Flair Woman: Angel Investor Joanne Wilson

If you are a female entrepreneur looking for an angel investor Joanne Wilson should top your list. Chances are you probably know, have used, or purchased products from some of the companies she’s invested in such as Food52, Swoonery, Spring, Blue Bottle coffee, Willa and Phin & Phebes ice cream among others. (In her spare time, Joanne also has a blog, Gotham Gal, and is the co-founder of the Women’s Entrepreneur Festival.) Joanne is truly badass—a straightforward, funny, intense woman who any other businesswoman would be lucky to have in her corner. What makes a good entrepreneur and how are female entrepreneurs different than their male counterparts? Joanne shares her insights with TFI. 

Give TFI a brief trajectory of your career and how you got into investing in female entrepreneurs: I started out in the retail wholesale world, I was a buyer then moved to wholesale, ran a compay, built a company, had two kids, left the industry, moved to the suburbs, thought I was going to lose my mind, had a third kid and went back to work. My husband was just starting his fund and investing in this new thing we called the Internet. [Joanne’s husband, Fred Wilson of Union Square Ventures, invested in Twitter, Tumbr, Etsy and more.] He introduced me to Jason Calacanis and I went to work with him and helped him build his business. I was watching the next generation of the web start to percolate and I said to my husband ‘there are some companies that I think are really interesting and it’s unfortunate you won’t invest in them, because I really believe that there’s an opportunity here for you’ and he said, ‘well, you should invest in them.’ And that’s how I began. As I started investing all these women kept coming to me and talking to me. I realized that they weren’t getting money. They were connecting to me, and I thought I should make a concerted effort to just invest in women. That’s kind of where it all began.

What have you learned about investing in female entrepreneurs along the way?  I didn’t think genders were different when I was younger. I was told I could do anything I wanted to do. And then I had boys and girls and I thought wow, very different. And certainly with my children I see their differences and investing in women I see the differences. Women take longer to build their companies.

Why do you think that is? I think they’re scrappy. They are very methodical. Teams are important to them. They want to make sure they’ve built a very solid platform before they move forward. And they want to make sure they hit at every cylinder until the business starts really starts taking off and then they go out and raise big capital and hit the gas. And that is typically later on in life.

What do women female entrepreneurs do differently than men? I think women in general tend to build businesses that fill voids in their lives. I’m not saying that men don’t, but I think that men tool around with random back-end technology. And in general, that’s not what women tend to want to do. The reality is, if we want more women in STEM, we need to allow them to build products that interest them and have social responsibilities and are part of communities, because that’s how women operate. They don’t have to go and build the next robot browser, they can build something that means something to them. If we nurture that, I think we will see a big difference.

What do you look for in a company when investing? I’m so early the reality of what I’m really looking for is people. Of course I want to see businesses that I think are interesting, that are filling voids in markets, that don’t have a lot of competition in them. But on the other hand, I also am investing at such an early stage. Of the 90 plus businesses I’ve invested in, I gave 50% of them their first dollar, so you’re talking about a very different investment strategy.

What are key factors for being a good entrepreneur? What do you look for in the people whose companies you invest in? I look for people who listen, who are tenacious, who are drinking their Kool Aid heavily, who are scrappy and who are flexible.

What is the most important advice you try to give new entrepreneurs? Hmmm….Call me if you get in trouble. (Laughing) I always tell them I want to hear the good and I want to hear the bad—I’m here to help you.

Are you deeply involved with a lot of them? I am. Almost all of them. I try to help as much as I can. [As an entrepreneur] you have to listen to your audience and you have to be willing to make the hard decisions and to make the easy decisions as well. And if you don’t know you should feel free to reach out for advice. Don’t tell your investors everything is hunky dory when everything sucks; it’s not going to get you anywhere. I think women are pretty good at that.

What has been your biggest success? I still have a lot of companies out there and I think that’s certainly success. That they are all out there, that many of them are moving forward, all of these things are really important. I’ve had a few companies sell, but the reality is my first biggest hit was the first thing I invested in. And that shows you how long it takes, because it was over 10 years ago, but the company has been a phenomenal success.

What has been your biggest dud or failure and what did you take away from it? I had a major fucking dud. I think one of the things you learn the longer you do this, and I use Malcolm Gladwell’s Theory of Success—is the more times you do something the more you become a maven and get really good at it. I have two stories. One this company–I loved this company. I loved the concept, it was so community oriented, and I thought of a million things it could be doing. And the reality is, the guy was a shitty entrepreneur. He blew through four million in less than nine months and called me and couldn’t make payroll. And you know what, I saw the red flags from day one but I ignored them. I think a lot of people just don’t think about those things when they invest, because the people who invested in this were one name-brand angel investor after the next. So that was a learning experience–don’t be so impressed by names. Number two is when you see red flags open your eyes bigger. Trust your gut. I’m the kind of person who feels like they can save everything, that I can influence my super powers somehow and make it all work. It doesn’t happen. I think those experiences have made me a much better investor.

