Shane Neman. Secrets of Post-Exit Happiness
Episode - 34
Shane Neman. Secrets of Post-Exit Happiness
Shane Neman. He successfully built and exited two iconic businesses: JoonBug, a digital events powerhouse, and EZ Texting, the largest business SMS software platform in the US.
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.
What We Discussed:
00:00:16: Introduction of Shane Niemann
00:00:29: Shane's first business ventures
00:00:50: Shane's transition to real estate and writing his book
00:01:14: Shane's background and early life
00:02:12: Entering the nightlife industry
00:02:51: Failed startup and transition to Junebug
00:04:05: Early days of Junebug and the rise of ecommerce
00:07:12: Challenges in the nightlife industry and building Junebug
00:07:45: Decision to sell Junebug
00:08:33: Creation of Easy Texting
00:09:23: Running Junebug and Easy Texting simultaneously
00:09:51: Easy Texting's potential and selling Junebug
00:12:01: Burnout and decision to sell Easy Texting
00:13:09: Transition from founder to investor
00:15:54: Transitioning to a mindset of an investor
00:18:30: Learning and mistakes in investing
00:20:27: Importance of learning from experts and finding mentors
00:23:10: Initial real estate investment discussion
00:24:16: Early financial challenges after selling a company
00:25:03: Importance of a good financial advisor
00:27:17: The journey of becoming a better investor
00:28:05: Reviewing past decisions for better investment strategies
00:29:02: Balancing time between real estate and venture investments
00:30:09: Writing a book on investment lessons
00:32:03: Responsibility for personal wealth management
00:33:03: Long-term thinking in investment
00:35:17: Transition to personal life insights
00:35:22: Reflections on selling the business and initial joy
00:37:07: Post-sale financial planning stress
00:38:23: Accepting and managing change
00:39:41: Missing the business team and structure
00:40:57: Relocation and new family experiences
00:42:00: Health and wellness post-business sale
00:44:23: Introduction to athletic greens
00:44:41: Daily health habits and routines
00:47:08: Post-exit entrepreneurs and humility lessons
00:49:00: Learning decision making
00:52:01: Importance of introspection
00:55:11: Reflections on introspection and personal growth
00:56:28: How Shane wants to be remembered
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Shane Neman: [00:00:00 - 00:00:16]
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.
Anastasia Koroleva: [00:00:16 - 00:00:29]
Shane Niemann. He successfully built and exited two iconic Junebug, a digital events powerhouse, and easy tech stack, the largest business SMS software platform in the US.
Shane Neman: [00:00:29 - 00:00:36]
You know, I had an opportunity and I kind of said to myself, like, what's the magic number that would make me happy?
Anastasia Koroleva: [00:00:36 - 00:01:05]
Today he manages a substantial real estate portfolio, invested in over 50 startups, and authored the book called Nightlife, how I conquer the business of partying with tech. In this episode, Shane reveals the secret behind his transition from the daily stress of running two businesses to achieving contentment and impressive financial success. Shane, hi.
Shane Neman: [00:01:07 - 00:01:08]
Hi. How are you?
Anastasia Koroleva: [00:01:09 - 00:01:11]
Very well and very excited about this interview.
Shane Neman: [00:01:12 - 00:01:14]
Likewise, likewise.
Anastasia Koroleva: [00:01:14 - 00:01:48]
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 twenties in New York too, so I was very, very curious to compare notes and read it. But I would love you to share a little bit with my audience. That part of your life.
Shane Neman: [00:01:48 - 00:07:11]
I'm actually a native New Yorker. I was born in New York. I was born in Brooklyn. So 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 computer science and actually went to NYU med. I 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, you know, in the, in the early nineties, 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. I'm not sure if that's the case now. But anyway, I actually did a startup before Junebug for about a year and a half. 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.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. So I could always go back to med school, right? Anyway, got my taste of entrepreneurship through that roller coaster ride. Some. 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. And 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, I don't know, through a bunch of really weird twists and turns, what happened was that my girl, I moved into my girlfriend's dorm. She was going to fit at the time to save money, 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, and 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 kind of cliche in that respect. And we built a platform for basically nightclubs and bars. It's same as toast does for restaurants to run their business on. And then that grew, really became the de facto software stack that grew into a really large business. And 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. 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 2001, those things were not really happening and nothing, you know, we hit a niche. There was a need for it. It was easy to scale because there wasn't very many. No one was really thinking in that vertical about tech and nightlife, that kind of thing, was able to grow a really big business out of it and really learn how to get screwed in every possible way you can have screwed in business because that's, I mean, you're dealing with nightclub owners and unscrupulous people.
