Posts from musings

Hitting the Wall

hit-the-wallI have had so many different careers.  It is probably why I like start-ups because I am always looking to try something new and do something different.  It is also why I like real estate projects.  There is something that thrills me about the start and the growth.  In real estate, I do like closure.  In start-ups I like to opt out when the growth hits that point where the next level of growth is not as much about problem solving but a bit more like intelligent cruise control.  Not the best description but it is the time when it helps to bring in some experienced institutional investors.

This fall we took off for a blissful month.  We realized that we could take it down a notch and could still take the Wilson business on the road.  I am doing a fair amount of traveling this fall and perhaps that is why I am truly starting to hit the wall.  Maybe it is also the beginnings of seeing what life is starting to look like with our kids out of the nest.  Who knows.
Angel investing is something that many do without any involvement.  I do not think I am capable of that.  Yet in the world of angel investing you have to make a lot of bets each year for the model to work.  Maybe it makes sense to start thinking about only doing so many a year with the hopes that the ones from the year before get a little more mature.  I don’t know.  It isn’t like I am talking to all these businesses daily but I am aware of what is going on in all of them, some more than others, and of course I am always available, focused and am happy to help, talk and do whatever I can do for the entrepreneurs I have invested in. I also sit on several boards from start-up to non-profit.
The real estate is a whole other life.  One I rarely speak about but takes up a lot of space in my head.  Growing a portfolio takes time, management and obviously a lot of thought.
This past week I have been wondering am I hitting the wall?  I admit it is exciting to have built a new career and feel like I am making an impact on businesses and women.  That feels great. I have always been competitive and I always like to win but how much do I need to win?
Maybe I am describing something that many others feel but don’t talk about.  It is probably a feeling that most early stage entrepreneurs feel.  That feeling of there aren’t enough hours in the day, I won’t be able to get it all done, am I crazy to be doing all this, how do I take it down a notch, can I take it down a notch?  it feels great to be able to focus on thinking about businesses which I truly do love (start-up, real estate, and the rest) but I think that once this year ends, I am going to spend some time trying for a little more balance.
Practice what you preach, right?

It’s Brooklyn

Brooklyn1My first job out of college was running the cosmetics department for Macy’s in Kings Plaza Brooklyn.  I’d drive out there every day instead of taking public transportation which was a subway and a bus.  The hours were long and late so a car was definitely the way to go.  We were lucky that we had one which at one point became so dilapidated that we had to pay a tow truck to take it away and he was concerned that there might be a lean against the car.  But that is a whole other story.

I’d drive through Brooklyn many days instead of taking the main routes back to NYC.  Fred and I would also venture into the different neighborhoods to check them out and at one point lived in Cobble Hill and Brooklyn Heights.  So many of those neighborhoods were not places you would want to venture into at night or even day. A lot has changed.

I see the Brooklynization of cities across the globe.  The next generation has taken control of areas that needed some serious TLC.  Jonathan Butler Demby started Brownstoner sometime around 2006 when Curbed began.  Brownstoner wrote about the ins and outs of Brooklyn real estate among other things. Jonathan and Eric saw what was happening in Brooklyn and began the Brooklyn Flea in 2012 where they took the concept of a flea market and applied that with food (which was starting to dominate the Brooklyn start-up scene) and created a place for people would go to shop and mingle.  Out of that came Smorgasburg completely dedicated to food.  It is truly was brilliant and in many ways I think of both Jonathan and Eric as the self-appointed mayors of Brooklyn.

Fast forward, they both bought a building in Crown Heights and built a beer hall along with co-working spaces and singular places to rent for companies to put down their roots.  The beer hall is called Berg’n with food from Asia Dog, Mighty Quinns, Pizza Moto Slice Shop and Ramen Burger.  When I first saw the idea I knew it would be a success.  Located in Crown Heights surrounded by big open streets and beautiful brownstones.  The timing was right.

The other spots that have transformed areas of Brooklyn is the Royal Palms Shuffleboard in Gowanus.  An awesome large space with shuffle board in the middle of surrounding cabanas, a food truck of the night and dozens of games that can be used to play that evening.  It is a local community spot.

