#79 with Alexa von Tobel - From Dropping Out of Business School to a $375M Exit

Alexa, thanks for joining us uh on the podcast today. So we have special guest. Uh I'll let you do your intro because I really am terrible at introductions. But for those who don't know, what was Learnvest? Uh give us kinda like your your maybe two or three minute uh background so that people know who you are. Sure, I think so. Um I'll start from the beginning. I grew up in Florida, uh, and when I

Always been an entrepreneur, love entrepreneurs, love building companies. Um, went to Harvard undergrad and uh studied happiness, uh, which I I always mention because I actually think somehow it's been very helpful to to life. Um, ended up I uh going back to business school there, dropped out, bottom of the worst recession and originally eighty one years. Now I feel like this may be a uh our own COVID moment is is becoming obviously something that's worrisome. Um but I built a financial planning software company called Learn Vest with a really simple mission which was uh so Learn Vest became TurboTax for financial planning. So literally every American family for an affordable price, get get access to a financial plan and an advisor. Um and on our fifth birthday, uh on March twenty fifth of twenty fifteen, um sold the business to Northwestern Mutual for about three hundred and seventy five million dollars. Um, and then uh spent the next few years uh as part of that business uh at North Russian Mutual and through it all of that, wrote some books, uh best selling book uh uh called Financially Fearless and then Financially Forward. about the future of your wallet and I'm just a diehard entrepreneur. I love entrepreneurs and I love to build businesses and so now I'm the managing partner I run.

a two hundred million dollar venture fund called Inspired Capital, uh, which is headquartered in New York City and we pay it for it and we invest in seed and series A entrepreneurs of tomorrow building big ideas. Uh so it's really fun to get to have done both and um now I'm on the investing side. And that's me and I'm married. I live in New York City. I have three beautiful little babies, uh a five year old, a two year old, and a one year old, which means I'm completely crazy. Um, but that's who I am. Wow. Impressive. You're not in New York City right now. I see are you? I see greenery. No, I'm not. I'm which um no, so uh have been in Florida, um uh I'm actually sitting in my like high school bedroom, um which is which is uh bringing it all back full circle.

Um where we came, we came down here for spring break and just haven't gone back. Do you have like a Justin Timberlake poster on the wall or something? Or what what's what's in the high school room? No, but you know, it's amazing. Look at this. See, my mom has literally kept like all of the things and I'm some days I'm like, Mom, why didn't you throw some of this stuff away? But um she kept all my pictures and all my artwork and all my silly stuff. So I'll start because Sam's probably still blownway. He loves

Harvard, you had him at Harvard. Then he sold a company for three hundred seventy five million bucks and then financial planning, he's a total financial planning nerd, personal finance nerd. So Sam, do you need a moment to just sort of gather your thoughts or are you ready to go? No, he he's joking a little. I uh I did not go to Harvard, I wish, but I I do have an odd fascination with it. I people say I have a Harvard sweatshirt. People always say, Oh you went to Harvard? I was like Yeah, I went there. I I

I paid money and took a tour and they shook me around. Uh well I will just say uh while Harvard was a great education, I think there's lots of things in life that are much cooler than Harvard. Uh so excited to be here. Did you say you dropped out? I d so I graduated undergrad and I dropped out of Harvard Business School. Okay, gotcha. And you said you studied happiness, uh like w is that like one class? Like I took a class called Getting Rich and but I you know, that wasn't like my major, it was just one class. So I I actually I studied psychology. Um I I started in a track called Mind Brain Behavior and then ended up in psychology. Um, and specifically there was a happiness lab that Dan Gilbert was running, um, where we focused on like how people

make decisions, what makes us happy. And basically the headline of the whole uh you know, my my whole experience was We're really bad about making decisions that make us happy. We do things that we think will make us happy, but in fact like getting the fancy car doesn't make you happy'cause then you have to clean the car, or getting a bigger home out of the city doesn't have you know, necessarily make you happy because then you commute farther to your work. So it was just really, really, I think a a good perspective of um it's the little things that really make us happy. Love that. You know, uh this is very on topic. So so I remember back in the day there's a guy who was I think a professor at Harvard named Sean Anchor. Is that somebody who was Yeah, that was he was uh he was one of my teachers, Sean Acre. Um yeah, he's wonderful. And actually um his Court Professor Tal Ben Shahar.

Um, and Philip Stone were my my thesis advisors. So he he gave this TED talk. That's pretty great. I still remember it and I watched this thing like 10 years ago. That's kinda st you know, the some talks just stick with you. And it was called the I think the happiness advantage or or the sort of something like that. And If I remember correctly, the the thesis was Being happy is actually an advantage to uh getting great results. Some people think about it the other way, like if a great thing happens, then I'll be happy. And his advice if I what I remember from ten years ago was

If I am happy, I'll have better results. Is that a good Is that am I am I accurate or am I just totally misremembering? So The short term is at Um

In under extreme duress and extreme stress, you can outperform in the short term. If you're actually very happy and relaxed and fulfilled, you outperform the long call. So when you're building teams For long term success so you know Inspired capital to venture fund. Uh we have a really unique group of people that have come together to build this firm. Um and we're trying to build a long term fund. And so I'm very focused on let's make sure we have long term happiness because you outperform in the long run. And so um and the other thing is I think one of the things I learned from Sean and Tall, my my professors, is um

Positive energy and attitude are actually an undervalued resource. People are very naturally drawn to people that are positive. If you're super negative over and over People don't want to be around you. They don't want to work with you. They don't want to show up for you. Um, and so I think again, you know, one thing people always ask me is what would I tell high schoolers? And I'm like, Have a good attitude. It goes really far and it's it's part of that point of Happiness is an advantage.

