LearnVest: Alexa von Tobel When Alexa von Tobel was just 14, her father passed away unexpectedly, leaving her mother to manage the family's finances. The tragedy made Alexa determined to understand money – and help others plan for periods of uncertainty. In her mid-twenties, she founded LearnVest, a tool that simplifies financial planning and investing. Within three years, the company was providing support to millions of customers. In 2015, she sold LearnVest for a rumored $250 million. PLUS for our postscript "How You Built That," how Dillon Hill built Gamers Gift to help bed-bound and disabled patients enjoy a wide range of places and experiences —through virtual reality.
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LearnVest: Alexa von Tobel

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LearnVest: Alexa von Tobel

LearnVest: Alexa von Tobel

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ALEXA VON TOBEL: The plan for day one was, open my damn laptop and just start hustling. And I did. And I remember, like, I was taking anyone who would meet with me. I was asking for people who would give me advice. I was looking for advisers, just literally paying people in equity, which was all phantom because the company was worth nothing. And I had my first intern - literally hired her at a Starbucks. And I was like, do you want to work for my company? My company was, like, me inside the Starbucks (laughter).



From NPR, it's HOW I BUILT THIS, a show about innovators, entrepreneurs, idealists and the stories behind the movements they built. I'm Guy Raz, and on the show today, how a financial emergency in her childhood inspired Alexa von Tobel to create LearnVest, a company that simplifies financial planning, and how she went on to sell it for almost a quarter of a billion dollars.


RAZ: So most of us - you, me, your friends, your spouses, whoever - most of us do not know how to organize our finances. I mean, just think about it. The average U.S. household has $16,000 in credit card debt, and two-thirds of us have less than a thousand bucks in our savings accounts. And here's one more. The median amount of money the average American has saved for retirement is $5,000, which - and I hope I'm not freaking you out here. This is not enough money to get you very far after you stop working.

So Alexa von Tobel knew this. She knew that even her well-educated friends didn't think much about financial planning, especially because the whole process can seem intimidating, and frankly, something you do when you're older. And let's face it, it's kind of boring. But it's super important. And what Alexa saw back in 2006 was an opportunity - a big opportunity to build a company that could demystify financial planning, especially for young people and people without a lot of money. And a big part of the idea came from a traumatic experience that she had as a teenager. Alexa grew up in Jacksonville, Fla. Her mom was a nurse practitioner, and her dad was a pediatrician.

VON TOBEL: So I would go to my dad's office, and I would file. I would clean up all the toys. And actually, I think it was - in its own way, it was kind of brilliant. My dad wanted me to, like, observe other families going through challenges. And some days, I kind of pull on that more than I even realize, now that I have my own family.

But anyway, so that's what I would do. And he would pay me I think, you know, basic minimum wage so that I could fund things I wanted to. But yeah, I had a job really early. And actually, one summer, I even put it into an IRA, which - my dad kind of taught me early about financial planning in that way.

RAZ: So your dad was a doctor. Your mom was a nurse practitioner. So it sounds like you had a kind of a science-y (ph) type of family.

VON TOBEL: (Laughter) I did. Also, my mom was, like, a developmental specialist. So I always joke that I think my parents probably, like, secretly had me take, like, six or seven different tests - like, whatever they were trying out at work. Like, I remember just, like, a few times sitting down and people being like, hey, you know, just, like, take this computer test really quickly. I always joke that they were testing me for hyperactivity because I have so much energy.

But yeah, really kind of science-y - like, geekily (ph) science-y - like, my dad and I used to, like, make potions to turn fire in the fireplace, like, purple and blue. He was definitely putting some chemicals in it. I have no idea what they were. And that's kind of what I would do with my dad - is, like, geek out on that stuff. And I'm sure, in some very subtle way, that really influenced kind of my own path into technology.

RAZ: So - pretty stable childhood, right? I mean, you had a pretty kind of stable middle, upper-middle-class upbringing in in Jacksonville, Fla.

VON TOBEL: Yeah. So, I mean, I would say really stable except for when I was 14, my dad unexpectedly passed away. And I think that kind of - you know, it throws - and it was in an accident. So it was very much like noise stopped, sound stopped, time stopped. Can ask any child who's lost their parent - they - you unfortunately remember every minute, every day of that whole period of time. It's like it's burned into your soul.

