January 28, 2025 • 26 mins
At 23, Alexa von Tobel dropped out of Harvard to launch a financial education company, LearnVest, during the Great Recession. She put her life savings into starting the business. Years later, she sold it for $375 Million. This is her story.
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(00:00):
I think we had something like $54,000,000 ofcash.
(00:03):
This is Alexa von Tobel.
At 23, she dropped out of Harvard and founded afinancial education platform, which she sold
for 375,000,000.
Today, I had her at her studio in Manhattan andasked her to teach me her blueprint to become a
successful entrepreneur.
What's one rule you live by that most peopledon't?
It's really simple.
Get up, dress up, show up.
Is one of the most underappreciated assets thata human being can have.
(00:25):
What did you learn during that time on what itactually took to negotiate the multi
$100,000,000?
While I was the head negotiator, I was in areally interesting place.
Also, crazy fact.
Alexa, I wanna start this episode back in theyear 2009.
You're at Morgan Stanley, and all of a sudden,boom.
Lehman Brothers collapses.
(00:47):
The financial world is falling apart, and youdecide to take a massive leap of faith and
start your own company during the greatrecession.
Yep.
Why?
Right now in America, if you have lots ofmoney, it's very easy to get access to
financial advice.
If you have, again, 100 of 1,000, 1,000 ofdollars, people wanna give you advice.
If you don't have that, which by by by juststructure, most young people do not because
(01:10):
they have not had a job yet.
So if you're your age, 18, 19, 20, but even inyour early twenties and and late twenties and
early thirties as a person, you're buildingyour wealth.
And so when you're in that building phase,right now, financial planning is a luxury
product still, and that really pissed me off.
It got under my skin.
I was like, that's unfair.
(01:31):
It's if as if the health care system would onlysee you if you were healthy.
Right?
Let's I mean, think about that.
So in the financial system, you get a lot ofhelp when you're really healthy and have lots
of money.
And when you don't have any money and you can'tafford to make a mistake, you can't get access
to advice.
And I said to myself, this digital revolutionthat we were going through back in 2008 seemed
(01:52):
really obvious to me that, we could democratizeaccess to financial advice.
Learn best ultimately was TurboTax forfinancial planning.
It was extremely accessible, very affordable.
We were open 24 hours, 7 days a week.
And I said, let's go democratize access tothis, and that's what we did.
So now that you launched LearnVest, youmentioned you founded that in 2007.
You moved to New York City, and I heard thatyou started building it out of a Starbucks.
(02:15):
What were the first steps that you're taking tobuild out this platform?
So what's really cool now here in 2024 isthere's so many clear ways to build businesses.
You can go online.
There's literally, like I mean, I got pitchedrecently a tech platform that instantly builds
the business for you.
I mean, it's just such a different world.
Back in 2007, 2008, you know, you barely hadcompanies to be able to easily build, you know,
(02:39):
your business online with a website.
That was its own process.
Finding designers to imagine what the home pagecould look like was its own process.
You know, you can trip over a designer todayor, frankly, use tools like Canva and build
things yourself entirely.
So it it was really hard.
And it's just like, I think, you know, I sortof have a lot of a better understanding of how
(03:01):
people probably felt in 1999 when the Internetwas just coming, and people were like, yo,
building things was hard.
Getting online was hard.
In 2008, you know, there wasn't a lot ofinfrastructure to go after things, so you would
do a lot yourself.
I remember, you know, I'd just taken my 5 yearleave of absence from from Harvard Business
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School, and I remember telling my my bestfriends and family members and boyfriend that I
was like, I am literally I had to understandhow to become a lawyer, a designer.
I'm understanding engineering because I have tounderstand how to turn the website on.
I'm writing my own business plan.
I'm writing our own models.
I did do most jobs myself to be able tounderstand what needed to happen to get
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something online and then go find the rightpeople.
So it was really, really hard.
I remember looking back, you know, I absolutelystarted working at 7 o'clock in the morning,
wouldn't finish until 11, 12 at night mostdays, including the weekends.
I didn't do anything else.
I literally lived and breathed building thisbusiness every day, every minute.
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I had risked everything.
I dropped out of school.
I put in all my own savings, which is, by theway, not a great financial thing to do.
There were no other options.
There are people sitting in the audiencelistening to your story, and they're feeling
something very similar.
They're awake at 7, going to bed at 11, 12o'clock at night, but they're not getting
progress.
They feel this level that they might feelstuck.
(04:23):
They're constantly hustling, grinding, puttingin the grit, but it's not moving forward.
What would be your advice to them on how theycan get unstuck?
I think one of the things I I naturally did wasI wanted to win.
I wanted to be successful.
And so I would go to people that I reallytrusted their advice.
I thought they were smarter than me.
(04:43):
I thought they had better insights than me, andI would go and say, beat up my company.
What am I not getting right?
Why am I stuck?
What's happening?
And I had this simple rule of thumb, which wasgo find 5 of the smartest people around you and
ask them their opinion.
And if 3 or 4 say the same thing, you shouldprobably take that as pretty good advice.
(05:04):
And so, you know, you you don't want anyone toover rotate and, like, learn to only listen to
other people and not trust their own instinctsbecause I think as founders, you need to trust
your own instincts.
Like, you have an inner voice, a reason whyyou're starting.
There's you have a point of view.
So I don't want people to also learn not tolisten to themselves, but you should constantly
have a board of advisers around you of reallysmart people that tell you what you need to
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hear and then go do it.
When you're saying that you want them to beatup your company, what were some of the things
that you were learning from the top 5 smartestpeople that you had conversations with?
I remember really clearly.
I was talking to a really great guy, and I waslike, I'm gonna need to raise money.
And he's like, if someone's smiling at you andnodding and not at the end of it asking for
more information and following up and asking tomeet again, like, they're not giving you money.
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And I just remember such a simple and I waslike he's like, so don't let them waste your
time because they're not giving you money.
So move on.
Go find the people who are gonna give youmoney.
And that was, like, a really I just rememberthat was such a simple insight where it was
like, so ask them who else you should meet andmove on, and, like, don't waste any more time
with the people who are not actively writingchecks and helping give you money.
(06:11):
You know, I was building one of the things Ihad to decide really early was should LearnVest
become a registered investment adviser.
