It’s been 10 years since Alexa von Tobel offered her monetary planning startup LearnVest to Northwestern Mutual for a reported $375 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 Instances bestelling writer, 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 delivery of her first little one, 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 gained’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 are feeling proudest of?
First, Northwestern Mutual is an unbelievable firm, and our software program grew to become an extremely vital a part of the shopper expertise. And I’m so proud that so most of the LearnVest crew stayed at Northwestern Mutual for therefore lengthy, and it actually was only a merger of precise values. It’s simply superb how easy some issues are, it comes all the way down to the values of two corporations and the missions of two corporations.
I offered on a Wednesday and went into labor with my first little one that weekend. All jokes apart, I all the time say it took me a few yr to mentally simply recuperate from being, like, all programs had been go, my mind was being pushed to handle so many issues. Actually, I used to be having my first little one. It was just like the world threw a bus at me and I caught it.
So whenever you had been closing the deal, was there a ticking clock in your thoughts, that you just needed to end every part earlier than this complete different factor occurs?
In fact. If you concentrate on it, we actually signed on, I feel, 11am on March 25 after which we did a press tour with the CEO, after which the following day, we did a rise up with your complete crew, after which I went to sleep and actually awoke in labor.
Having your first little one is priceless. There’s nothing on the earth that’s extra invaluable to me than having my kids, nothing. And so I stored being like, “We now have to get this accomplished, as a result of I’m not leaving the hospital to return again and shut a deal. I truly have to deal with 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 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 greater than a product. [Northwestern Mutual’s] John Schlifske, he’s not CEO, however he is among the individuals I look as much as most on the earth, only a formidable human being. And he stored being like, “We’re gonna merge the businesses.” And I’d giggle — 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 part and merging it into the broader mum or dad firm. My CTO of LearnVest grew to become the CTO of the mum or dad 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 truly 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 essentially the most inviting time to begin an organization.
And I actually was searching for a capital associate that didn’t exist. I had this imaginative and prescient of what it ought to appear and feel like, this type of rigor and camaraderie and in-the-trenches-ness of what an early stage capital associate might 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 in the future, 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 in the future 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 in all places. 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 associate that you just wished you’d had. How do you place that into observe?
What was I searching for in that capital?
What had been you searching for, 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 period capital. It means once we again a founder, we actually put blinders on for 20 years. While you’re constructing an organization, there’s selections 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 crew’s fairly distinctive in that we’ve constructed and scaled greater than 10 companies which have touched tons of of thousands and thousands of customers world wide. That mentality is so completely different whenever 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 rather a lot, and we respect 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 your complete crew. At many corporations, you get one associate, that’s the individual they know, they know you, and if, God forbid, that associate leaves, it’s such as you’ve evaporated your social fairness that you just constructed up with that associate. 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 in control.
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 a lot of, many, many, many ways in which we can assist corporations get entry to issues which can be actually laborious to get as only a sole founder in your 20s or 30s, the place we are able to truly be an amazing enterprise accelerant to our corporations in a fairly 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 and so they’re like, “Right here’s a giant downside that’s dealing with a billion individuals. Let’s go repair it.”
I feel a number of the largest founders on the earth, 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 [thought], I by no means desire a household to really feel financially destabilized, and I needed to go construct the answer.
After we look again on the broader ecosystem over the past 10 years, one of many massive transitions is forsaking 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 strategy investing at Impressed?
So only a useful framework — Impressed is a full generalist fund. We are going to contact every part from deep tech to well being tech to shopper, searching for the largest, most vital concepts of the following 15 years. Daily, after I come to work, I actually mentally stroll into this workplace in 2035. And that’s how we’re fascinated by the place the world goes and the issues to be solved.
And I feel when ZIRP existed, many issues that I’d say weren’t enterprise bets, would get backed. And I nearly assume it could be complicated, since you’d be like: What classes are usually not enterprise classes? A number of classes are usually not enterprise classes by nature — if you concentrate on energy regulation, every part that we again ideally has an actual likelihood to be price $10 billion. There’s not a number 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 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 feel a number of issues bought funded over the past interval of, like, 2014 to 2021, that ought to’ve been getting a special 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 the moment. Monetary providers 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 earnings inequality, and growing poverty — particularly amongst older People — underscore the necessity for extra adaptive and inclusive monetary instruments. To not point out the speedy job loss because of AI.
This second presents a serious alternative for startups to reimagine monetary merchandise from the bottom up. We consider this wave as fintech 3.0. The following wave of innovation gained’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 handle it.
You launched LearnVest on-stage on the TechCrunch 50 convention in 2009. Should you had been a choose at our Startup Battlefield in 2025, what would you be searching for within the profitable crew?
I’d be searching for a founder who, primarily based on who they’re and their lived expertise, has a strong, distinctive perception to an issue that touches tons of of thousands and thousands of individuals, if no more. Two, I’d be searching for one thing that’s non-obvious. You realize, I feel a number of the largest and greatest concepts are non-consensus, individuals don’t assume they’re fascinating. Third, I’d search for an entrepreneur who’s residing and respiration a decade out. They see this very highly effective future.
And the ultimate factor I’d search for is the founder who has — there’s a spikiness, there’s a grit and resilience, but in addition a command, that you may sit with them and it’s palpable, that they’ll work out a option to succeed. These are the important thing substances that you just search for.
