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Be Bold: A Conversation with Joanne Solomon Wilson

Last week, I had a conversation with Joanne Solomon Wilson, one-half of the New York City power couple who has been a pioneer in the angel investment and venture capital sectors, in which her husband, Fred Wilson, is one of the co-founders of Union Square Ventures.

Joanne is one of those women who one might find slightly intimidating at first, but she was gracious enough to let me pick her brain and ask her for all sorts of questions from the most personal to common problems within the angel investment community. I got to know Joanne through her blog, Gotham Gal, an insanely popular blog that dissects all aspects of life from business, to feminism to cuisine and art. There are very few blogs in which women entrepreneurs, founders and investors are willing to be candid and open about their lives, and I find Joanne's viewpoint a refreshing one from those that are written by publicists only portraying a censored point of view, if at all. To know Joanne is to admire her, as she has the kind of career and life that most women probably aspire towards.

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Joanne Solomon Wilson

I was curious about what Joanne was like as a teenager, as I recall my teen years primarily filled with ennui and apprehension. However, it doesn't seem as if Joanne has changed much from those early years, as she was a forward thinking, insanely driven, competitive senior in high school, who had single-handedly ran the Montgomery County school office, re-organised their entire office and even coached teams back then as well. I asked if she ever thought about becoming a Professor or a lecturer at a university? as I could see that her no-nonsense approach to life would probably inspire the next league of female entrepreneurs. Currently Joanne is an advisor to many startups, in addition to having a portfolio of 50+ startups in which she has made many investments in sectors such as advertising, media, mobile apps, travel, shipping and even ice cream. 

"I just have so many responsibilities right now, that I don't know if I have the time to teach. However, I would love to teach." Joanne was also the closing keynote speaker at my alma mater, Columbia University for their startup festival last year. 

One thing Joanne and I have in common is that we both have the same personality type, at least, according to the MBTI: we are intuitive thinker judgers. Since there are so few women with this type, it's fairly easy to seek them out because their actions and perhaps life history may closely align with your own. I have noticed that a lot of women in the Producers Guild of America, in which I am on the International Committee, also share this type of personality. It could be that personality types are attracted to certain sectors, and ours mainly flourish in the male-dominated ones. Of course, this isn't to say that personality type is an end-all-be-all, but it's an interesting theory that gives insight into understanding a person's interaction with others. Joanne and I discussed some of the top challenges a woman faces in the corporate and start-up world and she had this to say:

"There are so few women in the first place, that's the initial problem. Women, like men, need to find peers to connect with, develop camaraderie. I've tried to address this issue by launching the Women's Entrepreneur Festival.  It is a place where women can connect and be heard.  Although many of us may share similar qualities, generally, women network differently than men do. We have priorities, go home to see friends, need time for ourselves and tend to separate our social and personal lives from our professional lives. Men typically have less delineation of their lives and are happy to go to any event vs the few that are worthwhile." - Joanne Solomon Wilson   

Currently, Joanne and her husband are spending the winter in Los Angeles, which was also Joanne's hometown before her family moved to the East Coast. We discussed some of our favourite restaurants, Abbott Kinney Street and the various developments that are going on there and the inevitable gentrification. Joanne, too, prefers the West side of LA, near the beaches.

"It's a shame, there were many great independent brick-and-mortar retailers on Abbot Kinney that are now filled with chains."

I agreed. The rent for these independent shoppes are so high, in addition to other expenses and CA taxes that it makes it nearly impossible for small retailers to survive in California. Similarly, if one wants to open a retail shoppe, the best place to do it is in Texas, where there are no corporate taxes and low overhead. Whole Foods was initially launched and tested in Texas; anything that works in Texas will be a testament of success to the rest of the U.S. 

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One of the founding partners of Gjelina's, Robert Schwan, gave me a tour of the restaurant when it first opened on Abbot Kinney Street in Venice, California. The interior took approximately two years to design and all materials were from recycled or repurposed natural materials, with specific pieces in the Ladies' lavatories ordered from Italy.