And at first, we heard content, and we wentinto tools, and we were gonna give advice.
And I got compliance people and lawyers, and itwas sort of early for you know, Fintech was in
a category at the time.
There wasn't now it's like Fintech, and you canname 27 companies that are huge big businesses.
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It wasn't a category.
And so building a regulated entity online as,like, a digital kid, was a pretty novel thing
to do.
And so I went and chat to the appropriatelawyers, and they were like, you should become
a reg you should become a registered investmentadviser.
And I said because I was like, I don't ever getin trouble or go to jail.
I wanna do the right thing.
And they said, yeah.
Start there.
And so constantly putting people that werebetter and smarter and more informed around you
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is and and I look for that now with founders.
I look for them every day.
Like, are you hiring people that you don'tdeserve to hire, that are better than you are,
that have more insights, more experience sothat they can fill in your blind spots?
Because, you know, often entrepreneurs areyoung people with big ambition who wanna solve
a problem.
They're an engine.
They're visionary, but you wanna surroundyourself with people who also know how to
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execute.
I wanna play a scenario.
Let's say I'm an investor in that early stagewhen you're building out LearnVest.
You sit down.
We're having a conversation.
What would you say to me to try to get me toinvest in your company?
I mean, I always say actions speak louder thanwords.
I dropped out of Harvard Business School in thebottom of recession in 81 years when it was not
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cool to do.
People truly thought it was insane.
So I'd already put my, like, actual personal Icouldn't afford to lose.
I had literally made an extremely damningdecision to my personal trajectory.
I passed up major jobs that were gonna pay me 3x.
I mean, I was making nothing, so it's reallyeasy to have a job that's paying you more.
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I then taken all my own savings and put it intothe company.
So, again, like, I burned the bridge behind me,and I always say, I like to see people.
There's no plan b.
It's only plan a.
Like, they have to make it work.
And so so those two things are prettycompelling.
And then the third thing that was prettycompelling is I'd written a 75 page business
plan on my own.
No one asked for it about every single thing.
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I was probably more informed than most people,around financial literacy, the future of
finance, the categorization, the demographicsaround individuals and their wallet and what
was gonna happen and what I thought was gonnahappen.
And so I always said I had to be more informedthan anyone else sitting next to me because
that is what was gonna convince somebody that Iwas trustworthy enough to give me, some money.
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And what quickly happened is those three thingswere compelling enough that someone said, I'm a
take a risk on you.
And once that happens, it started to kickdominoes that then turned people to join me,
and this ball started snowballing.
And, you know, that snowball continued for thenext 7 years until we sold the company.
Yeah.
I like your point on plan a and plan b.
(09:11):
I met a founder.
He built out a company called Dandy.
So they're now, I think, a $1,000,000,000dental We're
in a better place.
Yeah.
So Tony Illoko.
And I have graphics with him.
And he asked the waitress, hey.
Could I get avocado toast?
And they're like, I don't think we still haveit.
Is there something else you want me to get you?
He's like, well, can you check?
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And they're like, okay.
Sure.
We'll check.
But is there something else as a backup thatyou want?
And he said, well, let's just stick with theavocado toast.
And if you can't find it, then come back andwe'll go from there.
They ended he ended up getting the avocadotoast.
It was a very small moment, but it it spoke alot to his story that he always will go with
plan a instead of plan b.
To be clear, we're an investor in Tony.
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He is fabulous.
And, we always say we look for founders who arerelentless and very, very demanding.
And those are the people you wanna work for andwork with.
They are gonna be the hardest working.
They're gonna have plan a.
They're gonna make plan a happen.
They're gonna turn the sails to make sure thatyou catch the wind so that plan a happens.
(10:15):
It's what you wanna see in someone who's tryingto change the world.
Elon Musk doesn't take no for an answer.
That's not to say he's perfect.
But if you want someone changing the world,that's a pretty good skill set to have.
Yeah.
Even with Jensen Huang, his employees have saidvery demanding, but you kinda have to be to
build a multitrillion dollar company.
Right?
When you were growing LearnVest, to get yourfirst 50 k sign ups, you started off with these
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financial boot camps.
Yep.
What were they, and how did they take off?
I mean, I literally invented it.
I I was the architect of our product because itwas great.
I was 20 3 when I started the company, 22 whenI 21, 22 when I was really coming up with the
idea.
And so I there I was.
I was like, I am a you know, I had a job atMorgan Stanley on their prop desk.
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I was making real money, and I kept being like,I wanna know what to do with my money.
And I want it to be seamless and obvious, and Iwant I want trusted advice.
I don't want you to sell me products.
And so I said, well, how do we educate 100 ofthousands of people in a short period of time
to trust us with their wallet?
Let's create these boot camps, and the bootcamps can be free.
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And we can get people to come and be dedicatedto 10 day programs online as a way to start
building our brand.
I wrote the content.
That's why I became a certified financialplanner.
I said, I can't teach this if I'm not literallya world class expert.
They weren't a product that even existed.
It was a 10 day program.
You would get an email in your inbox.
It would pull you back into the website.
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You would then finish the quizzes and the testsand the interaction to the forum of really
making sure that you understood importantconcepts.
And what was crazy at that time, and this wasliterally our first product that we launched,
we were content, tools, and then advice.
So content was the boot camps.
The tools became sort of our mint likemint.com, which is no longer existing, but you
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could link all your accounts, see all yourmoney.
And then we just connected experts there tothen start helping give you advice, and so we
built them in sync.
You know, first was the content, then thetools, then the advice.
And so the 1st boot camp, we started partneringwith magazines, like Real Simple and other
places where I kind of intuitively was like, Ithink people who probably really like Real
Simple like to be organized, so they probablywanna be organized on their money.
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Let's see.
And we got covered in a few places, and,literally, tens of thousands of people started
coming and signing up for LearnVest and tellingtheir friends about it.
And it was just a very different time.
We didn't pay for users.
We didn't acquire users through marketing andspend and anything.
It was all word-of-mouth.
But pretty quickly, when you start having tensof 1,000, 20,000 at a time, human beings
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saying, I wanna go through this program andthen showing up and loving it, I was pretty
clear that there were more people like me inthe world who wanted really good trusted advice
for their wallet who were young.
You became a world class expert online creatingcontent.
