I went through some really challenging personal stuff and family stuff. We’ve been through life together, not just the professional, but we have this…. It was almost that we were friends, but then we realized there was this deeper layer because of our careers versus we met through our career and found a deeper layer.
Joanne: I think about other partnerships that I know are in the venture world that are institutional investors. As you are, you take money from an LP, you are an institutional investor no matter the size of your fund and your thesis. I don’t know how many of them are really personal friends, because business relationships are funny. You meet the right business person, but it doesn’t necessarily mean you know how many children they have.
Kara: Yes, that’s right.
Joanne: I don’t know if that’s women different, or men.
Kara: I was going to say, I think that’s…. We ask people how many children they have.
Joanne: I do too.
Kara: We are definitely…
Joanne: Women want to know things. You connect differently.
Kara:We made a conscious decision to be women, we’re women. This is why we’ll never be … I’m not calling them out specifically. I could say 10 names, I’ll say Excel. We’re never going to be Excel. We’re never going to be a primarily white male led Silicon Valley fund. We’re never going to be that.
Joanne: I actually think one of the things I notice when I started investing is that women would tell me things. Then they would say, god, I’ve never had this kind of conversation with anyone.
Kara: We hear it all the time.
Joanne: Right. I’m sure it’s the same thing because you’re asking them, and you’re connecting, and they feel a comfort that they don’t need to be on-guard when they are talking to you, even though you have money to give them.
Kara: That’s right.
Lizzie: It’s not an act. I think for us, what was so eye opening about that is when we actually look at people that we invest in, is at the stage where it is really a lot about the people and a lot of character they have. For us to actually really pull back the layers and the approach that we take, we get to meet a lot of great people, and really get to understand what makes them tick, and that really helps us when we make our decisions.
Joanne: For sure. When did you guys decide, you know what, we’re talking to all these amazing people, maybe we should start a fund and see that we should invest in all these women and brilliant people?
Lizzie: Actually, it’s a long answer to this but it’s worth it.
Kara: It’s worth it to us. We love telling our own story. We can talk about it all day.
Lizzie: Kara and I have been talking about doing something, whether or not it was… I think at the time we were more geared towards let’s start a business, get a more traditional sense that we know. We both started multiple companies. Let’s build a venture backed business, and let’s think about something we really want to do. About four and a half, five years ago, we went to a magical place called Miraval, which–
Joanne: It’s in Arizona, right?
Joanne: I went there with my daughter last year.
Kara: Did you do the horse thing?
Joanne: We did do the horse thing. We both are not horse fans. I remember when she was a kid, she hated the stink and the whole thing of the horses. So, we both decided we’re not doing the horse thing, but we did go …
Kara: Ropes course.
Joanne: We did… what’s it called when they shoot you across and you’re ….?
Lizzie: We did that too, where you hold the bar and shoot…. I forgot what it’s called.
Joanne: We did ziplining. We did want to go to the drum thing, because you can get out your anger. We did a lot of stuff where you sat by the pool and chilled and talked and had massages.
Kara: Really important work.
Joanne: Yes, it was very important, we had a great time.
Lizzie: I think what you just nailed was you take time out of the routine that you’ve created, which is manic, and you leave your kids at home and you leave your 24/7 jobs at home. Kara had just had one company go public, and just sold the other one to AOL, and had been on planes, trains, and automobiles nonstop 24 hours 7 days a week and just had stopped it. Because she realized she did actually have two children and a husband.
Kara: I was a quivering heap of humanity at that point.
Joanne: That’s hard to keep up.
Kara: Yeah, and the pros of it are less than cons at some points in your life, right? When you’re 25, it’s fun.
Kare: Less fun when you’re 40.
Joanne: Sure, and also if you have children.
Lizzie: Yeah, you miss them.
Joanne: That makes it the hardest, it’s hard on the relationship with your partner and it’s hard on the relationship with your children.
Kara: It’s amazing, when I think about that time, when I think about it in telling my professional story or my timeline on my professional life, I think about the fact that Rubicon Project went public in the beginning of 2015 which was four months after AOL bought adap.tv for 450 million. I left Rubicon, gone to adap.tv to take them through their IPO. I got there, sat down, and helped Tim Morse who was CFO start writing the S1. We were ready, and then AOL swooped in, which in retrospect thank you, Lord, Tim Armstrong, for appearing in that moment. But when I think back on that time, from a LinkedIn profile sense, from explaining why and why I understand startups, literally in a four-month period I had an IPO and a major exit. It was insane.
Joanne: You start hyperventilating when you start looking backwards?
Kara: When I look backwards, I don’t think about that. It’s not like oh my god, remember that time I went to Singapore for 14 hours? It’s a 42-hour round trip flight.
Joanne: Right, that’s what you had to do.
Kara: That’s the reality. The headlines aren’t your day to day.
Joanne: You guys took off went to Miraval, and you chilled.
Lizzie: We did.
Joanne: And talked.
Lizzie: We had this realization, because we stopped and took a pause, that if you sort of, I think, all of us grew up in a way that you weren’t rewarded for actually being a mom or being realistic about ….