RAZ: Do you remember the day that you found out about what happened? It was 1998.

VON TOBEL: Yup. June 9 of 1998 - my dad had gone to work. I was supposed to go to work with him that day, and I didn't because I was - you know, that, like, beginning to be an adolescent. And I was like, hey, I actually want to go and, you know, hang out with friends today. And I remember kind of pulling up to my house, just seeing tons of police lights. And, frankly, it was like, literally felt like a horror scene. And I just knew something was really, really bad. And my dad had gotten in an accident and passed away. And I remember literally processing, this is my worst nightmare, this is my worst nightmare.

And, you know, as the kind of weeks went by after, the biggest thing that really stuck with me is life is literally so short. Like, one second you can breathe, and the next second it can just literally be over. And I think that was the thing that I was grappling with the most in those few days because I wasn't physically present. You know, I didn't see the accident, and so it was just like, wait, but he was here this morning saying goodbye to me, and then all of a sudden I'm coming home and he's not here.

RAZ: I know we're going to get to this later on. You're a mom, and you're married and you've had this successful career. Is there a day that goes by that you don't think about your dad?

VON TOBEL: It's such a good question. And the absolute truth is, like, no. Not a day goes by. It's like the - (laughter) totally getting choked up. The truth is, every day. And it's really, really simple - small things, big things, the songs that we sing to my daughter now are songs that he loved. So, no. And I think any person who's lost someone they really, really love knows that.

RAZ: I think when we think about losing somebody in our lives, we obviously - and of course we think about the emotional impact of that - there are things that we don't think about, we don't sort of talk about, which is the impact on how a family functions. I mean, oftentimes there is one parent who kind of handles things like finances and bills and just the household stuff, and it's complicated when one of them passes away.

VON TOBEL: Exactly. Hence, and kind of this is where some of the idea for LearnVest and kind of my own, like, entrepreneurial crusade was really born, which is - first of all, you know, as you kind of alluded to, both my parents - very skilled, very, very capable people. But still, tradition has its ring on a family, right? So like, my mom managed the budget. It's definitely where I get my skill of being very frugal from. And then my dad managed all of our investments and kind of the bigger picture.

And to be clear, my mom's a tough cookie. Like, she's very brave, very bold, very, very smart. There's nothing that she really shies away from. But she didn't manage our investments. So I think that's the best way to put it. And I think that's true for millions of households. But when my dad passed away, one of the really clear things I remember was my mom just didn't have a really clear handle on where everything was and what the picture looked like. I just remember my mom being like, not quite sure, like, how money was going to work.

RAZ: I mean, I have to imagine that's a potentially paralyzing thing for any family.

VON TOBEL: Sure. So I think this is one of the things, Guy, that's really stuck with me, is just - 14, you know, just knowing that, like, my mom was even questioning that, like, it kind of made me sick to my stomach that there was one other thing that she had to worry about. And so it really left a lasting impression. When your life is crumbling and, like, you are devastated, whether it is an illness or an unexpected accident that, like, takes away a loved one, or losing your job, or your partner walking out on your life, whatever it may be, all the things that crush people, I don't want you to have to worry about money. I don't want money to even be a question. In those times, I want it to be, like, you're good, right?

Which, if you fast-forward, and when I went to college and I started getting - you know, studying things I'm interested in, I ended up literally, like, thinking to myself, I just want to take, like, some financial planning classes. Like, (laughter), like, how many credit cards should I have? And, you know, how do I think about these things? And, like, you know, just basics. And there was no class. And there were no - there wasn't a program. And I just remember kind of being appalled that I can't teach myself this life skill easily. And, you know, that kind of is some of the seedlings of, like, really where LearnVest was truly born.

RAZ: And did you - I mean, did you have, like, an entrepreneurial kind of mind in college? I mean, were you thinking, I'm going to be rich. I'm going to start a business. Like, was that even part of your thought process?