Another spot is coming to Gowanus is called Threes Brewing.  Besides brewing a variety of their own beers which are fantastic there will be food, coffee and music from breakfast to late night.  Opening 12/1 and certainly local beers at your favorite bars soon.  It is a great space with a big outside area in the back with a bar and a grill.  The building spreads back and forth from one street to another.

We are investors in all three.  It feels so great to know that each of these spots are creating local watering holes for the neighborhoods of Brooklyn.  The neighborhoods are filled with young people, young families and a DIY vibe that stems from the young tech communities and the food purveyors.  It is great to feel apart of
that beat of the street in areas that not long ago felt vacant.

Let’s hope for change in the medical world

imgresOn Friday night I started coughing about 9pm.  No idea where that came from but I was obviously getting sick.  Could be that I have run myself ragged the last month, it could be the change of weather, it could be a variety of things.  That night I woke up a few nights wheezing.  I was a bit concerned.  The next morning Fred said you were wheezing all night long.  Ugh.

We were out at the beach so I made sure I was the first person at the local clinic when it opened on Saturday morning.  It is a great clinic that I found out later has been run by several groups.  It is changing hands one more time in January and being run by the hospital in Southhampton.  It is hard to make money on the clinic and each group got tired of all the back end of running the business vs the real business at hand; treating patients.

Anyway, I got in quickly and saw a young energetic doctor.  She called in some meds and gave me a treatment while I was there.  It was really efficient.  We started to talk about how difficult it is to make money as a doctor and how these clinics, although great, are financial losers.  She was working at the clinic on the weekends and worked somewhere else practicing medicine during the week.

I told her about Captureproof.  Captureproof is HIPAA approved (which is key for doctors) so she could track and follow patients through the app after the initial visit which based on the results that CP has got it cuts down on the second visits by 80% and saves insurance companies almost 80%.  That is a win win for everyone.  The doctor wanted to understand how she would get paid on the second visit if it was through a photo and a quick message.  I didn’t know the answer but I am assuming that she will gets paid a co-pay based on the insurance.

This doctor has $300K in debt.  She went into medicine because she loved it and wanted to help people.  We need more people like her and yet our medical system remains a mess.  She is not only dealing with providing care she is dealing with the front end of a business to make sure she makes money.  That includes chasing down insurance companies for the co-pay.  It is utterly ridiculous.  We need to make doctors lives seamless so they can concentrate on what they set out to do and that is not being a business person.

I look at Captureproof, and have been part of the journey signing up hundreds of doctors including Blue Cross Blue Shield and Kaiser Permanente.  I hear the data that comes back to help make the medical world more affordable and seamless.  This is the beginning of a massive change that will happen over the next ten years.  Technology will hopefully allow doctors to be doctors and make sure that every one has access to preventive healthcare.  At least let’s hope so.

The future of transportation…

imagesTransportation is changing.  You still need a vehicle to get from point A to point B but what type of vehicle is in question.  Electric is in our future and so is a lot more.

One of the greatest things about city life is that you don’t need to own a car.  The public transportation system is good and could be better but it exists underground and above ground.  Citibike announced a huge expansion this week in and around the boroughs of NYC.  Then of course there is Uber.  There is also Hailo, Lyft, Sidecar and a few others but Uber seems to have taken NYC by storm.  There is something brilliant about being able to order a cab or black car from your phone, get the information on the driver and then track their trip to pick you up.

I would hope that the next Presidential administrations will take a hard long look at investing huge amounts of capital on transportation.  As urban areas become more expensive there is a need for high speed trains.  Why can’t someone live two hours outside of the city and still work in the city.  It shouldn’t take two hours to get from one location to the other, it should take 30 minutes tops. That is a game changer.

The cities can not afford to build underground but with less cars on the road but they can certainly afford to build rails above ground.  Why isn’t there a railway that moves freely around Brooklyn and Queens.  It would also be a game changer for the neighborhoods that have already changed dramatically where the transportation is far from seamless.

Cars.  Zip-car changed the need to rent a car or even own a car in the city.  It was the beginning of the shared economy although the cars are owned by Zip-car they are shared by many with the ease of entering your info into your phone and finding a car near you.

