Shane Neman. Secrets of Post-Exit Happiness

0:00Welcome to the Exit Paradox podcast, where we discuss how to build a fulfilling and meaningful life after selling a business. I'm Anastasia Koroleva, an exited founder who spent the last 13 years researching and collecting stories about life after a successful business sale. If I didn't want to start another business, I had to learn how to become a good investor, which is diametrically different than being a good operator. Because you tend to do a lot, and the more you do as an investor sometimes really is harmful. Shane Neiman. He successfully built and exited two iconic businesses, Junebug at Digital Events Powerhouse and Easy Texting, the largest business SMS software platform in the US.

0:47You know, I had an opportunity and I kind of said to myself, like, what's the magic number that would make me happy? Today, he manages a substantial real estate portfolio, invested in over 50 startups, and authored the book called Nightlife Lessons, How I Conquered the Business of Partying with Tech. In this episode, Shane reveals the secrets behind his transition from the daily stress of running two businesses to achieving contentment and impressive financial success.

1:21Shane, hi. Hi, how are you? Very well and very excited about this interview. Likewise. Shane, when I first met you at that boat event in Miami, you came across as a very, you know, solid, stable family man. So I was quite surprised when I later found out that you spent most of your life with a strong reputation of a party animal and even wrote a book called Nightlife Lessons about partying in New York. I spent my 20s in New York too, so I was very, very curious to compare notes and and read it um but i would love you to share a little bit with my audience that part of your life i'm actually a native new yorker i was born in new york i was born in brooklyn so um i grew up my entire life in new york initially queens and then long island and i went to nyu for undergrad and i studied i studied computer science and i actually went to NYU Med.

2:27I was pre-med right after. So I had a, you know, the thought of like going into the nightlife business was never my aspiration. I was kind of like a nerd. Let's just put it that way a little bit. Computer nerd. And I really just did computer science actually as a fallback if i didn't get into med school because at that time uh you know in the in the early 90s um you know it was still like real i don't know how it is now but it was like really really hard and being a doctor was like the ultimate goal uh i'm not sort of sure if that's uh the case now but um anyway uh i actually did a startup before junebug um for about a year and a half uh that was a failed startup my roommate was at Goldman Sachs at the time and he convinced me to drop out of med school and join the dot-com boom he's like he said he said well look I can raise all this money you know how to program we can make a great team let's try and do this and I don't know I couldn't argue with that.

3:46So I could always go back to med school, right? So anyway, got my taste of entrepreneurship through that roller coaster ride. Some people thought, some investors thought it was a good idea to give a bunch of 22-year-olds millions of dollars. And we built basically what what you would call Microsoft 365 now, but through Citrix. So a lot of those words that are used now, like cloud and app store and SaaS, you know, just really didn't exist. And like, there wasn't even really broadband penetration that much in the early, in the late nineties. And so, you know, we built a great product that was really too early for its time.

4:37And then the.com bust happened. And we went down with the ship, just like many others. And I actually had lost all my savings too, because I had been programming on the side and, you know, making money during college. And I put my money where my mouth was investing in the company as well. and then um i don't know through a bunch of really weird twists and turns um uh what happened was that my girl i moved into my my girlfriend's dorm she was going to fit at the time to save money um and she was working at some nightclubs on the side to make money and i would go and pick her up or go with her sometimes.

5:26And like, you know, she was getting paid at three in the morning. And it was really kind of backwards the whole, there was no, there was no systems in place. It was all pen and paper. It didn't really make a lot of sense. And I actually saw an opportunity there. So Junebug basically built, I went back to not my dorm room, but her dorm room, and I was coding. So it was like kind of a cliche in that respect. And we built a platform for basically nightclubs and bars, same as like Toast does for restaurants to run their business on. And then that grew really, we became the de facto software stack that grew into a really large business.

6:20And then it really took off when we added ticketing. And there were really no, sorry, there were really no, like Ticketmaster was not serving smaller venues. And there was no event, right? You have to understand this is like a pre-MySpace, pre-Facebook, pre-camera phone time, right? People can't remember that time, right? But like 19, you know, 2001, those things were not really happening. Um, and nothing, you know, uh, we, we hit a niche. Um, there was a need for it. It was easy to scale because there wasn't very many, there were, no one was really thinking in that, in that vertical about tech and nightlife and that kind of thing.