So is positivity. Yeah. I I always talk about this, uh enthusiasm is sort of in in complete under supply. Amongst successful people. So you know, when you're trying to compete and you're trying to be successful, I'm like the stupidest, most enthusiastic person. Obviously you bought in on this. What I'm saying is that for most people or most of the environments I've been around, whether it's like, you know, entrepreneurs, investors, right now I'm at a bigger company because my company got acquired. It's like the execs at this company.

In some ways enthusiasm, I think people see it as like a low status thing to do. It's like, oh, you know, sort of Being reserved is somehow more Prestigious or powerful in some way. Uh, and I've gone the complete opposite direction, where I'm I'm overly enthusiastic. And I've I'm like, dude, I have one tenth of the skills of all the people that have been around me

But I've been able to go so far because I think enthusiasm is uh such a superpower that most people could tap into and totally don't for whatever reason. I I mean I totally uh agree with you. Um and beyond not only do I totally agree with you, I also think it's worth saying that Um

It is a skill that we can all adopt, right? Like just trying to have a positive outlook is something you know, I can't grow taller or I can't get better at um, you know, a certain trait that I just don't have, but um, trying to be positive and trying to to to be joyful. I think actually It's something we can all put on. It may not be easy for everybody to do it, but it is possible. Sam, are you an enthusiastic guy?

Uh I think I am. I think that's why people like this. Podcast so We have a a very loyal audience and I think it's because people feel as though the Sean and I have a little bit of a contagious Energy and yeah, it is it is positivity. It's very positive. But I I think some of my co workers will say that I'm kinda grumpy.

Because I I've gotta be the bad guy, unfortunately a lot of times, and I'm pretty blunt. I think you have like a angry enthusiasm. Uh you flip the your switch flips from like in extreme enthusiasm and it's super infectious to like quickly very angry or grumpy about something and then you s you you switch back sort of effortlessly, but for the people around you they're probably just getting rocked by it. Yeah, I uh like Yeah, maybe you were like this uh But like I will fight with my like executives at my company.

But then I can we can just hug it, we're good. We're good, but I'm definitely like that. Um Can we talk about Larn Vest a little bit? So I used to I used you guys when you first came out. What uh what was the premise behind the business? Because I think it Kinda pivoted a fair once or twice, right?

Um, so we started it was um the business plan was always the same. It was content, tools, and advice. Uh and I started it out of my own savings. Uh so we started with content because uh back in two thousand eight in New York City. I actually founded the company in two thousand seven. Uh Great.

you could do a free newsletter and just kinda get going. And so we started creating a brand. We started trying to talk to our users, um, and just have a really authentic voice to say, Yeah, for me it was pretty It was pretty stupefying that I could graduate from a great school Yeah, I worked on Wall Street. I was really good at math, really good

Um at economics. But when it came to just the basic questions of my wallet, how many credit cards should I have? What's a credit score exactly and how do I make sure I keep it safe? What are the activities I need to do? in to to make sure my wallet is strong. How do I, you know, how much can I afford in rent? Really basic questions. The fact that There were not very clear answers was kind of wild. So we started with content and then we always said it would be content tools and advice. And so

Um once we finally raise enough money to build proper tech team. We started with a budgeting app. I which uh was a place for you to see all your finances in one place. Um and then Well we quickly realized was people wanted advice and I had no idea what advice looked like. Chat what it look like phone calls a call center open twenty four hours a day.

I had no idea. And we just said we'll follow the customers. Um And we originally started uh when you build content, you wanna focus on on an audience, a specific one. So we started with um Female millennials. And then what we quickly, by the time we got to advice, we just served households. So it was never a pivot. It was very much just like an extension of what we were doing. Um and by the time we get to advice, we actually built financial planning software that could take any family and ingest sixty data pointly

What we call GPS for your money. So literally a living and breathing financial plan. Um, and then we connect you to I I'm a certified financial planner and Uh I We connect people to uh trusted advisors that worked full time for us. And so that's what we did. And it was a subscription service. And then by the end, we had companies buying learn best software for all their employees as a a a benefit, uh you know akin to uh your health benefits and your four one K benefits. And so

That's what Learn Best became. We became the the the largest, fastest growing online financial planning company. So I don't know if you know uh about my business. Uh we we're we're hosting this podcast. It's called The Hustle. It's content as well. And we're we're also building tools for it. So I I'm I'm very familiar with the content game and the strategy. Um I think it's great. But most people fail at it, I think. It's quite hard. How long did it take to go from content to creating your pro products? Um, so we started content in uh

I May of two thousand seven is when I founded the company. Um my then boyfriend's now he's my husband. Um his dad was our lawyer, so shout out to him, he was the best. Uh, and my mom was a secretary, literally, like signed the formal paperwork. I'll never forget it. Um, and then I'd written a seventy five page business plan. And then by the time that I dropped out of HBS, it was december eighteenth of two thousand eight. Moved to New York and started

I remember I gave myself Christmas. I said you get basically a week and then it's go time. And uh so started building January first of two thousand nine. And then by the time we launched the company, like truly launched to our first 10,000 users, was the following January. We launched, uh we launched these things called boot camp. Which were ten day programs that people could go through to learn about their wallet. Um, and they were free and

Mm. we quickly one day realize holy smokes ten thousand people have signed up. Uh in a week. to go through one of these programs. And from there we just kept building and we kept talking to our customers and saying

What kind of tools do you want? What what do you want advice to look like? And one day I started noticing every night people would write in and say, I really want to talk to a customer or sorry, to I really want to talk to somebody. I have questions. I have questions. And so Cuida.

keep in mind it's a regulated business, um, to become a financial advisor. And so we had to go get regulated and became a registered investment advisor. And we then opened it up that you could pay to talk to an advisor. And we said, let's make it super honest, really transparent. No hidden cost, just on the site, exactly what it costs. Um, and while like you step back, it seems really logical. Like what we were doing was never illogical. But it actually flipped the whole industry on its head. The industry used to pretend to give advice away for free, but then charge you deeply on all the products that they would give you. And all those fees. actually be pretty material. So if you had a hundred thousand dollars, you're paying two thousand dollars a year for advice

And That didn't always feel good. People were very distrustful and so we just said flip it over. Make it five hundred dollars for the year to get access to unlimited advice. And will sell no products.