What do you think that says about theimportance of becoming an expert in your
industry through content online to be able tobuild out a b to b business?
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It was truly just like a very simple strategyof like, okay.
How do we find people?
And I was like, well, we gotta create content.
And where should the content go?
It should go where people are spending time,which at that time was, like, magazines and
content sites.
And, so we literally started creating 50articles a week that we would share all across
the Internet to bring people back to learn bestto then create an account and know that we
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could be a home where you could come start tomanage your finances.
And so it was really scrappy.
I wrote a book the weeks before my wedding.
Like, that's a crazy thing to do if you're,like, a bride to be.
Like, I was a different version of abridessela.
Like, I was like, I gotta go write a book.
So that's what I'm gonna focus on.
And I think that just gives you a sense of,like, we didn't there weren't playbooks.
We were inventing our own playbooks of how dowe get out there so that people know about
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LearnVest and can come and manage theirfinances.
So what if you're out there building a companyright now, think about things other people
aren't doing.
That's what I would say.
It's like we did things no one else was doing,to find really smart ways to go find customers
that authentically would like us and gravitatetowards us.
And how were you able to rapidly gain marketshare against incumbents like Charles Schwab
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who had, like, the trust and and brandalignment and the moat and the experience?
Yeah.
It was sort of an unfair advantage, which isthat they couldn't easily create content, for a
bunch of reasons.
The first is they were trying to sell youproducts, and so it's really hard to trust
their advice because it's not unbiased.
We didn't sell products, and that was sort ofour unfair advantage, which is we we literally
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said, just advice.
That's it.
Like, that's what we're here for, and it madeus, like, a very neutral party.
And so, actually, we got those types ofcompanies to start taking our content.
And so, we had partnerships early with TDAmeritrade and, Fidelity and, many, many other
sites because they were like, we'll take yourcontent because it's more trusted than us.
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And so it became a really trusted brand inpersonal finance content.
It is a very different switch when you'refocused on helping and not selling.
That's right.
It it's actually it is, being authenticallysomeone's teammate is a very good way to do
business.
And I look back, and I think one of the thingsI'm most proud of is we built millions of users
without spending.
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We never had huge marketing spend.
We used a lot of partnerships, and, we thoughtabout other brands that we thought were really
good brands for ours at the time, lululemon.
Like, young people loved lululemon.
So we were like, let's do things with them.
Like, we truly thought about brands that wewere like, let's figure out if they'd partner
with us and do something smart.
And, punchline, they were they also wanted toget in front of smart people.
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So we just used we hacked it all.
And fast forwarding a few years, NorthwesternMutual approaches you and wants to acquire the
company.
Yep.
How did that happen, and what were some of theconversations that were taking place behind the
scenes?
They'd come to us.
We'd not approached them.
They had actually emailed us and said, hey.
We really would like to invest and learn more.
And so very quickly, I started realizing thatour bet on building something for the masses
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that didn't exist, prioritizing everydaypeople, it was scale of the country, was a
really good thing to do.
And so North Russian Mutual emailed us a fewtimes, and finally, we I took the meeting, and
they invested and and stayed close to us, andthe rest was history.
What did you learn during that time on what itactually took to negotiate a multi $100,000,000
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deal?
Well, I was the head negotiator at the age of29, 30.
I was authentically doing it the way only way Iknew how, which is being myself.
And so, yeah, I mean, it was, it wascomplicated with a few, potential parties who
had sort of come around, and I'd just raisedcapital, so we did not need, this number's
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directionally.
Right?
I think we had, like, something like$54,000,000 of cash, which is a lot of money
back then.
Like, that I mean, today, like, some some, youknow, coming out of the 2021, 2022 window, that
was we we barely used even the capital, butbecause we were so scrappy and frugal.
So we also didn't need to sell.
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So it kinda gave us a really interesting I wasin a really interesting place.
Also, crazy fact, I was also 9 months pregnant.
I sold our company on a Wednesday and had ourdaughter, Toby, that weekend.
So that's also pretty
unusual.
Crazy.
Yeah.
It was like, I always joke there's pretty goodnegotiating leverage because I truly was like,
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I have to either we get this done before I havethis baby or not, but, like, I am not gonna, I
can't pick up the phone, you know, in thehospital.
Yeah.
It reminds me.
So I'm interviewing Ankur Nagpal from Teachablelater today, and his business got acquired for,
I think, 250,000,000.
He had a acquire approach to them as well, andthey didn't need to acquire.
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They didn't need to sell.
They weren't looking to sell at all.
They actually weren't even interested inselling the business.
But that did give them a lot of leverage to thepoint where I think there were 4 months in
negotiation.
And he's just like, hey, I'm not going to keepflying back and forth from New York to Brazil
or or or New York, to to your offices.
Let's just close this over 4 days.
We'll just bang it out if you really wannaclose it.
(18:24):
Otherwise, we're not gonna go through.
They closed the deal in, like, 4 days becausethey had to leverage because they they had it.
I mean, I think the the thing I tell foundersevery day is you can never sell a company if
you're trying to a company.
Yeah.
Build a company that you'd want to own forever.
Right?
And not
That's the only way to build something.
And I would have been per perfectly happy notselling LearnVest.
Northwestern Mutual, the acquirer, wasactually, your dad's life insurance policy
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when, he passed away when you were younger.
What did it mean for them to be the ones thatacquired
the business?
Well so I hadn't told anybody that.
And, actually, it kinda gives you a sense of,who I am, which is I had lost my dad
unexpectedly when I was 14, and I remember tothis I mean, I'll never forget it, when my mom
(19:12):
realized he'd bought a great life insurancepolicy that was gonna really protect my family.
And so, one, we didn't need to sell.
I just said it re really clearly.
We had tons of cash.
But I actually knew firsthand what it meant tobe a policyholder when a crisis happened.
And, also, as a financial planner,predominantly one of the biggest things you do
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for your clients is you plan for a crisisbecause real crises can happen.
You can get sick.
You can get cancer.
Someone can die unexpectedly.
You can lose 2 jobs unexpectedly, and familiesget really crunched.
So it was a pretty beautiful moment, which is Iwaited until after we signed all the documents,
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and the board sent me the video, approving andsigning.
And then our board approved, and I signed.