Anastasia Koroleva: [00:07:12 - 00:07:14]
I can imagine a very special kind of crowd.
Shane Neman: [00:07:14 - 00:07:47]
Yeah, yeah. You know, really short sighted people. Hard to convince, hard to monetize on. So if you can really crack that market, 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 and it's a doggy dog kind of industry, for sure. Very, very, very fickle.
Anastasia Koroleva: [00:07:47 - 00:07:50]
So why did you decide to sell? How did that happen?
Shane Neman: [00:07:50 - 00:10:16]
I was getting a little bit older, so I had started Junebug when I was, let's say, like 24. I remember something like 23 or 24. It was a few years after med school and the failure of that company. I had been doing it for about eight or nine years at that point. And what happened was, is that actually during, in 20050 six, what happened was that we realized that we had phone numbers for a lot of people, and we also built like a marketing 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. I built it initially internally for our company 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. And I ran those two for like a year or two together, 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 June Bug wasn't a big business, but it was also the shiny new object had been doing that one for the other, the other one for eight years. And so we just called up our competitor 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 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 years.
Anastasia Koroleva: [00:10:16 - 00:10:22]
So you didn't take any break in between them because you already had the second company to run.
Shane Neman: [00:10:22 - 00:10:34]
Yeah, I had a successful company that was actually making money, and so I had a lot of drive to build that business as well.
Anastasia Koroleva: [00:10:34 - 00:10:42]
So by the time you sold easy texting, it had been like 20 years of nonstop building, wasn't it?
Shane Neman: [00:10:43 - 00:10:49]
Yeah, yeah, it was almost. Yeah, yeah, it was. It was like 19 years or something.
Anastasia Koroleva: [00:10:50 - 00:10:56]
And that's when was the first time when you had a chance to stop and actually think it about your life, wasn't it?
Shane Neman: [00:10:56 - 00:11:33]
I don't think I really thought about much else than work, to be honest. 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 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.
Anastasia Koroleva: [00:11:33 - 00:11:39]
Cool from the outside. For most people, it looked like you were partying all day long.
Shane Neman: [00:11:40 - 00:11:41]
No.
Anastasia Koroleva: [00:11:41 - 00:11:43]
Because of the industry you were in.
Shane Neman: [00:11:44 - 00:12:00]
No, it's very hard to do that and, you know, have a multimillion dollar company with, 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.
Anastasia Koroleva: [00:12:01 - 00:12:08]
So, Shane, fast forward to your exit from easy texting. Why did that happen?
Shane Neman: [00:12:08 - 00:13:06]
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, and 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. Um, you know, I had a team in, 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 that constantly come, come up and, um, you know, so it.
Anastasia Koroleva: [00:13:06 - 00:13:09]
Was your burnout, essentially. You got tired and it was burnout.
Shane Neman: [00:13:09 - 00:14:54]
I tried to replace myself, you know, and, you know, take that classic advice and delegate, and I guess I just wasn't too good at it, just to be honest. In retrospect, I tried hiring people that I thought could replace me. It was easier said than done. Nobody kind of really fit the bill. And then I tried to delegate, and that didn't work too well for me either. 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. It had like 60 70% margins. We were profitable. No one had seen something like that. Yeah, so, um, 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, easy taxing is much bigger than when I ten years ago, and I would have had a much bigger company, arguably, and many other things, but I would have never given it up because I was able to experience so many other things.
Anastasia Koroleva: [00:14:55 - 00:14:58]
So no regrets? No regrets.
Shane Neman: [00:14:58 - 00:16:07]
No. I mean, like, if you looked at it only financially, it would be regrettable, possibly. But I got to move to Miami, first of all. I would have never been able to do that from New York. I had my first child ten years ago, and I was really, truly present for her, and I got to experience that. And then 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 sometimes because you tend to do a lot, and the more you do as an investor sometimes really is harmful. And also just learning how to shift your mindset into an investor's mindset versus a builder's mindset is very different. Yeah.