Joanne: You were newly pregnant; did you say that already?
Lizzie: No. I was newly pregnant and looked 20 months pregnant.
Kara: It was amazing, she invented a whole new kind of pregnancy.
Lizzie: I did.
Kara: She did 23 months. It felt like 10 years.
Lizzie: We just realized, why are we apologizing for the reality with these amazing….
Lizzie: Exactly, reality women and we had these successful careers, it’s not feasible to fly 42 hours to do a 14-hour meeting and still have a meaningful relationship with your family. It’s very hard, really difficult. I was at the time gestating, which had taken many years to do, our son Jackson. It was an exciting moment, I thought you know what? I just do not want to go back to that and miss out. It’s taken me years and many doctors, and a lot of money to get this little person in me. What are we doing? What is this rat wheel? From there we promptly did not do anything, but at least planted the seed and talked about what we’re going to do much more seriously. After Jackson was born, ….
Joanne: To create something around your lifestyle?
Lizzie: Exactly. We just decided…
Joanne: A lifestyle you wanted to live.
Lizzie: It was lifestyle, but it was also a bit of having felt as women in technology, like it was a perpetual game of square peg round hole.
Kara: I think on that trip, we didn’t mention your sister was with us too.
Kara: Lizzie’s sister Margaret Francis is phenomenal, she’s a VP of Product at Heroku. She one of the only VP level at the sales force organization. Margaret is amazing too. She was going through her own major life event at the time, you were newly pregnant, I was a quivering heap of humanity. It was a very powerful time where we had to be stripped down to just who we were, because we were too wiped out by what…. We had to be real, we had to be honest about it, we just thought what if we didn’t try to not be women? What if we didn’t try to…. I mean, quite frankly I admire her so much, but I always held Sheryl Sandberg in this place of shouldn’t I be going the Sheryl Sandberg route? Shouldn’t I be trying to be that where I’m a very senior executive at a very big company and have major influence over people. To realize, just like Excel and the boys starting the venture funds, that’s not me either.
Joanne: Well, it’s an interesting topic. Sheryl is someone to look up to for many women in regards to her job and her level and influence over one of the largest companies in the globe. Yet, she’s not an entrepreneur, so it’s a very different role. If you read her book, it’s the one that she had been interested in since she came out of the womb, and that’s who she is. But I think most of the women I talk to, and that you talk to, and who you are, are entrepreneurs, it’s a very different mindset. You can own your life at that level, and you’re certainly intrapreneurial, because if you’re not you can’t have that role. But it’s very different when you are jumping into the pool by yourself in order to create something for yourself.
Lizzie: We actually embrace that, to your point around and Kara’s point about why we apologize for being women. We said, we can start something, we love being entrepreneurial, but we can actually jump…. We also are at this point in our careers where we are really good at what we did. Yes, and if felt like not dialing it in, but don’t we want to learn something new? We want to be intellectually challenged. We thought, okay, let’s be entrepreneurial. Let’s jump to the other side of the table, and let’s learn something new. We’ve raised hundreds of millions of dollars between us from venture capitalists, let’s change the narrative and use our narrative to do that together, and that’s what we did. We agreed to do it one morning after I accepted a job. Called Kara immediately after I accepted and said, I made a terrible mistake and I don’t want to do this. She said, we start tomorrow. I called him back and said, I’m not taking the job and I actually have a much better person for you, and he actually ended up taking the job. We met, and I still can remember, we went to End Street Kitchen in Santa Monica, toasted and started on our values. Just talked about what are the values we want.
Kara: We still at that point…. We had been talking venture for a long time, but we…. Listen, if some great business startup concept came to us, we would have done that too, right?
Lizzie: We did sort of do that, actually.
Kara: Well, accidently.
Lizzie: Along the way.
Kara: We might have accidently also done that. But literally, we just said, okay, let’s not start with what we’re going to do, let’s start with how we’re going to do it. That I think, getting back to the partnership, and the kind of people we are ….
Joanne: Also, that really creates your thesis.
Kara: It really does.
Joanne: I think that the most successful firms that are investing in companies, it could be PE, it can be microfunds, Angels, I don’t care what it is, you need to have a thesis. Because without a thesis, you don’t become an expert and you don’t have something that you can stand to. If you fall back on that thesis again and again and again, it helps you make the right decisions.
Kara: Absolutely. The day we decided, because originally, we were going to be all a female founders founder built by girls, something along those lines. We actually realized through a great conversation with Mark Schuster who listened to our pitch. I’ve know Mark for years, we went and had a casual conversation with him, took him through what we were doing. At the end, very Mark style, he was like can I be your pitch coach? We said, sure. He was like, it sucks.
Joanne: That’s hilarious.
Kara: He said, you came in here and told me a story about investing in women that any two women who’ve been in this business for a few years can come in and tell. That’s not what differentiates you. It’s amazing how we’re both marketers and we would say the exact same thing when it comes to yourself – doctor heal thyself.