And, they asked me to send a quick video abouthow I felt, and that was actually when I told
them, that I had been a firsthand recipient ofa policy and that that's why I was agreeing to
sell my first baby, my you know, LearnVest, myfirst solely founded company, to them because I
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felt that, if we could take our software andhelp tens of millions of more people,
understand the need to plan and have insurancewhen they need it, that that would be a really
proud thing for me to do.
And so it absolutely felt like it was it wasright.
And, you know, for me, I always said your jobas CEO is actually not to do what's in your
best interest.
(20:41):
It is factually, fiduciarily to do what's inthe best interest of all shareholders, all
employees, all customers, and then finally, allinvestors.
And when I finally have the space, which was,you know, after all was said and done to make
my own decision, the decision had made itself.
(21:02):
It was the right thing for for for me to do.
And when the wire finally hit the account, howdid that feel for you?
It's funny.
Obviously, you know, as a young person, havinglife changing wealth hit your bank account is a
is a is a great moment.
But it's funny.
That that wasn't even, the moment I actuallyfeel like.
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It was the moment where, I got to tell theentire team that, like, our work had been, so
meaningful and valued and valued by others.
It was amazing.
The CEO, whose name is John Slitsky, who's anincredible person and actually to this day,
probably one of the best mentors, I've had.
(21:43):
We got to go tell press together, and we wenton I mean, I was literally 9 months pregnant.
I looked like I was gonna go into labor thatday.
We went and told 10 outlets about what we weregonna do teaming up.
Those are the sort of things that were prettypretty for me, it was when I got to tell my own
family.
Those were the the moments that I thought weremore special.
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The last thing I'll say is it was the emails Iactually got from the team where they told me
what the equity value of what we just createdwould do for their kids and their family.
And as a nerdy financial planner who doesn'tneed a lot of money to be happy, that is quite
literally how I am wired.
You don't become a financial planner to hoardmoney.
(22:26):
You plan in in those types of things.
It really was just watching all all of theincredible good that we could do.
That was that was awesome.
And, also, really awesome, my husband and I,like, would celebrate those moments together.
It was really exceptional.
And before we wrap it up, have a few closingquestions.
Sure.
1st, what's the best piece of advice you'veever received?
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Surround yourself with people who are gonnatell you what you need to hear, not what you
wanna hear.
What's one rule you live by that most peopledon't?
Get up, dress up, show up.
It's really simple.
Get up early.
I'm a early riser.
I've always been my whole life.
I I get out of bed with, like, a spring in mystep and ready to tackle the day.
Get up, dress up, get dressed, get dressed sothat you feel your best, and show up with a
(23:12):
positive attitude.
And I think if you, like if you think about it,it's really simple mantra, but, like, get up
early, outwork people.
Like, dress up.
Like, put yourself together.
Feel your best.
Do whatever that means for you, and then, showup for people.
Show up for yourself.
Show up for the people you love.
I'm a huge fan.
My best friends will tell you, like, I believein showing up for people, particularly in their
(23:35):
tough moments, and then show up for yourself.
And positivity is, I think, one of the mostunderappreciated assets that a human being can
have.
People are attracted to people who are verypositive and who wanna do things and believe in
things and will things into existence, and Ithink your best founders are people who will
things into existence.
And if I slid you over a phone and you couldcall your 20 year old self, would you call?
(23:59):
And if so, what would you say?
I absolutely would.
I would remind her what she was already good atand just, which is don't follow the pack.
I've always been comfortable not following thepack.
And I have 3 little kids, and we teach them notto follow the pack.
And probably the thing I was most proud of isyesterday, my son, who's 6, the teacher showed
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a screenshot of every kid and what theirpredictions were, and he was the only one with
a weird prediction.
And he was alone.
And I took a screenshot of it, and I'm like,don't follow the path.
You don't get anywhere in life following thepath.
You gotta chart your own path.
And so I would tell 10 year old Alexa, 15 yearold Alexa, 20 year old Alexa, like, trust your
instincts.
Keep doing what you're doing.
I don't need people to understand me orappreciate me.
(24:44):
Like, I I'm comfortable following my own path.
You secured a $330,000,000 fund for fund 3 forinspired.
What's your goal with with the capital?
What what do you wanna do?
Yes.
So first, we wanna meet founders who are readyto absolutely go and powerfully change the
future.
We're generalist fund.
We back any and every big idea.
(25:04):
We're looking for people.
I wanna see people dream crazily big, crazilybig.
Not a little bit.
Don't give me incrementality.
Give me epically big innovation going aftersome of the world's biggest problems.
And sitting here on the morning after anelection, all I can say is we got a lot of work
to do as a society, sort of free from politics.
Like, we've got a lot of work to do to makethis country, what we know we should and be,
(25:30):
thriving as a global leader.
And so I want people with huge ideas, crazyideas, solving some of the biggest problems
facing the future of wealth and health andsociety and technology and AI to come show up
and let us give you capital and swing big.
I noticed that some of the best founders andmost successful in the world founders in the
(25:52):
world have a crazy amount of delusion, but alsocrazy amount of ambition.
I met with this 17 year old kid who I justinterviewed who runs an app that makes
$1,000,000 a month.
He was just featured on Forbes.
And I asked him, like, what's your long termgoal?
Like, what do you wanna be?
And he said to my face, I wanna be the nextElon Musk.
I was like, yeah.
(26:12):
You're gonna go far.
Yeah.
I mean, you want people I always tell people ifsomeone's like, I'd love to be a lawyer.
I'm like, why not be a supreme court justice?
Like, if you whatever you wanna do, swing to bethe best at it in the world.
Not not I always say it inspired we are nothere to run the marathon.
We're here to win the marathon.
There's very different levels of training thatgo into something if you're there to be number
(26:34):
1, not number 100.
And I think that's you only get to live once.
This is in the dress rehearsal.
So show up for yourself and swing big.
Awesome.
Well, I think that's a great way to end it.
Thanks, Alexa, for taking the time to join theshow.
We'll have a link to Inspired Capital in theepisode description down below if any founders
interested are checking it out.
Well, thanks, Alexa.
Appreciate it.
For having me.
You're awesome.
I think we had something like $54,000,000 ofcash.
(00:03):
This is Alexa von Tobel.
