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. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:04Speaker 00

  The plan for day one was open my damn laptop and just start hustling. And I did. And I remember I was taking anyone who would meet with me. I was asking for people who would give me advice. I was looking for advisors, just literally paying people in equity, which was all phantom because the company was worth nothing. And I hired 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.

• 0:37Guy Raz?

  From NPR, it's How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 0:48Guy Raz?

  I'm Guy Raz, and on today's show, how a traumatic experience 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 a rumored quarter of a billion dollars.

• 1:06Guy 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 US household has $16,000 in credit card debt. And 2/3 of us have less than $1,000 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,

• 1:50Guy Raz?

  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, Florida. Her mom was a nurse practitioner and her dad was a pediatrician.

• 2:29Speaker 00

  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, a, 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.

• 3:06Guy Raz?

  So your dad was a doctor, your mom was a nurse practitioner. So it sounds like you had a kind of a sciency type of family.

• 3:14Speaker 00

  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. I remember just like a few times sitting down and people being like, hey, you know, just like, look, take this computer test really quickly. I always joked that they were testing me for hyperactivity because I have so much energy. But yeah, really kind of sciency, like geekily sciency. 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 go geek out on that stuff.

• 3:55Speaker 00

  And I'm sure in some very subtle way, that really influenced kind of my own path into technology.

• 4:01Guy Raz?

  So, so pretty stable childhood, right? I mean, you had a pretty kind of stable, middle, upper middle class upbringing in Jacksonville, Florida.

• 4:13Speaker 00

  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, throws, and he 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, into your soul.

• 4:40Guy Raz?

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

• 4:47Speaker 00

  Yep, June 9th 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, like a, 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.

• 5:28Speaker 00

  And, you know, as the kind of weeks went by after, the biggest thing that really stuck with me that 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, he's not here.

• 5:55Guy Raz?

  I know we're going to get to this later on. You're, you're 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?

• 6:06Speaker 00

  It's such a, a good question. And the absolute truth is like, no, not a day goes by. It's like the, the, and totally getting choked up.

• 6:21Speaker 00

  The truth is every day. And it's really, really simple.

• 6:27Speaker 00

  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.

• 6:42Guy Raz?

  I think, 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 we don't, we don't think about, we don't sort of talk about, which is the impact on. On how 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.

• 7:13Speaker 00

  Exactly. Hence, and kind of this is where some of the idea for Learn Invest and kind of my own like entrepreneurial crusade was really born, which is, first of all, 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.

• 7:56Speaker 00

  There's nothing that she really shies away from, but she didn't manage our investments. 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.

• 8:20Guy Raz?

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

• 8:27Speaker 00

  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, when I went to college and I started getting, you know,

• 9:09Speaker 00

  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, 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 Learn Best was truly born.

• 9:37Guy Raz?

  And did you, I mean, did you have like an entrepreneurial kind of mind in, in college? Were you thinking, I'm going to be rich, I'm going to start a business? Was that even part of your thought process?

• 9:51Speaker 00

  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. And because I just find them so, so interesting and I just want to learn everything. That coupled with, if you ask my mom, my mom would tell you I was an entrepreneur at like age four. Because I was, instead of having a lemonade stand, I was actually, 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. And I got in a lot of trouble a handful of times because I once took a piece of art off the wall that I just didn't think we needed. And I sold it.

• 10:37Guy Raz?

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

• 10:43Speaker 00

  Correct.

• 10:44Guy Raz?

  As a trader?

• 10:45Speaker 00

  Yes. Well, so I kept being like, okay, this is like a good foundational job that will give me the foundation of what I think I want to do. But, 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 Learn Best 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?

• 11:16Guy Raz?

  But I guess I'm just wondering, like, I mean, because I'm trying to 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, 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 twenties, and it just seems like a boring thing at that point in life.

• 11:55Speaker 00

  No, it's so boring. I'm not, I was like, here I am. So I'd accepted the job at Morgan Stanley. I remember sitting there being like, I work at like a great financial firm, you know, as like on a trading desk, and I am sitting here struggling with like, do I put money in my 401K or my IR, right? 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.

• 12:36Speaker 00

  Young, old, money, no money, people who had like huge, you know, golden parachutes from their family, et cetera. And from that, I was like, this is an idea.

• 12:46Guy Raz?

  And, and that was the beginning of Learn Best?

• 12:49Speaker 00

  Yeah. That's how I started working on it. And I, 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 go 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 just, I was like, I was hooked, and I was stuck, and I had to go do it.

• 13:14Guy Raz?