Kara: He said, what I know about you guys is that you’re the two marketers that anyone in LA and anywhere would ….
Joanne: Would acquire.
Kara: Consumer businesses all want to hire Lizzie, and enterprise businesses all want to hire Kara. You guys understand… He said, marketing. Then we met with Ann Winblad the next week and told her the story. She said, it’s go to market. You guys understand how to take entrepreneurial ideas to market. When we were able to leverage that, the substance not just being women, it’s who we are as our values, our experience, and then put the overlay of we understand commerce. She understands the front end of it, I understand the back end of it, and we focused in on that transforming the future of commerce thesis, with a strong and conscious bias.
Joanne: So, you had to formulate your thesis.
Kara: Towards brilliant diverse leadership teams.
Joanne: It also helps you formulate how you’re going to pitch to LPs and what separates you from other people they’re going to invest in.
Kara: Our whole life got easier after that.
Joanne: Right, because you were articulate. It was very easy because that’s what you’ve done.
Lizzie: Also, as marketers, it’s what we’ve done building brands our whole career. How do you get your value proposition crisply out there? How do you tell the story? As soon as we did it, it just felt so natural. Instantly, like a second skin which is amazing.
Joanne: This is great. You started raising money, which is always fun. I actually have to say, I’ve raised money all the time for every company I’ve invested in, but that’s a different thing. I think it’s really healthy for venture funds to raise money, because then they know what it’s like for their companies to raise money, and it’s just not pretty. It sucks, and it’s very hard particularly on your first fund but the key, as we know, is that you want to have the right investors that are interested in you for your third fund, because they’re not fly by night LPs. They’re long term investors and they’re interested to make sure that if they’re going to do it now, they know they’ve got four funds to invest in.
Kara: Absolutely. My mom who is a remarkable woman, one of the first women at Yale Law School, minority, was in class with Marian Wright Edelman and Eleanor Holmes Norton when it started. The only job she’d get after law school was in the government, and then she joined a law firm as a partner in D.C. The piece of advice I always remember that she gave me about her own business, because she’s a business woman too, was it’s very hard for us to bring in associates who are all bright and brilliant and intellectually curious and great at their craft and take them on the journey where they realize at the end of the day 80% of their job is sales and 20% of it is the hard-intellectual work. It’s what cut the wheat from the chaff is that they moved associates into partnership. I think the exact same thing applies to people who are, as I’ve discovered, starting their own investment firm. We’ve raised so much money behind concepts we love, business we’ve built, but they’re all easier when it’s an idea. It’s easy to get someone excited about function, or SaaS technology that’s going to change how they make profit and margin their business. To have to sell yourself….
Joanne: Is very different.
Kara: … is a very different skill set. People have warned us beforehand about how hard it was and how you had to just become sales people. I remember thinking about my mom’s story and how much that applied, because we’re marketers which is a really nice bow and a nice way of saying sales, which we’ve done our whole career.
Joanne: I don’t care what field you’re in, if you’re an artist, you’re a product person, musician, anything. Yes, the cream rises to the top, but if you’re a salesperson, that is really a very key component in order to getting your work out there. It just is. All right, so you guys decided let’s go, figured out your thesis.
Lizzie: Well, we practiced, I should not say practiced, we first did something we raised money for an SPV. We wanted to really understand….
Joanne: I remember you did that. I hate those.
Lizzie: Actually, we liked it.
Joanne: I think it’s very frustrating because you’re herding sheep on a daily basis when you find those businesses, and you can’t commit.
Kara: Here’s the thing. We found a great one, it was a wonderful deal and it’s a wonderful company. I’ll tell you what it is in a second. What was deceptive about it was that it was very easy to sell. We raised a lot of money in ….
Joanne: For that particular company.
Kara: … in one week for that company. Based on that, we thought if we can do this….
Joanne: We can do it for anyone.
Kara: Our fund is going to be … God, how are we going to handle it when people want in. We’ve hit our hard cap, people started talking to us about the hard cap. Do you remember that?
Lizzie: I do, that’s funny.
Kara: That’s so funny.
Lizzie: We did prove a point in….
Kara: The hard cap is the end of the rainbow. We’re climbing through, where is the…
Lizzie: Our hard cap changed a lot.
Joanne: That’s okay.
Kara: Our hard cap got softer and softer.
Lizzie: But it did prove that idea we had that it’s easier to sell a thing to people, a great business idea, than it is to sell an investment firm. Once we nailed down the thesis to your point, and had done this for fundraising experiment, which went…
Kara: By the way the company was Tamara Mellon brand which is a luxury footwear company direct to consumer founded by named after its founder who was the founder Jimmy Choo.
Kara: Everything about ….
Joanne: had a success.
Kara: This was an easy win.
Joanne: A slam dunk.
