It’s been 10 years since Alexa von Tobel bought her monetary planning startup Learnvest to Northwestern Mutual for $250 million.
Since then, von Tobel grew to become 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 writer, and she or he’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 baby, and when she knew it was time to begin 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 in every of her pre-Impressed fintech investments, Chime, simply went public.)
“We consider this wave as fintech 3.0,” von Tobel mentioned. “The following wave of innovation received’t come from superficial tweaks however from elementary 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. Trying again, what do you’re feeling proudest of?
First, Northwestern Mutual is an unimaginable firm, and our software program grew to become an extremely necessary a part of the client expertise. And I’m so proud that so lots of the LearnVest crew stayed at Northwestern Mutual for therefore lengthy, and it actually was only a merger of precise values. It’s simply wonderful how easy some issues are, it comes all the way down to the values of two corporations and the missions of two corporations.
I bought on a Wednesday and went into labor with my first baby that weekend. All jokes apart, I at all times say it took me a few 12 months to mentally simply recuperate from being, like, all programs have been go, my mind was being pushed to handle so many issues. Actually, I used to be having my first baby. It was just like the world threw a bus at me and I caught it.
So once you have been closing the deal, was there a ticking clock in your thoughts, that you just needed to end every thing earlier than this complete different factor occurs?
After all. If you consider 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 arise with the complete crew, after which I went to sleep and actually awakened in labor.
Having your first baby is priceless. There’s nothing on this planet that’s extra precious to me than having my kids, nothing. And so I stored being like, “We’ve to get this carried out, as a result of I’m not leaving the hospital to come back again and shut a deal. I truly have to deal with this human being that I’m bringing into the world.” I at all times joke that the legal professionals took me very critically.
When individuals on the surface discuss an acquisition, clearly, the very first thing they discuss is normally the financials, after which one of many indicators of success is the product. LearnVest as a product doesn’t exist anymore, nevertheless it sounds prefer it was much less about having LearnVest as a standalone product and extra about remodeling Northwestern Mutual.
It was a lot larger than a product. [Northwestern Mutual’s] John Schlifske, he’s not CEO, however he is likely one of the individuals I look as much as most on this planet, only a formidable human being. And he stored being like, “We’re gonna merge the businesses.” And I might snicker — 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 grew to become the corporate’s first ever chief digital officer, after which chief innovation officer, and it was actually about taking every thing and merging it into the broader father or mother firm. My CTO of LearnVest grew to become the CTO of the father or mother firm.
You stayed for 4 years?
Yeah, [my last day] was principally finish of January 2019, and that day we launched Impressed.
How do you know it was time to go away, and the place did the concept for Impressed come from?
I’m at all times at my finest once I’m constructing one thing that I want existed for me. And I’ve mentioned many instances that the concept for Impressed truly occurred once I dropped out of enterprise college, and I used to be a extremely all-in entrepreneur in each method — I dropped out principally December 18 of 2008, on the backside of the worst recession in 81 years, not essentially the the essentially the most inviting time to begin an organization.
And I actually was on the lookout for a capital accomplice that didn’t exist. I had this imaginative and prescient of what it ought to feel and look like, this form of rigor and camaraderie and in-the-trenches-ness of what an early stage capital accomplice may very well be, and I didn’t see it available in the market. That was New York in 2008, 2009, and I had this long-term plan of at some point, I need to come again and construct that.
Quick ahead to 2018, 2019 I’d began actually actively dreaming about what that might appear to be. And at some point I used to be like, it has to occur, it’s now.
We’re now nearly seven years in. We’re a devoted early stage enterprise fund, generalist, headquartered in New York, however investing all over the place. And I really feel like I’ve been right here for one minute. It actually is the perfect job I’ve ever had.
You talked about having this concept of a capital accomplice that you just wished you’d had. How do you set that into observe?
What was I on the lookout for in that capital?
