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 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 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 delivery 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 in all 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 received’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 are feeling proudest of?
First, Northwestern Mutual is an unimaginable firm, and our software program turned an extremely necessary a part of the client 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 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 youngster that weekend. All jokes apart, I all the time say it took me a few 12 months to mentally simply get better from being, like, all techniques have been gomy 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 have been closing the deal, was there a ticking clock in your thoughts, that you just needed to end all the pieces earlier than this complete different factor occurs?
In fact. 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 get up with all the crew, after which I went to sleep and actually awakened in labor.
Having your first youngster is priceless. There’s nothing on the earth that’s extra worthwhile to me than having my youngsters, nothing. And so I stored being like, “Now we have to get this finished, as a result of I’m not leaving the hospital to come back again and shut a deal. I truly must concentrate on this human being that I’m bringing into the world.” I all the time joke that the legal professionals took me very significantly.
When folks on the skin 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 larger than a product. (Northwestern Mutual’s) John Schlifske, he’s now not CEO, however he is likely one of the folks 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 opposite 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 pieces and merging it into the broader dad or mum firm. My CTO of LearnVest turned the CTO of the dad or mum firm.
You stayed for 4 years?
Yeah, (my final 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 all the time at my finest 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 approach — 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 in search of a capital companion 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 companion could possibly 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 someday, I wish to come again and construct that.
Quick ahead to 2018, 2019 I’d began actually actively dreaming about what that would appear to be. And someday 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 every single 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 companion that you just wished you’d had. How do you set that into apply?
What was I in search of in that capital?
What have 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 totally 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. If 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 received’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 lots of of thousands and thousands 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 so much, 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 all the crew. At many companies, 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 all the portfolio, so that everyone’s in control.
After which the ultimate factor, due to (Impressed 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 can assist corporations get entry to issues which might be actually arduous to get as only a sole founder in your 20s or 30s, the place we are able to truly be an incredible enterprise accelerant to our corporations in a reasonably distinctive approach, 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 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 an enormous drawback that’s dealing with a billion folks. Let’s go repair it.”
I believe a few of the greatest 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 used to be like, I by no means need a household to really feel financially destabilized, and I wished 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 way in which you method investing at Impressed?
So only a useful framework — Impressed is a full generalist fund. We’ll contact all the pieces from deep tech to well being tech to client, in search of the largest, most necessary concepts of the subsequent 15 years. Daily, after 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’d 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 lot of classes are usually not enterprise classes by nature — if you concentrate on energy regulation, all the pieces that we again ideally has an actual probability to be price $10 billion. There’s not lots 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 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 lots 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 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 at present. 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 growing poverty — particularly amongst older People — underscore the necessity for extra adaptive and inclusive monetary instruments. To not point out the fast 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 subsequent wave of innovation received’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. When you have been a choose at our Startup Battlefield in 2025, what would you be in search of within the successful crew?
I’d be in search of a founder who, based mostly on who they’re and their lived expertise, has a strong, distinctive perception to an issue that touches lots of of thousands and thousands of individuals, if no more. Two, I’d be in search of one thing that’s non-obvious. You understand, I believe a few of the greatest and finest concepts are non-consensus, folks don’t suppose they’re attention-grabbing. Third, I’d search for an entrepreneur who’s dwelling 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, which you can sit with them and you may prefer it’s palpable, that they’ll determine a method to succeed. These are the important thing components that you just search for.