At 23, she dropped out of Harvard and founded afinancial education platform, which she sold
for 375,000,000.
Today, I had her at her studio in Manhattan andasked her to teach me her blueprint to become a
successful entrepreneur.
What's one rule you live by that most peopledon't?
It's really simple.
Get up, dress up, show up.
Is one of the most underappreciated assets thata human being can have.
(00:25):
What did you learn during that time on what itactually took to negotiate the multi
$100,000,000?
While I was the head negotiator, I was in areally interesting place.
Also, crazy fact.
Alexa, I wanna start this episode back in theyear 2009.
You're at Morgan Stanley, and all of a sudden,boom.
Lehman Brothers collapses.
(00:47):
The financial world is falling apart, and youdecide to take a massive leap of faith and
start your own company during the greatrecession.
Yep.
Why?
Right now in America, if you have lots ofmoney, it's very easy to get access to
financial advice.
If you have, again, 100 of 1,000, 1,000 ofdollars, people wanna give you advice.
If you don't have that, which by by by juststructure, most young people do not because
(01:10):
they have not had a job yet.
So if you're your age, 18, 19, 20, but even inyour early twenties and and late twenties and
early thirties as a person, you're buildingyour wealth.
And so when you're in that building phase,right now, financial planning is a luxury
product still, and that really pissed me off.
It got under my skin.
I was like, that's unfair.
(01:31):
It's if as if the health care system would onlysee you if you were healthy.
Right?
Let's I mean, think about that.
So in the financial system, you get a lot ofhelp when you're really healthy and have lots
of money.
And when you don't have any money and you can'tafford to make a mistake, you can't get access
to advice.
And I said to myself, this digital revolutionthat we were going through back in 2008 seemed
(01:52):
really obvious to me that, we could democratizeaccess to financial advice.
Learn best ultimately was TurboTax forfinancial planning.
It was extremely accessible, very affordable.
We were open 24 hours, 7 days a week.
And I said, let's go democratize access tothis, and that's what we did.
So now that you launched LearnVest, youmentioned you founded that in 2007.
You moved to New York City, and I heard thatyou started building it out of a Starbucks.
(02:15):
What were the first steps that you're taking tobuild out this platform?
So what's really cool now here in 2024 isthere's so many clear ways to build businesses.
You can go online.
There's literally, like I mean, I got pitchedrecently a tech platform that instantly builds
the business for you.
I mean, it's just such a different world.
Back in 2007, 2008, you know, you barely hadcompanies to be able to easily build, you know,
(02:39):
your business online with a website.
That was its own process.
Finding designers to imagine what the home pagecould look like was its own process.
You know, you can trip over a designer todayor, frankly, use tools like Canva and build
things yourself entirely.
So it it was really hard.
And it's just like, I think, you know, I sortof have a lot of a better understanding of how
(03:01):
people probably felt in 1999 when the Internetwas just coming, and people were like, yo,
building things was hard.
Getting online was hard.
In 2008, you know, there wasn't a lot ofinfrastructure to go after things, so you would
do a lot yourself.
I remember, you know, I'd just taken my 5 yearleave of absence from from Harvard Business
(03:21):
School, and I remember telling my my bestfriends and family members and boyfriend that I
was like, I am literally I had to understandhow to become a lawyer, a designer.
I'm understanding engineering because I have tounderstand how to turn the website on.
I'm writing my own business plan.
I'm writing our own models.
I did do most jobs myself to be able tounderstand what needed to happen to get
(03:41):
something online and then go find the rightpeople.
So it was really, really hard.
I remember looking back, you know, I absolutelystarted working at 7 o'clock in the morning,
wouldn't finish until 11, 12 at night mostdays, including the weekends.
I didn't do anything else.
I literally lived and breathed building thisbusiness every day, every minute.
(04:03):
I had risked everything.
I dropped out of school.
I put in all my own savings, which is, by theway, not a great financial thing to do.
There were no other options.
There are people sitting in the audiencelistening to your story, and they're feeling
something very similar.
They're awake at 7, going to bed at 11, 12o'clock at night, but they're not getting
progress.
They feel this level that they might feelstuck.
(04:23):
They're constantly hustling, grinding, puttingin the grit, but it's not moving forward.
What would be your advice to them on how theycan get unstuck?
I think one of the things I I naturally did wasI wanted to win.
I wanted to be successful.
And so I would go to people that I reallytrusted their advice.
I thought they were smarter than me.
(04:43):
I thought they had better insights than me, andI would go and say, beat up my company.
What am I not getting right?
Why am I stuck?
What's happening?
And I had this simple rule of thumb, which wasgo find 5 of the smartest people around you and
ask them their opinion.
And if 3 or 4 say the same thing, you shouldprobably take that as pretty good advice.
(05:04):
And so, you know, you you don't want anyone toover rotate and, like, learn to only listen to
other people and not trust their own instinctsbecause I think as founders, you need to trust
your own instincts.
Like, you have an inner voice, a reason whyyou're starting.
There's you have a point of view.
So I don't want people to also learn not tolisten to themselves, but you should constantly
have a board of advisers around you of reallysmart people that tell you what you need to
(05:27):
hear and then go do it.
When you're saying that you want them to beatup your company, what were some of the things
that you were learning from the top 5 smartestpeople that you had conversations with?
I remember really clearly.
I was talking to a really great guy, and I waslike, I'm gonna need to raise money.
And he's like, if someone's smiling at you andnodding and not at the end of it asking for
more information and following up and asking tomeet again, like, they're not giving you money.
(05:50):
And I just remember such a simple and I waslike he's like, so don't let them waste your
time because they're not giving you money.
So move on.
Go find the people who are gonna give youmoney.
And that was, like, a really I just rememberthat was such a simple insight where it was
like, so ask them who else you should meet andmove on, and, like, don't waste any more time
with the people who are not actively writingchecks and helping give you money.
(06:11):
You know, I was building one of the things Ihad to decide really early was should LearnVest
become a registered investment adviser.
And at first, we heard content, and we wentinto tools, and we were gonna give advice.
And I got compliance people and lawyers, and itwas sort of early for you know, Fintech was in
a category at the time.
There wasn't now it's like Fintech, and you canname 27 companies that are huge big businesses.
(06:35):
It wasn't a category.
And so building a regulated entity online as,like, a digital kid, was a pretty novel thing
to do.