VON TOBEL: It's so funny. Being rich was never something that seemed, like, exciting, if that makes any sense. That said, I always thought, like, CEOs of companies were like rock stars because I just find them so interesting, and I just want to learn everything. That, coupled with - if you asked my mom, my mom would tell you I was an entrepreneur at, like, age 4 because I was - instead of having a lemonade stand, I was actually, (laughter) I was taking things out of my house that I wasn't allowed to have and selling them, like, on the street, like, up our neighborhood (laughter). And I got into a lot of trouble a handful of times 'cause I once took a piece of art off the wall that I just didn't think we needed, and I (laughter) just sold it (laughter).

RAZ: So your first job out of college was with Morgan Stanley, right?

VON TOBEL: Correct.

RAZ: As a trader?

VON TOBEL: Yes. Well, so I kept being like, OK, this is, like, a good foundational job that will give me the foundation of what I think I want to do. But at that point, I kind of, I had this really constant energy of, like, I want to build, I want to create, I want to make. And I would keep these, like, really wild notebooks of, like, lists of ideas, of things I was excited about. And the idea for LearnVest had already been kind of born in my head of, like, why don't we learn about money? Why isn't there a better way to do this? Why isn't there something out there?

RAZ: But I guess I - I'm just wondering, like, I mean, because I'm trying think back to when I was in college, and I really wasn't thinking about financial planning. Like, I'm being honest with you. Like, I wasn't - it wasn't something that would have ever crossed my mind - not - I mean, maybe I was irresponsible or maybe I was just not that intelligent. But I just didn't think about it. I thought, what's going to be interesting? I like studying history. It's interesting. Like, that was the extent. So I'm trying to figure out how it was that you thought, you know, financial planning - this is something that more people should know about because you're like in your early 20s. And it just seems like a boring thing at that point in life.

VON TOBEL: (Laughter) It's so boring. I'm not - I was, like, here I am. So I accepted the job at Morgan Stanley. I remember sitting there being, like, I work at, like, a great financial firm, you know? Like, I'm on a trading desk. And I'm sitting here struggling with, like, do I put money in my 401K or my IRA? - like, basics. I just was, like, if I feel this way, and I don't even have a family - I don't even have a mortgage - I don't even have kids. Like, I feel pretty lost with my financial planning. How do other people feel? So I started asking. I asked everyone who would talk to me. How do you feel about your wallet? Is it stressing you out? And literally, it was amazing. Everyone I would ask would say, I have no idea what I'm doing - young, old, money, no money, people who had, like, huge, you know, golden parachute from their family, etc. And from that I was like, this is an idea.

RAZ: And that was the beginning of LearnVest?

VON TOBEL: Yeah. That's how I started working on it. And it's - I never embarked on this being, like, this is the sexiest idea because, Guy, there was another part of me that struggled with, I want to do something that is so cool. This wasn't cool. I knew that. But it honestly spoke to this core part of me that just cared so damn much that that's what was driving - it's just - I was like - I was hooked. And I was stuck. And I had to go do.

RAZ: You were at Morgan Stanley writing the business plan?

VON TOBEL: Yes. So I was at Morgan Stanley. And essentially, I gave up having a real social life. Like, nights and weekends, I would, like - I put together the 75-page-ish business plan that nobody read. But it was all my thoughts in one place on what this future LearnVest company - LearnVest stood for learn, earn, invest - even though, by the way, Guy, I had no damn idea what I was going to build, what it was going to look like. But I started feeling like, I get it. Like, this is what I'm meant to do.

RAZ: This is around 2008, 2009?

VON TOBEL: Two thousand six.

RAZ: Two thousand six - so - OK. So you've got this idea for LearnVest. And you leave Morgan Stanley. But I guess right about this time, you actually started going to Harvard Business School, right?

VON TOBEL: Yeah. So I entered business school September of 2008. And I actually took my leave of absence from business school on December 18 of 2008. So I was there about 90 days. And I'd written my business plan. And when, basically, the economy crashed - like, if you remember, Guy, that fall of 2008 was a bloodbath. It was a nightmare. And that actually kicked my courage into even higher gear because I said to myself, this is literally a time when anyone in my family, anyone I knew was like, should I be selling my - you know, all my retirement into cash. Like, people were putting money under their mattresses. Like, everyone was terrified.

