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

alex alexa and thanks for joining us on the podcast is we have a special guest i'll let you do your intro because i'm really in terrible at introductions but for those who don't know what was learn vest give us kinda like your your maybe two three minute background so that people know who you are sure i think so i'll start from the beginning i grew up in florida and when i always been an entrepreneur love entrepreneurs love building companies went to harvard undergrad and studied happiness which i i was mentioning because i actually think somehow it's been very helpful to to life ended up i going back to business school there dropped out bottom of the works recession and originally eighty one years now i feel like this maybe a our own covid moment is is becoming obviously something that's worrisome some but i built a financial planning software company called learn das with a really simple mission which was so learn best became turbo tax for financial planning so literally every american family for an affordable price could get access to a financial plan and an adviser and on our fifth birthday on march twenty fifth the twenty fifteen sold the business to north northwestern mutual for about three hundred and seventy five million dollars and then spent the next few years as part of that business at north northwestern mutual and through all that wrote some books best selling book i called financially fearless and then financially forward about the future of your wallet and i'm just a diehard hard 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 which is headquartered in new york city and we pay it forward and we invest in seed in series a entrepreneurs of tomorrow building big ideas so it's really fun to get to have done both and now i'm on the investing side and that's me and i'm married i live in new york city i three beautiful little babies a i old to year in a one year old which means i'm completely crazy but that's who i am wow in person you're not in new york city right now i see are you i see greenery no i'm not i'm wish no so have been in florida i'm actually sitting in my like high school bedroom which is which is bringing it all back full circle where we came we came down here first spring break and just haven't gone back do you have like a justin timberlake lake poster on the wall or something or what what's what's in the high school room but you know it's amazing look at this see my mom has literally kept like all of the things and some days i'm like mom why didn't you throw some of this stuff away but she kept all my pictures and all my artwork worked and all my silly stuff so i'll start because sam probably still blown away he loves harvard you had him at harvard then he sold a company for three to 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 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 was yeah i went there i i i paid money and took a tour and they took me around well i will just say while harvard was a great education i think there's lots of things in my that are much cooler than harvard so excited to be here did you say you dropped out i so i graduated underground and i dropped out of harvard business school okay gotcha and you said you studied happiness like was is that like one class classic like i took a class called getting rich and but you know that wasn't like my major it was just one class so i i actually i studied psychology i i started in a track called mind behavior and then ended up in psychology and specifically there was a happiness lab that dan gilbert was running where we focused on like how people make decisions what makes us happy and basically the headline of the whole 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 it doesn't make you happy and you have to clean the car or getting a bigger home out of the city doesn't you know necessarily make you happy because then you can commute farther to your work so it's just really really i think a as good perspective of it's a little things that really keep make us happy i love that you know 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 was he was is one of my teacher sean acre yeah yeah he's wonderful and actually his court professor tal shah in phillip stone were my my thesis advisers so he he gave this ted talk that's pretty great i still remember it and i watched this thing like ten years ago that's you know kinda you know some talks just stick with you and it was called that i think the happiness advantage or the sort of something like that and if i remember correctly the the thesis was being happy is actually an advantage to 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 am i am accurate or am i just totally mis remembering so the short term is that in under extreme du and extreme stress you can outperform in this short term if you're actually very happy and relaxed and fulfilled you outperforming the long call so when you're building teams for long term success so you know inspired capital to venture fund we have a really unique group of people that have come together to build this firm 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 the long run and so and the other thing is i think one of the things i learned from sean and tal my my professors is 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 wanna be around you they don't wanna work with you they don't wanna show up for you 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 in advantage so as positivity yeah i i always talk about this 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 a strong person i'm like the stupidest modes enthusiastic well obviously you bought in on this what i'm saying is that for most people are mostly 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 as somehow more prestigious or powerful in some way 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 it is such a superpower that most people could tap into and totally don't for whatever reason i i mean i totally agree with you and beyond not only do i totally agree with you i also think it's worth saying that 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 you know a certain trait that i just don't have but trying to be positive and trying to to to be joyful i think actually 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 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 feels though the sean and i have a little bit of a contagious energy and yeah it is it is positivity but it's very positive but i i think some of my coworkers will say that i'm kinda grumpy because i've gotta be the bad guy unfortunately a lot of times that i'm pretty blunt i think you have like a angry enthusiasm you flipped 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 you you switch back sort of effortlessly but for the people around you they're probably just