The Independent Consigliere To Founders


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Joanne Wilson Started With Founders, But Now She’s Funding Movements Too

Joanne Wilson, better known to her fans as “Gotham Gal” for her enduring blog of the same name, has been a fixture of New York investing for nearly a decade. She’s an independent voice unafraid of controversial points of view, and coupled with her husband and Union Square Ventures founder Fred Wilson, comprises one of the most powerful couples in venture finance.

But Joanne Wilson runs her own shop, focusing on very early stage seed financing, with more than 100 investments so far, more than half of which are run by female founders. Recently dismayed by the shift in our national politics, the Wilsons have spearheaded a new approach to philanthropy as well, working to fund organizations fighting what they consider to be misguided policy from inside Washington. This coming week (May 3), Wilson and her colleagues will roll out one such effort, focused on supporting Planned Parenthood, which was recently targeted by President Trump. Below are both the video and text transcript of our recent conversation in New York, edited for clarity and length.

John Battelle: You’ve developed a reputation as a unique kind of investor, both in the ecosystem here in New York and around the world. What do you think that difference is?

Joanne Wilson: Probably because I don’t have any LPs (limited partners). I don’t have anyone to report to.

…you get Joanne.

Yeah. You get what you get. I think it’s a combination of things, though. The thing that I care most about is having a success. Everyone does when they put money in something. They’re not expecting to go down a big black hole and just think — that was a great experience. I do care more about the founder and helping them create the success they saw with the company they wanted to build.

Also, because I am an angel, yet I operate like a venture capitalist in some respect, it’s a full‑time job, and I know the ecosphere of technology, and investors in CPG or in the fast‑food casual world, so there’s this huge network of people are supporting these companies.

I’m never the million-dollar check, and because of that, I think I’ve become the consigliere to every single founder.

How did you get started doing this? Was it before or after you started your blog, which really is how I came to know you?

It’s after my blog. The blog really started because I had been involved in the first generation of the Web, and we all watched it (get) overvalued, implode, a million different mistakes and not enough successes.

I was watching the next generation (of founders). I’d stepped back for a while, and I was like, “OK, well, how do I stay connected to this world that I just left, but not go back and work in it yet, because there’s nothing to work in?”

I had three kids at home, and I really did not want to start my own company or work in a startup. I was trying to figure out, “What does that look like?” for myself, and then blogging started. I was like, “Oh, well, this is a great medium. No one owns it but me. Who knows what will happen? I’ll continue that connection to people.”

The reality is, most people left the industry after that first generation, never returned. It was the next generation that started reading my blogs, so really, it was all new people.

Did some of your early investments come from people who you wrote about and/or connected with through your site?

Some totally did. It was really the next generation of the Web that I was watching percolate, watching new companies enter the market, and I was fascinated with them, because what I loved about this generation of the Web is that the founders grew up with technology.

The first generation of founders did not grow up with technology. They just knew there was something really amazing there they had to get into. These (new) people understood how to create something that would become part of their daily lives, and I thought it was a much more creative group of people.

Yet, you’ve told me that recently you feel like a lot of the companies that were founded in the Web 2 era are now becoming more mature, and they’re getting better at prosecuting all of these opportunities. You say that maybe some of the companies you’re seeing now feel like they’re not differentiated.

No, they’re really not. I think that a lot of the investments — in ’08, ’09, ’10, ’11 — who have had deep pockets, they’re really building. It takes a long time to build a company. Certainly we read about the ones that, boom.

Yeah, everyone wants to be Instagram.

Right, but the really successful companies, someone thought about it for a long time. It takes time to grow these companies, a lot of the mature companies, and I think that a lot of the next generation of deals and decks that I’m seeing are that long tail of “everyone wants to be an entrepreneur.” It’s easy to access. There’s open source. It doesn’t cost that much. I’m not so sure they’re doing their homework. They just feel like, “Oh, another mousetrap, better mousetrap,” and it’s just not that interesting.

You said you were also a little tired of the young founder syndrome.

I come in so early. I’d say 60 percent, if not more, of the investments I’ve made, I gave the first dollar to the founder, so we’re talking early. Because of that, it takes a long time, and I do get really involved. I am available, and I will answer any email. There’s times when I talk to someone every single day. When they have, really, no chops or experience, you’re like, “OK, I hope they didn’t stop in that pothole and just pissed away $200,000.” You’re really involved, and after a while, it’s exhausting so…

You’re finding yourself backing more mature founders?

Yeah. Which is nice on so many levels, because they operate with you in a very different way. They know your value, and you know they know how to find the bathroom.

Of course, the myth of the young college drop‑out founder is so strong, particularly in the Valley.

That’s one in a million. Come on.

You live in New York. You call yourself Gotham Gal, which is…

A New Yorker.

What do you make of the Valley and the whole ethos of the Valley?

