It’s been 10 years since Alexa von Tobel offered 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 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 start 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 stated 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 stated. “The following wave of innovation gained’t come from superficial tweaks however from basic deep product reinvention — instruments that meet the wants of a altering financial 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’re feeling proudest of?
First, Northwestern Mutual is an unbelievable firm, and our software program grew to become an extremely essential a part of the client expertise. And I’m so proud that so lots of the LearnVest crew stayed at Northwestern Mutual for thus lengthy, and it actually was only a merger of precise values. It’s simply superb how easy some issues are, it comes right 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 at all times say it took me a couple of yr to mentally simply recuperate from being, like, all techniques have 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 if you have 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?
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 rise up with your complete crew, after which I went to sleep and actually awakened in labor.
Having your first little one is priceless. There’s nothing on the planet that’s extra priceless to me than having my kids, nothing. And so I saved 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 have to deal with this human being that I’m bringing into the world.” I at all times joke that the attorneys took me very severely.
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, 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 saved 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 complete 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 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 depart, and the place did the thought 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 stated many occasions that the thought for Impressed really occurred once I dropped out of enterprise college, and I used to be a extremely all-in entrepreneur in each means — 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 searching for a capital companion that didn’t exist. I had this imaginative and prescient of what it ought to feel and look like, this kind of rigor and camaraderie and in-the-trenches-ness of what an early stage capital companion 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 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 would 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 perfect job I’ve ever had.
You talked about having this concept of a capital companion that you just wished you’d had. How do you place that into observe?
What was I searching for in that capital?
What have been you searching for, and the way did you get everybody on the on-board with that imaginative and prescient?
So, once I discuss to entrepreneurs, I at all times say Impressed is totally different for 4 key causes. The primary purpose is that we’re extraordinarily lengthy length capital. It means once we again a founder, we really put blinders on for 20 years. Whenever 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 more durable 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 more durable 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 a whole bunch of hundreds of thousands of customers all over the world. 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 lots, and we recognize the contours. It’s virtually like seeing 3D versus 2D.
The third factor is that our crew operates like one unit. So once we again an organization, you really get your complete crew. 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 just 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 complete portfolio, so that everyone’s on top of things.
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 can assist corporations get entry to issues which can be actually arduous to get as only a sole founder in your 20s or 30s, the place we will really be an amazing enterprise accelerant to our corporations in a reasonably distinctive means, with entry to tech and authorities and plenty of different vectors.
So briefly, 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 and so they’re like, “Right here’s a giant downside that’s dealing with a billion individuals. Let’s go repair it.”
I believe a number of the largest founders on the 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 need a household to really feel financially destabilized, and I wished to go construct the answer.
Once 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 couple of 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 part from deep tech to well being tech to client, searching for the largest, most essential concepts of the subsequent 15 years. Daily, 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 virtually assume it will 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 part 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 straightforward enterprise. It was regulated, there have been so many different issues that have been actually arduous about what we have been doing. I actually like arduous 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 concerning the state of fintech in 2025? The place are there nonetheless alternatives for startups?
I’m feeling each pressing and optimistic concerning the state of fintech in the present day. Monetary companies stay foundational to a functioning society, however they haven’t saved tempo with the fast technological, demographic, and social shifts we’re experiencing. The rising federal debt, rising revenue inequality, and rising poverty — particularly amongst older People — underscore the necessity for extra adaptive and inclusive monetary instruments. To not point out the fast job loss attributable to 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 gained’t come from superficial tweaks however from basic deep product reinvention — instruments that meet the wants of a altering financial 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. If you happen to have been a decide at our Startup Battlefield in 2025, what would you be searching for within the successful crew?
I might be searching for 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 searching for one thing that’s non-obvious. You already know, 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 dwelling 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, that you may sit with them and you’ll prefer it’s palpable, that they may determine a solution to succeed. These are the important thing substances that you just search for.