RAZ: So in the midst of all this chaos, you thought, hey, leave business school and start a business?

VON TOBEL: Yeah. And I was, like, this is a time when America needs more financial planning than ever. And it literally was the scariest big decision that I had had to make personally. And so December 18, I walked into the admissions office. And then I said, I'd like to take a leave of absence where you get, like, a one-year. And then you keep extending it. And I did that. And then I literally said to myself, I was taking a plane ride from there to New York. And I said - I literally cried the entire plane silently. I was like one of those - you know when you see people crying on the street, and it's like a silent street sob? You're like, that person's having a bad day. I was just crying on this plane to myself, being like, what the hell did I just do?

RAZ: Yeah. I mean, that's the thing. Like, you were an A student. You went to Harvard Business School. Clearly, you are a good student. Clearly, you followed rules. But you don't strike me as a kamikaze risk-taker.

VON TOBEL: I'm not (laughter).

RAZ: So what happened? What was it that you said, no, i'm just - I'm going to give up the stability and just go into chaos?

VON TOBEL: I'm laughing because the truth is I am a rule follower. But I think there's this other really - there's this other really, really deep part of me, Guy, that is where I go to to make my decisions, which is - I always say there's a little - so one of the things I learned in psychology is that if you ask a bunch of 90-year-olds to say, hey, what do you regret? They never regret the stuff that they did. They never regret that I kissed this boy, or I quit this job, or I did these things or spent this money - ever. You ask 90-year-olds - they always regret the risk they didn't take.

RAZ: So you leave business school. And you move to New York to start LearnVest.

VON TOBEL: Correct. That's where our offices were going to be. That's where I was going to hire people. New York is the finance capital of the world. It was - very early startup days, so really important to say out loud, like, there isn't a lot of, like - there - like, there was not a startup community truly in New York. And I kind of basically - I always say I had this - my entrepreneurial Cinderella moment, which was I about nine months of savings with my own kind of basic financial plan. I knew that if I hadn't raised money, like an angel round, to actually get going, I wasn't going be able to fund this out of my pocket.

RAZ: How much money did you have?

VON TOBEL: So I had, from all my bonuses and everything from Morgan Stanley, about $75,000.

RAZ: Which wasn't really enough to - I mean, you could start it with yourself. But it wouldn't be enough to give you that much runway.

VON TOBEL: One engineer was about $10,000 a month - one really high-quality engineer in New York.

RAZ: And you knew this was going to be a tech company. It was going to be web-based or...

VON TOBEL: Well, I knew - at the time, I wouldn't have said it was going to be, like, a technology company. I was, like, I'm building a consumer, you know, internet company, right? Like, I needed to hire engineers. I need a CTO. And they all made at the minimum $150-200,000 a year. So like, my money wasn't denting anything.

RAZ: So how did you get the seed money to start?

VON TOBEL: Yeah. So the goal was to raise $750,000. The plan for day one was open my (expletive) laptop and just started hustling. And I did. And I remember, like, I was taking anyone who would meet with me. I was asking for people who would give me advice. I was looking for advisers.

And little by little over the next few months, I started gaining this actual confidence because I always said me working 30 percent or 40 percent full time on a startup does one thing. Me working 100 percent of my time, like, literally not doing anything else, you just - I just started seeing results. And it felt like this little bit of snowball. And this was actually my husband's speech at our wedding - is - he's, like, everyone always thinks, you know, Alexa had this, like, pure success. He's like, but I watched it. He had a nice, big joke as he would come home from work, like, in a suit at, like, 11 p.m. And I'd be, like, furiously still working.

And one of two things was happening. I was either clutching, like, a bottle of wine or some days about a wine and a cookie. And he, like, knew if I had both (laughter) that it was just, like, a really bad day. And I was dressed, like, heads down and, like, just literally paying people on equity, which was all phantom because the company was worth nothing. And I hired my first intern who was, like, a Princeton, you know, like, student who took the train up. And I literally hired her at a Starbucks. Her name's Annie Shapiro. And I was like, do you want to work for my company? My company was like me inside Starbucks (laughter).