Lizzie: Then we just started shaking the trees, our personal network trees. I will tell you, I would probably grade us at an awkward D or maybe even like an easy F on some of those first conversations. I cringe when I think back about them. It’s not that we didn’t feel comfortable discussing our thesis, I think it was such a different pitch than anything we’d ever done. But to your point, we found fantastic LPs who believed in us and believed in what we were investing in, and are waiting for the results, but believe enough…
Joanne: It takes a long time to. I think that is one of the, I don’t know if they’re dirty little secrets or romantic fallacies, which is that it takes 10 years to show that you are a good investor. Obviously, once in a blue moon there’s some incredible hit. I’ve met some angels that just hit the right team at the right time. I have to say, some of them that I know I understand why they invested in those, and I understand why they came across their desk. For me, that wouldn’t be of interest. It’s like, yeah, that’s a money maker but I’m not interested in just knowing … It’s a money maker, there’s more to it. That’s the same thing for both of you. Why don’t you talk about what your thesis is?
Kara: Yeah, and I think you really keyed in on something Joanne that I think is so important. A lot of this stuff we’ve been talking about today and the conversations in general lately are about …. Sorry, seems like I’m going off course.
Joanne: No, you’re not.
Kara: But it’s about how we do thing differently as women, or maybe more broadly as people who didn’t come to it through the track. We didn’t go to business school, get degrees in finance, work at Goldman, and then go into venture, or whatever the track. I don’t even know what you call it.
Joanne: I don’t think there is a track.
Kara: There isn’t a track.
Joanne: It’s actually really hard to get into venture.
Kara: It’s really hard. What I noticed about all of these things is that knowing who you are, what you stand for, what you believe in, what your thesis is, is so focusing and helpful. How many times have I sent you stuff and you’re like oh my god, no. It’s like you’re not really an entrepreneur unless Joanne Wilson has smacked your ass down. It’s like, no, I’m not doing that. But I think what’s great about that is you are beautifully unapologetic, such an inspiration to us in that role. You’re beautifully unapologetically doing what you’re doing.
Kara: You’re doing it your own way and on your own path. I think that is so advantageous, because I think what happens when you get into the venture capital industry world is people are like I don’t want to miss the great deals. Of course, but have you ever seen a company that you’ve passed on. I know the answer, this is a leading question. Have you ever seen a company that you passed on end up being wildly successful, having a major exit, and thinking good for them I’m still okay with my decision?
Joanne: Absolutely. I never look back. I’ve seen the couple and I’m like I think I talked to them at the beginning. I go through my email and I’m like wow, I did. I’d still pass on it.
Kara: Exactly, because you…. I think there is this …
Joanne: It’s also a perfect storm.
Kara: Of course.
Joanne: We’re looking at deals that are so early. I think the hardest thing about these early stage deals, not that it’s not difficult in later stage deals, but more early stage deals is the capital. The reality is, unless you have a $50 million fund that you can say no worries. If you get into trouble, I believe in you. What you’ve done in the past 18 months is amazing and I don’t know why these people don’t see the same thing I do, which happens 99% of the time. I’ll write you the check, not a worry. For me, I am not in the position to do that. That has been my largest frustration over the past decade, and makes me rethink my thesis, because it’s exhausting for the founder, but it’s also frustrating for me as an investor.
Kara: Yeah, absolutely. I think that’s right. Our thesis is bringing together capital and our expertise, our deep understanding of how do you bring these companies – technology and data driven companies – in and around commerce to market. We’re really looking at the companies transforming the future of commerce. We think about that in three ways – we look for three substantive aspects of these early stage businesses – and we invest in the seed and preseed visits. One is transformation around people, commerce around people. By that we mean, separate from assessing a team which is of course critically… in terms of what the company is doing. Are they meeting or newly meeting or better delivering on the needs of new emerging or previously underserved audiences? Great example of that is a company we invested in recently with Arlan Hamilton for Backstage Capital called Haute Hijab. They’re based in New York. They are bringing a westernized brand approach to the hair covering scarf that many observant Muslim women wear, the hijab.
Joanne: Right, I’ve talked to them.
Kara: The Muslim population is expected to grow 70% in the next 30 years. I mean, talk about emerging. Emerging is a funny word because …. but growing, fast growing. Right now, Muslim women are observant covering their hair, successfully running medical practices, attorneys, and starting business, and not really having a right. It’s really not the right thing, and it’s not something stylish at the level of everything else she’s wearing. They started that company, so that’s a great company in the people category.
The next category we look for around transformational commerce is products. People who are bringing or applying technology and data to deliver product in new better way. I would put Parachute Home in that category.
Kara: RevCascade with what they’re doing now. Skylar Body, you know, Cat Chen in the way she can create value out of data and technology in selling her natural care fragrance line is incredible. That’s sort of the product focus around commerce.
Then the third is process, that really gets to the fact that we invest not only in consumer facing businesses, but enterprise and business B2B companies. Those are companies like Happy Returns, which is tackling the logistics around all the returns, what I call the pile of boxes that we all have in our houses it seems like these days. They’re addressing the pile of boxes and turning that into a more positive experience for the consumer, but a revenue center versus a cost center for the modern commerce retailer.
Joanne: Are you mostly focused, is it LA focused?
Kara: We’re a lot of 60s and 40s, 60 LA, 40 New York.