And so that's what Learn Best did and again it seemed At the time it was actually pretty groundbreaking. To build financial planning software um for everybody and for the masses. And so we also said we'll take you if you have thirty thousand dollars in income or thirty million. Um, again. Not that wild, right? It just lets be let's be a good business that takes care of people.

But What we realized is that alone that brand positioning was pretty powerful. How many employees Did you have uh like in the first two years or so to build all that.

Uh, so we were small in the beginning, you know, we got to about fifty employees by call it the first real like two to three years up and running. And by the time we got acquired, we were about a hundred and fifty people, which um you know, uh we're real business. And so that for me, uh meant just like so much personal growth, so much you know, being a young entrepreneur, You don't know what you don't know. And so um it seemed really big to me at times.

So how how big was the audience before you started launching those m uh the the products and the advice? So how because you're what I'll call an audience first. uh company which is first build it through content Loyalty. Um and then when you have a service to offer or product or tool to offer Uh you got your customers sitting there, you just need to convert X percent of them. So how big was the audience?

Um, by the time that we got acquired, uh, we were about two and a half million users. What what's a user? I was somebody who had signed up for to to make an account. Wow, that's a ton. Yes. No, it's I mean and and we so it's funny, we're really old school. We actually didn't

We didn't ever spend on advertising. We I I think by the the year we got acquired We hadn't even spent a million dollars on advertising. Um, it was really old school. We were very focused on like That's

Let's go and find customers. through business partnerships and relationships and creating content and you know, we wrote books and we did all these other things to really build a following. Um, and then we kept converting them into that. So, you know, for the for the tools where people would link all their finances and we would see their full wallets. We had about half a million of those. Um

And then on the paying customer side when we got acquired we had about Uh, depending on how you cut it, we had about a hundred thousand uh customers on the paid side. And this is before Facebook, too. Um, so uh Mark Zuckerberg uh went to college undergrad with me. I was his same classmate, and so Facebook definitely existed before I was starting Learn Best. Um but I yeah.

two thousand seven, two thousand eight when I was starting the idea. Facebook I think was founded in like two thousand four. Um so it existed, but it was very much, you know, you weren't building your business on Facebook at that time. Right, that's that's what I meant. So hold hold on. You were at Harvard when he launched Facebook at Harvard? Yeah, I was his like same classmate. Well what was that like? Do you remember when you heard about Facebook?

Do we remember? Are you kidding? You like could never have forgotten. Um, you know, I remember at actually at the end of your uh username what would be the number of Facebook user you were, and I was like in the hundreds. Um so I was like roughly around a hundred and fifty. Ah and you knew it because it was just the most helpful thing on the planet. It'd be like, Oh, what's that person's name again? I can look them up. Um And I was joked with my husband When my husband asked me out, I like couldn't look up who he was yet. He'd asked me out before Facebook existed.

And I remember being like oh I can't remember who he is like is it this guy or that guy It just like And my kids will never know a world where you like

can't look somebody up. I mean it's just it's really powerful. So Did you think at that time it's gonna be this is gonna be a big deal or were you like this is useful for Harvard and I mean like could you foresee that it was gonna be like a seventy five billion dollar company? Um I I I can't take credit for having like something that that was that kind of crystal ballish, but you knew it was a big deal. Um really quickly you could just tell it was like the amount of time you were spending on it, how quickly it was spreading. at when it went to other colleges and you could look up your friends at those schools uh when you could poke people I

It was Yep. to to the credit of of Mark, it was an incredibly infectious platform. And did you know him personally or no? So I didn't know him when we were in undergrad. I met him a handful of times and um I know his family and his siblings um pretty well. Uh, but no, when he was starting at undergrad, I did not know him.

And did you think about joining when It was it's like, Hey, this thing has kind of taken off. I'm a student at Harvard, you were thinking about drop you know, you dropped out of business school anyways to start a business. I actually was thinking at that time of dropping out of Harvard to start Learn best basically. So my mom convinced me to graduate. I said to her, I wanna go start a company. I know I need to

Um, and my mom was like, Can you just graduate pretty please? I'd gotten into Harvard Business School and my mom was like, Can you sh at least graduate from from college. Um, and to my mom's credit, I did. I'm glad I did. Um, but I that That itch to go start something was like pretty alive and I you know, to the credit of like a Mark Zuckerberg

When you are so close to seeing businesses get built. You know, I think they called it the face bip effect, which is When you can see how powerful the Internet can be. And if you're a uh you a hardworking person who has skills, you're like, huh, maybe I should go do something. Um, but I uh so so yes, and I will definitely say I think Facebook spawned an entire uh, you know, set of entrepreneurs. And then you got you said you got acquired when you guys had

Um I forgot how many but I've read a blog post where which was like hey Learnvist gets acquired for whatever hundreds of millions of dollars. And it seemed to me when I was doing my kind of back of the envelope math, I was like So they were doing sort of like there's my my my math showed me You guys are doing like less than ten million in revenue and got acquired for you said three hundred seventy five million.

Um That's a huge multiple. So uh first am I did I just did I lose a zero somewhere? And then secondly, why did you get such a big outcome? So we're definitely doing a lot more in revenue than that, but Um, you know, I think what we developed was uh a pretty powerful software. So Uh we had about eight patents on our software. Um, we built cash flow based financial planning software.

Uh, which didn't exist, which is really silly if you think about it. Um, most of the financial planning software out there was focused on Helping Yeah. People who are quite wealthy.

Think about how to build more wealth, but it didn't have to ever net can you pay your bills. But for ninety five percent of the country, you know, right now seventy eight percent of the country lives paycheck to paycheck. So actually That software that existed would never have worked for The majority Of the entire country.