RAZ: When we come back, how Alexa went from hiring that one person in Starbucks to managing hundreds of employees and millions of users. Stay with us. I'm Guy Raz. And you're listening to HOW I BUILT THIS from NPR.


RAZ: Hey. Welcome back to HOW I BUILT THIS from NPR. I'm Guy Raz. So before Alexa could actually launch LearnVest, she, of course, needed to raise some of the money to do it - $750,000 to be exact. But in 2009, she actually raised more than that - $1.1 million. And the way she did it - she met with everyone, any connection she made during those 90 days at business school - connections from her time at Morgan Stanley and anyone else she could think of.

VON TOBEL: And, you know, I would pay for them to get coffee with me and bring them lunch. And like - I was like, I mean, I was like a gopher. I was a whoever will meet with me, you really grind. And there were a lot of people waste my time now for sure who were like totally uninterested. And those sucked. And I would leave and I feel like, ugh, demoralized. Then I'd have to suck it up because five minutes later I had my next meeting. And I actually had to run.

RAZ: Yeah. And how did you make the pitch? How did you convince people? I mean, even you with all of your intelligence and talent were so young at that time.

VON TOBEL: I was. And I will tell you - I - you know, I just turned 25. I was not proven. I'd never done this before. But I think one of the things that I kind of really rested on, Guy, was that I had written this 75-page business plan. Like, I researched it. I knew my stuff. And if there was going to be someone in the space that you could care about, you know, like, I was all in.

RAZ: In that - in a sort of nine months of trying to raise money - this was like - this is collapse. I mean, the country's collapsing. There's huge bailouts and stimulus packages. And people are freaking out...

VON TOBEL: Freaking out - freaking out, Guy.

RAZ: I mean, this is a really - so I'm trying to figure out how you were able to convince people to give you money at a time when I can imagine nobody wanted to take risks because...

VON TOBEL: You've nailed it.

RAZ: ...Right?

VON TOBEL: You nailed it. I would say it was, like, a year - year and a half of, like, just taking people's names and following up with them and staying persistent. And one guy who actually said no to me then came back and, by the summer, was, like, you know what? I'm in. Like, you're crazy. Like, you're totally committed. Like, I'm in. And one of the things that I really held onto through that time is I, you know, had a few people that were like mentors to me, who were great entrepreneurs ahead of me. And they were, like, listen. If you can do it in this environment, you can do it any time.

RAZ: Yeah. Yeah.

VON TOBEL: Like, they were, like, the entrepreneurs who survived through this. It's like a gauntlet, right? It's like - literally, it's like multiple, like, jumping through knives and hoops. And if you can get through it, like, you can actually thrive. And it was true.

RAZ: But you were saying to people, I'm going to offer what?

VON TOBEL: So what I was saying to people is, we are going to go after a younger millennial audience and we are going to be the solution for their money, for them understanding everything to do with their money. And everything was - sounds really broad. But the point was it was content. We're going provide them the education then the tools - so we built our own tool where you could aggregate all of your money in one place.

And then we launched advice. And advice was where you could call in and talk to someone. So you would talk to one of our planners. And the idea was we were going to apply super modern world today, so open 24 hours a day, super, super fresh. and if you think about it, banks at the time had these stupid ads on TV that were like were open on Saturdays from, like, 11 to 2 when you were like, what? Like, that's so irrelevant for a young person who doesn't even want to walk to a bank.

RAZ: So you launched the site, I think, in 2010? And how did it go?

VON TOBEL: So yeah. January of 2010 - like - just like all good founders have the story, site went up. Daily Candy covered us. Some other news outlets covered us. Site crashes. We had 4,500 people, I think, around that the first day - the next day. We get the site back up. Another few thousand people signed up. And in that first month, we had about 10,000 people who had signed up. And just to your point, this is personal finance. This is boring.

RAZ: But was it - like, you say Daily Candy and other people, like, wrote about it. Was it pitched as a, hey, this is for young people or this is for women or this is - like, how did - how was it...

VON TOBEL: It was literally pitched as, like, for anybody who wants to get their butt kicked about their wallet in a way that's like plain English and easy, go to LearnVest. And we had a boot camp, which was, like, a 10-day email program that was basically going to give you, like, a simple overview on what every young - and I had to define young - very - I think 40 is young - any person - young person who needs to understand their wallet.