Lizzie: I think there’s a really close tie between LA and New York.
Joanne: You can pretty much cut the middle of the country and smoosh those two, which appears what Trump wanted to do.
Lizzie: That might be the only thing we agree on. I’m down, let’s do this.
Joanne: Certainly, that seems to be…. Those are the two state he really decided he didn’t like. There definitely is a synergy I think between New York and LA and has been forever.
Lizzie: Do you feel like there’s that same string between Boston and San Francisco, likewise LA and New York? That’s where we split our time.
Joanne: Yeah, that makes sense. Asia is booming too. I don’t know if any of you speak Chinese.
Kara: Right, we should work on that. Let’s add that, we’re going to do that.
Joanne: You can go do Duolingo.
Kara: We’re going to do that.
Joanne: And play around with that.
Kara: Note to self, tweet Joanne tomorrow in Mandarin. Joanne, we nailed it.
Joanne: That’s great.
Kara: These are all visions and pie in the sky. We said on our list of values that we didn’t publish was build some business that will eventually need an office in Paris. Is that so wrong?
Joanne: No, it’s okay, it’s okay. I totally get it. Thank you guys for coming, Brilliant Ventures, brilliant. It’s nice to see where you guys are versus where you were a couple years ago.
Kara: Oh, that’s nice of you to say, thank you. It’s good to hear that. Sometimes when you’re in it, you’re not sure if you’ve, no, we have.
Joanne: You have, you’ve raised money, you make investments. Yeah, you’re venture people.
Kara: It’s been incredible.
Lizzie: Thank you.
Kara Thank you so much.
Joanne: Thanks guys.
Our thanks to Lizzie and Kara for joining us on the podcast this week. You can learn more about Brilliant Ventures by visiting their website brilliant.ventures. That is brilliant.ventures not .com. Thank you to all of you listeners for joining us this week. Stay up to date with Positively Gotham Gal. You can find us on Facebook and Twitter. You can subscribe to our podcast on SoundCloud or iTunes. See you next week.
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This week’s episode features Amanda Eilian, Co-Founder & President of Videolicious — a video creation service for enterprise businesses and companies. Amanda and I talked about her early days as a teenage radio host, her transition into investment banking, and what led her to starting Videolicious in the first place. Most interesting, perhaps, is that Amanda and her co-founder ignored a lot of early advice they received about what direction they should take their company in — and it paid off.
Design that Speaks to a Rising Ride, Rachel Berks, Otherwild, Podcast #49
This week I chatted with Rachel Berks, owner of Otherwild and designer behind the insanely popular ‘The Future Is Female’ t-shirt. Rachel had a lot to say about the unexpected reach of her design work, the steps she took to get enough freedom in her business to create, and how she’s dealt with having her work copied by other artists.
Listening to Customer #1, Jordan Salcito, Ramona, Podcast #48
Jordan Salcito is the sommelier and entrepreneur behind two successful beverage ventures — Bellus Wines and RAMONA. To kick off 2018, Jordan and I sat down to talk about her path towards entrepreneurship, and how she really followed herself as potential customer #1 to drive the ideas behind each of her businesses.
Conquering the New York Restaurant Scene, Victoria Freeman, Restauranteur, Podcast 47
Victoria Freeman has a successful career as a New York City restaurateur — a feat in and of itself. Her restaurants include Cookshop, Vic’s, Shuka, and Rosies. This week we sat down to talk about her career path, and the challenges and triumphs she’s had along the way. Positively Gotham Gal will be on hiatus for the rest of this holiday season — enjoy the remainder of your 2017, and we’ll be back on Monday, January 8th with a brand new episode.
What Drives Me? Olivia Young, Box + Flow, Podcast #46
Olivia Young is the Founder of Box + Flow, a fitness location and lifestyle brand based on the principles of personal balance and enjoying life. For the podcast this week, Olivia and I sat down and got straight to business — from what it took for her take the plunge into her first entrepreneurial venture, to how she brings a unique perspective to the exploding wellness industry, and everything in between.
Trust What You Chose, Abbey Warsh, Harbor Market & Kitchen, Podcast #45
After over a decade of being a full-time mom, Abbey Warsh decided to take a calculated leap into entrepreneurship — she partnered with Chef Paul Del Favero and Susan Del Favero to open the Harbor Market & Kitchen in Sag Harbor, Long Island. Abbey shares with me how trusting her gut led her to the right opportunities and collaborators, and how this mindset continues to influence her business today, as well as her plans for the future
Empowering Women with Tech, Fereshteh Forough, Code to Inspire, Podcast#44
Empowering Women with Tech – Fereshteh Forough Description: This week I sat down with Fereshteh Forough, Founder & CEO of Code to Inspire — a nonprofit committed to teaching female students in Afghanistan how to code. Fereshteh talks about her journey from Afghan refugee, to international advocate for women’s education and equality.
If you like what you hear, please support what Fereshteh is doing. She has a campaign going right now for Code to Inspire. Click here.
