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?

Kara: Yeah.


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.


Lizzie: Yeah.


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.


Kara: Yeah.


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.


Joanne: Imploding.


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.


Joanne: Yeah.


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?


Lizzie: Yes.


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.


Kara: Ziplining.


Lizzie: Ziplining.


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.


Joanne: Right.


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 for 450 million.  I left Rubicon, gone to 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….


Kara: Why?


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.

Lizzie: Yeah.


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.


Joanne: Yes.


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.


Joanne: Exactly.


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.


Joanne: Yeah.


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.


Lizzie: Yeah.


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.


Lizzie: RevCascade.


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  That is 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.


Comments (Archived):

  1. Pranay Srinivasan

    So much movement towards a quasi-Betaworks type of VC model. Balancing higher ownership with more involvement with a smaller number of investments seems to be the movement du jour right now.Of course, the more women entrepreneurs you can fund, the better – And if its in non-creepy, non-white male environments, maybe this kind of hands-on support is exactly what founders need to grow.Also it is interesting but if someone did a survey, I am SURE it would show that female-founded companies turn profitable faster, with a lower headcount, less investment and grow faster than a comparable one by men.Maybe thats a better metric to shoot for and have optionality *whether* to raise an A, instead of *having* to raise an A.I definitely learnt that lesson the hard way.

    1. Gotham Gal

      I think your data point could be correct.

  2. jason wright

    how do you get this transcribed?

    1. Joanne Wilson

      We use a freelance transcriber. Let me know if you’d like her info.

      1. jason wright