7:08Uh, was able to grow a really big business out of it, um, and really learn, um, how to get screwed in every possible way. you can never get screwed in business because uh that's i mean you're dealing with nightclub owners and unscrupulous people i can imagine a very special kind of crowd yeah yeah uh you know really short-sighted people hard to convince hard to um monetize on so if you can really crack that market um you know they say like you know if you in new york if you can make it there you can make it anywhere they should change that for like if you can make it in nightlife in new york you can make it anywhere because the hustle is real um and it's a dog-eat-dog kind of um industry for sure um very very very fickle so why did you decide to sell how did that happen i was getting a little bit older uh so i had started joombug when i was like let's say like 24 I remember something like 23 or 24 it was a few years after med school and and the failure of that um company I had been doing it for about eight or nine years at that point um and what happened was is that actually during in 2005-6 uh what happened was is that we realized that we had phone numbers for a lot of people and we also built like a marketing uh stack where people could send emails out and sell their tickets and market and we realized we had everyone's phone number and there was no way to text them and texting was just really starting to kind of take off in the united states with blackberries and that kind of stuff and and so you know if you can't find it you build it yeah i built it initially internally for our company um used it it was like it was like a silver bullet magic cut through all the clutter of the inbox and spam and no one was really doing it and had crazy open rates and response rates and people were asking me how did you do that how did you do that and then I realized that that could become a business in itself if you can imagine like a MailChimp or a constant contact for texting you know just didn't didn't exist and so we spun that out it was called easy texting yeah and so i ran those two for like a year or two together um and then i realized that easy texting had much more potential it was a really it could become a really really big business and not not that nightlife you know not like not not like joonbug wasn't a big business but it was also the shiny new object i had been doing that one for the other you know the other one for eight years and so we just called up our competitor and that was always kind of nipping at our heels and said hey look it's either now or never if you've always wanted this opportunity we're willing to sell and then i took a lot of the the capital from the sale of that of junebug and kind of pumped it into easy texting and then did that for another like eight or nine year so so you didn't take any break in between them because you already had the second company to run yeah i had a successful company that was actually making money um and so i had a lot of um drive to to build that business as well so by the time you sold uh easy texting it had been like 20 years of non-stop building wasn't it close yeah yeah it was almost yet yeah it was it was like 19 years or something and that's when it was the first time when you had a chance to stop and actually think about your life wasn't it i don't think i really thought about much else than work to be honest uh work and then you know i had time to kind of go out and you know be young and party a little bit and you know that kind of stuff but I mean as a practical matter even though I was in the nightlife business I really wasn't like going and drinking and doing crazy stuff I mean I would go out but like any normal person would but um I went to the office at like nine in the morning like everyone else and I had employees and that kind of I might have had access to certain things that people didn't have which was cool from the outside for most people it looked like you were you were partying all day long no because of the industry you were in no it's very hard to do that and you know have a have a multi-million dollar company with you know a lot of employees and that kind of stuff and well i mean i guess you can build it like that but to maintain it you know it'll fall apart if you don't.

12:18So Shane, fast forward to your exit from easy texting. Why did that happen? So I think like a lot of people who get to a certain level, I was, you know, always constantly under the stress of my business. I lived and breathed my business.

12:42and I had just met my current wife. I had, you know, and I wanted to have a family. I wanted to see her more, obviously, because it was craziness. Like, you know, I'm sure just like a lot of startup founders, you know, experience, you know, you're working all hours. You know, I had a team in Ukraine. we had a whole office in Ukraine so that time zone was different um there are emergencies that you have to put out um you know that they're constantly come come uh up and um you know it was the your burnout essentially you got tired and it was like burnout I tried to replace myself you know and you know take that classic um advice and delegate and and I guess I just wasn't too good at it just to be honest uh in retrospect um I tried you know hiring people that I thought could replace me um it was easier said than done nobody kind of really fit the bill and then um I you know I I tried to delegate and you know that that didn't work too well for me either uh and and I had an opportunity to sell because someone you know I was getting approached because I had a company that was a SaaS company that was growing, you know, at least 40, 50 % a year.