When You Fall in Love with the Work, Amanda Merrow & Katie Baldwin, Amber Waves Farm, Podcast #43
This week features the Co-Founders and farmers of Amber Waves Farm, Amanda Merrow, and Katie Baldwin. Located in Amagansett, NY, their mission is to bring sustainability, education, and a highly curated food experience to the farm to table market. Amanda & Katie’s story takes us from their first connection during a farming apprenticeship to opening their own, one-of-a-kind, grocery store.
The Payoff that Comes with Starting Small, Jessica Banks, RockPaperRobot, Podcast #42
Jessica Banks has a career path that did not go the way she thought it would — after having to abandon her dreams of becoming an astronaut, it took this Founder & CEO of RockPaperRobot awhile to find the right place to put her feet on the ground. But once she did, she took off. Jessica’s plan of honing in on one product before expanding her business has paid off big-time and is definitely an idea we can all find use from.
Putting in the Time to Build Traction, Carissa Waechter, Carrisa’s Bakery, Podcast #41
This week’s episode features Carissa Waechter, the entrepreneur, baker, and pastry chef behind Carissa’s Bakery in East Hampton, NY. Carissa takes us through her career path from culinary school to starting her own business, and why it was so important for her to make sure she took the time she needed before launching her retail store.
It’s All about Creating an Emotion – Zara Tisch, Terez, Podcast #40
Zara Tisch is the Founder & CEO of the playful leggings and accessories company, Terez. Zara sat down with me this week to talk about how she’s built her company by focusing on products that create positive emotional experiences for her customers.
Business as a Force for Good in the World, Susan McPherson, Podcast #39
Turning Your Lowest Moment into Your Biggest Opportunity, Jane West, Podcast #38
This week’s episode features CEO Jane West, one of the women entrepreneurs who has pioneered the cannabis industry since Denver’s legalization in 2014. Her story is full of plot twists, and Jane shares with us how she saw each let-down, misdirection, and mistake as an opportunity to try something new.
Play to Your Strengths, Megan Grassell, Yellowberry, Podcast #37
Megan Grassell founded her company, Yellowberry, when she was just 17. This week, I sat down with the millennial entrepreneur to talk about what inspired her business, the smart moves she made throughout her journey, and her vision for the future of her company.
Put Your Idea Out Into the World, ItsbyU, Christine and Caroline Strzalka, Podcast #36
Sisters and Co-Founders, Christine & Caroline Strzalka, are the duo behind the soon-to-be-released floral subscription service, Itsbyu. This week they shared with me a ton of insights from their mad dash to hit the ground running with a brand new startup
Christine Vachon, It’s So Much About Risk, Podcast #35
This week’s episode features acclaimed American film producer and Co-Founder of Killer Films, Christine Vachon. Christine and I discussed her trajectory from New York’s experimental film scene to the Oscars, and the big risks she took along the way. Definitely an inspiring story for any entrepreneur looking to take on a fresh perspective on how to conquer their corner of the market.
Donna Zaccaro, You Need to See It In Order To Be It, Podcast #34
Donna Zaccaro is the director of the upcoming documentary film, ‘To A More Perfect Union: U.S. v Windsor” — set to have its world premiere at the Woodstock Film Festival this October. Donna is also the founder of Dazzling Media. She joined me in conversation to talk about her films, her empowering influences, and a career full of decisive twists and turns that led her to a life that allows for her impactful, creative endeavors today.
Podcast #33, 10 Years in the Making, Jen Bekman, 20×200
This week’s episode features Jen Bekman, art gallerist, and Founder of 20×200 — an online marketplace that makes art accessible to everyone. Just in time for 20×200’s ten year anniversary, Jen shares some insights on playing the long game in your business — from re-evaluating your steps, to honoring your successes, and everything in between.
Failure can make you Fearless, Harleen Kahlon, Bolde, Podcast #32
Failure can make your Fearless – Harleen Kahlon This week features a conversation with Harleen Kahlon, Founder of bolde.com, an editorial-driven lifestyle company for millennial women. Harleen’s path to founding her company took her through many career milestones, and down some unexpected avenues — it’s a great example of being unafraid to embrace new directions and looking at missteps as new opportunities
Start Small, Think Big, Podcast #31, Kelsey Recht, Venuebook
Kelsey Recht, the Founder and CEO of Venuebook joins me on the podcast this week to talk about everything from the dedicated sense of drive she developed as a competitive junior figure skater, to how motherhood made her a better CEO. Kelsey’s approach to creating a new platform for event booking benefited from her mindset of ‘start small, but think big’- something we can all get a benefit from.
Get Focused On Your Mission, Christine Quinn, Podcast #30
I have known Christine for years and we sat down to sat down to discuss everything from her career in politics to coping with failure, and how to bring entrepreneurship into all aspects of life. She has learned a lot over the years and her transparency around all these topics is impressive. Christine lets us in on some valuable insights into the political sphere and what we can do to create change in our own communities. She is definitely back on her game. A very timely conversation.