I am an investor in Scoot.  Scoot is the zip-car of electric scooters.  When you travel in Europe scooters are everywhere.  They make a lot of sense for large cities when people need to get from point A to point B without a car or a bus or a subway.  Basically a motorized bike.

Here is the future.  You live 2 plus hours outside a major urban area, let’s make it NYC.  Financially it makes more sense for you to live there and you actually prefer the solitude and community.  You jump on the bus or share a car or take your bike down to the train station in the morning.  You get there around 8am, jump on the train and you are in the city by 830.  Your office is on the other side of town and you much prefer being above ground and being solo.  So you walk over to the 40 Scoots parked right outside the train station and jump on one.  You choose the Scoot on Wednesdays because you generally move around a lot on Wednesdays for meetings and it is the most efficient way to get around the city.  Thursdays you take a Citibike because you just go to the office and back and you like the exercise.  You run your errands and at the end of the day instead of going home you decide to go meet a friend for dinner just outside of the major city hub, let’s say Brooklyn.  You park your Scoot and leave it there for the next rider and jump on the ferry to get across the river.  Once you are there you jump on the railcar and go a few stops into Brooklyn where there used to be zero transportation.  You have dinner and get back on the railway which takes you into Queens where you can pick up the train that hooks up with the train that takes you home for the night.  Although if you are really not in the mood you might just Uber it to the train in the new fleets of electric vehicles that have been deemed mandatory in the city because there are no longer any gas stations.  Or you decide to just stay in Brooklyn for the evening and had planned ahead by booking an Airbnb the night before and packing a small bag for the night.  If you forgot something you could always get Postmates (driving their Scoot) to get it for you and meet you at the restaurant before getting to your Airbnb.

This is not so far around the corner.  It might be bumpy getting there but I believe that we will get there sooner than we think.

The hook-up generation

No-means-No-300x172We have all read about the escalation of rapes that have taken place on college campuses.  There are so many conversations to have on this topic.  Are college campuses educating incoming freshman about safe sex and rape.  It is refreshing to see that women are actually coming out and saying this person raped me vs sweeping it under the carpet.  Unfortunately most campuses are not equipped to deal with the aftermath of these abuses as they would prefer to continue to sweep a rape under the carpet.

Education is obviously key. Sexual education should begin at a very young age and in many schools it does where as in other schools there is none.  Sex is one of those topics that parents rarely talk about.  They realize that they should talk to their kids about drugs and alcohol but when it comes to sex many just want to know if they are using birth control.

The reality is that once your kid reaches a certain age they are more than likely going to become sexually active because of the hook-up culture that is essentially the long tail aftermath of the sexual revolution.  Birth control has given women the same opportunity as men when it comes to having casual sex.  Because both men and women are having one night hook-ups there seems to be this broken communication around when no means no.  What is incredible is because so many women are now empowered to have casual sex and feel comfortable about the one night hook-up that they also feel powerful enough to say I have been raped.  They are not holding back but putting it out there because they realize that they were raped, it is a crime and it is not ok.  I applaud every single one of these women who have come forward.  However the system has to get better at gathering information and investigating rape.  After all, in our country you are innocent until proven guilty and you have to prove a crime in order to prosecute those individuals.

Let’s go back to the importance of education.  Young men ( and women ) have to understand that no means no.  Make sure that you are both consenting to having sex.  Communicate and if  someone is so wasted that they can not communicate I would take that as a no.  Second is use protection.  Third is sex is a two way street.  These are conversations that should be taking place at home not only at school.  Respecting each other when it comes to sex is an important lesson to learn young.

Colleges should be talking about rape, educating incoming freshman about no means no and understanding that there will be repercussions, prosecution and immediate suspension if someone was found to have raped another individual.  Colleges should be safe places where you can go wild among friends and are free to have a one night hook-up without fear of being raped.

Raising good eaters

kidThe NYX magazine section a few weekends ago focused on the question “what should children eat”.  To some it might seem like an absolutely ridiculous question but to others it is a real concern.  This could be a stretch but I believe that children who are good eaters generally come from a family of good eaters.

There is no doubt that we all have different taste buds and there are just some things that do not taste good but in general it is about being exposed to tastes and textures from early on.  Mark Bittman wrote an article in the magazine about how him and his wife raised their two daughters and although I was not writing a cookbook as he was when raising our kids we basically did what they did.  We ate everything and there was never this conversation of us begging them to try something because we swear it tastes good.  They ate what I gave them and if they were unsure at least they would try it.