14:11It had like 60, 70 % margins. We were profitable. No one had seen something like that. Yeah. So, you know, we had, we, you know, I had an opportunity and I kind of said to myself, at what point, like, what's the magic number that would make me happy, essentially. And I'd be willing to kind of give this up and like, you know, figure something else out, you know, that kind of thing. And, you know, it happened, someone was willing to give me, you know, my number. And I was going to be happy with that, and with my decision. And in retrospect, now, Now, Easy Taxi is much bigger than years ago. And I would have had a much bigger company, arguably, and many other things.

15:07But I would have never given it up because I was able to experience so many other things. So no regrets? No regrets? No. I mean, if you looked at it only financially, it would be regrettable, possibly. um but i got to you know move to miami first of all i would have never been able to do that uh from new york uh i you know i i had my first daughter my first child 10 years ago and i was really truly present for her and i got to experience that um and then you know i i really pivoted at that point because i realized that if i didn't want to start another business I had to learn how to become a good investor, which is diametrically different than being a good operator.

16:02Right. Sometimes because you tend to do a lot and the more you do as an investor sometimes really is harmful. and also just kind of learning how to shift your mindset into an investor's mindset versus a builder's mindset is very different um yeah what helped you in your transition because at least to me you look like an exceptionally successful investor and this seems you seem to be very happy being one and that's not necessarily very common in in our post-exit founder community as you know lots of people feel very miserable yeah investing instead of building yeah so i think there's a couple of things first of all i think a lot of people fall into the trap of identifying themselves with what they do um or their company um i thankfully really never had that thing like i never like saw myself as easy texting or i never saw myself as june bug i saw it more of like ends ends to a means like it's what i did it wasn't who i was yeah um not that i didn't i i liked what i did i didn't i mean i liked i loved aspects of what i did but like as a founder you do a lot of shit that you really don't want to do just to be honest And that what makes you a good founder is like your willingness to do things that other people won't do.

17:36Right. So I think, you know, you're looking at something that's 10 years in the making. Right. So possibly in the beginning, I don't think you would have said the same thing like looking at me. It was a process for me. I had to learn. I made a lot of mistakes. There were a lot of times where I kind of had these false starts where I thought that I would start a new business. And then I had to kind of hold myself back and be like, wait, did I this? Am I sure I want this? You know, is this extra X amount that I possibly could make going to make me happy? Or, you know, do I value my time and being able to control my own time, which I can now, right?

18:27For the most part. I mean, you know, there's always exceptions to the rule. But I think that, you know, it's just as hard as, you know, initially of, you know, doing a startup in terms of, you know, finding your footing. And it's a lot of mistakes and learning from your mistakes. uh so what were the biggest mistakes in terms of types of investments not necessarily you know we don't necessarily need all the details but what for example if i if if i just sold my company and i would be asking you can you please tell me what to avoid investment wise what would you tell me I think what I would say is there isn't like a particular type of investment that I think you should avoid.

19:25I think all investments can be all different asset classes can be good investments if you know what you're doing. I think what you really need to do is truly figure out, figure out. I think the key is figure out who really are, who's really good investor and who really knows what they're talking about. of who's an expert in that field and, you know, learning from them. And I think that, you know, if you really like to learn, bless you. Yeah. If you really like to learn and you bring yourself to a place where, you know, you're, you're curious about everything, you know you can you can become interested and i think listen people like what they're good at right and so once you kind of get some small successes right under your belt you start to like it better obviously you don't like it when you lose and you know it doesn't feel good right but when you're winning it feels good and um you know some people you know all of a sudden win and then think they're like a genius right and they don't realize that you know a lot of luck goes into it too uh but i think i think instead of trying to avoid uh certain asset classes and saying this asset class is bad or whatever i think the better idea is trying to surround and by the way you know if you're in ypo or tiger 21 or any of these other kind of organizations um there's so many people who made it in all these different industries that you can leverage um and speak to and you know like uh for me i'm in tiger right i'm in i'm in a few other things as well and you know there's there's a couple there's there's a few guys that i met that like you know are really crypto guys right and you know if you ask people at different times you know crypto could have been the worst asset class or the best asset class you could have been in right uh so it all really depends on anything but like i really you know pick their brain i talk to them i'm interested i learn i maybe take small bets so i can learn um and and that kind of thing before i kind of come up with my own um thesis thesis or i also think that one of the things that i did that was um very important that I think was a building block at my success was that I found initially a wealth manager that was willing to teach me not just kind of like just do it and then like I had to listen to them they they were willing to sit down and tell me why they were doing certain things or why they thought something was a good investment and really take me through it and you know I did that for a few years initially until i could feel confident about myself being able to do that later on and it was a it was like you know it was a process it was a few years but now i do that myself and i feel confident enough um that i can kind of take bets in a way that uh you know but it sounds like it took it sounds like it took you years to identify those people and then learn what you needed to learn right oh yeah and i made a lot of mistakes there were a lot of a lot of people who i thought were um were experts um yeah and and you know like you know people tell you real estate's safe well i made like three or four real estate investments that went to zero if you can believe that right wow yeah because you know i was lp i got you know i got wiped out as pref equity but because the the or i bought office you know we bought office like six seven years ago right and and and um you know it's it's gonna go to zero right um and so and then there were really there were other real estate guys that i did business with that like you know i made tons of money with and they were right um so you know i think it's unavoidable um i think you have to kind of uh Also, think of it as a game and, you know, not take it too seriously.