And so we built cash flow based financial planning software, which actually would say, How much cash do you have? And can you pay your bill? And if you have something left, then where do we go put it? And so it was a pretty profound technology platform and in fact

I even chatted with somebody else the other day who's trying to build like a a similar company learn best because There's still demand for these software platforms. by the these big financial institutions and they're really hard and they're Very tedious to build. Um so

So no, and then North Russian Mutual Also, it's just an incredible business and They have you know uh five million plus families across the country that they serve. And for them to be able to take our software and go deliver, you know, plans to everybody. Was a very

powerful concept uh that the CEO had. So Um So yeah. So I I wanna come back to you were saying that you're talking to people who are building similar tools. I want to come back to that in a second. But I have two questions for you. Um were you profitable when you guys sold?

Um, we were like within profitability, meaning like we depending on how we were spending, um, we were near profitable. And we could have been profitable. So one thing that's worth saying, um, we we were incredibly lean in how we had run. We had just raised thirty five million dollars. So My mandate was to continue growing and build out business units at that time. Um but again I I'm a recession entrepreneur in my DNA. We always lived as though we didn't have extra money.

And it was just I you know, I think we went through a moment at post twenty ten where it was all about growth and get as big as you can. Um with no mindset to profitability. My roots, first of all, are like I'm naturally, you know, very, very frugal, very scrappy, every dollar I every dollar we started spending was my own money. Um, in the early days, it ties to the company up. And so that was and I'd read a few different founders saying that that's the best way to be a founder. And I

I lived it because I felt like it was the right way to run the business. Um, and so even when we were spending, like there were no dollars that were not going somewhere. Um I'm gonna get this number. This number will be roughly right, but We'd something like

Forty five million dollars of cash when we got acquired. um uh on the balance sheet, uh and m meaning that um we just we were never spending that much money. So why why raise so much? If you had just raised thirty million dollars, you had forty five million dollars in the bank, that means you had some like ten or fifteen million dollars when you raised your last round, and if you're making good revenue Why raise in the first place and also why sell? So great question. Um so I think first of all we so we'd literally just raised uh when we got acquired.

Um and North Cross Mutual actually had had just invested and then they came and said, Actually we'd like to we'd like to acquire you guys. Um, so so that's that. And then um Why sell? So what we were building uh to be able to go get it to, you know, uh our direct to consumer business. Uh

was growing. But I remember every day we were, you know Signing up forty families a day, forty households a day to get financial plans or You know, some days we do two hundred, but it was And I I remember thinking we built this incredibly valuable asset and we built it because we really believe that it should be something that should go as quickly as we can across the country. But getting people financially plan is really hard. It's not like anybody walks down the street and says

Oh, I can't wait to go get a financial plan today. That concept didn't exist and I always joked. Um, I actually was telling an entrepreneur today, I was like, God, I really did run a hard business to build, which In retrospect, I think made it I'm like an even scrappier entrepreneur than I thought, if that makes sense. Like if I was selling shoes online, like holy smokes, how much fun would that be? And I feel like that's an easy business to build, but I was selling something that was hard. Right.

And we're productizing a financial plan that nobody ever was super excited about. Uh and There was some part of the population that loved it, but you know, we were we were telling people, hey, financial plan's gonna make you better. And then once they tasted it, they loved it. So our customers were super sticky. Um but I remember thinking to myself, Oh my goodness, North Rash and Mutual has eight thousand financial advisors. That

passionately care about the mission in the same way I do. that can actually go and use this platform to get to more families faster. And if I really believe in our mission. Cut. probably the right thing to do actually for this business is if you could tell me that I could go

From Hundred thousand. To five milyen in a short period of time. And like guarantee that that would happen. Like that

actually is a better use of what I built. So then did it does make sense. And so did the company uh Northwestern Mutual did they acquire you Based off of Was the the frame or the valuation based off of How many customers you currently had, or did they just say ah that's a we don't really

you know, the behemoth of the company. We don't really care about your users, but what we want to do is just take what you built and plug it in on our back end. Yeah, I mean I think and again I can't speak for how they valued the company exactly. I wasn't part of those conversations on the back end, but um I think that what they viewed it as uh was they'll say that there were three really powerful things. Um the first was an incredible software that they could plug in that could go uh to to their customers. Um The second was our entire platform and if you go in North Russian mutual dot com, you know, today I was it's effectively learn best. We just

moved over the tech stack, made it so you could log in, see your finances, um, use a lot of the tools. We launched their mobile apps, everything, uh leveraging all of that. When they offered, were you just like Hell yeah, in or uh because you had just raised I mean, it it if you said yourself you it sounds like you had a It was a slog a little bit. If I'm kind of reading between the lines, like you're like, Oh my God, it's forty users a day, like this is really

Friggin' hard. Where and they offer you that where you're like, Yup. And or uh What was that like? No, um, it wasn't that simple. Um, we had a handful of other acquirers at the table. Uh and I actually took my job very seriously, which was um

My your job as CEO in those moments. uh if you take your job seriously and maybe this is just how I'm wired My job was actually to go get All of the opportunities. And

unemotionally bring them to the board. And to say here are all the different paths that we can take forward. And then the board came together and made a decision of what we thought was best for us. Um, and I actually waited until that day, which was the morning that we signed to make my decision because my job was gathering all the different opportunities to bring them to the board and say

Here's what we have in front of us. We can go this path, this path, or this path. Um, and to be crystal clear It was never like a stressful decision in that staying private also was a really good decision. Like we had, as I said, about fifty million dollars of cash. Actually think it was fifty two million if I remember correctly, um, of cash on the balance sheet. Um, we were growing. Uh it was starting to get easier and easier because we had launched Learn Best at work, which was growing rapidly and we were selling the software subscription in tens of thousands. That's way more fun than you know, a hundred a day. Um, way more fun. You're like, great, I can do this.

