It’s been 10 years since Alexa von Tobel sold financial planning startup Learnvest to Northwestern Mutual for $250 million.
Since then, von Tobel has become Northwestern Mutual’s first Chief Digital Officer and then Chief Innovation Officer, and has since launched her own inspirational capital early stage venture, along with former U.S. Secretary of Commerce, Penny Pretzker. She is also the author of Basetelling for The New York Times and is about to launch a new interview podcast, “Inspired by Alexa von Tobel.”
In a conversation with TechCrunch, Von Tobel recalled the busy period around the acquisition a few days before the birth of her first child, and when she learned that it was time for her to start her own company.
Von Tobel became the investor she dreamed of when she was the founder. And although Inspired is a generalist company, she said she feels both “urgent and optimistic” about Fintech, the sector in which she began her career. (Chime, one of her pre-inspired fintech investments, has just been published.)
“We consider this wave to be FinTech 3.0,” von Tobel said. “The next wave of innovation comes not from superficial fine-tuning, but from the reinvention of basic deep products. It is a tool to meet the changing economy and the needs of a more diverse and digital native population.”
The following interviews have been compiled for length and clarity.
Congratulations on the 10th anniversary of the acquisition. Looking back, what are you proud of?
First of all, Northwestern Mutual is an incredible company and our software has become a very important part of the customer experience. And I’m very proud that so many Learnvest teams have been staying at Northwestern Mutual for a long time, and it was really just a merger of actual values. It’s amazing how easy it is to do some things. That comes down to the values of both companies and the mission of the two companies.
I sold it on Wednesday and went to work that weekend with my first child. All jokes aside, I always say it took me about a year to recover mentally, as all systems went, as my brain was being pushed to manage so many things. Literally, I had my first child. It was like the world threw a bus at me and I caught it.
So, as you conclude the deal, did you have a ticking clock in your heart?
of course. If you think about it, I think we literally signed on at 11am on March 25th and then we went on a press tour with the CEO. And the next day we stood up as a whole team and then I was literally awakened to labour about sleep.
Having your first child is valuable. There is nothing in the world more valuable than having my children. So I’m kidding me that “we have to accomplish this because I’m not leaving the hospital and coming back and closing the deal, so I really need to focus on this person I bring into the world.” I’m always kidding that my lawyers have taken me very seriously.
When outsiders talk about acquisitions, obviously, the first thing they are talking about is usually finances, and one of the signs of success is the product. Learnvest as a product no longer exists, but Learnvest is rarely used as a StandAlone product, and there doesn’t seem to be much of a change in Northwestern Mutual.
It was much larger than the product. (Northwestern Mutual’s) John Schlifske, he’s no longer the CEO, but he’s one of the people I admire most in the world and just a formidable person. And he continued to feel that “we’re going to merge the company.” And I laugh – one is a $400 billion annual company, and (the other) a bit of a small Learnvest. But he really meant that. He was like, “We’re going to use this as a catalyst.” This was the catalyst for the entire digital conversion.
I became the company’s first Chief Digital Officer and then Chief Innovation Officer. It was really about taking everything in and merging it into a wider parent company. My CTO at Learnvest has become the CTO of my parent company.
Have you stayed for four years?
Yes, (my last day) was basically the end of January 2019, but that day I launched Inspired.
How was it time to leave and where did the inspiration ideas come from?
When I’m building what I want to be there for me, I’m always at my best. And I have said many times that the ideas that inspired me when I dropped out of business school actually happened. I was truly an all-in entrepreneur in every respect – I basically fell out on December 18, 2008, at the bottom of the worst recession of 81.
And I was looking for a capital partner that really didn’t exist. I had this vision of what it should look like. It’s this kind of rigour and trench sexiness about what friendship and early stage capital partners are, and I didn’t see it in the market. It was 2008 New York in 2008 and I had this long-term plan one day, I would like to go back and make it.
Fast forward to 2018, 2019, I started dreaming really aggressively about what it would look like. And one day, I was, it must happen, now.
We’ve been in nearly seven years now. We are a dedicated, early stage venture fund and generalist, headquartered in New York, but investing everywhere. And I feel like I’ve been here for a minute. It’s literally the best job I’ve ever had.
You mentioned that you have this idea of a capital partner you wanted. How do you put that into practice?
What were you looking for in that capital?
What were you looking for, and how did you put all the people with that vision on?