Anastasia Koroleva: [00:16:07 - 00:16:25]
What helped you in your transition? Because, at least to me, you look like an exceptionally successful investor, and you seem to be very happy being one, and that's not necessarily very common in our post exit founder community. As you know, lots of people feel very miserable.
Shane Neman: [00:16:26 - 00:16:26]
Yeah.
Anastasia Koroleva: [00:16:27 - 00:16:28]
Investing instead of building.
Shane Neman: [00:16:30 - 00:18:36]
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 or their company. 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 to a means. Like, it's what I did. It wasn't who I was. Yeah. Not that I didn't. I liked what I did. 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. Right. So I think, you know, you're looking at something that's ten 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 is. 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? For 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. It's. It's a lot of. A lot of mistakes and learning from your mistakes.
Anastasia Koroleva: [00:18:38 - 00:18:59]
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 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?
Shane Neman: [00:19:00 - 00:19:41]
I think what I would say is there isn't, like, a particular type of investment that I think you should avoid. I 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, who's an expert in that field and learning from them. And I think that, you know, if you really like to learn. Bless you.
Anastasia Koroleva: [00:19:41 - 00:19:42]
Thank you.
Shane Neman: [00:19:42 - 00:22:33]
Yeah. If you really like to learn and you bring yourself to a place where, you know, 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, 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, of course. But I think, I think instead of trying to avoid certain asset classes and saying this asset class is bad or whatever, I think the better idea is trying to survive. And by the way, if you're in YPO or Tiger 21 or any of these other kind of organizations, there's so many people who've made it in all these different industries that you can leverage and speak to. And, you know, like, for me, I'm in tiger, right. 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? 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 and that kind of thing before I kind of come up with my own thesis. Thesis. Or. I also think that one of the things that I did that was very important, that, that I think was a building block in 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 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 that I can kind of take bets in a way that, you know, but it sounds like.
Anastasia Koroleva: [00:22:33 - 00:22:40]
It took, it sounds like it took you years to identify those people and then learn what you needed to learn, right?
Shane Neman: [00:22:40 - 00:24:15]
Oh, yeah. And I made a lot of mistakes. There were a lot of. A lot of people who I thought were experts and, you know, like, you know, people tell you real estate safe. Well, I made like, three or four real estate investments that went to zero, if you can believe that. Right? Yeah. Because, you know, I was lp, I got, you know, I got wiped out as prep equity because. Or I bought office. You know, we bought office like six, seven years ago. Right. And I. And, you know, it's gonna go to zero, right. 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. So, you know, I think it's unavoidable. I think you have to kind of also think of it as a game, and I, you know, not take it too seriously. Some people are really kind of too. Too focused on not losing and instead of learning. So 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.
Anastasia Koroleva: [00:24:16 - 00:24:48]
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, but it almost never happens because that learning is always costly. Did you find that true for yourself as well?
Shane Neman: [00:24:48 - 00:24:57]
Yeah, of course. I went down before I went up, and I was freaking out, by the way, when we went, just, you know.
Anastasia Koroleva: [00:24:58 - 00:25:00]
Same happened to me. I totally understand.
Shane Neman: [00:25:03 - 00:25:52]
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 that kind of, 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 a buffet or some of these other guys, I mean, they're on the spectrum, right? So they don't. They don't, like, experience emotion like, like most people do, and so they're able to make judgment calls emotionless without emotion. And it serves them very well in investing. It's very hard to be like that.
Anastasia Koroleva: [00:25:53 - 00:26:11]
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.
Shane Neman: [00:26:11 - 00:26:28]
It over time, whether it's greed, whether it's whatever it is, whether it's just altruism or whatever it is that's driving them, it's the extreme of that that makes them successful, and it's actually the downfall of the investor. Right.
Anastasia Koroleva: [00:26:28 - 00:26:37]
So from the practical standpoint, how did you turn yourself into a Warren Buffett type and stop being emotional, by the.
Shane Neman: [00:26:37 - 00:28:56]
Way, I am not nearly. That is, like, really not what I am. I 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 ten years ago. Let's just put it that way, which I think is just the key to being, you know, a pretty decent investor. But 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 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. You know, I. I keep a decision journal when I make major decisions, and so 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, and 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 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, you know, if you waited long enough. Right. Or vice versa, it was great in the short term, but turned out to be bad in the long term. 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.
Anastasia Koroleva: [00:28:56 - 00:28:58]
How did you get yourself excited about it?
