The Hillary Clinton of Investing - OZY | A Modern Media Company

The Hillary Clinton of Investing

The Hillary Clinton of Investing

By Farah Halime


Because an investor with an agenda can be an interesting type to watch.

By Farah Halime

She was once known as the wife of a very powerful man. Now she’s a heavyweight in her own right, making a big play on her own. Sound familiar? It’s the story of more than a few women, but this time we’re talking about one you probably haven’t heard of: Joanne Wilson, the investor every startup wants behind them.

At 53, Wilson, wife of successful investor Fred Wilson, is the queen of a financial empire mostly hedged on women. She’s grown her portfolio from just a handful of companies to 75 and counting, including San Francisco’s Blue Bottle Coffee; Nestio, a real estate company that helps people find housing easily; and TaxiTreats, a startup that sells vending machines to taxi cabs. Only three of her startups have failed. She calls herself “a champion for women,” and that’s the ethos of her angel investing venture Gotham Gal, as well as all her other projects — the Women Entrepreneur Festival, an incubator for wannabe women investors which hosts people like Diane von Fürstenberg, and even her blog, also called Gotham Gal, in which she writes about everything from investing to restaurants.

Vanessa Pestritto, program director at New York Angels, which invested $6 million in early-stage companies last year, says she never stops hearing about Wilson from entrepreneurs looking to raise money. “Either they want to talk to her or be introduced to her,” Pestritto said. 

When we reach her, Wilson has just returned from wintering in Los Angeles, where things are a little “more chill” compared to Manhattan, she says. Except “chill” for Wilson means eyeing another handful of companies for a possible investment while spending time with her three kids and the rest of her “children” (that hefty portfolio). Though she absolutely looks the part now — professional, close-cropped hair, winning smile and a sharp (in a good way) demeanor — her power-woman status sprung from humble beginnings. She worked her way up from a sales assistant at Macy’s to managing a staff of a few hundred at the store by the time she was 22. Her boss told her she’d need to work at least another four years to get to vice president. Her response: “Are you kidding me?” She quit and spearheaded sales for a startup magazine and events company called Silicon Alley Reporter (it sold to Dow Jones in 2003) and grew another from $1 million to $15 million.

She’s a hard-nosed, tough-cookie type, whose M.O. is trying to own 1 percent of every company she invests in. That’s a lot. And it’s not your standard strategy: Many investors would rather own, say, half a percent of a $10 million company than 1 percent of a $5 million company. Wilson, though, is a boutique-style investor who likes to be “scrappy with the $750,000” before upgrading to the “big check.” She opts for small teams, skeptical of the behemoths like Twitter and Facebook that dot today’s tech landscape and, in her view, often don’t live up to their big-time valuations. It’s not a perfect plan, of course. Some investors wouldn’t consider this the best strategy; it limits the type of companies you can back.

Because of all this, Wilson is becoming one of those pedestal-ized, women-in-biz types — both a blessing and a curse. She’s featured in a new film called Dream, Girl about the new era of female business stars. She’s definitely part of a new boom. In 2013, female angel investors represented 19.4 percent of the U.S. angel market, a significant jump from 12.2 percent in 2011, and it’s continuing to go up, experts say. And in the business world of women and men alike, Wilson is a standout, says Angela Lee, founder of 37 Angels, a New York-based network of women investors funding early-stage startups. In fact, the tight-knit women’s investing community — “All the women investors know each other!” Lee says — might actually help.

It can also be a pain: The Wilsons and the Lees get accosted with startup pitches focused on hair and beauty all too often. Lee adds that women will likely never make up even a third of the angel market share. There’s also the truth that the world of rich people investing off their own money is nebulous: Are they powerful because they already were, or because they’re succeeding in a big way? Because Wilson’s investments are often under-the-radar, we’re still waiting for her mega-boom, her next Blue Bottle, to prove she’s no one-hit wonder. She wouldn’t tell us her average rate of return or how much money she’s managing.

We turned to one of her founders-mentees, Mara Zepeda, who heads Switchboard, a Portland, Oregon-based online community service that’s been likened to Craigslist without the creeps or flakes. With Wilson’s investment and guidance, and a couple of extra investors thrown in, Switchboard raised just over half a million dollars in its first round. More recent investments: The Mighty, a media company that calls itself a “virtual shoulder to cry on,” shining a light on disability and disease, and coUrbanize, which helps residents work better with city planners and real estate developers.

Wilson plans to keep being loud about the gender issue at a time when people are suddenly more willing to hear that narrative. And because she “doesn’t mind being pigeonholed.”

Correction: an earlier version of this story misstated the age at which Wilson worked at Macy’s.


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