And we had 10,000 people sign up. And the open rates and engagement with the site were massive. And I remember being like, wow, this data is really compelling. And we had a bunch of advertisers jump at us. And so by February 15, I remember because it was right around that Valentine's Day - literally, we were in a where we had tons of the best venture firms in the valley and in New York being like, I want to fund your next round. And. I was like, wow OK. So we ended up taking just under $5 million from Excel Venture Partners and a bunch of other really cool people. And entrepreneurs threw in some money at that point.

And in short, what we built was Turbo Tax for financial planning, so a way for you to come, very affordably get a financial plan. Most financial plans cost $2-5,000. I don't know about you, Guy. but if you're in your 20s and 30s, you're not really ready to go spend, you know, $5,000 on a financial plan when you're trying to figure out what to do with the $5,000 you have that's extra.

RAZ: So is it - I mean, so you didn't have to hire lots and lots of financial advisers, like, people to say, here's what you should do - here's what you should do - because you were developing essentially a software that could could give you answers based on the data that you put in?

VON TOBEL: Correct. And think about that - developing software is not an easy or an expensive thing to do. And you need - not just, like, 10 engineers - you need tens of engineers, very sophisticated engineers with certified financial planners to develop this software. So essentially, what we started doing was - we started asking people - you, know we had their data saying, what are the questions you have? - and really listening. And eventually we developed a software that - I like to think of it as GPS for your money. It gives you a real sense. And then from there, we then kicked your butt. We would hold you accountable. We would send you action items. Go close this account. Go open this account. And what we would see was it was just a very innovative way to deliver a financial plan.

RAZ: And so your entire business model was built around subscribers rather than getting, you know, a commission from, like, steering people into a specific investment or fund?

VON TOBEL: Correct. And then on the business-to-business side, we sold LearnVest@Work. And that was where really big companies started coming to us. And actually, it kind of shows you, like, the nimbleness of an entrepreneur. I remember we had a really big, big brand name company come to us and say, hey, could we buy this for our employees? And being an entrepreneur, you say, yeah. Of course, we can figure that out.

RAZ: But 2012, like, you guys had raised $25 million or even more. I mean, you were growing so fast. You were getting so much attention. I have to imagine that this, like, caught the attention of big companies, Charles Schwab and other, you know, or other companies offering financial planning advice.

VON TOBEL: Yup. So what I would say by, like, 2012, 2013, 2014, we were having active conversations with either - for business partnerships or sponsor - huge sponsorship deals or they wanted to license or white label our software. So all of a sudden, lots and lots of business interests coming to us...

RAZ: But nobody was saying, we're going to compete against you?

VON TOBEL: I think what we did was really radically different. And so no one was quite set up the way we were, which was highly human. So we still really believed in the power of humans and still do to this minute. And we were just really convicted because of our principles of, you know, every American deserves a financial plan. It needs to be cheaper. It shouldn't - you know, one thing I said over and over is, financial planning should not be a luxury product. You know, the big brokerage firms don't really want to talk to you unless you have over $250,000, which, most of America doesn't. And I just said, wow, what if we could tip that on its head and really make this a mass consumer product?

RAZ: Do you - is any part of you motivated by competition? Like, do you want to win?

VON TOBEL: This is a really good question. I'm hyper motivated. I get up. I get up with, like, a spring in my step. I want to go do things. But, my whole life, I've always been - like, I don't feel competitive, if that makes any sense. What I figured out is, there's two types of people. There's competitors, and there's achievers. And achievers wake up with their own to-do list of things that they want to do by the end of the day and kind of focus on getting those things done. And it's very much, like, you know, within your own swim lane. Competitors, actually, are looking to the people in the other swim lanes and want to beat them. I'm not a competitor. The achiever in me is super focused on, you know, raising the bar for myself and things I think I can accomplish. And anyways, it's just a really good distinction. And one of my best friends, she goes, I wouldn't be your best friend if you were a competitor.

RAZ: All right. So you guys are off to the races. You're doing really well, you're growing. And then 2015, you get acquired by Northwestern Mutual. Was that part of your plan from the beginning, that you would have that exit strategy?