Shane Neman: [00:28:58 - 00:31:20]
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 and. 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, 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 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 I invested in or how I use it in my everyday investing now, 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 thinks so. I think the key is that, you know, spending, doing what you have to do, right? Like, I have to do the other 40% because it's still very important. I don't love it. I don't hate it, but I don't love it. And it's a necessary thing for me to do, to be able to spend the other 60, 50% of my time doing stuff that I really love and I'd like to do.
Anastasia Koroleva: [00:31:20 - 00:31:32]
So you basically have the sense. You basically have the sense of responsibility for your wealth, and that's what drives that 40%. And then 60% of your time is.
Shane Neman: [00:31:32 - 00:32:03]
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 gonna care the most, right? Because it directly affects you. So how could you not? You know, it's. You have a. You have a real responsibility to make, you know, to yourself to make that happen.
Anastasia Koroleva: [00:32:03 - 00:32:11]
And venture investments mostly come from love, or you also feel that it's a good investment decision if you're in a.
Shane Neman: [00:32:11 - 00:35:17]
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. I think, you know, a lot. It's very hard to live, you know, for people to think in long scale time frames. But it was. It was. It was funny. I actually went, you know, I listened to. Went to a dinner, and Michael Saylor was, you know, he's like, a bitcoin maximalist microstrategies. I don't know if this is a public company they own mostly. And he spoke at the dinner. It was actually at his house. And so he lives here in Miami, and he got up in the middle. It was like, 40, 50 people in his house. It was a big ballroom. And he's like, yeah, I just got my house appraised for, like, $48 million. 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. Now, 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. 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, 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 allocation to venture, right? Or much larger, let's just say, to venture, because they're really thinking, you know, 50 years out, 60 years out, maybe 100 years out. And so you have to get alpha in order to maintain wealth over time, because the value of your money is being destroyed. Unless Michael Saylor gets his way and bitcoin becomes the universal currency, and then inflation would stop. But I don't know. That's a totally different bet.
Anastasia Koroleva: [00:35:17 - 00:35:46]
Shane, switching away from investing to your personal life. 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 heal from whatever it is you may have hurt. During 20 years of grinding, how did you feel on that day when you sold it?
Shane Neman: [00:35:46 - 00:38:27]
I felt really happy. I'm not gonna lie. It was amazing. I saw a lot of money in my bank account. I was newly married, and I just saw a lot of potential. I saw a lot of potential ahead of me. And then I would maybe say a month later, you know, reality kicks in again. Nothing really changed. Nothing's really changed. Yeah. I don't know. For me, I was never, like, 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. Like, you know, but I'm not, like, doing it for that. I think everyone likes nice things, right? Like a nice vacation or whatever, you know, that kind of thing. But, like, I wasn't, like, ever thinking to myself, you know, like, I want to buy a boat or I want to buy, 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. 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 would need to happen pretty quickly because, you know, all of a sudden, I was on payroll. I 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 gonna 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 gonna do that. So that that became another source of stress, let's just say a different short 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 and didn't, like, you know, all consume me, let's just say. So, listen, there's problems on each side, right? It's just you have to choose. Choose which problems you want, basically.
Anastasia Koroleva: [00:38:27 - 00:38:41]
Did you feel sad that you no longer had the team and the structure and the family environment and the business that was growing? Was sadness part of your. How you felt at the moment?
Shane Neman: [00:38:41 - 00:40:38]
I had a hard, like, a pretty hard childhood. 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. 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, you know, obviously, for me, it was my mom, because, like, she was able to accomplish a lot, being really ill her entire life. And, you know, I kind of really understood the concept of, you know, non permanence of things, let's just. Let's just say. And being able to accept change at a rapid pace. 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, 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 the times. So the impermanence of things kind of, you know, was a staple in my life. Maybe I learned that earlier in life. So I don't know. I think, you know, be. For me, it was. It wasn't that difficult to deal with change because I had that a lot happen to me earlier.
Anastasia Koroleva: [00:40:38 - 00:40:39]
Makes sense.
Shane Neman: [00:40:40 - 00:41:05]
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, you know, I kind of replaced it with things that, you know, occupied me, essentially.
Anastasia Koroleva: [00:41:05 - 00:41:12]
Yeah. Yeah. It sounds like you had a lot on. On your hands. Didn't have the luxury to feel sad, right?