24:02Some people are really kind of too focused on not losing instead of winning.

24:13So that's not to say to take these crazy bets where, you know, if you lose, you know, you lose everything. The idea is to, you know, take as many good bets as you possibly can and you can play a perfect poker hand and still lose. Right. But you have to kind of come to terms, come to terms with that. Right. So, Shane, in my own experience and my observation so far is that for most people, they first lose quite a lot, not necessarily quite, but some of their exit wealth before it starts growing. So most people expect when they sell the company and then they calculate what kind of rate of return they want, they expect that curve to go straight up.

24:57But it almost never happens because that learning is always costly. Did you find that true for yourself as well? Yeah, of course. I went down before I went up. And I was freaking out, by the way. Yeah. Just like, you know. Yeah, same happened to me. I totally understand. You know, and I think that's actually where a good financial advisor is a big asset, is more so not telling you what to buy or explaining it to you, but kind of keeping you emotionally in check. Yeah. And not doing things that you're not supposed to do. You know, I think being an investor, you know, I mean, if you look at the best investors like the Buffett or some of these other guys, they're on the spectrum.

25:50Right. So they don't they don't like experience emotion like like most people do. And so they're able to make judgment calls emotional without emotion. And it serves them very well in investing. It's very hard to be like that. Yeah. Also, you can't be a successful entrepreneur like that because you actually have to have lots of passion. So other people catch that passion from you and get energized by you. I totally agree with you. Most entrepreneurs, if anything, are very emotional, even though they learn not to show it over time. here whether it's greed whether it's whatever it is whether it's like just altruism or whatever it is that that's driving them it's the extreme of that that makes them successful and it's it's actually the downfall of the investor right so so from the practical standpoint how did you turn yourself into uh a warren buffett type and stop being emotional i'm by the way i am not nearly That is like really not what I am.

27:01I think I've done pretty well, but I am not. Listen, I think like every other entrepreneur, right, I'm always hardest on myself, but I'm by far not the best investor. I think, you know, I'm constantly learning and I still make a lot of mistakes. But now I think I make fewer mistakes than I did 10 years ago. Let's just put it that way, which I think is just the key to being, you know, a pretty decent investor.

27:36But look, I think I think I do a lot of things that a lot of people don't want to do because it's not fun to do. Right. It's just, you know, it's the same thing as being an entrepreneur. Right. Like you do a lot of things that, you know, like I would sweep the floors if I had to in you know in my in my startup there was nothing beneath me to do um you know i i keep a decision journal when i make major decisions and so and then every three months every quarter i review the decisions and i and it's like a giant pain in the ass to do it takes like a long time it's like you know tedious and i have my own methodology of how to do it but i use like my note app and I go back and I and I re-go back to even decisions that I made years ago and I try and learn from them so that I can make better things or actually it shifts my perspective sometimes because sometimes a decision that I may may have made a few years ago in the short term might have the outcome of it might have been perceived as bad let's just say but it actually turned out to be really good uh you know if if you waited long enough right or or vice versa it was great in the short term but turned out to be bad in the long term um and that might still change too by the way in like five years from now um so i think you know doing those types of things um it's hard to do it's a giant pain in the ass and a lot of people will think of it as pointless how did you get yourself excited about it i'm not like excited about real estate let's just put it that way right Like I do real estate and like I'm pretty good at it, let's say, because I have a lot of experience with it and it makes money.