I asked Joanne what some of the common mistakes she has noticed within her own set of entrepreneurs (male or female) whom she had invested in? 

"I've noticed there are initially some red flags, mainly to do with execution. That is why I invest in people, not ideas. There was one entrepreneur whom I wasn't sure was capable of executing what I thought was a great idea, and yes, it didn't work out in the end, but it's important for me to invest in an entrepreneur who can surround herself or himself with great people, stick with their thesis and be a scrappy, tenacious decision maker, and not be prone to analyse something to death; to be a big picture thinker, and be able to build a team to get things done." 

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We also spoke about the past and some things we could've done differently or any regrets Joanne has had:

"I believe everything happens in the natural sequence it was supposed to. Everything is a learning experience that brings closer insight to where you are right now...but, sometimes I do think about having the opportunity to go to grad school. Fred did his MBA and at the time I thought about what if I had done mine as well...but I didn't and that is fine. I made the best decisions at the time that I felt were right for me."
-Joanne Solomon Wilson

Women and the work-life balance is one of the hot topics within corporate and entrepreneur circles, and I imagined that having two people in a happy marriage who both had demanding, high profile careers is something of unicorn or even a fairytale these days that most women could only wish for and asked Joanne what she thought were some of the most important qualities in making that kind of ideal relationship work?

"Respect is number one, the single most important thing to have for each other. Without respect, a relationship is doomed. It is also understanding that we are better as a team than being apart, and we're able to fill in each other's shoes, should something happen. At one point, I had made 3x the money that Fred was making. It's also important to have a similar life perspective and to enjoy doing things together. Fred and I love to travel together, explore new cities and restaurants together and we raised our kids with the same morals and values; these things lead to less strife." - Joanne Solomon Wilson 
Joanne also added, "If you're a vegan, you have to marry a vegan. You can't marry someone who loves meat and BBQ all the time; those things may initially work out, but not in the long run...You have to be with someone who holds the same values as you do." 
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Joanne Solomon Wilson and Fred Wilson. Shared values are one of the many things that keeps them together.

We also discussed some of the valuations of companies, such as Uber. I asked Joanne if she thought there were a tech bubble?

"Absolutely not. There is no tech bubble. There are always companies that are overvalued and undervalued, but back in 2008, we also had the implosion of the banking industries, and now you can't build a company without technology. I am not an investor in Uber, but it will certainly be interesting to see where Uber is 10 years from now." - Joanne Solomon Wilson

There was also a seed round recap blog post that Joanne had made which I found very impressive as well as alarming. If founders made it a habit to recap seed rounds then that sets a bad precedent for investors and creates a negative atmosphere for angel investment. I asked Joanne what was the outcome of that incident?

"I think it's important that as a Founder to be transparent and honest and if you're evasive, it gets you nowhere. However, I can understand in that situation that particular Founder I had invested in felt it was necessary to go out and get as much money as possible, especially for an early stage company. I still want to see that Founder succeed even if I got screwed.  We even had a chat for 10 minutes the other day when I was asked for advice, however, I do not condone that kind of behaviour, as it's not something I think Founders should do because it creates less trust within the angel investment community." 

I asked Joanne about the future of eCommerce, what her thoughts were on brick-and-mortar shoppes?

"I don't think brick-and-mortar will go away. It's in a state of transition. For brick-and-mortar shoppes to stay relevant in the eCommerce era, there has to be an experience you want to go into, have excellent customer service, the ability to take classes. People want to be part of a community, breathe fresh air, do stuff with their kids. It can't just be  about selling and buying, there has to be an experience that you can't have while clicking buy on online shoppes." 

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Shoppes must be more than a click-and-buy experience, according to Joanne Solomon Wilson

On a final note, I asked her what advice she would give to budding entrepreneurs?

She said with authority: "Be Bold. Being afraid of failure gets you nowhere. Failure is part of learning and experience." 

Joanne Solomon Wilson is an angel investor, wife, mother of 3 children, speaker at many events, founder of Women's Entrepreneur Festival and sits on the Board of Directors for more than a handful companies including the High Line. She also makes legendary chocolate chip cookies.