Whatever I made for dinner we all ate.  I was not a short-order chef.  If I was making a leg of lamb with a greek salad or a curry noodle soup or a chicken in the pot then that is what we all ate for dinner.  We didn’t do chicken fingers and frozen pizzas.  Sure I kept string cheese and some of those packaged products that kids love to eat for a snack but in general I made cookies and served a healthy meal.  They knew nothing else and were always amazed when their friends came over.  BTW, I converted many of their friends by just giving them what we were eating and prodding them to try it.

When Emily was about 13 months we have a picture of here sitting in a high chair at my Mom’s house with a stalk of broccoli in her hand chowing down.  I remember the moment quite clearly.  She just kept eating the stalks.  My Grandmother was still alive and was not only amazed at the eating frenzy but concerned she was putting away way too much broccoli.  She obviously liked it.

I even remember going to Barcelona with Josh when he was ten and the people at every restaurant were absolutely blown away with what he was eating and with what he ordered.  One place brought him out a few desserts on the house to acknowledge what he ate.  It was hilarious and the chatter among the wait staff.

Fast forward, all of our kids cook and bake.  They all eat about anything except for a few things here and there because they just don’t enjoy them.  They eat healthy and certainly enjoy a good meal.  Food is an integral part of our family life.  So in regards to the question what should kids eat I believe that they should eat everything and taste everything as soon as they can.  Don’t treat them as kids but as another mouth at the table.  Otherwise you could end up with picky eaters for life.

the investment life.

VC-Stock-ImageI don’t know if I have come in to my own as an investor or somethings just piss me off but it could easily be a combination of the two.

I am always learning in this business.  I have certainly learned that nothing is standard when it comes to investing. A few things happened recently that I truly learned on.
I have a thesis which is that I want to own 1% of the company from the very beginning which based on that amount I like to put in I pretty much have to put money into the very first round.  Not an idea but a real live product that I get excited about and an entrepreneur I believe can grow the beginnings of something into something larger.  That means hiring a team, raising money, thinking out of the weeds, making tough decisions and being completely out of their mind focused on success.
I always get a side letter that insures that I can continue to invest to keep my pro-rata share at every capital infusion until I choose to opt out.  At one point I have too much exposure (probably around the Series B) and then I choose to pass.  Then I look at the amount I have in the company not as a percentage but as a dollar amount that will hopefully have a multiple exit.  It is purely a head switch.
So here is how I screwed up.  I forgot to get a side letter with a company I invested in.  At the beginning I wasn’t on top of this but I finally figured it out.  I think that I was in between figuring out the side letter thing and this company might have been the last one without it.  Alas because one of the things I have noticed is in SF they like to raise notes over notes over notes.  What that means is when they finally do get their Series A and the note converts into stock what you believe you own is not what you own.  Needless to say I was pissed, I had a pissy fit and then I blamed myself.  Lesson learned.
Move forward on to other things that piss me off.  There are a few investors out there, not angels but funds that I refer to as micro-funds that love to get some sweet deal that is better than everyone else in the round because they can write a larger check.  It is that or they demand some kind of advisor shares on top of their investment.  Everyones money is the same in each round as far as I am concerned.  Some investors are more active others and some are completely passive but that money helps the entrepreneurs get to the next stage of their business.  The good news is that in my side letter I negate getting screwed by the micro-VC who comes in with their better terms than everyone else in the seed round.
So returning to reality after being off the grid for a full on month has been quite a whirlwind.  Perhaps while I was gone I found my voice but maybe it is just the last 9 years of investing and seeing some really not great stuff out there that I just do not like and I just help not holding back my anger.

Being Authentic

imagesA group of amazing people who I have had the pleasure of meeting through the investing world came up with this great idea of doing founders breakfasts.  As small as the start-up tech community is many of the founders do not know each other.  The concept behind this breakfast is to get a group of founders we each know (rarely is there any cross-over) get together and discuss what is top of mind in regards to the trials and tribulations of growing a company.