  You were at Morgan Stanley writing the business plan.

• 13:17Speaker 00

  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 Learn Invest company, Learn Invest 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.

• 13:44Guy Raz?

  This is around 2008, 2009?

• 13:46Speaker 00

  2006.

• 13:46Guy Raz?

  2006. So, OK, so you've got this idea for Learn Invest and you leave Morgan Stanley, but I guess right about this time, you actually started going to Harvard Business School, right?

• 13:59Speaker 00

  Yeah, so I entered business school in September of 2008 and I actually took my leave of absence from business school on December 18th 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 of my retirement into cash? Like, people were putting money under their mattresses, like, everyone was terrified.

• 14:39Guy Raz?

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

• 14:44Speaker 00

  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 18th, 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 can 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. It was like one of those, you know, when you see people crying on the street and it's like a silent street sob and 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?

• 15:25Guy 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.

• 15:32Speaker 00

  I have to say.

• 15:33Guy Raz?

  Like, you don't strike me as a kamikaze risk taker.

• 15:36Speaker 00

  I'm not.

• 15:36Guy Raz?

  So what happened? What was it that you said, "No, I'm just, I'm gonna give up this stability and just go into chaos"?

• 15:44Speaker 00

  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 risks they didn't take.

• 16:17Guy Raz?

  So you leave business school and you, you move to New York to start LearnVest?

• 16:24Speaker 00

  Correct. That's where our offices were gonna be. That's where I was gonna 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, 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 had 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 gonna be able to fund this out of my pocket.

• 16:55Guy Raz?

  How, how much money did you have?

• 16:57Speaker 00

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

• 17:02Guy Raz?

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

• 17:09Speaker 00

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

• 17:14Guy Raz?

  And you knew this was gonna be a tech company? It was gonna be web-based, or?

• 17:19Speaker 00

  Well, I knew, I, I, I mean, I, at the time, I wouldn't have said it was gonna 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 needed a CTO, and they all made at the minimum $150,000 to $200,000 a year. So like, my money wasn't denting anything.

• 17:36Guy Raz?

  So how did you get the seed money to start?

• 17:39Speaker 00

  Yeah, so the goal was to raise $750,000. 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 advisors. And little by little, over the next few months, I started gaining this, like, actual confidence. Because I always said, me working 30% or 40% full-time on a startup does one thing. Me working 100% 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. Because he's like, everyone always thinks, you know, Alexa had this, like, pure success. He's like, but I watched it. And he and I's big joke is he would come home from work,

• 18:24Speaker 00

  like, in his suit at like 11:00 PM. 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, a bottle of wine and a cookie. And he, like, knew if, like, I had both, that it was just like a really bad day. And I was just, like, heads down and, like, just literally paying people in 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 the Starbucks.

• 19:06Guy 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.

• 19:31Guy 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 connections she made during those 90 days at business school, connections from her time at Morgan Stanley, and anyone else she could think of.

• 20:04Speaker 00

  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 like, whoever will meet with me, you really grind.

• 20:12Guy Raz?

  Yeah.

• 20:12Speaker 00

  And there were a lot of people who wasted my time, for sure, who were like totally uninterested. And those sucked. And I would leave and I'd be like, oh, demoralizing. And then I'd have to suck it up because five minutes later, I had my next meeting and I just had to run.

• 20:24Guy 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.

• 20:35Speaker 00

  I was. And I will tell you, 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.

• 20:59Guy Raz?

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

• 21:11Speaker 00

  Freaking out. Freaking out, Guy.

• 21:13Guy Raz?

  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.

• 21:24Speaker 00

  You nailed it.

• 21:24Guy Raz?

  Right?

• 21:25Speaker 00

  You nailed it. I would say it was like a year, a 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 on to 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 anytime. Like, they were like, they were like, the entrepreneurs who survive 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.

• 22:07Guy Raz?

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

• 22:13Speaker 00

  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, was, sounds really broad, but the point was, it was content. We're going to provide them the education and 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 are going to apply super modern world to this. 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, we're open on Saturdays from like 11 to 2. And you were like, what?

• 22:55Speaker 00

  Like, that's so irrelevant for a young person who doesn't even want to walk to a bank.

• 23:00Guy Raz?

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

• 23:06Speaker 00

  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 got the site back up, another few thousand people signed up. And in that first month, we had about 10,000 people.

• 23:26Guy Raz?

  Wow.

• 23:26Speaker 00

  Who had signed up. And just to your point, like, this is personal finance. This is boring.

• 23:32Guy Raz?

  But was it, 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 was it?

