Anthony Ha
11 min read
It’s been 10 years since Alexa von Tobel sold her financial planning startup Learnvest to Northwestern Mutual for $250 million.
Since then, von Tobel became Northwestern Mutual’s first chief digital officer, then chief innovation officer, before launching an early-stage venture firm of her own, Inspired Capital, with former U.S. Secretary of Commerce Penny Pritzker. She’s also a New York Times bestelling author, and she’s about to launch a new interview podcast, “Inspired with Alexa von Tobel.”
In a conversation with TechCrunch, von Tobel recalled the hectic period around the acquisition, which closed literally days before the birth of her first child, and when she knew it was time to start her own firm.
Von Tobel explained that she created Inspired to be the investor she’d dreamed of — one with a “cultish commitment to entrepreneurship” — when she was a founder herself. And while Inspired is a generalist firm, she said she feels both “urgent and optimistic” about fintech, the sector where she launched her career. (One of her pre-Inspired fintech investments, Chime, just went public.)
“We think of this wave as fintech 3.0,” von Tobel said. “The next wave of innovation won’t come from superficial tweaks but from fundamental deep product reinvention — tools that meet the needs of a changing economy and a more diverse, digitally native population.”
The following interview has been edited for length and clarity.
Congratulations on the 10-year anniversary of the acquisition. Looking back, what do you feel proudest of?
First, Northwestern Mutual is an incredible company, and our software became an incredibly important part of the customer experience. And I am so proud that so many of the LearnVest team stayed at Northwestern Mutual for so long, and it really was just a merger of actual values. It’s just amazing how simple some things are, it comes down to the values of two companies and the missions of two companies.
I sold on a Wednesday and went into labor with my first child that weekend. All jokes aside, I always say it took me about a year to mentally just recover from being, like, all systems were go, my brain was being pushed to manage so many things. Literally, I was having my first child. It was like the world threw a bus at me and I caught it.
So when you were closing the deal, was there a ticking clock in your mind, that you had to finish everything before this whole other thing happens?
Of course. If you think about it, we literally signed on, I think, 11am on March 25 and then we did a press tour with the CEO, and then the next day, we did a stand up with the entire team, and then I went to sleep and literally woke up in labor.