VON TOBEL: So I always say that good entrepreneurs, it's not that you don't ever think about an exit strategy, but it's not your goal. The goal was, let's continue to stay in business and get bigger and bigger and deliver more and more plans and keep making this work. So fast-forward 2014, literally Northwestern Mutual had emailed in asking to invest. And, you know, my board said yes, and so they invested, and that was in April of 2014. By that Thanksgiving, the CEO, John Schlifske, reached out to me and said, hey, can we spend some time?

We a really good conversation, and it quickly turned into him saying, hey, we both believe in the same things, which is we believe in the power of human advice, and we really believe that Americans deserve access to plans. And he was like, what if we teamed up? That was now December, and the next thing you know, we're signing a term sheet to be acquired on March 25th.

RAZ: So Alexa - and you don't have to confirm this, but - the reported number of that sale was a quarter of a billion dollars. Now, when you were 14 and your dad passed away, your mom was, like, sort of left to figure out the finances and the finances of the family, which obviously created some instability. And that decision in 2015 that made you and presumably others around you financially secure for life, I mean, what did that mean to you?

VON TOBEL: I mean, I think a few things. And this was, like, a very personal story that I actually told the board after we signed the document. I sent them all a video - the board of Northwestern Mutual - I sent them a three-minute video. It was kind of surreal at the time 'cause I actually didn't intend to do this, but it just felt right and I just went with my instincts. But when my dad passed away, it was actually a Northwestern Mutual life insurance policy that stabilized my family, and I knew the power of what financial stability really provides to a family actually in their worst minutes. And I just sent them a video and said, here's why I'm doing this. Here I am, having helped build this great product that helped America innovate on financial planning, and if I can put it in the hands of their 8,000 financial planners to provide more of what I felt at 14, I can really get behind that.

RAZ: You are in your early 30s. You're a mom. You've got a 2-and-a-half-year-old and then one on the way.


RAZ: You have, like, your whole - your whole life is ahead of you. Like, you're in the age where most entrepreneurs start their first business. And, obviously, right now you still have a role at Northwestern Mutual. You're the chief digital officer. Is that right?

VON TOBEL: Correct.

RAZ: But I mean, do you think you'll ever go on to do something else? Like, would you start a new business?

VON TOBEL: I don't know. Right? I kind of like to solve problems all the way through. That's kind of what I care about, right? If I'm going to start something, I want to finish it. So I'm quite busy right now. I will say that. I've got a very, very, very full plate. Hundreds and hundreds of employees and a lot of work on my horizon. And for me, I like big, big meaty challenges. And that's the one thing I know about myself. So what's next? I don't know. I've been really, really honored to have lots of exciting options, but I want to see things through, and I still have work to do.

RAZ: You've heard me ask this question before to other people on the show. I'm going to ask you the question. How much of your success do you think is due to your intelligence and hard work, and how much of it is due to luck and circumstance?

VON TOBEL: So I know there's all the cliches of, like, people always, like, assign too much to luck and blah, blah, blah. And I would say definitely not my intelligence, and definitely not luck. I would say it was, you know, attributed to an incredibly powerful team of passionate people who, frankly, saw through walls, and we saw a better life. And for me, having had such a traumatic experience when I was younger, what I really learned was kind of the fragility of life when, like, someone that you love that's really important to you is alive one second, and literally minutes later gone. It kind of helps you just get rid of a lot of the - your focus gets really clear, and in fact it's almost given me a superpower in some way because I now process things a little differently, which is, does this really matter? Right? When, like, a really big, stressful, stupid thing is happening, I'm like, are we alive? Are we breathing? OK, next. (Laughter).

RAZ: Yeah.

VON TOBEL: At some point, when you shift into that perspective that, like, there's still oxygen in your veins, you're still breathing, the people you love are still alive, like, nothing's that big of a deal, I think you do your best work.

RAZ: Alexa von Tobel, founder of LearnVest. She's now the chief digital officer for Northwestern Mutual. And, by the way, something Alexa did not mention is that in high school she was a competitive diver and was actually recruited to compete at the Division I level in college. Even though...