Learning through Play, Ayah Bdeir, littleBits, Podcast#29
Learning Through Play – Ayah Bdeir Founder and CEO of littleBits Ayah takes us through her journey of a curiosity-filled upbringing in Beirut, to her inspiring years at MIT’s Media Lab, and how her path led her to create Little Bits — technology kits composed of electronic building blocks that have seemingly limitless creative potential for tinkerers and learners of all ages.
Pairing Knowledge with Possibility, Erica Jain, Podcast #28
Co-founder & CEO Erica Jain talks about how a massive void in the market led her to create Healthie, an all-in-one, HIPAA-compliant platform for nutritional healthcare. Erica’s out-of-the-box approach to client acquisition, and what led her down that path, provide great insights for entrepreneurs in any market.
From Friends to Founders – Claire Mazur & Erica Cerulo, Podcast #27
Claire Mazur and Erica Cerulo are the Co-Founders of Of A Kind, a hand-curated e-commerce site that connects consumers with artists and designers that create unique and small-run finds. Claire and Erica explain how their business was born from friendship — and how an idea hatched late at night during a resume writing session, became the new model for finding one of a kind pieces online and beyond. They also have a killer podcast.
Being Deliberate About Your Path, Alice Cheng, Podcast
Alice Cheng is the Founder & CEO of Culinary Agents, a company that connects food industry professionals to hiring companies and restaurants. Alice’s path to entrepreneurship was anything but linear — in our conversation, she discusses how thirteen years at the corporate giant, IBM, gave her the opportunity to learn the skills she needed for the next phase of her career.
Katherine Powers, Muses and Marketing, Podcast
This week’s episode features Katherine Power, Co-Founder & CEO of Clique Media Group — a parent company of leading content sites and brands. Katherine shares her unique strategy for inviting customers to be both muses and marketers for their favorite brands, and how that’s led to success across platforms today.
Jean Brownhill, Nothing is Standard, Podcast
This week’s conversation is with Jean Brownhill, Founder & CEO of Sweeten — a network that connects people with renovation projects to general contractors and assists them with project management throughout the process. I invested the first dollar in Sweeten, and you’ll understand why when you hear Jean’s story of hard work mixed with an openness to the possibility of opportunity — this woman has followed her gut from a high school babysitting business to the Harvard Loeb fellowship, with tons of informative lessons in between.
Lolly Daskal, Lead from Within, Podcast
Lolly Daskal, sought-after executive leadership coach and founder & CEO of Lead from Within, sat down with me this week to talk about her unconventional path to a sustainable career as ‘the navigator’ for some of the world’s biggest CEO’s. Lolly’s independent spirit led her to break out on her own at a young age, and it’s that same boldness that informs her ability to empower others in their business leadership. She has some great insights that are sure to be useful for everyone.
Flipping the tables on the podcast this week, it is me. #23
Episode 23: Turning the Tables – This week we’re turning the tables and putting me, the Gotham Gal in the hot seat. I am interviewed by Alexandra O’Daly, who works with me every day and we talk about the path that led me to become the investor I am today, what informs my passion for investing in women entrepreneurs — and gives some insights into my ‘take no bs from anyone’ attitude.
Tami Forman, Path Forward, Getting Mom’s Back to Work, Podcast
This week, Tami Forman discusses the work her organization is doing to help women return to the workforce after taking time away for motherhood or other family care giving. As Executive Director of Path Forward, Tami has poured her personal passion for gender equality at home and at work into a nonprofit organization with a vital mission.
We Couldn’t NOT Do It, Joanna McFarland, Hop Skip Drive, Podcast
Co-Founder & CEO of HopSkipDrive, Joanna McFarland, chats with us about how all roads led to quitting her job and diving into the startup world with the idea of creating a safe and dependable ride service for kids. Joanna shares her interesting career path, one in which she leveraged her fears and uncertainties into success — making it a point to explore and understand anything that intimidated or confounded her. Joanna’s measured approach to risk taking is certainly one to take a few pointers from.
Linda Ong, A Brand is an Ideology, Podcast
Linda Ong, branding powerhouse & Chief Culture Officer of Civic Entertainment Group, sat down with me this week to chat about how her own “mish-mash” of cultural identities informed her career — one in which she’s created cultural identities for companies and media networks alike. Linda breaks down how she approaches the building of a brand identity with her own clients, and her insights are not to be missed!
Tracy DiNunzio, Tradesy, From Learning to Closing, podcast
On episode #18 of Positively Gotham Gal, we talk with Tracy DiNunzio, Founder and CEO of Tradesy, an online platform where women can buy and sell from their own closets. Tracy’s scrappy approach to success is both tenacious and endearing — a great inspiration story for anyone in need of a swift kick in the pants in the start- up world.
Alexis Maybank, Changing Direction Can Be A Good Thing, Podcast
This week’s conversation features Alexis Maybank, Co-Founder & CEO of Project September, the first entirely visual shopping platform. Alexis lets us in on her previous experience as the Co-founder of the luxury e-commerce site, Gilt, and how she let changes in consumer behavior, and new ideas, influence her in a positive way to start her latest venture.
