Shane Neman - Serial Entrepreneur & Founder of Neman Ventures | The Business of Partying

There was no solution for texting, which was shocking. I built it, sent out the first text, and literally, I had every nightclub owner promoter of everyone call me and be like, how the hell did you just do that? Shane Neiman, CIO and General Partner of NAMM Inventures, has built his career on finding value where others dealt. From backing over 50 startups like Impossible Foods, Flexport, and Kraken, to investing in real estate gems like Pacific Park and the Racket Lounge, Shane has a unique approach to seizing asymmetrical opportunities. We had an app store, he saved your stuff in the cloud, and we were a SaaS company, but none of those words existed. That was my first taste of building something, and then just getting punched in the face and falling down again. In this episode, Shane reveals how he's cultivated a keen eye for high growth investments across venture capital, real estate, and private equity. The better decision maker you are, the better you tend to do. It's very hard for a 20-year-old to understand how much can happen in 10 to 15 years, and how much money can compound. Welcome to Success Story. I'm your host, Scott Clary. The Success Story podcast is part of the HubSpot podcast network. I'm also a big user of HubSpot products. I've supported the show for over three years now, and for all entrepreneurs I need you to go back to a time and place when building businesses as tough as it is can be sometimes a little bit fun. When you're marketing, it should be fun, but marketing is not so fun anymore because it's very time-consuming, it's very difficult, and it feels like there's just a lot of friction. Content was simpler to make, leads were easier to capture, and we weren't all spread so thin. As marketers, as entrepreneurs, the bottom line is that marketing used to be fun, it's not so fun anymore. But with HubSpots newly launched marketing and content hubs, I've been using it myself. It brings a little bit of fun and creativity back into marketing for your business. They're going to generate better content, they're going to generate more leads, and next level results which really make marketing fun again. So with tools like Content Remix, you can turn existing assets into all new pieces with just one click. Lead scoring helps you shine a light on the leads that are most likely to purchase and analytic suites they built out will help you with reports, KPIs, and just a gold mine of AI-powered insights. It's quick to get your results, it's easy to use, it connects all your teams in your data, so put the fun back into your marketing funnel with HubSpot. Visit HubSpot.com to get started for free. Shane, I'm glad we finally got to sit down. This has been a lockdown. It's been, it's been a lot of fall starts, but yeah, listen, I was in the middle of a move. That's okay, congratulations on your move. Beautiful home, beautiful studio. I'm very happy for you and your family. Yeah, now we're getting more entrenched in Florida. Yeah, well, I mean, for LaRielle to Miami, it's like now you're a real Miami and a real Miami. Listen, like this was a lot of effort for the past two months, but it's worth it, so I'm happy. Well, anyways, it's beautiful. Not about me. Enjoy it. I will enjoy it. It's the first of many. I know I know we're only going to do like a little one this afternoon, but you'll have to come on again, and then when you don't, you don't have to go run off for your kids, you invite me. I'll come the old browns. Yeah, well, you do a lot of cool stuff. So I think it's going to be, there's going to be a lot of future stuff to talk about too. You're not done quite yet. No, I don't think so, but we'll see. Let's kick it off for people that don't know you. We'll talk a little bit about your background where you came from. I think you have an interesting story. So you were, well, your parents were immigrants from Iran, and they came over at the end or at during the revolution or right before I guess they came during in the in the late 70s. I guess right before it kind of really tipped, and I was born here in the United States. So I was lucky in that in that manner. And you know, kind of classic immigrant story, they're Jewish, so they definitely had to leave because at that time being Jewish in Iran was not, not that it's working now, was not much better than that, but it was definitely not a great place to be. And they came to New York and they started over. They had a great life in Iran, you know, probably upper middle class family. My dad was an architect. My mom was a teacher. And I was an only child at the first child, their first child. And so yeah, you know, I watched them go from zero. I mean, I was sleeping at the foot of their bed until I was, I don't know, 10. So when they came over, it was pure immigrant mentality, immigrant hustle. They had to start from scratch or absolutely. So my my dad couldn't be an architect. He'd have to go back to school again to get the licenses and everything, which just didn't make any sense. So he decided to go into clothing because he had design skills and you know, started very humbly selling clothes to boutiques and then open their own boutique and then open their own knitwear manufacturing company. And then about a decade later, finally, was able to buy their own house. And you know, kind of American immigrant story where I remember, I remember falling asleep in our basement at two o'clock in the morning, watching