And so I went and chat to the appropriatelawyers, and they were like, you should become
a reg you should become a registered investmentadviser.
And I said because I was like, I don't ever getin trouble or go to jail.
I wanna do the right thing.
And they said, yeah.
Start there.
And so constantly putting people that werebetter and smarter and more informed around you
(06:59):
is and and I look for that now with founders.
I look for them every day.
Like, are you hiring people that you don'tdeserve to hire, that are better than you are,
that have more insights, more experience sothat they can fill in your blind spots?
Because, you know, often entrepreneurs areyoung people with big ambition who wanna solve
a problem.
They're an engine.
They're visionary, but you wanna surroundyourself with people who also know how to
(07:22):
execute.
I wanna play a scenario.
Let's say I'm an investor in that early stagewhen you're building out LearnVest.
You sit down.
We're having a conversation.
What would you say to me to try to get me toinvest in your company?
I mean, I always say actions speak louder thanwords.
I dropped out of Harvard Business School in thebottom of recession in 81 years when it was not
(07:44):
cool to do.
People truly thought it was insane.
So I'd already put my, like, actual personal Icouldn't afford to lose.
I had literally made an extremely damningdecision to my personal trajectory.
I passed up major jobs that were gonna pay me 3x.
I mean, I was making nothing, so it's reallyeasy to have a job that's paying you more.
(08:06):
I then taken all my own savings and put it intothe company.
So, again, like, I burned the bridge behind me,and I always say, I like to see people.
There's no plan b.
It's only plan a.
Like, they have to make it work.
And so so those two things are prettycompelling.
And then the third thing that was prettycompelling is I'd written a 75 page business
plan on my own.
No one asked for it about every single thing.
(08:27):
I was probably more informed than most people,around financial literacy, the future of
finance, the categorization, the demographicsaround individuals and their wallet and what
was gonna happen and what I thought was gonnahappen.
And so I always said I had to be more informedthan anyone else sitting next to me because
that is what was gonna convince somebody that Iwas trustworthy enough to give me, some money.
(08:49):
And what quickly happened is those three thingswere compelling enough that someone said, I'm a
take a risk on you.
And once that happens, it started to kickdominoes that then turned people to join me,
and this ball started snowballing.
And, you know, that snowball continued for thenext 7 years until we sold the company.
Yeah.
I like your point on plan a and plan b.
(09:11):
I met a founder.
He built out a company called Dandy.
So they're now, I think, a $1,000,000,000dental We're
in a better place.
Yeah.
So Tony Illoko.
And I have graphics with him.
And he asked the waitress, hey.
Could I get avocado toast?
And they're like, I don't think we still haveit.
Is there something else you want me to get you?
He's like, well, can you check?
(09:31):
And they're like, okay.
Sure.
We'll check.
But is there something else as a backup thatyou want?
And he said, well, let's just stick with theavocado toast.
And if you can't find it, then come back andwe'll go from there.
They ended he ended up getting the avocadotoast.
It was a very small moment, but it it spoke alot to his story that he always will go with
plan a instead of plan b.
To be clear, we're an investor in Tony.
(09:53):
He is fabulous.
And, we always say we look for founders who arerelentless and very, very demanding.
And those are the people you wanna work for andwork with.
They are gonna be the hardest working.
They're gonna have plan a.
They're gonna make plan a happen.
They're gonna turn the sails to make sure thatyou catch the wind so that plan a happens.
(10:15):
It's what you wanna see in someone who's tryingto change the world.
Elon Musk doesn't take no for an answer.
That's not to say he's perfect.
But if you want someone changing the world,that's a pretty good skill set to have.
Yeah.
Even with Jensen Huang, his employees have saidvery demanding, but you kinda have to be to
build a multitrillion dollar company.
Right?
When you were growing LearnVest, to get yourfirst 50 k sign ups, you started off with these
(10:36):
financial boot camps.
Yep.
What were they, and how did they take off?
I mean, I literally invented it.
I I was the architect of our product because itwas great.
I was 20 3 when I started the company, 22 whenI 21, 22 when I was really coming up with the
idea.
And so I there I was.
I was like, I am a you know, I had a job atMorgan Stanley on their prop desk.
(10:57):
I was making real money, and I kept being like,I wanna know what to do with my money.
And I want it to be seamless and obvious, and Iwant I want trusted advice.
I don't want you to sell me products.
And so I said, well, how do we educate 100 ofthousands of people in a short period of time
to trust us with their wallet?
Let's create these boot camps, and the bootcamps can be free.
(11:19):
And we can get people to come and be dedicatedto 10 day programs online as a way to start
building our brand.
I wrote the content.
That's why I became a certified financialplanner.
I said, I can't teach this if I'm not literallya world class expert.
They weren't a product that even existed.
It was a 10 day program.
You would get an email in your inbox.
It would pull you back into the website.
(11:39):
You would then finish the quizzes and the testsand the interaction to the forum of really
making sure that you understood importantconcepts.
And what was crazy at that time, and this wasliterally our first product that we launched,
we were content, tools, and then advice.
So content was the boot camps.
The tools became sort of our mint likemint.com, which is no longer existing, but you
(12:00):
could link all your accounts, see all yourmoney.
And then we just connected experts there tothen start helping give you advice, and so we
built them in sync.
You know, first was the content, then thetools, then the advice.
And so the 1st boot camp, we started partneringwith magazines, like Real Simple and other
places where I kind of intuitively was like, Ithink people who probably really like Real
Simple like to be organized, so they probablywanna be organized on their money.
(12:23):
Let's see.
And we got covered in a few places, and,literally, tens of thousands of people started
coming and signing up for LearnVest and tellingtheir friends about it.
And it was just a very different time.
We didn't pay for users.
We didn't acquire users through marketing andspend and anything.
It was all word-of-mouth.
But pretty quickly, when you start having tensof 1,000, 20,000 at a time, human beings
(12:48):
saying, I wanna go through this program andthen showing up and loving it, I was pretty
clear that there were more people like me inthe world who wanted really good trusted advice
for their wallet who were young.
You became a world class expert online creatingcontent.
What do you think that says about theimportance of becoming an expert in your
industry through content online to be able tobuild out a b to b business?
(13:13):
It was truly just like a very simple strategyof like, okay.