getting rocked by it yeah i like maybe you like this but like i will fight with my like executives at my company but then i think we could just hug it we're good we're good but i'm definitely like that can we talk about learn learn invest a little bit so i use youtube i used you guys when you first came out what what was the premise behind the business because i think it kinda pivoted a fair once or twice right so we started it was the business plan was always the same it was content tools and advice and i started the out of my own savings so we started with content because back in two thousand eight in new york city i actually found the company in two thousand seven 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 and just have a really authentic voice to say you know for me it was pretty it was pretty that i could graduate from a great school you know i worked on wall street it was really good at math really good as economics but when it came to just the basic questions of my wallet how many credit cards should i have what's the credit score exactly and how do 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 forward 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 once we've finally raised enough money to build a proper tech team we started with a budgeting app which was a place for you to see all your finances in one place and then what we quickly realized was people wanted advice and i had no idea what advice look like chat would it look like phone call call center open twenty four hours a day i had no idea and we just said we'll follow the customers and we originally started on when you build content you wanna focus on on an audience a specific one so we started with female millennials and then what we quickly by the time we get to advice we just serve household so it was never a pivot it was very much just like an extension of what we were doing and by the time we i get to advice we actually built financial planning software that could take any family and ingest sixty data point what we call gps for your money so literally a living and breathing financial plan and then we connect you to i'm a certified financial planner and we connect people to trusted adviser that worked full time for us and so that's what we and it was a subscription service and then by the end we had companies buying learn best software for all of their employees as a a a benefit you you know akin to your health benefits in your four zero one k benefits and so that's what learned best became we became the the the largest fastest growing online financial planning company so i don't know if you know about my business we we're we're hosting this podcast it's called the hustle it's content as well we're we're also building tools so i i'm i'm very familiar with the content game and this strategy 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 prod products so we started content in i i may of two thousand seven is when i founded the company my then boyfriend now he's my husband his dad was our lawyer so shout out to him he was the best and my mom was a secretary literally like like signed the formal paperwork i'll never forget it and then i'd read the seventy five page business plan and then by the time that i dropped out of h b 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 at go time and so started building january first of two thousand nine and then by the time we launched the company like truly launched to our first ten thousand users was the following january we launched we launched these thing called boot camp which were ten day programs that people could go through to learn about their wallet and they were free and we quickly one they realized holy smokes ten thousand people have signed up in 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 really wanna talk to a customer or sorry to i really wanna talk to somebody i questions i questions and so we that keep mind it's a regulated business 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 adviser and we said let's make it super honest really transparent no hidden costs just on the site exactly what it cost and while like you step back it seems really logical like what we were doing was never the logical but it actually flipped the whole industry on its head the industry used to pretend to give advice weight for free but then charge you deeply on all the products that they would give you and all those fees but actually be pretty material so if you had a hundred thousand dollars we're paying two thousand dollars a year for advice and that didn't always feel good people were very dis and so we just said flip it over make it five hundred dollars for the year to get access to unlimited advice and we'll sell no products and so that's what learn invested did and again it seemed at the time it was actually pretty groundbreaking to build financial planning software for everybody and for the masses and so we also said we'll take you a few thirty thousand dollars in income or thirty million again not that wild right it it just let's beat let's be a good business that takes care of people but what we realized is that alone that that brand positioning is pretty powerful how many employees did you have like in the first two years or so to build all that 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 a acquired we're about a hundred and fifty people which you know we were real business and so that for me meant just like so much personal growth so much and being in entrepreneur you don't know what you don't know and so you know it seemed really big to me at times so how how big was the audience before you started launching those the the products and the advice so how because you're what i'll call an audience first company which is first build it through content loyalty and then when you have a service to offer or a product or tool to offer you got your customer sitting there you just need to convert x percent them so how big was the audience by the time that we got acquired 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 yeah no i mean and and we so it's funny we're really old goal 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 it was really old school we were very focused on like let'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 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 and then on the paying customer side when we got acquired we about depending on how you cut it we'd about a hundred thousand customers on the paid side and this is before facebook too so mark zuckerberg i went to college undergraduate me i was his same class may and so facebook definitely existed before i was starting wearing invest but i you know two thousand seven two thousand eight when i was starting the idea of facebook i think was founded in like two thousand four so it existed but it was very much you know you weren't building a