I think there’s a lot of positive things about the Valley. It’s like one big MBA program. I think what’s great about it is that a lot of the investors do have the mentality, which is, “You know, let’s give it a whirl. Let’s see how this thing works. If it sticks, it sticks. If it doesn’t, it doesn’t.”

I don’t think New Yorkers, in general, think like that. I think they’re much more cynical, and they’re much more reluctant to just throw money at something. That’s a good thing and a bad thing. I think one of the bad things is valuations are out of control. We’re talking about companies that have shit, and are valued at $12, $15 million, (when) $3 million is the right number. I think that’s a problem.

The other thing that I think it’s created, for good or bad, is that — and I do think this is changing in the next decade — you have these really, really smart people getting out of Stanford, or schools in the area, or came out of a startup and are starting their own startup. They’re still super young, and they have these ideas. They’re not necessarily fleshed out, but they want to be an entrepreneur. That’s fine, but I think what we’re seeing now, not only in entrepreneurs, but also in investors, is that the concept of being a generalist for the last 10 years worked.

I think now, you’ve actually got to spend some serious time in verticals. I have heard of investors chasing something in the ag(riculture) space, when they’ve never touched ag, but they are known investors, and they get in there, and they charm the founders who’s 30 years old and has spent their entire career in ag, and is like, “Oh, this is great.” It’s like (the investors) know nothing about agriculture. They just see the opportunity.

More and more, I talk to people in certain deals, like when I talk to someone in the farming industry, my first question is, “Tell me about your past history.” If they’re like “Well, we’ve spent 10 years in the farming industry,” I’m like, “OK, good. That’s a great answer.”

What do you focus on when you invest?

I think at the end of the day, the one thing I’ve learned over the past decade plus is I really invest in people. You’re talking about first dollar. Those companies don’t always remain what the original concept was, they evolve into something bigger.

I’d say I look for survivors, people that I think are going to survive, no matter what comes their way. They’re open to conversation. They obviously have a good business, too. I tend to invest in things that no one is really doing in a space that makes sense to me.

That’s hard to find, isn’t it?

I get a lot of stuff that comes in to me, and it is hard to find, but I just feel like I still like to look at things that are brand new in a space.

Do you have companies in your portfolio that are emblematic of your investment philosophy, either they’ve had exits, or they’re on their way, or they’re new investments you’re excited about?

Yeah. Curbed Media, my first one. No one was really creating that as a media platform, and no one ever really has done the same thing that they’ve done. Union Station, which is a completely vertical operation of renting bridesmaid’s dresses. No one has done that completely vertical. I’m invested in Clue, even though everyone was doing it. She was the only female creating a period tracker app. To me, I felt like a female should be running that company.

You’re a very strong advocate for female founders.

I’m a huge advocate for female founders, and females, in general. I think there’s a lot more out there than anybody realizes.

The data’s not good, right?

Yes, but there’s still plenty of female founders out there, and also, dollars are fungible. Where’s that money coming from? Is that money from the top VCs in this country? Does that include the family offices? Does that include P&E? There’s a lot of, “Where is it all going?”

I’ve invested in 60‑65 female founders, and what I find is that women network differently. They’re not out there on Twitter. They’re not out there using their social media platforms. They should, but they don’t.

They put their heads down, get their job done, and grow their companies. They’re more methodical. They really like teams. They cross their t’s, they dot their i’s, good or bad, and they will take longer, if it takes longer, to get those milestones before they hit on the gas.

Do you think that the traditional venture investing culture gets in the way of female founders?

I think they can get in the way of any founder. It comes back to what I was saying before, that there are these opportunities that are really interesting. But if you don’t understand it, and you’re expecting these companies to grow at a clip in order to return what your LPs expect in seven to eight years, then sometimes you’re pushing these companies, not upward, but upward to a big crash.

We’re seeing a lot of that right now.

We’re seeing a lot of that, and it’s unfortunate, because I think a lot of these companies could have been successful. They might not have been billion dollar companies, but they could have been really successful companies that employed people and created an economy.

You actually started an event, The Women’s Entrepreneurial Festival. How long ago did you start that?

Eight years. It was before its time.

You were ahead of your time, and then you put it on hiatus. Because it’s a lot of work to do events?

It’s one of those things. We did it with NYU. My co‑founder is a professor at NYU at the ITP Department. ITP tends to be 50/50 gender, which is phenomenal, and that particular year (that we started), she had two classes that were more males than they were females. The dynamic in the classroom completely changed, and she was extremely frustrated by it. She’s like, “There’s not enough women in technology.”

I was like, “There’s plenty of women in technology. I talk to these women all day long.” She was like, “Well, I want to do an event to amplify them.” At that point in my life, “Yeah, I’ll do it with you.”

We started this event, and we knew from day one we had stumbled onto something. We continued it at NYU for five years. The impact was even bigger than I even know. I’ve bumped into people that still have meet‑ups from the first one, with a group of women.