How do we find people?
And I was like, well, we gotta create content.
And where should the content go?
It should go where people are spending time,which at that time was, like, magazines and
content sites.
And, so we literally started creating 50articles a week that we would share all across
the Internet to bring people back to learn bestto then create an account and know that we
(13:35):
could be a home where you could come start tomanage your finances.
And so it was really scrappy.
I wrote a book the weeks before my wedding.
Like, that's a crazy thing to do if you're,like, a bride to be.
Like, I was a different version of abridessela.
Like, I was like, I gotta go write a book.
So that's what I'm gonna focus on.
And I think that just gives you a sense of,like, we didn't there weren't playbooks.
We were inventing our own playbooks of how dowe get out there so that people know about
(13:59):
LearnVest and can come and manage theirfinances.
So what if you're out there building a companyright now, think about things other people
aren't doing.
That's what I would say.
It's like we did things no one else was doing,to find really smart ways to go find customers
that authentically would like us and gravitatetowards us.
And how were you able to rapidly gain marketshare against incumbents like Charles Schwab
(14:21):
who had, like, the trust and and brandalignment and the moat and the experience?
Yeah.
It was sort of an unfair advantage, which isthat they couldn't easily create content, for a
bunch of reasons.
The first is they were trying to sell youproducts, and so it's really hard to trust
their advice because it's not unbiased.
We didn't sell products, and that was sort ofour unfair advantage, which is we we literally
(14:42):
said, just advice.
That's it.
Like, that's what we're here for, and it madeus, like, a very neutral party.
And so, actually, we got those types ofcompanies to start taking our content.
And so, we had partnerships early with TDAmeritrade and, Fidelity and, many, many other
sites because they were like, we'll take yourcontent because it's more trusted than us.
(15:05):
And so it became a really trusted brand inpersonal finance content.
It is a very different switch when you'refocused on helping and not selling.
That's right.
It it's actually it is, being authenticallysomeone's teammate is a very good way to do
business.
And I look back, and I think one of the thingsI'm most proud of is we built millions of users
without spending.
(15:26):
We never had huge marketing spend.
We used a lot of partnerships, and, we thoughtabout other brands that we thought were really
good brands for ours at the time, lululemon.
Like, young people loved lululemon.
So we were like, let's do things with them.
Like, we truly thought about brands that wewere like, let's figure out if they'd partner
with us and do something smart.
And, punchline, they were they also wanted toget in front of smart people.
(15:47):
So we just used we hacked it all.
And fast forwarding a few years, NorthwesternMutual approaches you and wants to acquire the
company.
Yep.
How did that happen, and what were some of theconversations that were taking place behind the
scenes?
They'd come to us.
We'd not approached them.
They had actually emailed us and said, hey.
We really would like to invest and learn more.
And so very quickly, I started realizing thatour bet on building something for the masses
(16:10):
that didn't exist, prioritizing everydaypeople, it was scale of the country, was a
really good thing to do.
And so North Russian Mutual emailed us a fewtimes, and finally, we I took the meeting, and
they invested and and stayed close to us, andthe rest was history.
What did you learn during that time on what itactually took to negotiate a multi $100,000,000
(16:33):
deal?
Well, I was the head negotiator at the age of29, 30.
I was authentically doing it the way only way Iknew how, which is being myself.
And so, yeah, I mean, it was, it wascomplicated with a few, potential parties who
had sort of come around, and I'd just raisedcapital, so we did not need, this number's
(16:57):
directionally.
Right?
I think we had, like, something like$54,000,000 of cash, which is a lot of money
back then.
Like, that I mean, today, like, some some, youknow, coming out of the 2021, 2022 window, that
was we we barely used even the capital, butbecause we were so scrappy and frugal.
So we also didn't need to sell.
(17:18):
So it kinda gave us a really interesting I wasin a really interesting place.
Also, crazy fact, I was also 9 months pregnant.
I sold our company on a Wednesday and had ourdaughter, Toby, that weekend.
So that's also pretty
unusual.
Crazy.
Yeah.
It was like, I always joke there's pretty goodnegotiating leverage because I truly was like,
(17:39):
I have to either we get this done before I havethis baby or not, but, like, I am not gonna, I
can't pick up the phone, you know, in thehospital.
Yeah.
It reminds me.
So I'm interviewing Ankur Nagpal from Teachablelater today, and his business got acquired for,
I think, 250,000,000.
He had a acquire approach to them as well, andthey didn't need to acquire.
(18:03):
They didn't need to sell.
They weren't looking to sell at all.
They actually weren't even interested inselling the business.
But that did give them a lot of leverage to thepoint where I think there were 4 months in
negotiation.
And he's just like, hey, I'm not going to keepflying back and forth from New York to Brazil
or or or New York, to to your offices.
Let's just close this over 4 days.
We'll just bang it out if you really wannaclose it.
(18:24):
Otherwise, we're not gonna go through.
They closed the deal in, like, 4 days becausethey had to leverage because they they had it.
I mean, I think the the thing I tell foundersevery day is you can never sell a company if
you're trying to a company.
Yeah.
Build a company that you'd want to own forever.
Right?
And not
That's the only way to build something.
And I would have been per perfectly happy notselling LearnVest.
Northwestern Mutual, the acquirer, wasactually, your dad's life insurance policy
(18:50):
when, he passed away when you were younger.
What did it mean for them to be the ones thatacquired
the business?
Well so I hadn't told anybody that.
And, actually, it kinda gives you a sense of,who I am, which is I had lost my dad
unexpectedly when I was 14, and I remember tothis I mean, I'll never forget it, when my mom
(19:12):
realized he'd bought a great life insurancepolicy that was gonna really protect my family.
And so, one, we didn't need to sell.
I just said it re really clearly.
We had tons of cash.
But I actually knew firsthand what it meant tobe a policyholder when a crisis happened.
And, also, as a financial planner,predominantly one of the biggest things you do
(19:35):
for your clients is you plan for a crisisbecause real crises can happen.
You can get sick.
You can get cancer.
Someone can die unexpectedly.
You can lose 2 jobs unexpectedly, and familiesget really crunched.
So it was a pretty beautiful moment, which is Iwaited until after we signed all the documents,
(19:57):
and the board sent me the video, approving andsigning.