The breakfast this past week one of the men brought up something that I have never heard uttered out of a mans mouth.  He said he is hiring people that are better engineers than him, better at many more things than him and his fear is that he will be discovered out that he essentially knows nothing.  It was amazing.
Women, for whatever reason, tend to have this inner voice saying to think there are days when they feel like someone will realize that they are totally faking it.  They know nothing.  It was seriously refreshing to hear a guy come out and say that.
Then the conversation turned into creating a culture in your company.  It was really interesting to listen to each entrepreneurs transparency, leadership and expectations with their team.  It was really interesting to hear what works for one might not necessarily work for the other.
What I believe this all comes down to is the importance of being authentic. Everyone does it differently.  There is no right or wrong way of how you build the culture in your company.  Company culture is essentially an extension of the entrepreneur who started the company.  I think the key is being authentic.  Be true to who you are because it will come across to your team.  When you are not authentic that comes across too.  Be yourself because it is a helluva lot easier than pretending to be something that you aren’t.  Also…on a side note, I have thought for years I be would found out that I have been totally faking it.

Generational differences

imgres-1When Elvis came around and kids went gaga their parents freaked.  When the Beatles came to town and kids went bananas their parents freaked.  The generational differences between the youth and the older adults seems so vast and almost comical looking back at it.  It appears that this generation of parents and adults are much more connected to the youth.  There is a blurred line of parenting vs a friendship which is a whole other blog post.  Yet as technology has encroached on our life through social media the lines appear to be more divided than you think.

Perhaps some people move forward and others don’t.  I do not know if it is about curiosity or it is just innate.  My Grandmother was still reading Vogue at 85 and paying attention to the latest fashions and buying them.  I have always been interested in the latest and greatest from fashion to food to home design to music to technology to trends.  Personally I think it keeps you young.

Yet there are many people I know who are still listening to the same music they listened to in college, that are wearing the same clothes, have pretty much the same haircut, etc.  There are others who are all over the latest stuff and because of that they can connect with the youth.  They are using social media, they understand the impact it has on their businesses and the world around them, they are paying attention to the culture and the shifts.

It is almost the start-up vs corporate America.  The big corporations, at least some of them, seem to have a disconnect but at some level realize that they do and are not sure how to move forward.  Someone told me a story about going to do a freelance job for a huge corporation around marketing and branding as they move forward into 2015.  They actually asked if they could help them get into the hip stuff.  It made me laugh because I know exactly what they mean.  They understand that there is a movement but they aren’t quite sure how to get on that band wagon.

It is almost a digital divide that is purely generational from the users and the non-users.  My guess is that back in the day some parents thought Elvis and the Beatles were awesome.  At least I hope so.

Women conversations

imgresMy friend and I were talking about women events and listservs and the conversations that take place on them this weekend.  Having just launched the Women’s Entrepreneur Festival applications for 2015 it was relevant to my personal reflections on the event each year.

I have been watching the conversations on the recently launched and have always been fascinated with the conversations that take place at the festival and listserv’s that I am on.  The topics are vast depending on the listserv.  I was expecting a lot more conversation around business and what I found is that those talks certainly take place but most of them are relegated to female fodder.  What I mean by that is anything from does anyone have a favorite cookware line to what is the right attire for a conference to best shopping sites to where to get a blow out in Chicago to how do I ask for a raise.

We are all looking for a connection to other women that we can talk about anything from where did you get those fantastic shoes to how do you get food in the fridge for your kids when you are in the middle of launching your start-up to damn I had a shitty day.  Finding those women who in the same space you are in your life is important or having women mentors who have been through it before.

I see it at the Festival because the ages span from 18-60+.  When you get a room of women together the conversations go everywhere and sometimes they are really taking a deep dive at your business and other times they are about the best place you just recently dined.

I guess I wonder if there were any listservs out there for men what kind of conversations would take place.  It probably would not be all business either but their fodder might be more relegated to sports, music or a good meal.  I am purely guessing here and perhaps being judgmental but I see those convos take place among the men I know.  They are generally not asking about where they got those amazing shoes.

Thinking of all of this at a birds eye view this is exactly why it is so important for companies to have an even balance of men and women in each area of the workplace because men and women both think differently, have different daily interests and are brains are just wired in a totally different way.  I just find it interesting.