them work, literally making clothes on stop. Yeah. And I was in third grade, fourth grade. You know, and then if you look back like you, obviously you've built businesses now, you're an investor and you look back at your whole life and there's been lots of season, different seasons to your life. What was that? Was it was it them working exceptionally hard? There was a major influence on you. Was it because they were super entrepreneurial? They had the restart that like light the fire. Was it like, what was that inflection point in your life? I think the inflection point for me was actually there were there were many inflection points in my life. I had some pretty significant things happen to me earlier in my life. My father passed away when I was 13. So that taught me and he was 44. He was young. He was very young. He got stomach cancer, died within three months. And my mother was not the breadwinner, but had to learn and start over. So I learned that from my mother and she was actually perpetually ill. Her entire life, she had a lot of, she had renal disease and had a few kidney transplants and she had a lot of health issues. And despite that, despite that, she was a very successful businesswoman. Went into real estate after my dad passed and by against all odds made it really kind of pushed through, never had any excuses. So I saw these things. I understood how how fleeting and unfair life could be. Let's just say. And my dad passed when he was 44. So that was the measuring stick for me. I was like, I got to get everything done before 44. Because I don't know if I'm going to make it so it's actually very scary when you see that. When that's your reality. Yeah. Yeah. You're like, you're in high school, okay? You're 15, 16, 17. You're going off to college, university, you're turning 20, like my life's half. Oh, absolutely. It actually, it sounds really messed up, but that's the way I thought about it. I didn't. I kind of really understood the value of hard work in the beginning of college. So I went to NYU and I was pre-med actually and I took my first chem exam and I thought I was smart until I took my first chem exam. And I got an F which literally was a punch in the face to me, ego wise and everything like that because I had kind of coasted by in high school without having to work too hard. And then I realized that that's not going to really work in the real world. Like, let's just put it that way. I actually had to save. I was like, university was like a slap to the face because in high school, I could do whatever I wanted and soak it. I was partying all the time hanging out with my friends doing my homework last minute, you know, studying right before the test and I thought that that would fly, you know, when there are 600 other kids in my class that are infinitely smarter and work a lot more than I do. And that actually was a tipping point and inflection point for me. I literally realized at that point that I can't do that and I went into this kind of like crazy work mode. I went into founder mode. Yeah, yeah. The Paul Graham founder and you like, but that was so just back up for a second. Why did you go into med school in the beginning? Um, well, because med school is not founder mode. Med med is like, no, but getting into med school is founder mode just to be honest because it's so I don't know how it is now, but I'm talking about 25 years ago, almost, right? And more, it's more than 25 years ago. So at that time, it was still kind of like respectable to want to be a doctor and there was prestige and there was honor in it, which actually, by the way, I think there is, I think that being a doctor is probably the most noble profession you can be in. It's very important, but I think that people who do it now really have to love it because doctors are overpaid, I mean, underpaid, underpaid, overworked, right? And underappreciated. And I think that also what you're what you're saying is very true. So 25 years ago, I would say that entrepreneurship is not a thing the way it is now. No. So it was a glamorous is like doctor lawyer is pretty much the epitome of career success. Being an entrepreneur was not now. It's like popular. It's all over YouTube and everybody wants to be an entrepreneur of it. Yes, they don't realize how much it really sucks, but that's another conversation. But yeah, I came from an immigrant family, doctor, lawyer, you know, I also had, you know, my father passed and my mom be sick her entire life. And so, you know, I was, I was motivated by that, let's just say. But, you know, to get into med school is very difficult, was very difficult. I don't know how it is right now. It was very competitive. And you had to study a lot. You had to take pre-med classes and you had to take an MCAT, which was really crazy hard to and to get into a top medical school was not easy. And so I made that my mission and that was my goal and to achieve that goal, I had to really work hard at it. But then you chose to not go down that path. So I actually went to med school. I studied computer sciences at back up in college. Like an undergrad or yeah, an undergrad. So you can, you can actually major in whatever you want, English, you know, span it, you could do anything, actually, home economics or whatever you want to do, right? As long as you take the pre-med classes and you take the pre, the MCAT, you can get into medical school. So I actually did computer science because as a backup of like getting a job in case I didn't get into med school, right? It's a lot of bad backup. 