They met their partner, and they built a business, or they still have friends, or it’s their number one client. It’s pretty amazing, and the women that come are female entrepreneurs. The people on the panels, you might now know of, but they have had series As or series Bs, and because of that, the people in the audience can look at those people and go, “OK, I can do it, because she did it.”

I would hope that those people on the panel, when they do sell and become public, they amplify themselves every day in the public eye so that more people say, “Oh my God, look at all these successful women and what they have done.” You can’t be it if you can’t see it, and it’s important for our young boys and girls to see that.

After five years, I was like, “I’m done.” I think five years is good. I was going to close it down, and actually it was my husband and my sister who were like, “You can’t close this thing down. You made this huge impact,” and my sister said, “Well, I’ll run it with you. I’ll be your producer,” and she’s perfect for that. She’s insane, like detail‑oriented, takes a deep dive, very process‑oriented. I said, “Great.”

We took it out. We did it at One World Trade Center. I sold all the sponsorships, did all the panels, figured out the whole thing. She executed on it brilliantly. It was an amazing event. It was profitable. It was awesome.

I couldn’t help myself. I was like, “Oh my God, world domination. Let’s do this in LA. Let’s do it in Berlin. We’re going to do all these great things,” and… The timing wasn’t right, because the election was crazy. People were cutting back on budgets. … I was like, “I can’t do this.”

Plus, how many companies have you invested in now?

Like a hundred.

So your phone rings a lot.

Yeah. I was like, “You know what? Let’s put this on hold, and we’ll see where it goes.”

You and your husband, Fred, have been extremely involved in politics, for as long as I’ve known you, and certainly before, and philanthropy. I want to talk about both those things, because they’re related. What you guys did with Brad Feld and Amy Batchelor for the ACLU — how did that come about?

I think Brad actually emailed, and they were thinking of doing this, and we’re like, “We would do it with you guys.” I think that we were all blind‑sided by the government that we have in place at this point.

We realized, “OK, what can we do from a grass roots level that can impact the organizations that are going to ensure that democracy remains?” They were fighting it from the outside, because just like start‑ups, you can’t change anything inside. Everything has to be changed from outside, and we believe in that philosophically with anything.

We decided every month over the next year we will create a day where we will put out there something. First, it was the ACLU — that we will match. I think we each put in $10,000, and we will match, so we would raise $40,000. That thing took off, because people then said, “Hand me the baton, and I’ll do it.”

It became almost a relay race. People were like, “OK, now, we’re going to put down a matching grant,” and then the community would donate, and then the matches would happen, and then it would fill. It was like, “OK, who’d going to do it next?”

Boom. Yeah, it was amazing. I think in total, we raised like $150K. It was amazing how many people from Canada emailed me and donated.

Yeah, they don’t want a neighbor that’s blowing up.

Exactly. Again, three months ago, when we started this…we did the ACLU first. We did an organization that legally supports immigrants, and then last month, we did Earth Justice. I think the hardest part of what we’re doing is that we’re trying to choose organizations that are appropriate for the craziness that’s happening today, but it is like Whack‑a‑Mole.

There’s plenty of craziness.

Plenty of it. Last Thursday we decided, “OK, he just signed this terrible thing again, rolling back all the things that have to do with our climate and everything connected to that.” We’re like, “We’re ready to go.” It was Saturday morning, and then on Friday, it was like, “Oh my God, they’ve taken all the money away from Planned Parenthood.”

So maybe next month it’ll be Planned Parenthood.

Next month it’ll be Planned Parenthood. They’re having a huge gala on May 3rd, and so we’re going to do something in conjunction with that.

That, obviously, directly relates to politics. You guys have been pretty involved politically. I think the question that a lot of people have, given what seems to be objective insanity in Washington right now, is what can we do? There’s a certain frustration and despair. It’s like, “I’m one person. I’m happy to give money to the ACLU, Earth Justice, or Planned Parenthood, but what can I do?”

There’s many new organizations out there, like I think it’s Indivisible, where you can go to a town hall and do that thing.

It’s interesting you say, “I’m only one person.” I watched an amazing documentary a couple of weeks ago with Vik Muniz, who went into this huge garbage dump, which is the largest one in the world, outside of Sao Paulo. He interviews all these pickers. There was this one guy that really stuck with me. He said, “One makes the difference. 99 is not 100.” I thought, “Wow, that says it all.”

One of the things that I do believe in this country is everyone believes in the Constitution. You might interpret it differently, but that is the core of our government, and the core of our nation. That Constitution’s written for and by the people, and so I think what we can do is “power to the people.”

We need to be out there supporting organizations that are going to make a difference. We need to be going to town halls. We need to be writing our senators and governors, and if you have an interest in politics, run. By the way, the one thing you can do is frickin’ vote. [laughs] If everyone voted, then we wouldn’t be where we are now…and we would know what the majority of the people wanted.

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