Thanks to an introduction from our friend Nihal Mehta at Eniac Ventures, I sat down with Alexa von Tobel soon after Inspired Capital announced the close of its $450 million Fund IV.
Alexa founded LearnVest, sold it to Northwestern Mutual for a reported $250 million-plus, and in 2019 started Inspired with her co-founder Penny Pritzker, the former U.S. Secretary of Commerce. Fund IV brings the New York firm to more than $1.3 billion in total assets under management, and almost seven years in, Alexa says the job still feels brand new.
What we covered:
- Why the size of Fund IV matters less to Alexa than you might expect
- The four reasons founders should pick Inspired
- A team Inspired passed on, and why those same founders called Inspired first the next time around
- What Alexa is looking for in her next hire, and what they can’t fake
Watch the full conversation, or keep scrolling for the highlights 👇
The following content is for informational purposes only and should not be construed as personal legal, tax, investment, or financial advice. Quotes have been edited for length and clarity.
Fund IV, same team, same strategy
Alexa told me, “The size of the fund in our eyes doesn’t really matter,” because nothing about how the firm invests is Fund IV, same team, same strategy
Alexa told me, “The size of the fund in our eyes doesn’t really matter,” because nothing about how the firm invests is changing. It’s the same team and the same strategy Inspired has run since its first fund, which Alexa calls “napkin to Series A, generalist tech.” The firm is headquartered in New York, and she says half of its companies are on the West Coast and half on the East Coast.
Fund IV will back roughly 10 companies a year with checks between $1 million and $15 million across AI infrastructure, healthcare, defense, fintech, robotics, and consumer. Alexa said each fund holds about 30 bets, deployed over roughly three years, and Inspired usually leads and takes a board seat when founders want the firm as their core partner. The firm reports 10 portfolio companies valued at $1 billion or more, 10 companies past $100 million in revenue, and 10 exits.
“We’re a high conviction firm… We back a few things a year, eight to 10 deals.”
Alongside Alexa and Penny, Inspired’s investment partnership includes Mark Batsiyan, Charlotte Ross, Kamran Ali, and Chris Brown.
The four things that make Inspired different
Before a founder pitches, Alexa tells them the same four things. She walked me through all four:
1. Incredibly long duration. “We really do think in decades,” Alexa said, and that horizon is what lets Inspired back “really big ideas, scary, kind of audacious, high-convexity bets” and then execute on them “for 15 plus years with all of our might.” She described some of Inspired’s LPs as “truly multi-decade, in some cases hundred-year” venture backers who are fine with a strategy that isn’t chasing short-term results.
2. Our team’s really different. Inspired has fewer than 20 people, and Alexa says that together they have built 10 companies that scaled to hundreds of millions of users. “That’s just really different, John,” she told me. “It’s (not having an investor with operating experience) like getting parenting advice from someone with no kids. You wouldn’t do that.”
3. One team approach. The full team runs top to bottom through the whole portfolio every Monday, Wednesday, and Friday. “You literally get the entire team, you get all of us on every deal,” Alexa said.
4. Penny Pritzker. Alexa calls her co-founder “an unhirable asset.” As Secretary of Commerce, Penny’s job was to know every CEO in the country, and she has sat on Microsoft’s board.
“We can’t promise to get you to everybody on the planet, but we’re pretty darn sure we can get pretty close.”
Alexa says Inspired’s LPs understood that pitch from day one, “but now the results are really proving it.”
From Restaurant Robots to Defense Tech
I was curious about Allen Control Systems (ACS), one of Inspired’s defense tech companies, because it’s also in the portfolio of a fund I’m invested in. ACS was most recently valued at $2.2 billion and builds systems that shoot down drones. Alexa said its product is “literally on the battlefield right now,” and that Inspired was “the first dollars into this company.”
Inspired’s history with the founders goes back to the month the firm launched. Steve Simoni and his co-founders were running Bbot, a restaurant robotics startup, and Alexa loved the team. “They just had so much magic among the three of them,” she said. Inspired still passed.
DoorDash acquired Bbot in 2022. Alexa said Inspired would have made money on the deal, but it wasn’t “an Inspired enough swing.” Steve liked the Inspired team so much that when the founders decided to keep the band together and go after a far bigger problem (getting “human beings off the front lines of war”), they called Inspired first, and Inspired invested. That early position is now worth “a few hundred million dollars,” and Alexa says ACS has more exciting updates coming.
What Alexa looks for in a hire
Inspired is hiring a VC Investor in New York. Alexa told me exactly what stands out to her:
- You love doing the work. “Don’t become a chef if you don’t like making food.”
- You’re exceptionally hardworking and really, really clever. She called those a given.
- You have street hustle. Even with degrees from Harvard and Harvard Business School, Alexa says “street smarts are everything.”
- Your interest in technology is authentic. The type of person who studies esoteric areas of tech, like quantum computing, for years in their free time. (In this case, that someone was Alexa!)
- You’re already living in 2036. She wants people thinking a decade out about how technology will change our lives.
There’s more in the full conversation, including how Inspired works with other firms, why Alexa thinks the best founders “will the future into existence,” and her advice for aspiring podcasters from eight seasons of her own show and five years hosting a radio show on Sirius. Watch it above.
And for the finance side of Inspired, read our Office of the VC CFO interview with Inspired’s CFO, Chris Huether.