What have been you on the lookout for, and the way did you get everybody on the on-board with that imaginative and prescient?
So, once I speak to entrepreneurs, I at all times say Impressed is completely different for 4 key causes. The primary cause is that we’re extraordinarily lengthy period capital. It means once we again a founder, we really put blinders on for 20 years. While you’re constructing an organization, there’s selections it’s a must to make as a CEO, which is, “Do I do the factor for subsequent month in order that issues look good, or do the more durable factor that received’t look good subsequent month, perhaps it pays off in three years, or not?” And what we at all times say is, “Do the more durable factor, do the factor that’s creating way more long-term worth and fear much less about artificial outcomes.”
The second factor is, our crew’s fairly distinctive in that we’ve constructed and scaled greater than 10 companies which have touched tons of of tens of millions of customers all over the world. That mentality is so completely different once 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 lots, and we admire the contours. It’s nearly like seeing 3D versus 2D.
The third factor is that our crew operates like one unit. So once we again an organization, you truly get the complete crew. At many corporations, you get one accomplice, that’s the particular person they know, they know you, and if, God forbid, that accomplice leaves, it’s such as you’ve evaporated your social fairness that you just 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 the 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 wish to say that, there are various, many, many, many ways in which we may help corporations get entry to issues which are actually laborious to get as only a sole founder in your 20s or 30s, the place we will truly be an incredible enterprise accelerant to our corporations in a reasonably distinctive method, with entry to tech and authorities and lots of different vectors.
So in brief, that was the agency I needed.
I needed a deeply cultish dedication to entrepreneurship. We at all times discuss this Impressed future — one of many issues I really like a lot about entrepreneurship is, no nice entrepreneur exhibits up and is like, “Let’s make the world worse,” proper? They present up and so they’re like, “Right here’s a giant drawback that’s going through a billion individuals. Let’s go repair it.”
I believe a number of the largest founders on this planet, their corporations 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 used to be like, I by no means desire 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 huge 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 best way you method investing at Impressed?
So only a useful framework — Impressed is a full generalist fund. We are going to contact every thing from deep tech to well being tech to client, on the lookout for the largest, most necessary concepts of the subsequent 15 years. Every single day, once I come to work, I actually mentally stroll into this workplace in 2035. And that’s how we’re occupied with the place the world goes and the issues be solved
And I believe when ZIRP existed, many issues that I might say weren’t enterprise bets, would get backed. And I nearly assume it could be complicated, since you’d be like: What classes are not enterprise classes? A lot of classes aren’t enterprise classes by nature — if you consider energy legislation, every thing that we again ideally has an actual likelihood to be price $10 billion. There’s not a whole lot of these.
I constructed LearnVest on the backside of the worst recession in 81 years, and truly LearnVest was not a simple enterprise. It was regulated, there have been so many different issues that have been actually laborious about what we have 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 whole lot 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 this time. Monetary companies stay foundational to a functioning society, however they haven’t stored tempo with the speedy technological, demographic, and social shifts we’re experiencing. The rising federal debt, rising revenue inequality, and growing poverty — particularly amongst older Individuals — underscore the necessity for extra adaptive and inclusive monetary instruments. To not point out the speedy job loss resulting from 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 following wave of innovation received’t come from superficial tweaks however from elementary 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 have been a choose at our Startup Battlefield in 2025, what would you be on the lookout for within the profitable crew?
I might be on the lookout for a founder who, based mostly on who they’re and their lived expertise, has a robust, distinctive perception to an issue that touches tons of of tens of millions of individuals, if no more. Two, I might be on the lookout for one thing that’s non-obvious. You realize, I believe a number of the largest and finest concepts are non-consensus, individuals don’t assume they’re attention-grabbing. Third, I might search for an entrepreneur who’s residing and respiratory 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, you could sit with them and you may prefer it’s palpable, that they are going to work out a technique to succeed. These are the important thing elements that you just search for.
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