25 years ago was not as popular. Again, you were kind of out of the curve on a lot of this stuff because the computer science now, it's like, yeah, you won't hear kids to be able to code. But 25 years ago, I got, I don't even, well, kind of computers were you coding on 25 years ago. I learned on Turbo Pascal, which was like just an IBM worked on like a regular IBM PC type. So I learned, I think it wasn't like still in the early, early days, but you know, there was, it was, it was pretty advanced at that time. And then Java came out. And so there was object oriented programming and stuff like that. But I, it was crazy because actually, you're right. Most of the classes I had to take were graduate level classes because they didn't have enough classes in undergrad to kind of constitute a computer science major. And anyway, so I learned, and I actually worked on the side. I got into med school early, like in my junior year, I did early decision and I got into NYU. And so I ended up kind of having a relaxed time sort of for the last two years. And I worked as a web programmer. And at that time, that was really in demand. I was getting paid like a lawyer would get paid probably like 500 an hour or whatever it was. Yeah, I was making a lot of money for my age, ended up saving a bunch of money. I also was a TA and that kind of stuff. So I had a little bit of the entrepreneurial spirit at that time. But then when I got into med school and I started med school, it was, I don't know, months and, you know, I was about four or five months into med school when my roommate at the time was working at Goldman. And he's like, what the hell are you doing, dude? We can make like millions of dollars and you're sitting here and reading biochemistry on a Sunday, you know, and he had been parting all night the night before. It's like, I know how to raise millions of, this is during the dot com boom, right? So he's seeing it everywhere. Oh, yeah. And I'm like in this apartment on park Avenue in 36th Street and literally like just studying all day long. And I don't know, something, when he said it to me that way, clicked. And I just called my mom and I said, listen, I'm not going to go to med school on my day. She's like, why are you sure? And I'm like, yeah, and I said, I'm going to try this. I had saved up a little bit of money. He had saved up money too. And we tried a dot com. And someone, there were venture capitalists that were dumb enough to give 22 year olds, you know, a few million dollars to pursue something that was really actually, we basically tried to create Microsoft 365 through using Citrix. So at that time, apps were not web based. They were mostly like Windows based, but there was a way to use Citrix to kind of run your apps, look, you know, on a server. And we had an app store and we saved your stuff in the cloud. And we were a SaaS company, but none of those words existed. None of those words that I just said to you existed. You were making it with blue ocean. You were trying to build in a category that didn't exist. Yeah. And so sometimes you have a great idea. And this is obviously will lead into the VC portion of things, but you're just great idea, just really bad timing. And, you know, we built something that people actually use, but there were lots of reasons why we failed, not just because we were early. There wasn't enough broadband penetration. There was a lot of other issues. And then, you know, the dot com bubble bursts and people would not continue to fund us. And so anyway, that was my first taste of building something that I thought was amazing. And then just getting punched in the face and falling down again, right? But that must have been, so that that's probably raising venture money and then failing is probably the most stressful thing a 20 some year old can go through. Oh, absolutely. Because now all the investors want their money. They're asking you what's going on. And not even that. I mean, just the tension between founders. Also, because, you know, you end up kind of having disagreements of what should be done. If I wanted to just walk away, they didn't, you know, and there was another founder involved. And, you know, the dynamics of it is is is a lot more complicated than that. What what how did you get out of that? Because that that's I just gave I said, well, here are my shares. Have a nice day. You guys, if you want to continue to do it, do it. But I don't see a light at the end of this tunnel. And so my options of that time was going back to med school or maybe starting something else. And I wasn't sure exactly what I would want it to do. And even if I wanted to go to back to med school, I had to wait until, you know, matriculating for the next year and that kind of stuff. So then when did and how did Junebug start? Because that was that was that's the one. I mean, you wrote book about it. Yeah, I wrote the book about it because I learned the most about it about about life and and business. It's just so funny because you were med school. You did a SaaS startup and then you go into night life. And you and the way you enter night life is I mean, eventually there was tech components built out. But at the beginning, it was like a very much like a non tech business. I think even from the so so let me kind of so so at the time I actually moved in with my girlfriend at the dorms. She was going to FIT. How old are you? No, I must have been 23 or 24 at that point. And and she, you know, she was still