business on facebook at that time right that's a that's what i meant so hold on you were at however when he launched facebook at harvard yeah i was just same classmates well what was that life do you remember when you heard about facebook do we remember are you kidding you like could never have forgotten you know i remember at actually at the end of your username what would be the number of facebook user you were and i was like in the hundreds so i was like roughly around a hundred and fifty and you knew it because it was just the most helpful thing on the planet would be like oh what's that person's name again i can look them up 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 for facebook existed and i remember being like oh i can't remember who he is like is it this guy or that guy and 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 where you're like this is useful for harvard and yeah like could you foresee that it was gonna be like a seventy five billion dollar company you know i i i can't take credit for having like something that that was that kind of crystal ball but you knew it was a big deal 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 when you could poke people i it was you know to to the credit of of market was an incredibly infectious platform and did you know him personally or no so i didn't know when we were an undergrad i met him a handful of times and i know his family his siblings pretty well but no when he was starting an undergrad i did not know him and did you think about joining when it was it's like hey this thing is kind of taken off i'm student 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 next basically so my mom convinced me to graduate i said to her i wanna go start a company i know i need to and my mom was like can you just graduate pretty please i gotten into harvard her business school my mom was like huge a elise graduate from from college to my mom's credit i did i'm glad i did 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 facebook effect which is when you can see how powerful the internet can be and if you're you know a hardworking person who has skills you're like maybe i should go do something but i so yes and i will definitely say i think facebook spawned an entire you know set of entrepreneurs and then you got you said you got acquired when you guys had i forgot how many but i've read a blog post where which was like hey learn v acquired for whatever hundreds of millions of dollars and it seemed to me when i was doing my kinda back at the envelope math i was like so they were doing sort of like does 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 that's a huge multiple so first am i that i just did i lose a zero somewhere and then secondly why did you get such a big outcome so we are definitely doing a lot more in revenue than that but you know i think what we developed was a pretty powerful software so we had about eight patents on our software we built cash flow based financial planning software which didn't exist which is really silly if you think about it most of the financial planning software out there was focused on helping you know 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 is paycheck 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 bills 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 other day who's was trying to build like a a similar company to 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 so so no and then north russia mutual also is just an incredible business and they have you know 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 that the ceo had so so yeah so i i wanna come back to you were saying that you're talking to people who are building similar tools i wanna come back to that in a second but i have two questions were you were you profitable when you guys sold we were like within profitability meaning like we depending on how we're spending we were near profitable and we could have been profitable so one thing that's worth saying 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 but again i i'm a recession entrepreneur entrepreneurial in my dna we always lived as though we didn't have extra money and it was just 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 with no mindset to profitability my roots first all like i'm naturally you know very very frugal very scrappy every dollar every dollar we started spending with my own money in the early days it ties start the company app 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 and so even when we were spending like there were no dollars that were not going somewhere i'm gonna get this number this number will be roughly right but we had something like forty five million dollars of cash when we got acquired on the balance sheet and meaning that we just we were never spending that much money so why why raised 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 or you raised your last round and if you're making good revenue why raised in the first place and also why cell so great question so i think first of all we'd so we'd literally just raised when we got acquired and north northwestern mutual actually had had just invested and then they came said actually we'd like to we'd like to acquire you guys so so that's that and then why sell so what we were building to be able to go get it to you know our direct to consumer business 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't across the country but getting people a 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 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 scrap your 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 are product a financial plan that nobody ever was super excited about and there some part of the population that loved it but you know we were we were telling people hey financial plan is gonna make you better and then once they tasted it they loved it so our customers are super sticky but i remember thinking to myself oh my goodness north northwestern mutual is 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 that mission that's 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 million 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 did did it does make sense and so did the company 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 out that's a we don't really you know is the the behemoth of the company we don't really care about your users but what we wanna 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 wasn't part of those conversations on the back end but i think that what they viewed it as was they'll say that there were three really powerful things the first was an incredible software that they could plug in that could go to to their customers the second was our entire platform and if you go in north northwestern mutual talk com you know today was it's effectively learn best we