Nina Luu, Episode 16, Building a Diverse Team
Chatted with Nina Luu, Founder & CEO of Shippabo, about how she came up with the idea for her successful startup and what really sets them apart from other solutions in the marketplace. Nina’s approach to management and diversity in considering how to build her company’s team takes on unexpected difficulties that she shares with us here — it’s definitely worth a listen for anyone thinking about growth and culture.
A New Way to Tell A Story, Amanda Kludt, podcast
I have been fortunate to watch Amanda Kludt, Editor-in-Chief at Eater, grow into this role. I have known Amanda for almost a decade. Her insight into the food industry is worth listening to. She has always had her finger on the pulse. I highly recommend signing up for her weekly down-lows on the world of food. I loved this conversation.
Jean Poh, Changing One of the Oldest Industries, Podcast
Erin Bagwell, Choosing to be Your Own Distributor, Podcast
Erin Bagwell is the director, producer, entrepreneur and visionary behind Dream Girl. Dream Girl is a film that is about showing other women especially young girls that there are female entrepreneurs out there and that they can be too. This film has been shown around the globe. Erin’s approach to the film, the distribution including how she raised the capital is the new model. The next generation of film makers should be taking note. We sat down to talk about her endeavor to get this film made.
Dana Cowin, Lead and Exceed, Podcast
I met Dana Cowin more than a several years ago now. I was in London having dinner and she was a few tables over from me. I recognized her as I have been an avid subscriber of Food and Wine for now over 30 years. I went over to her table and introduced myself. We had a few friends in common and when I returned to NYC one of them reached out for us to connect and have dinner. We have been having dinner and more since then. Her birds-eye view of the food industry is like no other. It was really fun to sit down with her and chat about her career starting as an editor at Food and Wine to her next journey in the world of food. Highly suggest following her on Instagram for some fantastic photos.
Challenging the Health Care Model, Katherine Ryder, Podcast
I met Katherine after she left the venture world and was charting her life as an entrepreneur. She finally found the right path with Maven. Maven connects patients and providers with video or messaging. They are able to give advice, provide prescriptions and everything else in between. Think of it as a place for women to get care digitally. I love their tag line; prescriptions or advice by video appointment or private message. Whenever, wherever.
Katherine and I sat down to talk about her journey. An interesting path to get her to where she is today.
Positively Gotham Gal, Karen Cahn, iFundWomen
Karen is the founder of iFundWomen a crowdfunding platform for women-led businesses. Karen has been part of the tech industry of NY since the start. This platform is not only giving women a voice but capital to build on their ideas. They can tell their stories, raise capital and be part of a community. Karen is passionate about the women she is helping and her enthusiasm shows in our conversation.
Enjoy the podcast!
Podcast, Marianne Courville, The Alchemist of Entrepreneurship
Marianne Courville is the founder of The Hudson Standard, a line of small batch cocktail bitters and syrups.
Monday Podcast, Sara Chipps, Jewelbots, If Your Partner Wouldn’t Hire You, Then You Shouldn’t Hire Them.
Sara Chipps, Jewelbots
Podcast Monday, The Surprises Never Stop Coming, Amanda Hesser and Merrill Stubbs, Food 52
Podcast with Maiko Kyogoku, Restaurants Are A People’s Business
Today’s episode is with Maiko Kyogoku, the owner of the restaurant Bessou.
Positively Gotham Gal Podcast, Open and Honest Conversations with Caren Maio
This week’s Podcast is with Caren Maio, Founder and CEO of Nestio.
Podcast Monday is the new theme
I am going to start posting podcasts on Monday like I used to post entrepreneur of the week. This time instead of reading the piece you can listen. 20 minute sound bites.
This one is Just Build with Nancy Lublin.
One person can change everything….oh, and a new podcast
In a company one person can change everything. A sales person can join the team and the trajectory can change overnight. A new COO can join the team and take a look at the company from bottom up, shift a few things around responsibilities and all of a sudden you have a fine oiled machine.
One bad apple in a company can reek havoc on the culture. Some founders have a hard time firing that one person for fear of the team being upset, or hoping that tomorrow will be a better day but pretty much 10 times out of 10 when they do let that bad apple go the team sighs a huge gasp of relief. The question is always, “why didn’t anyone say anything?” The reality is most don’t. They are looking for leadership and believe in in the culture they are creating.
It isn’t easy being the founder. It is a tough job yet it is also an exhilarating job. I have also seen founders become paralyzed around hiring. It is hard to put the cart before the horse but in the start-up world those risks are weighed daily.
I have seen companies have 24 cents in the bank and boom they get funded and life changes. It is the same thing with people. One person can change the whole game.
Positively Gotham Gal
After writing over hundreds of Monday posts called Women Entrepreneur of the week it was time for a change. And so…I began a podcast. It is called Positively Gotham Gal which is an ode to Positively 10th Street, a podcast our family did on a weekly basis back in early 2000 that is unfortunately nowhere to be found.
The podcast will be around entrepreneurship. It is short, sweet with worthwhile tidbits. I will post them weekly and get a widget up on the blog.