29:26And but I don't like love real estate like some people might love real estate and I don't love stocks and bonds and I don't love, you know, certain things. But I really do love venture. Right. And so what I do is, you know, I allocate correctly for me and my tolerance and where I am. and I spend like 40 % of my time on stuff that I don't love, right? And then I spend 60 % of my time on venture, which I love. And that gives me the time with, let's say, really, really smart other founders, startup founders, early stage, late stage founders. and I look at a lot of different companies I read their decks I spend time with them I call them I invest and then I also you know help them along actually the book that I wrote was a result of the so much of the time that I spent saying the same stories over and over to them and I the way I structured it was you know each chapter was a lesson that I learned that's why it's called nightlife lessons and then i kind of circled it back to like how i use that lesson in another company that i either did or or i invested in or how how i how i use it in my um everyday investment which i thought which i thought would be helpful it's not just like kind of like bullshit advice that you hear that's like esoteric and like no one really um things so um i i think the key is is that you know spending doing what you have to do right like i have to do the other 40 percent because it's still very important um i don't love it i don't hate it but i don't love it um and and it's a necessary thing for me to do to be able to spend the other 60 50 percent of my time doing stuff that i really love um and i'd like to do so you basically have the sense you basically have the sense of responsibility for for your wealth and that's what drives that 40 and then 60 of your time is no one's gonna give a damn about your wealth except for you trust me no wealth advisor no one is gonna really give a damn because you know like you're really you and your family or you know your whoever else you know your significant other are the ones that are going to care the most, right?

32:10Because it directly affects you. So how could you not, you know, you have a real responsibility to make, you know, to yourself to make that happen. And venture investments mostly come from love or you also feel that it's a good investment decision? If you're in a position where you want to grow, have long-term wealth, right? You really have to have a pretty good exposure to things like venture or venture-like asset classes in order to defy wealth destruction just even if you were able to let's say maintain right um i think you know a lot it's very hard to live you know for for people to think in long scale time frames um but it was it was it was funny um i actually went uh you know i listened to i went to a dinner and michael sailor um uh was was you know he's he's like a bitcoin maximalist um micro strategies i don't know if you know it's a public company they own mostly and he he spoke at the dinner it was actually at his house and so he he lives here in miami and you know he got up in the middle it was like 40 50 people in his house it was a big ballroom and he's he's like yeah um i just got my house appraised for like 48 million dollars and you're like thinking yourself why is this guy telling me this but you know he's like i bought it for i don't know 30 million like five years ago or six years ago and then this house was built by a family who came here in the 1920s and they built this house in the house next door for$120 ,000.

34:00Now, the reason why I'm telling you this is that if they took that$120 ,000 and buried it in the ground and gave it to their grandchildren, their grandchildren right now wouldn't even be able to buy a square foot of my driveway with that$120 ,000. And so if you think about it, that's like just two generations, right? And so, you know, that's not going to happen with bonds, right? It's not going to happen with treasury, it's not going to happen with and i'm not saying you shouldn't have some you know in my in my opinion and by the way again i'm not like the best investor at all but i try and kind of emulate who i think are the better investors which if you look at like endowments or those types of people they have a really healthy um allocation to venture right or much larger uh let's just say to venture because they're really thinking, you know, 50 years out, 60 years out, maybe 100 years out sometimes.