just moved over the tech stack made it so you could log in see your finances use a lot of the tools we launched their mobile apps everything leveraging all of that when they offered were you just like hell yeah in or because you had just raised i mean and and if you said yourself you it sounds like you had a it was a s a little bit if i'm kinda reading between lines like you're like oh my god forty users a day like this is really freaking hard where and they offer you that were like yep and or what was that like no it wasn't that simple made a handful of other acquire at the table and i actually took my job very seriously which was my your job as ceo in those moments if you take your job seriously and maybe this is just how i'm wired my job is actually to go get all of the opportunities and emotionally bring them to the board and to say here all the different paths so we can take forward and then the board came together and made a decision of what we thought was best for us and i actually waited until that day which was the morning that we signed to make my decision because my job is gathering all the different opportunities to bring them to the board and say here's what we have in front of us we can do this path this path or this path 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 goes fifty two million dollars if i remember correctly of cash on the balance sheet we were growing it was starting to get easier and easier because we'd launched learn invest at work which was growing rapidly and we were selling the software subscription in tens of thousands so that's way more fun than you know a hundred a day 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 and 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 can't wait to eat our our salads like it was it was not anything like that but so i didn't make the decision till 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 of people have been part of the company 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 to behalf at knowing that some people be thrilled about an acquisition some people big 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 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 a i really i don't regret a single i have to say you know personally i got to grow a lot through it most times when a start up ceo gets acquired they like speak out the back door as quickly as they can and i care deeply that by the end of it that i i wanted to make sure they felt great and i wanted to feel like i had done what i i said i was gonna do and so i ended up saying four years because i such a good time and i think that that that speaks volumes to to north spectrum rachel which again i was chatting with a few friends who sell 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 they were really hard days 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've been a rep for a hundred and sixty three years and learn best was a tiny little brand and you know i was proud of that decision also because it was the right one for what we promised that we're gonna do so what are what are you looking at now so you invest now you gotta fund inspired capital what spaces are interesting to you nowadays so so inspired capital we're an early stage fund so seed series a we're totally generalist we're literally looking right now and everything from restaurant tech so food tech which is really interesting it's a mix of fintech and sourcing of any type of food that we will all eat from straight to agriculture you know farms to your coffee shops that we're pretty excited about we're really focused on the future of money movement and there's some really cool things we're working on there we are we just mess in the company and the the trucking logistics space which we think in hope can put lots of people to work and so you know really focusing on what is the next decade gonna look like we actually published today a future of work study 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 have just advanced the ball on who how and who we all are and how we will think and you're being a a working mom how amazing it 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 i it's 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 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 that's when innovators go nuts and this is like my favorite thing i talked to ten entrepreneurs a day and as you can tell them i'm honestly just a junkie for founders i i i love building businesses my brain loves nothing more than hard problem solving when i was just saying to a founder her before this you know companies have seasoned right you have spring summer fall in winter winter sucks right and as i just said i had plenty of winters at learn beth summers when it's fun and things are exciting and i like to say that you know the inspired capital team we 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 wanna be the best teammates you you talked about future of work and you think is a huge shift going on i think a lot of people right now are talking about this remote work what is what does that mean is this sort of permanent is this temporary what are the second secondary effects i'm curious what's something you know the peter till question what's something that you believe about the future work that is not sort of consensus right now it's not something that everybody is saying do you have any sort of original views or contra 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 use i don't know if about you guys but i used to like being in cab and running in uber in the subways and sprint 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 in gonna see you in the 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 equal utilizing household i actually think that this is this is a great equal everybody's part taking in so many parts of running a house hold these states because we were blocked in our homes and that's gonna create some permanent habits that i think are gonna be better and 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 around our home and i think that that's gonna be hopefully more normalized going forward as i think a lot of 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 seven hours a week if you want to and i think that we're gonna so the l only looking can out i'll say it's i'm not content 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 to in the morning wondering howard are fifteen million households gonna be absorbed when those jobs don't come back and i'm worried about that a lot so that's one thing i i'll say i don't i i sometimes wonder why more people aren't talking about what we're gonna do with the job that do not come back and that worries me a lot what type of what's your background your what part of florida are you from so i grew up in jacksonville florida i was born in kentucky i grew up in jackson