So when I talk to entrepreneurs, I always say that inspiration is different for four important reasons. The first reason is that we are very long-term capital. That means we will be truly blindfolded for 20 years when we support our founders. When you’re building a company, you have the options you have to create as a CEO. So, “Do what next month, make things look good, or what next month, do things that don’t look good, and what we always say is, “Do what’s difficult, create much longer-term value, and don’t worry too much about worrying about synthetic results.”
Second, our team is extremely unique in that we have built and expanded over 10 businesses that touched hundreds of millions of users around the world. We don’t necessarily have all the experiences, but we’ve lived a lot, so that mentality is very different when we’re sitting in the seat where we work with entrepreneurs. It’s like watching 3D vs 2D.
The third thing is that our team operates like a single unit. So when we support the company you actually get the whole team. In many companies, you get one partner. It’s the one they know, they know you, and if God forbids, if your partner leaves, it appears that it has evaporated your social equity you have built with that partner. We act like a flock that you get us all and actively stand up every week across our portfolio.
And the last thing is for (inspired co-founder Penny Pretzker), she was on the Microsoft board and was the US Secretary of Commerce. So, we can withstand a very unique business for our businesses, as we can help you access what is really difficult to get as the only founder in our 20s or 30s, and in fact, we can withstand a very unique business for our businesses, such as having access to technology and government and many other vectors in a very unique way.
In short, it was the company I wanted.
I wanted a deep voiced commitment to entrepreneurship. We will always talk about this inspired future. One thing I really like about entrepreneurship is that no great entrepreneurs appear and they’re like, “Let’s make the world worse.” They come in and say, “There’s a big problem facing a billion people here. Let’s fix that.”
Some of the world’s largest founders think their company was poured out from DNA. With my father passed away, I started Learnvest and my mother had to take control of our finances. And I wanted to build a solution because I didn’t want my family to feel financially unstable.
Looking back at the broader ecosystem over the past decade, one major transition remains a period of zero interest rate policy (ZIRP) for VCs and startups. Have you seen changes in the venture ecosystem over the past few years?
So, merely a useful framework – inspiration is a complete generalist fund. From deep technology to health technology to consumers, we are exposed to everything from deep technology to health technology, and we are looking for the biggest and most important ideas of the next 15 years. Every day, when I come to work, I literally step into this office mentally in 2035.
And I think there will be a lot of things that I say weren’t venture bets when Zirp was there and it’s going to be backwards. And I think it’s going to be confusing. Because you will be: Many categories are not essentially venture categories. When we think about the power law, everything we support is a real opportunity worth $10 billion. There aren’t many of them.
I built Learnvest at the bottom of the worst recession in 81, but Learnvest was actually not an easy business. It’s regulated and there were so many other things that really were difficult about what we were doing. I really like hard business because they have defensive potential. They have a reason to exist. They have few imitators.
I think a lot should have been funded during the final period from 2014 to 2021.
What do you think about the state of FinTech in 2025? Where are the startup opportunities still available?
Today, I feel urgent and optimistic about the state of Fintech. Financial services remain the foundation of a functioning society, but they are not responding to the rapid technology, demographics and social change we are experiencing. Increased federal debt, increased income inequality, and increased poverty, particularly among older Americans, underscore the need for a more adaptive and comprehensive financial tool. Not to mention the rapid unemployment caused by AI.
This moment offers a great opportunity for startups to rethink financial products from scratch. I think this wave is FinTech 3.0. The next wave of innovation comes from not from superficial fine-tuning, but from reinventing basic deep products. It is a tool to meet the changing economy and the needs of a more diverse digital native population. We are excited to see this challenge clearly and build bold solutions to address it.
We launched the Learnvest On stage at the 2009 TechCrunch 50 Conference. If you were a judge at the 2025 Startup Battlefield, what would you look for on the winning team?
I’m looking for founders who have strong and unique insight into the issues that touch hundreds of millions of people based on who they are and their living experiences. Secondly, I’m looking for something non-trivial. As you know, I don’t think some of the biggest and best ideas are non-consensual. People don’t think they’re funny. Third, I will be looking for an entrepreneur who has lived for 10 years and is breathing. They see this very powerful future.
And the last thing I’m looking for is the founder who has. They have spikes, grit and resilient, but you can sit with them and like it’s obvious. These are the important ingredients you look for.