LearnVest's Alexa von Tobel wants to boost NYC's VC scene with new fund

Last fall, Alexa von Tobel was mulling her next move. In early 2015, von Tobel had sold her personal finance startup LearnVest to Northwestern Mutual for $375 million; following the acquisition, she had taken a role at the financial services company, where she had spent three and a half years and had been promoted to chief innovation officer. Now it was time for something new.

Von Tobel (who also hosts the Inc. Founders Project podcast, under Fast Company' s parent company Mansueto Ventures) shared her idea with Penny Pritzker, the founder and chairman of investment firm PSP Partners and the former U.S. secretary of commerce under President Obama. "She was just a natural person for me to call, just to say, 'I'd really love your guidance on my career and life,'" von Tobel says. "I started telling her about this [venture capital] firm rooted in New York, investing across the country, that has an incredible mix of operator and investor DNA. I got her advice on it, but by the end, it was obvious that we should probably work together on it."

The result of their partnership is Inspired Capital, for which von Tobel and Pritzker are attempting to raise $200 million for their debut fund, which would make it one of the biggest funds helmed by women. (Von Tobel declined to comment specifically on fundraising, citing legal concerns.) Forerunner Ventures, which has backed prominent female-run companies such as Away and Glossier, recently raised a $360 million fund, but on the whole, 45% of female partners across venture capital are concentrated in funds that are between $25 million and $250 million, according to data from All Raise. Even at megafunds totaling more than $1.6 billion, women reportedly account for 11% of partners but control just 9% of capital.

Inspired Capital's investments will be industry-agnostic and span early-stage companies that are seeking seed and series A funding. Von Tobel and Pritzker have locked down partners such as Lucy Grayson Deland, the former chief operating officer of Paperless Post and a friend of von Tobel's, and Mark Batsiyan, who von Tobel worked with at LearnVest and then Northwestern Mutual, along with a growing portfolio of founders. Their pitch, as a firm created by entrepreneurs, is to be with their founders every step of the way. "It's not just about being good investors," says von Tobel. "We actually really care about helping the entrepreneurs win and succeed. One thing we say a lot is we've had the sleepless nights; we know how painful they can be and how lonely it can be to be a founder. And as a result, we really want to ask the hard questions early to our entrepreneurs because we want to help make sure that they have fewer of them, ideally."

Inspired Capital formalizes and builds on von Tobel's angel investments in companies such as workflow management platform Airtable and Chief, a private club for high-powered women. The latter is now one of the firm's first major investments; Inspired Capital co-led Chief's $22 million series A round earlier this year. The firm has also invested $1 million in series A funding toward Kindur, a fintech startup that helps baby boomers plan for retirement, and led a $5 million seed round for Rho, a digital business bank for entrepreneurs.

"Because [Alexa] has gone through this whole rodeo before and understands the trials and tribulations of being an entrepreneur, I walked out with such greater clarity [after] every conversation I had with her," says Chief cofounder and CEO Carolyn Childers, who first connected with von Tobel as she was exploring the market for Chief. "It was a little bit of a coaching session every time. I just really deeply valued the relationship and the guidance she was giving, and I knew she was starting Inspired Capital. So as we were starting to kick off our series A, it was just an obvious next conversation to have."

As a former entrepreneur, von Tobel wants to foster an environment that she wishes had existed when she started LearnVest 10 years ago. "When I dropped out of HBS in the fall of 2008, it was the exact same time that Lucy was working to help [start] Paperless Post," she says. "I worked out of Starbucks. There weren't angel funds and a bunch of seed funds. I think what Inspired Capital gets to leverage is the fact that in many ways, we've been part of the fabric of helping build an ecosystem [in New York City]."

That's why, while Inspired Capital will make investments across the country, it was important to von Tobel that her firm be based in New York. And for a founder like Everett Cook-the cofounder and CEO of Rho, which is based in New York-the firm's location was a big draw. "So much of the VC ecosystem is still based on the West Coast," he says. "We felt it was really important to be connected to a firm that is in our backyard. I'm from New York, and I want to play a part in helping grow the ecosystem."

Von Tobel believes the extensive network she and Pritzker have cultivated is a major selling point. "We know so many people, and we call them friends-they're not even just contacts," von Tobel says. "So not only do we plan to support our companies financially, but I would say emotionally in addition to that, through all the business relationships that we can bring to the table. We can open doors very quickly."

If von Tobel's background as a New York-based entrepreneur is a plus, so too is her perspective as a female founder leading a venture capital firm alongside Pritzker. "One of the great advantages that Inspired Capital has is that we do have a team of people that come from different backgrounds with different skillsets," Pritzker says. "I think the fact that we as an organization are in demand, not only by entrepreneurs but also by other venture capital firms, is because they know that we can bring to the table a point of view that they maybe don't have."