florida my mom side of the families from south bend indiana my grandfather was a welder who his whole life my grandmother i worked at at and t is like a the them doing the spinning motion she was literally for waiting super for it all and then my dad's side of the family it bon us as swiss belgian and so and then at both my parents were in the army as doctors and nurses and so my brother was born in germany and i was born kentucky and then so i'm from missouri and then i live in tennessee so i'm from a normal fam like not a silicon valley not a manhattan family i live in san francisco now 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 i mean the partner for your capital for your firm is like a pretty big deal the prince family does it feel ever like you're an outsider you said main street in wall street just does it feel more like you're connected to your roots where you grew up or do you identify more at i mean and i say this because i'm in this crew too a little bit like in this relatively tight circle i mean where are you or an outsider or do you think so glad you asked this question so glad for a bunch of reasons and i think what's really obvious to me is i think it is an incredible competitive advantage i think right now we're in a world where 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 direction there's days where i feel hopeful 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 a nurse practitioner my dad passed away when i was younger so my i was actually raised by a single mom with three older or sorry three kids i told the brothers we're also both doctors 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 well for a decade and the headline is people can't afford anything and everyone's stressed 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 for forget like saving for retirement if you don't know how you can actually feed people right now holy smokes and now that i've become apparent like that's so much more visceral and i actually think it's a real competitive advantage to remember that there's three hun three hundred plus million households in this in this country and that not everybody's on the same page and technologies and always moving everybody forward and so i think it's a major advantage to not forget that in and again i'm literally in jacksonville florida right now in chan 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 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 base i'm i'm a huge nerd in this i use wealth front i use personal capital i've used mint i use spreadsheets i love this stuff you know i think a few things at one the problem of our wallets for america is bigger than just like great software there's a lot of what i'm gonna call infrastructure problems that like tech can't solve what's the minimum wage how do we handle you know working mothers when twenty five percent of the country's moms are are single moms and how do we handle daycare care 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 i don't feel like learn best solved everything and in fact i i have this itch that we wanted to scratch for a long time around you know i was a part of the population where i i i wanted to talk to financial planner that for me there's a certain user type about twenty two percent of the country from our data that wanted to talk to an advisor in the country but about seventy eight percent country doesn't want talk to anybody they just want the problems of the 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 i think that's one of the things that you know we get pretty excited to talk about is you 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 looked like self driving wallet you've put rules and controls around it and say 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 dot com i i i i i've been toy around with that but what i learned was that it's it's a checking and savings account it's actually they used i forget what's whatever the biggest bank in like the world is it's like b i forget what it's called anyway they put their software on top of another bank's checking account and because it's opening up the bank is really hard is that what you would do i mean how would you go about solving this so i i i remember correctly simple got acquired by bb i think actually right before learn best firm remember correctly so the and again i don't wanna totally bore you but basically underneath it the problem with thomas wall wallet his money movement which is money doesn't move quickly from one bank to another it moves across ach 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 of come pieces papers as i call it actually liquefied money is the thesis 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 for two weeks is this like some something that i don't i have no idea it's a legacy concept some people get paid weekly but most of us get paid twice a month and if you think about that people have liquidity crunch in between those two dates but you work every day so why don't you get paid every hour yeah what do you think of the company i think it's called earn in i believe that solves that problem that tries to solve that problem cool they're solving a portion of that problem so what but no i think that there's a few of them there's earn there's dave there's a bunch of other there's a company called even which is but i'm i'm that they are solving elements of it 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 as we watch but basically getting paid like that so why don't i get paid by the second that i'm working it's just streaming into my bank account fractions basically of of value and there's crypto companies in it even more valuable k is not just the streaming in it's then what happens your credit card debt actually charges you interest every single night k 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 your bucks so 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 four one k 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 precarious of our economy but it also exposed the precarious ness of the american wallet and i think that we're going to be in a groundbreaking moment of how do we go fix it so any entrepreneurial listing i wanna talk to you alexa at inspire capital i wanna hear your ideas but these are the big monumental challenges we wanna solve what what would prevent that that's a that's a crazy idea i think that's a that's a cool idea for someone who wants to like it it's it's kinda like a go bigger 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 by i was just saying it's the the money movement huge because that i mean that is it money movement or is is it a cultural thing because i'm a business owner like i like the two weeks buffer for a small business when you're just getting started like business is are we we we take advantage of that right like you're like like oh alright