It’s been 10 years since Alexa von Tobel bought her monetary planning startup LearnVest to Northwestern Mutual for a reported $375 million.
Since then, von Tobel turned Northwestern Mutual’s first chief digital officer, then chief innovation officer, earlier than launching an early-stage enterprise agency of her personal, Impressed Capital, with former U.S. Secretary of Commerce Penny Pritzker. She’s additionally a New York Occasions bestelling creator, and he or she’s about to launch a brand new interview podcast, “Impressed with Alexa von Tobel.”
In a dialog with TechCrunch, von Tobel recalled the hectic interval across the acquisition, which closed actually days earlier than the start of her first youngster, and when she knew it was time to start out her personal agency.
Von Tobel defined that she created Impressed to be the investor she’d dreamed of — one with a “cultish dedication to entrepreneurship” — when she was a founder herself. And whereas Impressed is a generalist agency, she mentioned she feels each “pressing and optimistic” about fintech, the sector the place she launched her profession. (One among her pre-Impressed fintech investments, Chime, simply went public.)
“We consider this wave as fintech 3.0,” von Tobel mentioned. “The subsequent wave of innovation gained’t come from superficial tweaks however from basic deep product reinvention — instruments that meet the wants of a altering economic system and a extra numerous, digitally native inhabitants.”
The next interview has been edited for size and readability.
Congratulations on the 10-year anniversary of the acquisition. Wanting again, what do you are feeling proudest of?
First, Northwestern Mutual is an unbelievable firm, and our software program turned an extremely vital a part of the shopper expertise. And I’m so proud that so most of the LearnVest workforce stayed at Northwestern Mutual for thus lengthy, and it actually was only a merger of precise values. It’s simply wonderful how easy some issues are, it comes right down to the values of two firms and the missions of two firms.
I bought on a Wednesday and went into labor with my first youngster that weekend. All jokes apart, I all the time say it took me a few yr to mentally simply recuperate from being, like, all techniques had been go, my mind was being pushed to handle so many issues. Actually, I used to be having my first youngster. It was just like the world threw a bus at me and I caught it.
So if you had been closing the deal, was there a ticking clock in your thoughts, that you simply needed to end all the things earlier than this entire different factor occurs?
After all. If you concentrate on it, we actually signed on, I believe, 11am on March 25 after which we did a press tour with the CEO, after which the subsequent day, we did a rise up with your complete workforce, after which I went to sleep and actually awakened in labor.
Having your first youngster is priceless. There’s nothing on the planet that’s extra priceless to me than having my kids, nothing. And so I stored being like, “We’ve got to get this carried out, as a result of I’m not leaving the hospital to come back again and shut a deal. I really must give attention to this human being that I’m bringing into the world.” I all the time joke that the attorneys took me very critically.
When individuals on the surface discuss an acquisition, clearly, the very first thing they discuss is often the financials, after which one of many indicators of success is the product. LearnVest as a product doesn’t exist anymore, but it surely sounds prefer it was much less about having LearnVest as a standalone product and extra about remodeling Northwestern Mutual.
It was a lot greater than a product. [Northwestern Mutual’s] John Schlifske, he’s now not CEO, however he is likely one of the individuals I look as much as most on the planet, only a formidable human being. And he stored being like, “We’re gonna merge the businesses.” And I might chuckle — one is a $40-billion-a-year firm, and [the other is] little tiny LearnVest. However he actually meant it. He was like, “We’re gonna use this as a catalyst.” It was a catalyst for a whole digital transformation.
I turned the corporate’s first ever chief digital officer, after which chief innovation officer, and it was actually about taking all the things and merging it into the broader father or mother firm. My CTO of LearnVest turned the CTO of the father or mother firm.
You stayed for 4 years?
Yeah, [my last day] was mainly finish of January 2019, and that day we launched Impressed.
How do you know it was time to depart, and the place did the concept for Impressed come from?
I’m all the time at my greatest after I’m constructing one thing that I want existed for me. And I’ve mentioned many instances that the concept for Impressed really occurred after I dropped out of enterprise faculty, and I used to be a very all-in entrepreneur in each means — I dropped out mainly December 18 of 2008, on the backside of the worst recession in 81 years, not essentially the the probably the most inviting time to start out an organization.
And I actually was in search of a capital accomplice that didn’t exist. I had this imaginative and prescient of what it ought to feel and appear like, this type of rigor and camaraderie and in-the-trenches-ness of what an early stage capital accomplice might be, and I didn’t see it out there. That was New York in 2008, 2009, and I had this long-term plan of sooner or later, I need to come again and construct that.
Quick ahead to 2018, 2019 I’d began actually actively dreaming about what that might seem like. And sooner or later I used to be like, it has to occur, it’s now.
We’re now virtually seven years in. We’re a devoted early stage enterprise fund, generalist, headquartered in New York, however investing in all places. And I really feel like I’ve been right here for one minute. It actually is the most effective job I’ve ever had.
You talked about having this concept of a capital accomplice that you simply wished you’d had. How do you place that into follow?
What was I in search of in that capital?
What had been you in search of, and the way did you get everybody on the on-board with that imaginative and prescient?