• 23:42Speaker 00

  It was literally pitched as, like, for anybody who wants to get, like, their butt kicked about their wallet in a way that's, like, plain English and easy, go to Learn Best. 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 every young, and I define young very, you know, 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 the 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 15th, I remember, because it was right around that Valentine's Day,

• 24:27Speaker 00

  literally, we were in a spot 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, okay. 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 TurboTax for financial planning. So a way for you to come, very affordably get a financial plan. Most financial plans cost $2,000 to $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 that you have that's extra.

• 25:12Guy Raz?

  So is it, I mean, so you didn't have to hire lots and lots of financial advisors, 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 give you answers based on the data that you put in?

• 25:30Speaker 00

  Correct. And think about that, developing software is not an easy or inexpensive thing to do. And you need, not just, like, 10 engineers, you need tens of engineers, very sophisticated engineers, with certified financial planners.

• 25:46Speaker 00

  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.

• 26:02Guy Raz?

  Yeah.

• 26:02Speaker 00

  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.

• 26:18Guy Raz?

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

• 26:29Speaker 00

  Correct. And then on the business to business side, we sold LearnVest at 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.

• 26:54Guy Raz?

  By 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.

• 27:13Speaker 00

  Yep. So 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 interest coming to us.

• 27:31Guy Raz?

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

• 27:35Speaker 00

  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 a TED and really make this a mass consumer product?

• 28:16Guy Raz?

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

• 28:23Speaker 00

  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.

• 29:07Speaker 00

  And one of my best friends, she goes, I wouldn't be your best friend if you were a competitor.

• 29:12Guy 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, was that part of your plan from the beginning that you would have that exit strategy?

• 29:29Speaker 00

  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, I, 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 Shlifsky, reached out to me and said, hey, can we, can we spend some time? We had 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

• 30:13Speaker 00

  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 25.

• 30:24Guy 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.

• 30:37Guy Raz?

  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?

• 31:02Speaker 00

  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 because 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, you know, having helped build this great product that helped America innovate on financial planning.

• 31:47Speaker 00

  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.

• 31:56Guy Raz?

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

• 32:05Speaker 00

  Yep.

• 32:06Guy Raz?

  You have, like, 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?

• 32:21Speaker 00

  Correct.

• 32:22Guy Raz?

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

• 32:27Speaker 00

  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.

• 33:04Guy 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?

• 33:19Speaker 00

  So I know there's all the cliches of like people always like assigned 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 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 and like someone that you love that's really important to you is alive one second and literally minutes later, gone.

• 34:01Speaker 00

  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? Okay, next.

• 34:23Guy Raz?

  Yeah.

• 34:24Speaker 00

  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.

• 34:37Guy 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 one level in college, even though-

• 34:53Speaker 00

  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.

• 35:10Guy Raz?

  Please do stick around because in just a moment, we're going to hear from you about the things you're building.

• 35:18Guy 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 Dylan Hill. He's a student at UC Davis. And a few years ago, he co-founded a nonprofit called Gamers Gift.

• 35:32Speaker 02

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

• 35:42Guy Raz?

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

• 35:52Speaker 02

  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.

• 36:03Guy Raz?

  Chris eventually did get better, and he and Dylan stayed friends.

• 36:07Speaker 02

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

• 36:14Guy 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.

• 36:23Speaker 02

  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.

• 36:33Guy Raz?

  And Dylan 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 Dylan said, hey, I wonder what it would take to start our own charity.

• 36:48Speaker 02

  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.

• 36:59Guy Raz?

  Actually, some of this stuff does not sound so simple. But eventually, Dylan got his mom to guarantee a bank account for their nonprofit. And they became a 501(c)(3).

• 37:10Speaker 02

  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.

• 37:19Guy Raz?

  And so after they got it sorted out, Dylan 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 in other places in California, sharing VR and games with children and adults.

• 37:42Speaker 02

  So for example, there was this man Dominic, who's living with cerebral palsy. And he's always wanted to drive a race car. 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 race car.

• 38:00Guy 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.

• 38:10Speaker 02

  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.

• 38:37Guy Raz?

  That's Dylan 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 [email protected]. You can tweet us. That's at How I Built This. Our show was produced this week by Rachel Faulkner with music composed by Rantin Arablouei. Thanks also to Neva Grant, Sanaz Meshkhanpour,

• 39:22Guy Raz?

  Claire Breen, and Jeff Rogers. Our intern is Diana Mustak. I'm Guy Raz, and you've been listening to How I Built This from NPR.

• 39:54Guy Raz?

  Thanks.