35:03And so, you know, you have to get alpha in order to maintain wealth over time, because the, you know, the value of your money is being destroyed. Unless like Michael Saylor gets his way and like bitcoin becomes you know the the the the you know the the universal um currency and then you know then you you can't you know inflation would stop but um i don't know that's it's like it's a totally different bet shane switching away from investing to your personal life so sure can we go back again to that moment when you sold easy texting you are free from your businesses you have a chance to stop and think and and heal from whatever it is you you may have hurt during 20 years of grinding how did you feel in on that day when you sold it i felt really happy i'm not gonna lie it was amazing um i saw a lot of money in my account um i was newly married and um you know i i um i just saw a lot of potential i saw a lot of potential ahead of me um you know and then i would maybe say a month later you know reality kicks in again nothing really changed nothing's really changed yeah um i don't know for me i was never like um a person that like said oh if i get this i'm gonna buy a ferrari or i'm gonna buy you know like i was just never that person i never really cared i mean i like nice things don't get me wrong like yeah you know but i'm not like doing it for that um i think everyone likes nice things right like you know like a nice vacation or whatever you know that kind of thing but like i wasn't like ever thinking to myself i you know like i want to buy a boat or i want to by like a plane or like those things would just never were like things of that that were goals of mine let's just put it that way um but then the reality kind of really set into me being like wait how do i not only not lose this now right but how do i make this last forever right i had a really keen understanding of that that that would need to happen pretty quickly because, you know, all of a sudden, you know, I was on payroll.

37:41I stayed for like another year, let's just say. But like I wasn't getting paid anything close to like what I was getting paid before. And I was like, oh, well, my income's gone, right? So, you know, I'm going to either have to work again or try and figure out a way to make this last a really long time and grow it. And I didn't know how I was going to do that. So that became another source of stress, let's just say, a different source of stress. The only difference was that it wasn't like at all hours of the day and putting out fires. And it was a different kind of stress that was, I think, for me, at least, more manageable.

38:27And didn't like, you know, all consume me, let's just say. um so uh listen there's there's problems on each side right it's just you have to choose choose which problems you want basically did you feel sad that you no longer had the team and the structure and the familiar environment and the business that was growing was sadness part of your um how you felt at the moment i had a uh i had a hard like a pretty hard childhood that wasn't i mean i didn't have like a bad childhood but i had a pretty hard childhood you know i lost my father when i was 13 my mother was like perpetually ill her entire life i we lived a pretty comfortable life a good life you know like a middle class life kind of thing and you know my mom worked and I saw her kind of work despite her illness and like if she could make it like I could you know I could make it kind of thing like so a lot of people ask like who your mentor is or whatever uh you know it's obvious for me it was my mom because like she was able to accomplish a lot being really ill her entire life um and you know i kind of really understood the concept of um you know non-permanence of things let's just let's just say yeah and and and being being able to accept change at a rapid pace um you know my mom was you know was ill and in and out of you know the hospitals all the time and stuff like that so things would change for me a lot uh you know all the time and I would make plans and like go to go away and then I stopped making plans because like you know a lot of times it would get canceled because I was you know in the unknown a lot of times so the impermanence of things kind of you know was a staple in my life maybe i'd learned that earlier in in life um so i i don't know i think you know being for me it was it wasn't that difficult to deal with change because i had that a lot happened to me earlier makes sense um yeah but like yeah listen did i did i kind of miss it a little bit yes i did but thankfully i had other things that i had was like really grateful for like i had a child and i was having that experience and we moved to miami and i had that experience so um you know i kind of replaced it with things that you know occupied me essentially yeah yeah it sounds like you had a lot on on your hands didn't have the luxury to feel sad right yes i think that's actually something that i that i got from my mom you know she never like didn't she never was like felt sorry for herself because she never had the time she just you know pushed through right like i think that's maybe a coping mechanism that a lot of people use basically did you do anything for your health specifically because we get quite burnt out uh after entrepreneurial experience and as you know we have lots of common friends who go really really extreme into biohacking or extreme sports like really focus on on their health and physical development did that happen to you it did it did um and i still to a degree do it um so like i still do cold plunging i have a cold plunge i do sauna um but then i kind of like took it to a pretty extreme for a few years uh when i turned 40 like seven years ago six seven years ago um i got diagnosed with pre-diabetes and i wasn't even really that i wasn't obese or anything like that it was really shocking to be honest yeah um and going to med school like i understood how bad that really is for your prognosis let's just say of like all the bad things that can happen to you afterwards especially at the age of 40 is very young I think so I took it really seriously they were like telling me that I need to exercise more and they wanted to put me on metformin and at that time it wasn't like kind of known that metformin makes you live longer yeah now it's very trendy yeah now it's like trendy but like it was really scary for me at that point i'm like i'm not gonna go on on like diabetes med right um so people like microdose that now um but uh so i i um i found this program called mastering diabetes which um is like a health program with eating and exercise um it's it's low oil like very low oil all kinds of oil you can't really have oil that's considered a processed food so whole whole non-processed foods um and um so i i went on that and it was also vegan for a while for like many years after that um so that yeah that that that ended up working and then I started doing a bunch of weightlifting so I got a I got a trainer that kept me accountable and then you know I did like the other things that people do like I did I got like any IV nad but like I don't think yeah you know I did it a bunch of times I did it all yeah I did I did a bunch of those things and I was like on restreveral and a bunch of these other things that just i don't know i think i've like kind of whittled it down to one or two things i take athletic greens every every day um disclosure i'm an investor in athletic greens but i take it every day because it has a thing uh you know has so i take that every day and i take so it's like all the multivitamin and probiotics in it i take you know you know i take vitamin d i take like a few things like that um and then i do cold plunge and sauna pretty much and i work out i i work out i do weight weight training um but like i i kind of like did six or seven years of this like really extreme i got to like six percent body fat at one point oh wow uh which was like even crazier than when i was in high school not very healthy i was like all my stats i had a continuous there's CluClose Monitor.

