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 Instances 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 delivery of her first baby, 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 unimaginable firm, and our software program turned an extremely vital a part of the client expertise. And I’m so proud that so lots of the LearnVest group 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 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 couple of 12 months to mentally simply get better 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 baby. 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 every little thing earlier than this entire 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 your entire group, after which I went to sleep and actually wakened in labor.
Having your first baby is priceless. There’s nothing on this planet that’s extra useful to me than having my kids, nothing. And so I stored being like, “We’ve to get this completed, as a result of I’m not leaving the hospital to come back again and shut a deal. I really must deal with this human being that I’m bringing into the world.” I at all times joke that the legal professionals took me very severely.
When individuals on the skin 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, 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 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 complete digital transformation.
I turned the corporate’s first ever chief digital officer, after which chief innovation officer, and it was actually about taking every little thing and merging it into the broader mother or father firm. My CTO of LearnVest turned the CTO of the mother or father 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 depart, and the place did the concept for Impressed come from?
I’m at all times at my greatest once I’m constructing one thing that I want existed for me. And I’ve mentioned many occasions that the concept for Impressed really occurred once I dropped out of enterprise college, and I used to be a very 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 start out an organization.
And I actually was on the lookout for a capital companion that didn’t exist. I had this imaginative and prescient of what it ought to appear and feel like, this form of rigor and camaraderie and in-the-trenches-ness of what an early stage capital companion may very well be, and I didn’t see it out there. That was New York in 2008, 2009, and I had this long-term plan of in the future, I wish to come again and construct that.
Quick ahead to 2018, 2019 I’d began actually actively dreaming about what that might appear 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 all over the place. And I really feel like I’ve been right here for one minute. It actually is one of the best job I’ve ever had.
You talked about having this concept of a capital companion that you simply wished you’d had. How do you place that into apply?
What was I on the lookout for in that capital?
What had 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 totally different for 4 key causes. The primary motive 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 you need 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, perhaps it pays off in three years, or not?” And what we at all times 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 group’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 around the globe. That mentality is so totally 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 loads, and we recognize the contours. It’s nearly like seeing 3D versus 2D.
The third factor is that our group operates like one unit. So once we again an organization, you really get your entire group. At many corporations, you get one companion, that’s the individual they know, they know you, and if, God forbid, that companion leaves, it’s such as you’ve evaporated your social fairness that you simply constructed up with that companion. We function like a swarm, the place you get all of us and we actively do weekly stand ups on your entire 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 lots of, many, many, many ways in which we can assist corporations get entry to issues which are actually exhausting to get as only a sole founder in your 20s or 30s, the place we will really 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 wished.
I wished 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 reveals up and is like, “Let’s make the world worse,” proper? They present up they usually’re like, “Right here’s an enormous downside that’s dealing with a billion individuals. Let’s go repair it.”
I believe a few 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 [thought], I by no means need a household to really feel financially destabilized, and I wished to go construct the answer.
Once we look again on the broader ecosystem during the last 10 years, one of many massive 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 strategy investing at Impressed?
So only a useful framework — Impressed is a full generalist fund. We’ll contact every little thing from deep tech to well being tech to client, on the lookout for the largest, most vital concepts of the subsequent 15 years. On daily basis, once I come to work, I actually mentally stroll into this workplace in 2035. And that’s how we’re fascinated 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 nearly suppose it could be complicated, since you’d be like: What classes are not enterprise classes? A number of classes should not enterprise classes by nature — if you consider energy regulation, every little thing that we again ideally has an actual likelihood to be value $10 billion. There’s not plenty of these.
I constructed LearnVest on the backside of the worst recession in 81 years, and really LearnVest was not a simple enterprise. It was regulated, there have been so many different issues that had been actually exhausting about what we had been doing. I actually like exhausting companies, as a result of they’ve defensibility. They’ve causes to exist. They’ve much less copycats.
I believe plenty of issues acquired funded during the last interval of, like, 2014 to 2021, that ought to’ve been getting a unique 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 immediately. Monetary companies 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 earnings inequality, and rising poverty — particularly amongst older Individuals — underscore the necessity for extra adaptive and inclusive monetary instruments. To not point out the fast job loss because 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 handle 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 on the lookout for within the profitable group?
I might be on the lookout 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 tens of millions of individuals, if no more. Two, I might be on the lookout for one thing that’s non-obvious. You understand, I believe a few of the largest and greatest concepts are non-consensus, individuals don’t suppose they’re fascinating. Third, I might search for an entrepreneur who’s dwelling 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 in addition a command, that you may sit with them and it’s palpable, that they may work out a method to succeed. These are the important thing substances that you simply search for.
