Ten years after selling LearnVest to Northwestern Mutual for a reported $375 million, fintech founder-turned-investor Alexa von Tobel is back in the spotlight—this time as a backer of what she calls “Fintech 3.0.”
Now at the helm of early-stage venture firm Inspired Capital, which she co-founded with former U.S. Commerce Secretary Penny Pritzker, von Tobel is betting that the next generation of fintech will be defined not by incremental innovation, but by full-scale product reinvention. “We’re not looking at surface-level upgrades,” von Tobel told TechCrunch. “The most impactful fintech companies of this next wave will rethink core infrastructure to serve a more digital, diverse, and economically fluid population.”
Inspired Capital has already backed a range of startups across sectors, but von Tobel’s roots in fintech remain deep. Before launching the fund in 2019, she served as Northwestern Mutual’s first chief digital officer and later, chief innovation officer, where she helped lead a broad digital transformation following LearnVest’s integration.
That transformation wasn’t just cosmetic. LearnVest’s technology became deeply embedded in Northwestern Mutual’s platform, and many key team members—including its former CTO—transitioned into leadership roles at the parent company. Von Tobel calls the acquisition a “values-driven merger” that laid the groundwork for digital innovation at one of America’s oldest financial institutions.
In the years since, she’s authored best-selling books, become a mother, and most recently, announced the launch of a new podcast series, Inspired with Alexa von Tobel. As Chime—one of her earlier fintech investments—enters public markets, von Tobel is positioning Inspired Capital to back the next breakout category leaders.
“Fintech 3.0 is about solving for structural gaps,” she said. “And we believe this generation of entrepreneurs will build the tools that redefine how money works for everyone.”