One of your attributes that helps you succeed: I’ve been involved with businesses since the day I came out of the womb. I have been entrepreneurial, business-oriented, a little bit of bull in the china shop, or a lot of bull in the china shop. Always incredibly optimistic, and I have no problem with controversy and being honest with people. I think all of those things.

What motivates you? I’ve always been motivated by making money. But my husband said this the other day and I think he’s right: I’m at a point in my life, and even as I’ve done all this investing, and there’s no doubt I want to win–I want to make 10 times on all this capital I put out there. I want to be financially successful, BUT what I really care about, first and foremost, are the founders. I care more about them than the business, I care more about them seeing their businesses grow, realizing their dreams, building what they want to build. I think with that attitude, in the long run, you end up having the first thing you want, financial success.

Many women I know don’t have comfortable, or even good, relationships with money. Many female business owners don’t know how to ask for it, where to go, and often feel like they get ignored by the typically male VC world. Why do you think this is and how can it be changed? There are plenty of places to get cash. Men might a little more aggressive, women might be dotting their I’s and crossing their T’s to weigh ‘would that be the right investor for me’. So in a way they’re not plowing forward and throwing darts in a million directions. But the really good female entrepreneurs throw as many darts out there as men. I think the ones out there who aren’t getting funded probably have shitty businesses. Because a good business will always get funded. I do hear some women say, ‘I’ve pitched this to 25 people and blah blah blah’. If you pitched to that many people and no one is interested that says something about you or the company. It’s easy to blame on everyone else.

How hard would you say you work? How do you keep focused?  Ridiculously hard. Too hard. I’ve always been focused. I’ve always been a hard worker, very competitive and very much an over-achiever. It’s in my DNA. I’m trying not to work as hard. But my not working as hard is probably most people’s working too hard.

Three words that describe your work: Disruptive, supportive, futuristic

Three words that describe you: Bold, tenacious, good gut

Role models: Certainly my generation, no one thought about that stuff. I’ve seen people over years that I thought ‘god, I never want to be like that’ or ‘wow, I’d would love to be where she’s at’. But in general, the road that I followed, there was no blueprint. I made it up as I went along. So my role models in regards to how I invest and deal with people, I’d probably put my husband on top of that list.

Life goals: Being happy, healthy and having the opportunity to enjoy my children as they go on their roadmap of life. That to me is more important than anything else. Family first. 100%.

Daily goals: Try not to each too much!

Favorite inspirational/motivational read: I don’t read motivational books. Never been a fan. I mostly like to read new novels. Always reading the next, and I don’t go back and read again. I really loved Homegoing by Yaa Gyasi, a debut novel that follows a family from Ghana in the 1800s and you watch the culture clash and bigotry. Loved all the Karl Ove My Struggles. The Fire This Time: A New Generation Speaks Out About Race by Jesmyn Ward; Here I Am by Jonathan Safron Foer…I don’t watch TV I read.

Favorite sites/people you follow: I look at real estate and architecture sites and the cool-huntings sites of the world, and I read everything from Elle to New York magazine to the New Yorker. I’ve always been one of those people who reads a lot in terms of broad pop culture, probably a lot of stuff that’s nonsense for your head so you can go to a cocktail party and speak coherently.

Daily rituals: I read the New York Times cover to cover every single day except for the sports section and do the crossword.

How do you unplug: I used to do a lot of cooking and baking, but not so much anymore because I have an empty nest. But I found it incredibly soothing. On the weekend you can find me curled up on the sofa with the Saturday and Sunday crossword–that is an un-plugger. And I take vacations.

Hidden talent/hobby: I can sew, I can knit, I can crochet; I’m a skier and a boarder. I don’t think anything’s hidden there.

Do you collect anything. I’m a big art collector but mostly emerging artists. Now some who are little more emerged than emerging.

Biggest splurge you don’t regret: I think once you make that one splurge it’s easy to make others. I used to be super cheap. Now, when I see something I love I buy it. I really love fashion, but I buy fewer nicer things. Pieces of art, those are big splurges.

Coffee/Tea: Coffee. Black.

Morning/Night: Day, when I’m up I’m UP and then I’m down.

Truth/Dare: Truth

Heels/Flats: Flats

Pastel/Primary: Primaries

Manet/Mondrian: Mondrian

Cats/Dogs: Dogs, I’ve had a dog since I was born. I have a mini Golden Doodle who’s not that mini.

Follow Joanne: Twitter, @gothamgal