45:31Like I did like the whole thing, right? But like, again, you know, it all consumed me because I treated it like it was my startup. Exactly. That's where I was getting to because I think that's exactly what happens to lots of people. They focus on their health with the same intensity and fanatism as they did on the business. And in a way it helps. It's not bad, but it's just a curious phenomenon I find. Yeah. I mean, I think people get sort of lose interest. Burned out. They burned out of it. Yeah. Yeah. So I don't do it as extreme. I did that. I did get burned out. Although thankfully I didn't like let it all go.

46:15I still work out regularly and I do a few of the things that I think are the most impactful, but listen, it's a, it's a fun journey. If you, if you like it and there could be worse things that you do for sure. Absolutely. I'm absolutely with you. I guess I like to think about it as this momentum. You spend 20 years going full force somewhere. You create even bigger force and then you just keep going with that force after you exit. You have to send that energy somewhere. And sometimes people just go crazy with investing before they learn how to do it. I made that mistake. and lots of people we know do but other people channel it into health and maybe that's a big that's a better option if you have to channel it somewhere it should go to health probably than see a bad thing to do i mean if you do it overdo it on your health it's not a bad thing for sure um i think a lot of also So post-exit founders, let's just say post-exit people, they have this false sense of thinking that just because they had an exit that they're smart, let's just say, in every other field of everything that they do.

47:37True. So that also contributes to this investing thing where they make mistakes in investing. No, absolutely. It's like you mentioned your business would have like 60%, 70 % margin. And of course, it's very hard then to settle for what private bankers advise you to do. there are no um there are no asset classes really out there that you can both control largely and have this kind of return yeah you end up taking too much risk and just because like let's say if you're in tech you think you know tech right yeah and then you conflate you conflate good tech with a good business because those aren't necessarily two good things right I mean, they're not the same things.

48:37Yeah, 100%. And I guess you're trying to push the boundaries just like you did as a founder. And that doesn't work out too well for you in the short term, at least, unless you really know what you're doing. We all learn these humility lessons. um the most of these patterns and mistakes are quite predictable if you talk to to enough people so what would you say your main humility lessons were so i took a decision making course during covid um so if you think about it no one really kind of like teaches you how to make good decisions i've never taught that and which is the most important thing we do in life but no one teaches you a hundred percent and you know i went into this thing i paid like twelve hundred dollars for it um it's it's by this guy named shane parish uh it's called the knowledge project yeah of course yeah uh so so i listened to his podcast i really like him a lot very smart guy um and he has this course and i'm like you know what i don't know listen i didn't have much to do anyway during COVID let's just say you know and I'm like I'm gonna take this this this this thing and whatever I went into it really arrogant thinking that I am a um like one of the best decision makers out there and I know everything about decision like what is this guy gonna teach me and I realized that I really had no clue of how to make a good decision and I wasn't doing any of these things that I now do a lot right and um you know just basic things of like even kind of like categorizing the kind of decision that you're making is this decision reversible is it is it um is it really important you know is it um you know or you know is it binary or could there be a third option that could solve your problem um you know there's there's a lot of um techniques that you can use.

