Jessica Livingston Talks Female Founders, Business Cycles, and Her Favorite Event of the Year

On April 4th, Y Combinator cofounder Jessica Livingston will host the third annual Female Founders Conference at the Herbst Theatre in San Francisco, an event meant to empower female founders — and those who aspire to become them – though a powerful line-up of women who’ve been there and done that, so to speak.

Among the speakers at this year’s free, half-day event will be Russlynn Ali, founder of the six-month-old nonprofit XQ Institute, which is trying to reimagine American high schools; Kathryn Minshew, co-founder of the popular career and jobs site The Muse; and Laurene Powell Jobs, the founder of Emerson Collective, Jobs’s education-focused investment vehicle.

The first time Livingston organized this conference, 450 people packed in to the Computer History Museum in Mountain View, Ca. This year, she expects to host 1,000. I chatted with Livingston on Friday about what the audience can expect to see, as well as trends that are likely to come up during the show.

TC: You say that about half the people who come to this event are founders and the other half aspire to found a company. How many are women?

JL: One hundred percent. While men can apply, I’m saving every available seat for women first. It’s really my favorite event of the year. There’s just this amazing energy that’s hard to describe. It’s the way it used to feel at [YC’s] Startup School in 2005 and 2006 [when YC was first founded]. There are mostly but not exclusively Y Combinator alumni speaking, and the founders just really tend to lay it out there and be very honest with their struggles about what went right and wrong, which makes the event really special.

TC: It’s your observation that more female founders are becoming CEOs. What roles have female founders typically taken, and what’s changing?

JL: Yes, one of the more recent trends we’ve notice within YC’s ecosystem is more women serving as their companies’ CEOs, which we’re very encouraged by as we think it will help deepen the pool of role models as these startups grow and become better known; we don’t just want to see more women starting startups.

In the past, some became CTO. A lot of times they took operations and marketing roles and, by the way, there’s nothing wrong with that. That’s what I was [doing] at Y Combinator. But I’m very excited to see women now leading these companies, because it just didn’t happen [much] in the first six years of YC.

TC: Are you seeing it more because YC is searching it out?

JL: We were always looking for more female-led companies, but we never asked because we didn’t think it was something we should ask. When we did start asking applicants [about their] gender, it was because we felt like we needed to get a firm hold on the numbers . . . and when we first did it, we found that 23 percent of applicants had a female founder. As it turned out, 23 percent of the companies we founded in that particular batch had a female founder, too, so we felt good that the class reflected our applicant pool.

But I do think we’re seeing it more generally because startups are becoming more mainstream. It wasn’t a normal thing to do in 2006, and now more and different types of people are starting to do it. Maybe you have a scientist who wants to solve a problem but who wouldn’t have considered leaving her job back in 2006.

TC: Last week, I interviewed Adam Grant, an author and Wharton professor, who suggested that the most successful founders start their companies on the side, while holding down other jobs with income. I’m wondering if that’s something that more women are doing.  

JL: I’m not surprised to hear that; I think starting a startup on the side makes sense. In terms of the applicants we see, I don’t see a trend. [Then again] a lot of people are a lot further along now when they apply to YC than when when we first got started. Either way while I encourage doing that, at some point you do have to say, “I’m going to commit to this and quit my paycheck.”

TC: I’m curious if that’s harder for women, particularly given that they make less to begin with, so have less savings as a safety net. 

JL: I wrote a blog post three years ago about what stops female founders and I gave advice that I wish I’d known when I was 25. It is hard, but you have to save up a nest egg. My big mistake was spending all my money. I was living in New York. I could have never have left my job and if I’d been fired, I’d have been screwed. Some kind of financial backing is key.

Do I think it’s any different between men and women? I don’t know the answer. I think it depends on the person. I definitely think it’s hard for anyone to leave a job with a nice paycheck for zero guarantee of success.

I also think if you’re talking about younger people with no kids and no mortgage, I sort of think men might be okay with a lower standard of living [that their savings affords them]. I’ve seen some of the squalor that 25-year-old dudes are willing to live in.

TC: Do you ever worry about there being too few women in venture capital? I’m optimistic that the imbalance will right itself over time, but I’d love to know if you think it impacts your companies.

JL: I don’t know what the facts are for the whole startup industry, but our female founders are doing very well. From my little perch, I see the women who are executing well and demonstrating good growth in big markets having no problems raising money.

I do think having more female founders, who eventually go on to lead what become unicorn companies, should help [the VC imbalance]. And these cycles take a while. For any company to become a billion-dollar company can take four to seven to more years. VCs like to [hire] people who’ve had a successful exit, and that experience can take a decade. So it might take a while for that kind of change.

I can say that with all the wonderful coverage showcasing the problems in this industry, people are talking about it. They care. I do see more VCs who want more equality and who are consciously making an effort to [get there]. I also see many more [women] angels and more women-led firms like Cowboy Ventures. I really hope that trend continues, where women say, “I’m going to start a fund. I’m going to do this professionally.”

Readers can apply to attend the Female Founders Conference here.

Photo: Steve Jennings/Getty Images North America