And then our board approved, and I signed.
And, they asked me to send a quick video abouthow I felt, and that was actually when I told
them, that I had been a firsthand recipient ofa policy and that that's why I was agreeing to
sell my first baby, my you know, LearnVest, myfirst solely founded company, to them because I
(20:21):
felt that, if we could take our software andhelp tens of millions of more people,
understand the need to plan and have insurancewhen they need it, that that would be a really
proud thing for me to do.
And so it absolutely felt like it was it wasright.
And, you know, for me, I always said your jobas CEO is actually not to do what's in your
best interest.
(20:41):
It is factually, fiduciarily to do what's inthe best interest of all shareholders, all
employees, all customers, and then finally, allinvestors.
And when I finally have the space, which was,you know, after all was said and done to make
my own decision, the decision had made itself.
(21:02):
It was the right thing for for for me to do.
And when the wire finally hit the account, howdid that feel for you?
It's funny.
Obviously, you know, as a young person, havinglife changing wealth hit your bank account is a
is a is a great moment.
But it's funny.
That that wasn't even, the moment I actuallyfeel like.
(21:22):
It was the moment where, I got to tell theentire team that, like, our work had been, so
meaningful and valued and valued by others.
It was amazing.
The CEO, whose name is John Slitsky, who's anincredible person and actually to this day,
probably one of the best mentors, I've had.
(21:43):
We got to go tell press together, and we wenton I mean, I was literally 9 months pregnant.
I looked like I was gonna go into labor thatday.
We went and told 10 outlets about what we weregonna do teaming up.
Those are the sort of things that were prettypretty for me, it was when I got to tell my own
family.
Those were the the moments that I thought weremore special.
(22:05):
The last thing I'll say is it was the emails Iactually got from the team where they told me
what the equity value of what we just createdwould do for their kids and their family.
And as a nerdy financial planner who doesn'tneed a lot of money to be happy, that is quite
literally how I am wired.
You don't become a financial planner to hoardmoney.
(22:26):
You plan in in those types of things.
It really was just watching all all of theincredible good that we could do.
That was that was awesome.
And, also, really awesome, my husband and I,like, would celebrate those moments together.
It was really exceptional.
And before we wrap it up, have a few closingquestions.
Sure.
1st, what's the best piece of advice you'veever received?
(22:49):
Surround yourself with people who are gonnatell you what you need to hear, not what you
wanna hear.
What's one rule you live by that most peopledon't?
Get up, dress up, show up.
It's really simple.
Get up early.
I'm a early riser.
I've always been my whole life.
I I get out of bed with, like, a spring in mystep and ready to tackle the day.
Get up, dress up, get dressed, get dressed sothat you feel your best, and show up with a
(23:12):
positive attitude.
And I think if you, like if you think about it,it's really simple mantra, but, like, get up
early, outwork people.
Like, dress up.
Like, put yourself together.
Feel your best.
Do whatever that means for you, and then, showup for people.
Show up for yourself.
Show up for the people you love.
I'm a huge fan.
My best friends will tell you, like, I believein showing up for people, particularly in their
(23:35):
tough moments, and then show up for yourself.
And positivity is, I think, one of the mostunderappreciated assets that a human being can
have.
People are attracted to people who are verypositive and who wanna do things and believe in
things and will things into existence, and Ithink your best founders are people who will
things into existence.
And if I slid you over a phone and you couldcall your 20 year old self, would you call?
(23:59):
And if so, what would you say?
I absolutely would.
I would remind her what she was already good atand just, which is don't follow the pack.
I've always been comfortable not following thepack.
And I have 3 little kids, and we teach them notto follow the pack.
And probably the thing I was most proud of isyesterday, my son, who's 6, the teacher showed
(24:21):
a screenshot of every kid and what theirpredictions were, and he was the only one with
a weird prediction.
And he was alone.
And I took a screenshot of it, and I'm like,don't follow the path.
You don't get anywhere in life following thepath.
You gotta chart your own path.
And so I would tell 10 year old Alexa, 15 yearold Alexa, 20 year old Alexa, like, trust your
instincts.
Keep doing what you're doing.
I don't need people to understand me orappreciate me.
(24:44):
Like, I I'm comfortable following my own path.
You secured a $330,000,000 fund for fund 3 forinspired.
What's your goal with with the capital?
What what do you wanna do?
Yes.
So first, we wanna meet founders who are readyto absolutely go and powerfully change the
future.
We're generalist fund.
We back any and every big idea.
(25:04):
We're looking for people.
I wanna see people dream crazily big, crazilybig.
Not a little bit.
Don't give me incrementality.
Give me epically big innovation going aftersome of the world's biggest problems.
And sitting here on the morning after anelection, all I can say is we got a lot of work
to do as a society, sort of free from politics.
Like, we've got a lot of work to do to makethis country, what we know we should and be,
(25:30):
thriving as a global leader.
And so I want people with huge ideas, crazyideas, solving some of the biggest problems
facing the future of wealth and health andsociety and technology and AI to come show up
and let us give you capital and swing big.
I noticed that some of the best founders andmost successful in the world founders in the
(25:52):
world have a crazy amount of delusion, but alsocrazy amount of ambition.
I met with this 17 year old kid who I justinterviewed who runs an app that makes
$1,000,000 a month.
He was just featured on Forbes.
And I asked him, like, what's your long termgoal?
Like, what do you wanna be?
And he said to my face, I wanna be the nextElon Musk.
I was like, yeah.
(26:12):
You're gonna go far.
Yeah.
I mean, you want people I always tell people ifsomeone's like, I'd love to be a lawyer.
I'm like, why not be a supreme court justice?
Like, if you whatever you wanna do, swing to bethe best at it in the world.
Not not I always say it inspired we are nothere to run the marathon.
We're here to win the marathon.
There's very different levels of training thatgo into something if you're there to be number
(26:34):
1, not number 100.
And I think that's you only get to live once.
This is in the dress rehearsal.
So show up for yourself and swing big.
Awesome.
Well, I think that's a great way to end it.
Thanks, Alexa, for taking the time to join theshow.
We'll have a link to Inspired Capital in theepisode description down below if any founders
interested are checking it out.
Well, thanks, Alexa.
Appreciate it.
For having me.
You're awesome.
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