50:45Am I really finding, you know, do you think about the second and third order implications of any decision that you might make, right? Because, you know, you might change something in something that's working, but you don't know, like you never think through what like the implications might be that might have adverse effects for you or even positive effects for you. So, anyway, that was a really, you know, like kind of moment of clarity for me. You were probably thinking, how did I create two super successful companies and sold them without knowing how to make decisions, right? No, you really underestimate how much luck has to do with it.

51:32It really does. you know I think not that I was like like I wasn't the worst decision maker like but but I but but I certainly was not like let's say you know a really great one that I was able to do that so I think you know I can tell you about like the 50 bad decisions 50 bad investments I made and stuff like that or i don't even know um you know a bunch of really stupid things that i did in my businesses that i that i shouldn't have done or that kind of stuff that really kind of you know brought me back to earth um but i'm curious about a post exit when you you know You had two successes. You had all the right to feel you know it all.

52:28Then one amazing humility lesson you just mentioned, learning that you don't even know how to make decisions. I think it's brilliant. I love it. I also took a course by Shane, but it was on mental models, on creating mental models. I also thought it was very helpful. I read his book on mental models. Oh, you did? Yeah, yeah. They're really... He's, I mean, I think, you know, this is also the, you know, this is also part of that process is if you can be really introspective about yourself and be willing to change, that's a very good trait for any investor. And that's part of why I took these classes and I was amenable to doing it is because I wanted to kind of, you know, making better decisions is the same thing as making better investment decisions, right?

53:29Not just like your other decisions that you make in your life. And so I wanted to really maximize how I did that and improve myself. So, you know, I think, you know, the biggest humility thing was like I never in my other businesses, except for like my lawyers and my accountants and stuff, I never really relied on anyone. Let's just say. um yeah and and so like when when it came to relying on a wealth manager um that was a hard thing too because i don't know it's it's kind of messed up to say but like i was like looking at the guy i'm like this guy's telling me what to do and like i just like you know i just like sold this business and how does he know better than i do you know what i mean yeah of course i know exactly what you mean shane so um i don't know you know like i went through a bunch of wealth managers and they probably all thought i was a giant dick just to be honest with you in the beginning so uh but i had to change i had to change because a first of all nobody would want to deal with me and second i wanted to learn from that person i had to bring myself like you know bring that ego down and be like this guy obviously know something that i don't know and like i need to learn um or this girl or you know i would i say guy but you know i mean guy or girl you know you know shane i've been researching the whole post exit journey and talking to people for 13 years now and i came to to one conclusion i'm absolutely sure of that the root cause of all the mistakes is just not taking that time to introspect correct not doing it properly not doing it long enough not doing it deep enough all mistakes come from there so i'm so happy to hear about you taking the decision making course and doing it actually that explains a lot uh in terms of you now being in a much happier place yeah i i appreciate that um yes it's again it's it's like willing to do what a lot of people won't do right or they think stupid um it's tough it's tough introspection is very tough especially for people who spent most of their adult lives uh interacting with the reality and making decisions fast and being very action-driven and then suddenly shifting our gaze in inwards it's hard work it feels very unnatural it's funny i listened to a podcast by sid guru today i don't know if you follow him but he's um he's really amazing and at the end they were like what do you want everyone to like get from this and it was like a two-hour podcast it was live right he was giving a talk live and they're like what do you want people to do after this and he's like well i can't make anyone do but i want them to realize that the only way out is from within how do you want to be remembered honestly just like as a good dad and good husband um that you know made people that other people like let's just put it that way uh that that you know contribute to society and you know people like to be around and make they make other people feel good i mean i i i have no delusions that like anyone's going to even remember me in a hundred years from now because like i don't remember anyone from a hundred years from now that was my ancestor so um you know it's it's it's weird to think about it that way but it's actually like i don't understand the concept of legacy and those types of things because at the end of the day really maybe like now if somebody will remember you from like instagram or something i don't know but even that will probably go away at some point jane this is so beautiful i'll let you go so you can be a good person and a good father oh thank you so much thank you so much thank you so much i loved it a lot a great conversation great me too thank you so much appreciate it