Shane Neman: [00:41:13 - 00:41:32]
Yes. I think that's actually something 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.
Anastasia Koroleva: [00:41:32 - 00:41:55]
Did you do anything for your health specifically? Because we get quite burnt out 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 their health and physical development. Did that happen to you?
Shane Neman: [00:41:55 - 00:42:58]
It did. It did. And I still, to a degree, do it. So, like, I still do cold plunging. I have a cold plunge. I do sauna. But then I kind of, like, took it to a pretty extreme for a few years when I turned 40, like, seven years ago. Six. Seven years ago, I got diagnosed with prediabetes, and I wasn't even really that. I wasn't obese or anything like that. It was really shocking, to be honest. Yeah. 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, it's 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 knowing that metformin makes you live longer.
Anastasia Koroleva: [00:42:58 - 00:42:59]
Yeah, now it's very trendy.
Shane Neman: [00:43:00 - 00:45:24]
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, like, diabetes med, so people, like, micro dose that now. But. So I. I found this program called mastering diabetes, which is, like, a health program with eating and exercise. It's low oil, 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. And so I went on that and was also vegan for a while for, like, many years after that. That, yeah, 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, na iv nad, but, like, I don't think, you know, I did it a bunch of times. Yeah, I did. I did a bunch of those things, and I was, like, on restrep roll 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. Disclosure, I'm an investor in athletic greens, but I take it every day because it has a thing, you know, so I take that every day, and I take. So it has, 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, and then I do cold plunge and sauna pretty much, and I work out. I work out. I do weight training, but, like, I kind of, like, did six or seven years of this, like, really extreme. I got to, like, 6% body fat at one point, which was, like, even crazier than when I was healthy. I was, like, all my stats, I had continuous glucose monitor. Like, 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.
Anastasia Koroleva: [00:45:24 - 00:45:47]
Exactly. That's where I was getting to, because I think that's exactly what happens to lots of people. They. They focus on their health with the same intensity and fanatism as they did in the business. And in a way, it helps. It's not bad, but it's just a curious phenomenon, I find. Yeah, I mean, people get sort of.
Shane Neman: [00:45:47 - 00:45:49]
Lose interest, burn out. They burn out of it.
Anastasia Koroleva: [00:45:49 - 00:45:50]
Yeah.
Shane Neman: [00:45:51 - 00:46:11]
Yeah. So I don't do it as extreme. I did that. I did get burned out, although, thankfully, it didn't, like, let it all go. I 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 like it, and there could be worse things that you do, for sure.
Anastasia Koroleva: [00:46:11 - 00:46:50]
Absolutely. I'm with you. Yeah, I guess I like, to think about it as this momentum. You know, 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, you should go to health, probably, than.
Shane Neman: [00:46:51 - 00:47:34]
A bad thing to do. I mean, if you do it, overdo it on your health, it's not a bad thing for sure. I think a lot of also, um, post exit founders, let's just say, or post exit people, um, they. They have this false sense of, um, 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. Um, yeah, that also. That also, um, contributes to, like, this, know, investing thing, you know, where they. Where they make mistakes and investing. No, absolutely.
Anastasia Koroleva: [00:47:34 - 00:47:58]
It's like you mentioned, you, 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, there are no asset classes, really, out there that you can book of control largely and have this kind of return.
Shane Neman: [00:47:58 - 00:48:35]
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? And then you conflate good tech with a good business, because those aren't necessarily two good things, right? I mean, those are two. They're not the same things. Yeah, 100%. And I guess you're, you know. Yeah. You're trying to push the boundaries, just like you did as a. As a founder. And that doesn't work out too well for you in the short term, at least with. Unless you really know.
Anastasia Koroleva: [00:48:36 - 00:48:49]
We all learn these humility lessons, most of these patterns and mistakes are quite predictable if you talk to enough people. So what would you say your main humility lessons were?
Shane Neman: [00:48:49 - 00:49:03]
So I took a decision making course during COVID So if you think about it, no one really kind of, like, teaches you how to make good decisions. I never taught that, which is the.
Anastasia Koroleva: [00:49:03 - 00:49:06]
Most important thing we do in life, but no one teaches you 100%.
Shane Neman: [00:49:06 - 00:49:17]
And, you know, I went into this thing. I paid, like, $1200 for it. It's by this guy named Shane parish. It's called a knowledge project.
