Jennifer Fitzgerald grew up thinking she would travel the world for a career in international development. Instead, she wound up in insurance. After consulting for big financial companies at  McKinsey, Fitzgerald and colleague Francois de Lame co-founded online insurance broker Policygenius in 2014. The New York startup now has more than $10 million in annual revenue and $52 million in financing--but landing investors wasn't easy. Here, Fitzgerald discusses the mistakes, disappointments, and investor sexism she had to overcome to line up funding. --As told to Maria Aspan

After college, kind of on a whim, I decided that I was going to do the Peace Corps. I like to call that my first startup experience: You're dropped in your county or village, and you kind of have to figure it out. You don't have a boss. You don't have anybody telling you what to do. I was assigned to a municipal government in Western Honduras, where I helped develop a system for the government to collect property taxes--by moving from paper statements and filing cabinets to a computer database. It was a year-long project, and the municipality collected something like 30 percent more that year. It was awesome. 

When my co-founder and I decided, "Yep, there's enough here for us to leave McKinsey and build a company," we knew right away we needed to raise money. We can't build the product ourselves--neither of us is a software engineer, and we have to be able to pay salaries for our first couple of employees. Also, insurance is an expensive industry to build a business. Customer acquisition is expensive.

I wish we had done more research on it, because we went into it with a little bit of hubris and a lot of naiveté. When you see company after company raising money, you get the outside-in perception: "It's not that difficult if they can do it." Which is not the case.

We were two ex-McKinsey consultants, neither of us was technical, and we wanted to tackle insurance--every strike was against us. It was a very fruitless and frustrating few months.

Finally, we realized, "This is probably not gonna happen." We don't have the track record. We don't have the trust. We don't fit the patterns that early stage venture firms are looking for. But we know people who do trust us. So we got off the VC track and just raised our seed round with a bunch of small checks from friends and family.

Our target was $1 million. We fell short; we raised about $750,000, among about 50 different small investors. Which is a painful way to do it, but we had to get it done. 

We stretched that $750,000 as long as we possibly could. We built and launched the first iteration of Policygenius with a very small team, about four of us. We got some early customers and some attention from the personal finance community. We actually showed that we can build something and not just talk about it; but if we're going to continue the company, we needed to get some institutional investors. There's no way we could build the company we want with $10,000 checks.

It was an uphill climb again. I'm the CEO. I'm older, I was more senior at McKinsey than my co-founder, and in terms of our personalities, I like to be more outward facing. I'm good at public speaking. There was one meeting where the investor would keep asking questions directed at my co-founder. I would answer it, or my co-founder would say, "Well, Jen, do you want to answer that?" I would answer the question, and then the investor would direct his followup back to Francois.

That kept on happening. I'm not a shrinking violet. I've been in the business world for a long time, and I'd never seen anything like that before. For the first 10 minutes of the meeting I was wondering, "What's going on?" Then I realized, "Oh, shit. It's because I'm a woman."

So that was weird. We'd gotten pretty pointed and difficult questions from other meetings and other pitches. But I've never had somebody not want to talk to me directly. We still laugh about it.

It took, oh gosh, five months to find a VC investor who believed in us. We really clicked. He got it. He actually had to advance us some of the cash, because we were a month away from running out of money and not making payroll.

After we got that first term sheet in, it got easier. Investing can be very much a herd mentality, so as soon as you have one institutional investor who will say, "I believe in this company and I'm gonna lead the round," it's easy to round up other venture firms.

Other people have asked, "How do you know when you know enough to actually leave the cushy corporate job and do it?" I don't think you can know enough. You just kind of have to take a leap of faith, which is what I did when I decided on a whim to join the Peace Corps. You can always talk yourself off a cliff. But if you really want to jump, you just gotta jump.

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Published on: Oct 1, 2018