i've got like five days i gotta go collect this this client's money and then i can make payroll yeah it's no i that i think is sol i mean you have two leading edge companies you know i think in just the last week we saw a few companies say i'm work from home forever but you take a few more that then say we're gonna pair 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 why do we withhold from you a free loan to your employer and at some point that we'll break down but that's not the thing i'm i think is harder it's actually the money movement piece of because our wallets have been un bundled 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 zero one k etcetera you now just both of you names 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 ach aca trail that ach aca trail takes about five days or 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 helping me what was it called transfer i there's a company called transfer wise but then actually europe is miles ahead of us they're on real time payment rails and you can actually they've like let they're there there like a full decade ahead of us in terms of you don't even need v mounts as you can just pop money into each other's bank accounts a bank yeah india just also came out and they announced a whole monetary api basically a mandatory payments infrastructure right it's forgot called p i love how much you guys know about yeah tech and infrastructure i love it guys i could geek out with you well yeah i don't know if you've heard this podcast as but what we do is we brainstorm ideas we just shoot the shit and we brainstorm some 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 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 about a lot of topics a little bit only a little bit we know a little about a little yeah what 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 this french companies 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 because this like pretty hard to conceptualize right because we're like it's been done this way for who knows decades hundreds of years yeah i mean to be honest for the standard of what i wanna see built i don't believe that there's a company that is close there's a company 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 at and it you know he he was helping people he started with credit card debt pay off their credit card debt faster which was the core pain point and starting automation around it but you know i think i i wanna i wanna like fast forward the decade ahead where we actually get to instant streaming money you know i i call it liquefied money you're calling it streaming money 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 meaningfully changes the life of american families like meaningfully changes the lives i'll i'll challenge one thing which is so i've heard this idea before about basically hey the what what's the category of of what you built it's like p p p and personal finance manager and the theory is basically you have things like clarity money and what learn fast and others that we're 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 suggest to you how you should you know turn or change lanes the car changes lanes because it knows where you're trying to get as your destination and so i've heard before that what what we need is for to get that 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 what what you added on was the reason that can't happen right now is because the transfer is too slow 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 management much to your grant i'm sure so is it more about software deciding versus user deciding or is it more about liquefied money to liquefied money matters but then to your point 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 in to my you know my each trade account and i'm gonna stare it on my graphs and and you know look at things and i'm gonna talk to an advisor and tell them my goals and then like a lot of things are gonna be executed i always 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 the 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 do i almost think we visualize money based on what exists but imagine i thought exercise and i'll use an amazon alexa since it literally there's like seventeen in my brother's house and he just likes to yell at me all day he thinks it's so funny 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've rules that you've set around your wallet so has anyone broken my identity has anyone done anything bad or unto unsure restrictions that you put on so like my kids credit cards can eat only 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 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 and then everything else just optimize for me and that's math the thing i'd 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 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 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 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 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 vc i think you should go and start this you were very persuasive if i feel like i'm ready to like get behind you and say let's go to war great you're very that's you've got a very good pitch i i i had a one last question g are you a fan of ram seth teachings in his book i his book i can teach you he's a great guy and i will say like every financial planner out there that's doing good work to help help people between now and when this beautiful future software can exists 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 login into my bank account and then i i eventually created all these systems so it's like a little bit of paycheck here a little bit of interest this thing goes there the 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 just because from 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 wanna i hate it i don't like that and this is a perfect example of where you know i really do think you know i grew up of really normal life i grew up in jacksonville florida which is a wonderful place to grow up and i just think you know 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 to fintech but one thing i particularly like about fintech is in fintech any innovation is actually helping the customer right like you're not innovating in fintech in a way that like gauge the customer it's like they're constantly making their life better and cheaper and less expensive into 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 or we should wrap up alexa is there any you already gave your sort of email address 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 our fund is inspired capital but you can message me on instagram and i so one place i actively tried to respond as many that come through so alexa von 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 calling coming you very much