And that business was really taking off. And it was I just started to see the oxygen of it. Um Okay. I I think the point that I'm making is every minute to getting there

was a lot of work. It was never one of these businesses that just like overnight seven thousand people show up to Chipotle and can't wait to eat our our salads. Like it was it was not anything like that. Um, but so I didn't make the decision until that morning and it was really I took it so seriously because I had As I said, about a hundred and fifty employees. I had you know, hundreds of plus shareholders and people had been part of the company and at some point left. And then all of our investors. And so I had to think on behalf of hundreds of people.

And I felt like your CEO job is actually a really serious one, which is to bring it to the table and then make the best decision on everyone's behalf. Knowing that some people be s thrilled about an acquisition, some people be Why are you selling? This is such a good business, it's going well. And I just also knew it was a it was gonna be a big decision. What do you r what do you regret about that journey? I mean, would you take back

selling or are you happy with that? Would you take back raising all that money? Are you happy with that? Is there anything that you you're like, uh I really I don't regret a single thing. I have to say, um, you know, personally I got to grow a lot through it. Um most times when a startup CEO gets acquired They like sneak out the back door as quickly as they can. Um, and I care deeply that by the end of it, um that I I wanted to make sure they felt great and uh I wanted to feel like I had done what I I said I was gonna do. And so uh I end up saying four years'cause I had such a good time. Um and I think that that that speaks volumes uh to to North Western Mutual, which Uh again I was chatting with a few friends who sold their business in the last week and they were like

How did you stay four years? And I'm like, I loved it. And that doesn't mean there weren't hard days. There were brutal days. There were really hard days. Uh, you know, we shut down the Learn Best brand at one point because it really made more sense for it to live on the parent company because a parent I'd been a rat for a hundred and sixty three years and Learn Best was a tiny little brand. Um, and you know, I was proud of that decision also,'cause it was the right one for what we promised that we were gonna do. So what do you what are you looking at now? So you invest now. You got a fund, um inspired capital. What spaces are interesting to you uh nowadays? So so inspired capital, we're an early stage fund, so seed series A, uh we're totally generalist. We're literally looking right now at everything from restaurant tech, so food tech, um, which is really interesting. It's a mix of fin tech and sourcing of

Any type of food that we will all eat from straight to agriculture, you know, farms to your coffee shops. uh that we're pretty inside about. Um we're really focused on uh the future of money movement and there's some really cool things we're working on there. Um we uh are we just mess in the company in uh the the trucking logistics space which we think in hope can put lots of people to work. Um, and so you know, really focusing on what is the next decade gonna look like. We actually published today a future work study. Um And I heard this great quote, We basically started the year in twenty twenty and we're ending this year twenty thirty, just in how much we've just advanced the ball on who how and who we all are and how we will think. Um and you know being a a working mom

How amazing it is is it that I can actually excel at my job, truly excel, and actually see my kids probably an hour and a half to two. per day more. I mean, it's just I I will say I think we're living through one of the bit bit biggest seismic shifts. On our planet right now. ever, maybe the probably biggest in my lifetime. Um the global health world is collaborating in ways that you've never seen because we are all focused on a common enemy of Covid. And I just think the world is incredibly exciting. And I will say when you see asymmetric dislocation like we see right now because the world is on its tilt.

Um that's when Innovators go nuts. And this is like my favorite thing. I talk to ten entrepreneurs a day. And um, as you can tell, I'm honestly just a junkie for founders. I I I love building businesses, my brain Loves nothing more than hard problem solving. Um

And I was just saying to a founder before this You know, companies have seasons, right? You have spring, summer, fall, and winter. Winter sucks, right? And as I just said, I had plenty of winters at Larn Gus. Summer is when it's fun and things are exciting and I like to say that you know the Inspired Capital team, we c we are our best when it's winter and for a lot of businesses right now, this is a winter. It's a scary time. And so this is when we want to be the best teammates.

You uh you talked about future of work and you think there's a huge ship going on. I think a lot of people right now are talking about this remote work. Uh what is what does that mean? Uh is this sort of permanent, is this temporary? Uh what are the second secondary effects? I'm curious.

Um, what's something, you know, it's a Peter Thiel question, what's something that you believe about the future of work that n is not sort of consensus right now? It's not something that everybody is saying. Uh, do you have any sort of original views or contrarian views around the future of work? I mean We will go back to offices, so let's be clear. But I think a lot of the fat will be Cut.

And what I mean by that is We used uh I don't know about you guys, but I used to like Be in cabs and running and Ubers and subways and sprinting in planes and trains and like the frenzy of what I used to do. Because there's so many social norms. Like if I'm gonna see you in this city, I wouldn't be like, Hey, let me just zoom you, right? You'd be like, That's rude, come visit me.

Why? Like There so just I think the amount of what I'm gonna call like useless friction That we used to apply to our lives that now looks calmer. So that's great. I think

You know, I'm really bullish on just equalizing households. I actually think that this is this is a great equalizer. Um everybody's partaking in so many parts of running a household these days because we are blocked in our homes and that's gonna create some permanent habits that I think are gonna be better. And um, you know, I I I'm really fortunate to have a phenomenal partner and my husband, and we really do both a lot of everything uh around our home. And I think that that's gonna be hopefully more normalized um going forward as I think a lot of p parents are gonna realize It's not a choice stay home or work, like

There's this very powerful middle path. And so you know, I think the gig economy going into this intermittent work economy. is just exploding right now. Like you can work twenty hours a week if you want to. You can work seventy hours a week if you want to. Um And I think that we're gonna So the only other thing I'll I'll say that's I'm not contented.

I am deeply worried about how forty million Americans are gonna get back to work. And I don't think, you know, the markets right now, Main Street and Wall Street are completely disconnected. I honestly wake up at three o'clock it to In the morning. Wondering. How are fifteen million households gonna be absorbed?

uh when those jobs don't come back. Um, and I'm worried about that a lot. So that's one thing I'll say. Uh I don't I I sometimes wonder why more people aren't talking about what we're gonna do with the jobs that do not come back and That worries me a lot.