Anastasia Koroleva: [00:49:17 - 00:49:18]
Oh, yeah, of course. Yeah.
Shane Neman: [00:49:19 - 00:51:00]
So I listened to his podcast. I really like him. A lot. Very smart guy. And he has this course, and I'm like, you know what? I don't know. I didn't have much to do anyway during COVID let's just say. And I'm like, I'm going to take this thing and whatever. I went into it really arrogant thinking that I am, like, one of the best decision makers out there, and I know everything about decision. Like, what is this guy going to 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, 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. Is it really important? You know, is it, you know, or, you know, is it binary? Or could there be a third option that solve your problem? You know, there's. There's a lot of techniques that you can use. Am 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.
Anastasia Koroleva: [00:51:01 - 00:51:09]
You were probably thinking, how did. How did I create two super successful companies and sold them without knowing how to make decisions? Right?
Shane Neman: [00:51:10 - 00:52:00]
No. You really underestimate how much luck has to do with it. It really does. You know, I think, not that I was like, like, I wasn't the worst decision maker. Like, you know, but. But I. What? 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, you know, a bunch of really stupid things that I did in my businesses that I shouldn't have done or that kind of stuff that really kind of, you know, brought me back to earth.
Anastasia Koroleva: [00:52:01 - 00:52:26]
I was curious about a post exit. When you had two successes, you had all the right to feel, you know, it all. Then 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.
Shane Neman: [00:52:27 - 00:53:42]
I read his book on mental health. They're really. 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. And I was, like, amenable to doing it is because wanted to kind of, you know, making better decisions is the same thing as, like, making better investment decisions, right? Not just, like, you know, your, your other decisions that you make in your life. And so I wanted to really maximize how I did that and improve myself so that, you know, I think. 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.
Anastasia Koroleva: [00:53:43 - 00:53:43]
Yeah.
Shane Neman: [00:53:43 - 00:54:09]
And so, like, when, when it came to relying on a wealth manager, that was a hard thing, too, because, I don't know, 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?
Anastasia Koroleva: [00:54:09 - 00:54:12]
Yeah, of course. I know exactly what you mean, Shane.
Shane Neman: [00:54:14 - 00:54:47]
So 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. 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 knows something that I don't know. And, like, I need to learn. Or this girl or, you know, I say guy, but, you know, I meant. I mean guy or girl.
Anastasia Koroleva: [00:54:48 - 00:55:22]
You know. Shane, I've been researching the whole post exit journey and talking to people for 13 years now, and I came to one conclusion. I'm absolutely sure of, that the root cause of all the mistakes is just not taking that time to introspect, 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 that. You take in the decision making course and doing it, actually, that explains a lot in terms of you now being in a much happier place.
Shane Neman: [00:55:23 - 00:55:32]
Yeah. I appreciate that. Yes. It's, again, it's like, willing to do what a lot of people won't do, right? Or they think stupid.
Anastasia Koroleva: [00:55:34 - 00:55:53]
It's tough. It's tough. Introspection is very tough, especially for people who spent most of their adult lives interacting with the reality and making decisions fast and being very action driven and then suddenly shifting our gaze inwards is hard work. It feels very unnatural.
Shane Neman: [00:55:54 - 00:56:23]
It's funny, I listened to a podcast by Sid Guru today. I don't know if you follow him, but he's really amazing. And at the end, they were like, what do you want everyone to, like, get from this? It was like a two hour podcast. It was live, right? He was giving a talk live. 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.
Anastasia Koroleva: [00:56:23 - 00:56:26]
How do you want to be remembered.
Shane Neman: [00:56:28 - 00:57:24]
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 have no delusions that, like, anyone's gonna even remember me in a hundred years from now, because, like, I don't remember anyone from 100 years from now. That was my answer. So, you know, 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 somebody will remember you from, like, Instagram or something. I don't know, but even that'll probably go away at some point.
Anastasia Koroleva: [00:57:25 - 00:57:29]
Jane, this is so beautiful. I'll let you go so you can be a good person and a good father.
Shane Neman: [00:57:29 - 00:57:32]
Oh, thank you so much. Thank you so much.
Anastasia Koroleva: [00:57:33 - 00:57:36]
Thank you so much. I loved it a lot. Great conversation.
Shane Neman: [00:57:36 - 00:57:37]
Great. Me too. Thank you so much.