VON TOBEL: I don't love heights. That said, you know, I've gone bungee jumping and I've gone skydiving. And so I'm not, like, as scared as your average person probably with heights, but I don't love them, either. I think I just like to face fear.

RAZ: Please do stick around because in just a moment we're going to hear from you about the things you're building. But first, a quick thanks to one of our sponsors. Go to Webinar, a trusted webinar platform with over 55,000 customers who posted over 2.3 million interactive Web events to connect with their audiences. For more, visit gotowebinar.com.


RAZ: Hey. Thanks so much for sticking around because it's time now for How You Built That, and today we're going to hear from Dillon Hill. He's a student at UC Davis, and a few years ago, he co-founded a nonprofit called Gamers Gift.

DILLON HILL: Yeah. So our biggest thing right now is bringing virtual reality, the headsets, to children's hospitals, assisted-living facilities and people with disabilities.

RAZ: And this idea goes all the way back to the fifth grade, when Dillon's best friend, Chris, was diagnosed with cancer and had to spend months in the hospital.

HILL: I would visit him every single day, and what I saw was my friend was no longer the kid that I knew. And my solution was to bring the video games because I knew that those would make him smile.

RAZ: Chris eventually did get better, and he and Dillon stayed friends.

HILL: And that experience always stuck with me, and I remember looking back on it as, wow, those video games really helped us.

RAZ: So anyway, fast-forward to senior year in high school, and Dylan is now doing volunteer work in his spare time. But he's not all that happy with it.

HILL: I volunteered at a food shelter, and instead of spending time with the homeless, I was in the back packing bags. And obviously all these things, they help, but it just wasn't rewarding.

RAZ: And Dillon kept thinking about the video games. Maybe there was some way he could use them to help people. So one day he and Chris were doing a little random Googling, and Dillon said, hey, I wonder what it would take to start our own charity?

HILL: And we Googled how to start a nonprofit, and we saw, wow, this is simplified into six steps. First make an LLC, and then get in touch with the franchise tax board.

RAZ: Actually, some of this stuff does not sound so simple, but eventually Dillon got his mom to guarantee a bank account for their nonprofit, and they became a 501(c)(3).

HILL: I think we probably Googled every single line on the tax paperwork because we had no idea what a lot of it meant. But, I mean, we have the Internet, you know? We can figure out anything.

RAZ: And so after they got it sorted out, Dillon and Chris started to raise money to buy video games and VR headsets. First, they sold baked goods door to door. Then they got some donations through an online service. And by the spring of last year, they were starting to visit hospitals and other places in California sharing VR and games with children and adults.

HILL: So for example, there was this man, Dominic (ph), who's living with cerebral palsy, and he's always wanted to drive a racecar. Now, he's only able to communicate by moving his head up or down, but we can put a headset on him, and we can push his wheelchair around his living room and we can emulate him driving a Formula One racecar.

RAZ: Right now Gamers Gift has about 20 volunteers who have brought VR sets or computer games to nearly 40 facilities around California, and they're hoping to expand.

HILL: Yeah, I would love to because, you know, this technology and the time that we spend with people, it doesn't have to be limited to a particular geographical location. And I think the communities we're already serving are the ideal communities, especially people with disabilities, you know, because they will never be able to experience scuba diving, but we can take that to them. And there's no reason why that should be limited to California.

RAZ: That's Dillon Hill, who co-founded Gamers Gift along with his friend Chris Betancourt. There's a lot more to this story, and you can find out about it on our Facebook page. And of course if you want to tell us your story, go to build.npr.org. We love hearing what you're up to. And thanks for listening to the show this week. If you want to find out more or hear previous episodes, you can go to howibuiltthis.npr.org. Please also subscribe to this show at Apple Podcasts or however you get your podcasts. You can also write us at hibt@npr.org. You can tweet us. That's at @HowIBuiltThis.

Our show was produced this week by Rachel Faulkner, with music composed by Ramtin Arablouei. Thanks also to Neva Grant, Sanaz Meshkinpour, Claire Breen and Jeff Rogers. Our intern is Dayana Mustak. I'm Guy Raz, and you've been listening to HOW I BUILT THIS from NPR.

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