Wha what type of what's your background? You're what part of Florida are you from? So I grew up in Jacksonville, Florida. I was born in Kentucky. I grew up in Jacksonville, Florida. Uh my mom's side of the family is from South Bend, Indiana. My grandfather was a welder who I its whole life. My grandmother uh worked at A T as like a uh

Uh the the I'm I'm doing the spinning motion. She was literally operator. Um, and then my dad's side of the family, uh Von Tobel uh is I is Swiss uh Belgian. Uh and so And then uh both my parents were in the army as doctors and nurses. Um, and so my brother was born in Germany and I was born in Kentucky. And then uh So I'm from Missouri and then I lived in Tennessee. So I'm from a normal family like a not a Silicon Valley, not a Manhattan family.

I live in San Francisco now and I'm definitely on like the inside. of like a lot of the you know the San Francisco nerds and it sounds like you are on the inside of the Manhattan relatively elite circle. Um I mean the partner for uh your cap uh for your firm is like a pretty big deal, the Pritzer family. Does it feel ever like you're an outsider Uh you said Main Street and Wall Street. Um

Does does it feel more like you're connected to your roots of where you grew up? Or do you identify more at this I mean, and I say this'cause I'm in this crew too a little bit, like in this relatively tight circle. I mean, where Are you an outsider, do you think? So glad you asked this question. Uh so glad. Uh for a bunch of reasons. And I think What's really Obvious to me is

I think it is an incredible competitive vantage. I think right now we're in a World where Um the country is very disconnected. I'm actually hoping that COVID is something that like does unify us a bit more. There's days where I worry it's moving in the wrong directions. There's days where I feel hopeful. Um

I think the fact that I came from a really Again, my my dad was in the army as a doctor, my mom went to boot camp, was a nurse. My mom's a nurse practitioner. My dad passed away when I was younger. So my I was actually raised by a single mom Um with three older or sorry, three kids. I have two older brothers. Um who are also both doctors.

Um But like It reminds me every day that the bubble that we live in is completely ridiculous. And in fact, you know, I I am a certified financial planner who stared at America's wallets for a decade. And the headline is people can't afford anything and everyone's stress. And if you don't have dignity to be able to put food on a table for your family, guess what? That's a pretty stressful thing.

If you're not sure how you're gonna be for forget like saving for retirement, if you don't know how you can actually feed people right now. Holy smokes. Um and now that I've become a parent, like that's so much more visceral. And I actually think it's a real competitive advantage to remember that. Uh There's three h three hundred plus million households in this in this country and that not everybody's on the same page and technology isn't always moving everybody forward. And so I think it's a major advantage um to not forget that. And again, I'm literally in Jacksonville, Florida right now, in Panamitra. Um in like my childhood bedroom and I'm so proud of my roots and I'm so proud of my family and what they've helped me accomplish. Um

And Goodness gracious, do I feel like we need to do more bridging the country together. So and this is a good segue because earlier you said that people are actually still trying to solve the problem that you were trying to solve for. What opportunities exist in this financial planning, personal finance space. I'm I'm a huge nerd in this. I use wealth front, I use personal capital, I've used Met. I use spreadsheets. I love this stuff.

You know, I think a few things. I one The problem of our wallets for America is bigger than just like great software. Um, there's a lot of what I'm gonna call infrastructure problems that like Tech can't solve.

Uh, what's the minimum wage? How do we handle um, you know, uh uh working mothers when twenty five percent of the country's moms are are single moms. Uh, and how do we handle daycare, blah blah blah. There's a lot of other big problems around the wallet in America that like a cool technology app doesn't solve. That said, um, I don't feel like learn best solved everything, and in fact I I have this itch that um We've wanted to scratch for a long time.

Um around Yeah. I was a part of the population where I I wanted to talk to a financial planner, that for me, there's a certain user type about 22% of the country from our data. that wanted to talk to an advisor in the country.

But about seventy eight percent of the country Don't want to talk to anybody. They just want the problems of their wallet to be solved for them. And so I get really excited about the future of self-driving wallets because I actually think. Every hour that you have an extra dollar, penny ten dollars, one hundred dollars, one thousand dollars. It should go to the exact right pocket.

instantly. And so I believe more innovation will happen. Um And I think that's one of the things that you know we get pretty excited to talk about is Um uh you know, I wrote a book called Financially Forward. literally just to force myself to think about what the future of our wallets could look like. So what's that product look like?

Uh, self driving wallet. You've put rules and controls around it that say Uh my checking account always needs at least four hundred dollars in it, but every dollar above that, please go put it in the exact right place and Take care of it.

So what what would you do? Would you Would you so like I use Simple I like simple.com. I I I I I've been toying around with that. But what I learned was that It's it's a checking and savings account. It's actually they use I forget. What whatever the biggest bank in like the world is, it's like the I forget what it's called.

Anyway, the put their software on top of another bank's checking account. And uh because it it's opening up a bank is really hard. Um

Is that what you would do? I mean how would you go about solving this? So I I if I remember correctly, Simple got acquired by BB VA. I think actually right before Learn Best, if I remember correctly. Um So the and again, I don't want to totally bore you, but basically underneath it, the problem with uh autonomous wallets is money movement, which is money doesn't move quickly. Um, from one bank to another. It moves ac across ACA trails from nineteen seventy one and they typically take about five days to move the money. And so if you want wallets to actually be able to self drive

You actually have to fix money movement. So we've written thesis upon thesis papers. I call it actually uh liquefied money is the thesis. Um, which is also and I'll give you another example. Why do we get paid every two weeks? How does that make any sense? You work every day. Guess what for a normal American family getting paid every day? materially helpful. That's a pretty radical idea. That's kinda cool.