So, after I discuss to entrepreneurs, I all the time say Impressed is completely different for 4 key causes. The primary purpose is that we’re extraordinarily lengthy length capital. It means once we again a founder, we actually put blinders on for 20 years. If you’re constructing an organization, there’s decisions it’s important to make as a CEO, which is, “Do I do the factor for subsequent month in order that issues look good, or do the tougher factor that gained’t look good subsequent month, possibly it pays off in three years, or not?” And what we all the time say is, “Do the tougher factor, do the factor that’s creating much more long-term worth and fear much less about artificial outcomes.”
The second factor is, our workforce’s fairly distinctive in that we’ve constructed and scaled greater than 10 companies which have touched a whole bunch of hundreds of thousands of customers all over the world. That mentality is so completely different if you’re sitting within the seat working with an entrepreneur, as a result of we haven’t essentially lived each expertise, however we’ve lived quite a bit, and we admire the contours. It’s virtually like seeing 3D versus 2D.
The third factor is that our workforce operates like one unit. So once we again an organization, you really get your complete workforce. At many companies, you get one accomplice, that’s the individual they know, they know you, and if, God forbid, that accomplice leaves, it’s such as you’ve evaporated your social fairness that you simply constructed up with that accomplice. We function like a swarm, the place you get all of us and we actively do weekly stand ups on your complete portfolio, so that everyone’s up to the mark.
After which the ultimate factor, due to [Inspired co-founder Penny Pritzker], she’s on the board of Microsoft, was U.S. Secretary of Commerce. So we prefer to say that, there are a lot of, many, many, many ways in which we might help firms get entry to issues which are actually laborious to get as only a sole founder in your 20s or 30s, the place we are able to really be an amazing enterprise accelerant to our firms in a reasonably distinctive means, with entry to tech and authorities and plenty of different vectors.
So briefly, that was the agency I needed.
I needed a deeply cultish dedication to entrepreneurship. We all the time discuss this Impressed future — one of many issues I really like a lot about entrepreneurship is, no nice entrepreneur reveals up and is like, “Let’s make the world worse,” proper? They present up they usually’re like, “Right here’s an enormous drawback that’s dealing with a billion individuals. Let’s go repair it.”
I believe among the greatest founders on the planet, their firms poured out of their DNA. I began LearnVest as a result of my father had handed away, and my mother in a single day needed to handle our funds. And I [thought], I by no means need a household to really feel financially destabilized, and I needed to go construct the answer.
Once we look again on the broader ecosystem over the past 10 years, one of many large transitions is abandoning that interval of zero rate of interest coverage (ZIRP) for VC and startups. Have you ever seen a change within the enterprise ecosystem in the previous few years, and has that affected the way in which you method investing at Impressed?
So only a useful framework — Impressed is a full generalist fund. We are going to contact all the things from deep tech to well being tech to shopper, in search of the most important, most vital concepts of the subsequent 15 years. Day-after-day, after I come to work, I actually mentally stroll into this workplace in 2035. And that’s how we’re desirous about the place the world goes and the issues to be solved.
And I believe when ZIRP existed, many issues that I might say weren’t enterprise bets, would get backed. And I virtually suppose it could be complicated, since you’d be like: What classes usually are not enterprise classes? A number of classes usually are not enterprise classes by nature — if you concentrate on energy legislation, all the things that we again ideally has an actual likelihood to be value $10 billion. There’s not a variety of these.
I constructed LearnVest on the backside of the worst recession in 81 years, and really LearnVest was not a straightforward enterprise. It was regulated, there have been so many different issues that had been actually laborious about what we had been doing. I actually like laborious companies, as a result of they’ve defensibility. They’ve causes to exist. They’ve much less copycats.
I believe a variety of issues bought funded over the past interval of, like, 2014 to 2021, that ought to’ve been getting a distinct supply of capital.
How are you feeling in regards to the state of fintech in 2025? The place are there nonetheless alternatives for startups?
I’m feeling each pressing and optimistic in regards to the state of fintech at present. Monetary providers stay foundational to a functioning society, however they haven’t stored tempo with the fast technological, demographic, and social shifts we’re experiencing. The rising federal debt, rising revenue inequality, and growing poverty — particularly amongst older People — underscore the necessity for extra adaptive and inclusive monetary instruments. To not point out the fast job loss as a consequence of AI.
This second presents a significant alternative for startups to reimagine monetary merchandise from the bottom up. We consider this wave as fintech 3.0. The subsequent wave of innovation gained’t come from superficial tweaks however from basic deep product reinvention — instruments that meet the wants of a altering economic system and a extra numerous, digitally native inhabitants. We’re excited by founders who see this problem clearly and are constructing daring options to deal with it.
You launched LearnVest on-stage on the TechCrunch 50 convention in 2009. When you had been a choose at our Startup Battlefield in 2025, what would you be in search of within the profitable workforce?
I might be in search of a founder who, based mostly on who they’re and their lived expertise, has a robust, distinctive perception to an issue that touches a whole bunch of hundreds of thousands of individuals, if no more. Two, I might be in search of one thing that’s non-obvious. You realize, I believe among the greatest and greatest concepts are non-consensus, individuals don’t suppose they’re attention-grabbing. Third, I might search for an entrepreneur who’s residing and respiration a decade out. They see this very highly effective future.
And the ultimate factor I might search for is the founder who has — there’s a spikiness, there’s a grit and resilience, but additionally a command, that you could sit with them and it’s palpable, that they are going to work out a strategy to succeed. These are the important thing elements that you simply search for.
