It has been a decade since Alexa von Tobel sold her financial planning startup, Learnvest, to Northwestern Mutual for $250 million. Since the acquisition, von Tobel has taken on various roles, including becoming Northwestern Mutual’s first chief digital officer and then chief innovation officer. She has also launched her own early-stage venture firm, Inspired Capital, in partnership with former U.S. Secretary of Commerce Penny Pritzker. Additionally, von Tobel is a New York Times bestselling author and is set to launch a new interview podcast, “Inspired with Alexa von Tobel.”

In a recent conversation with TechCrunch, von Tobel reflected on the period surrounding the acquisition, which coincided with the birth of her first child. She also discussed her decision to start her own firm, Inspired Capital, which she founded to be the type of investor she had wished for when she was a founder herself. Von Tobel expressed her enthusiasm for the fintech sector, where she began her career, stating that she feels both “urgent and optimistic” about its future. One of her pre-Inspired fintech investments, Chime, recently went public.

“We think of this wave as fintech 3.0,” von Tobel explained. “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?

Von Tobel expressed her pride in the fact that Northwestern Mutual is an incredible company, and LearnVest’s software became a crucial part of the customer experience. She is also proud that many members of the LearnVest team stayed at Northwestern Mutual for an extended period, and the acquisition was a merger of values and missions between the two companies.

Von Tobel sold LearnVest on a Wednesday and went into labor with her first child that weekend. She noted that it took her about a year to mentally recover from the experience of managing multiple responsibilities, including the acquisition and the birth of her child.

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?

Von Tobel confirmed that there was a sense of urgency, as she wanted to complete the deal before the birth of her child. She joked that the lawyers took her seriously, and the deal was signed on March 25, with a press tour and team stand-up following the next day, before she went into labor.

When people on the outside talk about an acquisition, obviously, the first thing they talk about is usually the financials, and then one of the signs of success is the product. LearnVest as a product doesn’t exist anymore, but it sounds like it was less about having LearnVest as a standalone product and more about transforming Northwestern Mutual.

Von Tobel agreed, stating that the acquisition was about something much bigger than a product. She explained that Northwestern Mutual’s CEO, John Schlifske, wanted to use the acquisition as a catalyst for the company’s digital transformation. Von Tobel became the company’s first chief digital officer and then chief innovation officer, working to merge LearnVest into the broader parent company.

You stayed for four years? 

Von Tobel confirmed that she stayed at Northwestern Mutual for four years, until the end of January 2019, when she launched Inspired Capital.

How did you know it was time to leave, and where did the idea for Inspired come from?

Von Tobel explained that she had always wanted to build a capital partner that she wished had existed for her when she was a founder. She dropped out of business school in 2008 and was looking for a capital partner with a rigorous and camaraderie-driven approach. The idea for Inspired Capital was born out of this desire, and von Tobel started actively dreaming about what the firm could look like in 2018 and 2019.

Inspired Capital is a dedicated early-stage venture fund, generalist, and headquartered in New York, but investing everywhere. Von Tobel stated that she feels like she’s been doing the best job she’s ever had, and the firm is now almost seven years old.

You mentioned having this idea of a capital partner that you wished you’d had. How do you put that into practice?

Von Tobel explained that Inspired Capital is different for four key reasons. The first reason is that the firm is extremely long-duration capital, meaning they truly put blinders on for 20 years when backing a founder. The second reason is that the team has built and scaled more than 10 businesses that have touched hundreds of millions of users around the world. The third reason is that the team operates like one unit, with weekly stand-ups on the entire portfolio, so everyone is up to speed. The final reason is that the firm can provide access to things that are hard to get, such as tech and government, due to the presence of co-founder Penny Pritzker.

Von Tobel stated that she wanted a deeply cultish commitment to entrepreneurship, where the firm is all-in on the founder’s vision. She believes that some of the biggest founders in the world have companies that poured out of their DNA, and she started LearnVest because her father had passed away, and her mom had to manage their finances overnight.

When we look back at the broader ecosystem over the last 10 years, one of the big transitions is leaving behind that period of zero interest rate policy (ZIRP) for VC and startups. Have you seen a change in the venture ecosystem in the last few years, and has that affected the way you approach investing at Inspired?

Von Tobel noted that Inspired is a full generalist fund, looking for the biggest and most important ideas of the next 15 years. She believes that when ZIRP existed, many things that weren’t venture bets got backed, and it was confusing. Von Tobel likes hard businesses because they have defensibility and less copycats. She thinks a lot of things got funded over the last period that should have gotten a different source of capital.

How are you feeling about the state of fintech in 2025? Where are there still opportunities for startups?

Von Tobel expressed that she is feeling both urgent and optimistic about the state of fintech today. She believes that financial services remain foundational to a functioning society but haven’t kept pace with technological, demographic, and social shifts. This moment presents a major opportunity for startups to reimagine financial products from the ground up. Von Tobel and her team think of this wave as fintech 3.0, where the next wave of innovation won’t come from superficial tweaks but from fundamental deep product reinvention.

You launched LearnVest on-stage at the TechCrunch 50 conference in 2009. If you were a judge at our Startup Battlefield in 2025, what would you be looking for in the winning team? 

Von Tobel would be looking for a founder who has a powerful, unique insight to a problem that touches hundreds of millions of people. She would also look for something non-obvious, an entrepreneur who is living and breathing a decade out, and has a spikiness and grit that makes it palpable that they will figure out a way to succeed.