Why do we get paid every two weeks? Is this like some I don't I have no idea. It's a legacy concept. Some people get paid weekly, um, but most of us get paid Twice a month. And if you think about that

people have liquidity crunches in between those two dates. But you work every day, so why don't you get paid every hour? Yeah, w what do you think of the company I think is called Ernin, uh I believe that solves that problem, that tries to solve that problem? Well, they're solving a portion of that problem. So what um but no, I think that um there's a few of them. There's Ernan, there's Dave, there's a bunch of other. There's a company called Even, um, which is Uh but I'm I'm They they are solving elements of it. H have you seen the sort of crypto projects that are doing streaming money?

Which is basically like the way we you know, we don't download movie files anymore and play them. We stream it bit by bit. Uh as we watch. Um, but basically getting paid like that. So why why don't I get paid by the second that I'm working? And it's just streaming into my bank account, uh fractions basically of of value. And there's

Crypto companies do it. Even more valuable. Okay. It's not just the streaming in. It's then what happens. Your credit card debt actually charges you interest every single night. Okay.

So actually you paying your credit card bill nightly? would materially help save and keep mind the average family in America has between nine thousand and sixteen thousand dollars of credit card debt based on how you cut it. The average savings account is four hundred bucks. But if every hour you got paid And then you could pay your bills and live your life, but it would actually stream into your 401k and get the matching dollar that same hour. And then auto invest. Think about the like

That is what is the difference between and I always I feel like Covid exposed the precariousness of our economy, but it also exposed the precariousness of the American wallet. And I think that we're going to be in a groundbreaking moment of how do we go fix it. Um, so any entrepreneur listening, I want to talk to you, uh, Alexa at Inspire Capital, uh, I want to hear your ideas. Um, but these are the big monumental challenges we want to solve. What what would prevent that? That's a that's a crazy idea. And I think that's a that's a cool idea for someone who wants to uh Like it it's it's kinda like a go big or go home. That's a pretty cool idea. I like that. What would prevent that from working?

What are the barriers? It's the infrastructure layer that we I was just saying. It's the the money movement layer. Is it money movement or is is it a cultural thing?'Cause I'm a business owner. Like I like the two weeks buffer. for a small business when you're just getting started like

Businesses are we we we take advantage of that, right? Like you're like Like oh right, I've got like five days, I gotta go collect this this client's money and then I can make payroll. Yeah, um it's no, I I that I think is solvable. Uh I mean you have two le bleeding edge companies. You know, I think in just the last week we saw a few companies say, um work from home forever, but you take a few more that then say We're gonna pay our our employees daily. And in fact Uber started paying its drivers every ride. That's that's an example of you've worked.

You should get paid. Why do why do we withhold from you? It's a free loan to your employer. And At some point that will break down. Um, but that's not the thing I'm I think is harder. It's actually the money movement piece of um because our wallets have been unbundled. We used to have wallets at one place, let's say chase. And used to have your credit card there, your savings account there, your checking account, your four hundred one K, et cetera. You now just both of you have named while you've been on this call seven places that you have financial accounts. So it's money movement across those accounts. moves across an A C A trail. That ACA trail takes about five days or it mimics it.

And it'll look like same day. And sometimes that same day is really more of like a magic trick. It's not really there. So then to be able to pay it out to some other place is very hard. There's a European company I think who was doing something similar, uh helping wha what was it called? Transfer uh Uh there's a company called TransferWise, but then to actually Europe is miles ahead of us. They're on real time payment rails and you can actually Uh huh.

They they like li' they're like a full decade ahead of us in terms of you don't even need Venmo because you can just pop money into each other's bank accounts. Bank to bank. Yeah. I India just also came out and they announced a whole monetary uh API, basically a mandatory payments infrastructure, right? Uh UPI or I love how much you guys know about uh FinTech and infrastructure. I love it, guys. I could geek out with you. Well, y I don't know if you've heard this podcast, but what we do is we brainstorm ideas. Uh we just shoot the shit and we brainstorm ideas or we see something interesting and we say, Hey, this is cool. These guys are doing streaming money. What would you do with that? Hey, why do we get I think we literally had this conversation which was why do you get paid every two weeks? Uh that's crazy. It's a free loan to your employer.

And so that's what we do on this podcast twice a week. So that's yeah, we we we like to nerd out about this stuff. We know a medium amount amount about a lot of topics. A little bit. Only a little bit. We know a little about a lot of it. Yeah. What uh One of my favorite ways to brainstorm is I like to look at companies in other countries and just be like Do that in America. So like guilt group.

Kevin Ryan was like Oh, I see the spread company's doing this, let's just do that in America and we'll put a little spin on it. What's a European company or an Indian company? that is doing this quite well that I can go and learn about in order to see like how this is done.'Cause this this is like pretty hard to conceptualize, right?'Cause we're like Uh it's been done this way for uh who knows, decades, hundreds of years. Yeah, I mean to be honest, for the standard of what I want to see built, I don't believe that there's a company that is

close. There's a company in the United States that's starting to think about this and in doing a good job also called Tally, where the Jason, the founder, is wonderful. Um at and it, you know, he he was helping people, he started with credit card debt, pay off their credit card debt faster. Um, which was the core pain point and um starting automation around it. But Um, you know, I think I wanna I wanna like fast forward the decade ahead.

Where We actually get to instant streaming money. It you know, I I call it liquefied money, you're calling it streaming money. Um where your money can always be optimizing to the right place. And that gets pretty powerful when that begins to happen, but most importantly

Not only is it powerful, it mi meaningfully changes the life. Of American families like meaningfully changes. The lives. But I'll I'll challenge one thing which is

Um so I've heard this idea before about basically hey, the what's the category of of what you built? It's like P P PFM personal finance manager. And uh the theory is basically you have things like Clarity Money and uh what learn best and others that were basically all like Hey, we can suggest some things. We can show you some charts and analysis, but like fundamentally you the user make the decision. And what you're talking about is

The software makes the decision, right? Self driving, basically. Like it's not It's not you're sitting in your car and your car suggests to you how you should you know, turn or change lands, the car changes lands because it knows where you're trying to get as your destination. And so I've heard before that hey, what what we need is for um to get the A get AI basically to the point where it can actually Make the decisions and optimize the money for you so that the user doesn't have to make decisions. User says, I want I have these financial goals for myself. This is my income coming in, here's my bills.

And it basically does it. And W uh what you added on was The reason that can't happen right now is because The transfer is too slow. Uh, but it seems like there's a middle step, which is just right now

The software doesn't decide. The user decides. And most users don't want to think about that or make those decisions. That most people are not active. with their money. Much to your chagrin, I'm sure. So is it more about software deciding versus user deciding, or is it more about liquified money? Uh so liquefied money matters, but then to your point, um

So I'm gonna like I wanna answer that. with a with a visual question. When we imagine money right now, we imagine money by saying, Okay, I'm gonna log into my you know my uh E trade account and I'm gonna stare at all my graphs and

and you know, look at things and I'm in a talk to an advisor and tell them my goals and then like A lot of things are gonna be executed. Um. I almost think that we are thinking about the limits and the bounds of what technology offers today as opposed to what the customer really wants.

If you ask a customer what they really want. They want Enough money to do what they need to do and they want everything else to be taken care of. And like For most people, thinking about money all day long is actually not fun or exciting, and in fact it's quite stressful.

And so I almost think we visualize money based on what exists, but imagine A thought exercise and I'll use an Amazon Alexa uh since uh It literally there's like seventeen in my brother's house and he just likes to yell at me all day and he thinks it's so funny. Um, but basically let's use an Amazon Alexa. And imagine you could walk in your kitchen every morning and just say You have surveillance, so you have rules that you set around your wallet. So

Has anyone broken my identity? Has anyone done anything bad or unto? Um restrictions that you put on. So like my kids' credit cards can each only s you know spend fifty dollars a month and whatever it may be. And then you've already clearly Laid out goals.

And it just does it for you. And so you walk in like, Why do I even need to look at my money? All I care about. Is Are there any crises? No. Um are the rules I've set up

in place. So any extra money, you know, I I need four hundred dollars in my savings account for checking for, you know, if I need cash, we're gonna obviously go away from cash permanently at some point. Um And then Everything else. Just optimize for me. And that's math. The thing I love, you know, I am a math geek. I've always liked math growing up. I always loved it. Math is really beautiful because this isn't you know, we're not trying to cure something, a disease that we don't it this isn't

A Covid situation where we don't know that you we don't know what to do yet. We are looking for a vaccine to use that as an analogy. This is math. For every American wallet, I can mathematically tell you where their next dollar should go. To save to save them money, make their life better. Um, and outside of them telling us what their goals are, then the math can do it and it can do it every hour or every minute. And at some point when you get there, that is better for the American wallet. And so That's the vision of that that's literally the picture in the back of my head is like when do we get to a place

Where My money is just doing what it should do at all times. And right now there's Wild amounts of friction. Move it from here, put it in the savings account, sweep it into this, do this with this, pay off the credit card. To pay off your student loans, you have to make two payments and tell them please pay the principal, not just the interest. Friction everywhere. And at some point it will go away. And I want it to go away as fast as we can and it will be some of my life's work to help that happen. I don't think you should be a V C. I think you should go and start this. You're very uh persuasive. I feel like I'm ready to like get behind you and say let's go to war.

You're very you've got a very good pitch. I w uh I I had a one last question. Do you are you a fan of Ramid Sati's uh teachings and his book? I his book, um I Can Teach Igrich, he's a great guy. And I will say like Every financial planner out there that's doing good work to help help people uh between now and when this beautiful future software can exist, I'm excited about I just I I feel a lot of your pain and I understand where you're coming from because I I'm not poor anymore, but I remember being

poor and like so afraid to look at my log into my bank account and then I I eventually created all these systems. So it's like a little bit of paycheck goes here, a little bit of Interest this thing goes there, the there and I'm like I I like Jerry rigged this thing together. And even to this day, I'm still like I hate logging into my bank account.

' For me you're it's like PTSD, right? You're like It's so like I just don't even automate some stuff because I'm like I don't even want to I hate it. I don't like that. And this is a perfect example of where, you know, I really do think um you know I grew up a really normal life. I grew up in Jacksonville, Florida, which is a wonderful place to grow up. Um and I just think, you know, I I'm interested in technologies that can impact tens of millions of families. I and like really meaningfully make our life better. And one last thing, you know, I at Inspire Capital, we literally invest across all sectors. I just told you everything from trucking logistics to consumer software, um, to fin tech. But one thing I particularly like about fin tech is

In fintech, any innovation is actually helping the customer, right? Like you're not innovating in fintech in a way that like gouges the customer. It's like they're constantly making their life better and cheaper and less expensive. And the pressure it puts on the big incumbents to drive their prices down is really powerful. And I think that's pretty awesome. So I think it's a great place for me to use my brain. This is awesome. Love it. All right, we should wrap up. Alexa, is there any uh you already gave your sort of email address out. Where should people find you, who should find you, how do how do people connect with you? So on Instagram, I'm just Alexa Von Tobel, uh our fund is Inspired Capital. Um, but you can message me on Instagram and I uh it's the one place I actively try to respond to as many that come through.

Uh, so Alexa Vantobot Instagram. And thank you guys for having me. This is so fun. You guys are so wonderful and again, really honored you reached out. Great. Thanks for talking about it. Thank you very much.

What you see above is a preview of the first minutes. One unlock costs 3 credits and covers this episode forever: full segment and word-level timestamps on this page, plus .txt, .srt, .vtt and word-level JSON downloads, as many times as you like.