going to school. And then she worked at a couple of night clubs on the side to make extra money. And and so I would go and pick her up at three or four in the morning. And then you know, she got paid cash. And then I was looking around and I'm like, I don't understand. These guys operate this entire night club or this bar or whatever on paper and pen. It makes absolutely no sense. They don't even have they had no systems in place. And so also they would, I don't know if you remember this. I mean, it's pretty old school to do this. They would print out flyers and then there would be a person outside the club. Yeah, I mean, I was around for a minute when I had a long and they would give you a flyer. They would give you like a piece of paper and it would tell you about the next party that was next week or the New Year's party or whatever it is that they were trying to promote at that point. And so I was like, what 99% of those are on the floor because people just take it and throw it on the floor. And I'm like, these guys should be emailing people. They need to have systems in place. So we kind of, it started by us using tech to do an event and seeing if it if it makes certainly you are doing nightclub promotion, just nightclub promotion. I'll bet. No, so I was like, let me test this theory. Initially, we did a haul. I said to my girlfriend, look, let's do a Halloween party. I have an idea. We have email addresses. No one was doing e-vite. This is a pre-facebook, pre-camera phone, pre-my space, pre like event bribe, pre everything that you know today. None of that existed, okay? Not even like MailChimp, right? None of that existed. And so I'm like, I'm going to figure out we're going to do this website for an event. And that was like really, and then you're going to have a code to put it in. And you have to have the code to go in. And we're going to do this. And I had just moved at that point to the, to the, to, to sudden place, which is like near the Queensborough bridge. And there was a new place that a new restaurant that was built under the arches of the bridge that was beautiful. And it was like, it was like an ideal place to do a Halloween party. And so I'm going to, I'm going to give the whole book. But we do this event. And in one night, I make like 200 grand or something like that. Something crazy. And it was just, it was basically digital marketing. All through digital marketing. And that was novel. Yes, that was. Emails, emails. We made a credit card that had a Mac stripe on the back of it. People had to come and come and use that. And I figured out how to do sponsorships, which I had no idea how to do. And then I knew at that point, I had something. And so we ended up, it ended up becoming a lot more than that. So we ended up building the entire full tech stack that most of the night clubs and bars used. So they would use it internally. And then we, we became like a media arm for them. And just to give like an idea of some of like the numbers around the business. So that first event, what kind of money can running an event with a tech stack actually make you as an entrepreneur? Oh, well, I mean, it's mostly profit. Because if you sell tickets and then you guarantee a bar and you hit the bar numbers and then you get a piece of the bar. I mean, I don't know how it works now. This is like 25 years. I mean, sending emails costs nothing. I programmed it myself, right? And so, I mean, I don't know. We were selling tickets between 30 and 50 bucks and we had three or 4,000 people come. So you just do the math. It's not bad for one night. And you can do that at multiple and you did eventually do it at multiple venues, even some simultaneous. So we had the tech part of the business, where it was more like SaaS and media. So we sell media. We also built an email list that people would, you know, kind of pay to get on kind of like a daily can. I don't know if I remember daily candy, but at that time, there was a daily candy. But now there's like three lists and these other, these other ones that that kind of came out. We were the precursor to those types of things. And then we built a ticketing system. So if you can imagine, like ticket master was not, you know, selling tickets for a nightclub, which ended up becoming instead of like thousands of tickets. It's turned into millions of tickets because EDM really took hold and venues, you know, like Tau, Tau Group and bigger venues started to use this technology. And they wanted to pre-sell tickets because, you know, they were paying a lot to these DJs to come in. And so they wanted to make sure that they had their costs covered. And, you know, you just do the math. You sell millions of tickets and make two or three bucks on convenience fees. It's money out of threat thin air. And you basically built that. So all the tech that like the people would use now, including payment processing, would you do, would you build out your own payment processor? Yeah, well, that our systems, we didn't, we partnered with payment processing, but you'd still get a percentage. Absolutely. Because you're the one bringing in the business. And then we would sell ads. And then we were like, wow, these guys are making so much money on events. And we figured out that New Year's and Halloween are the two biggest money makers of every New Year's. I mean, everyone goes out on the years and people are willing to pay ridiculous prices for like the worst experience of their life. Okay. It's like, you know, just because like it's barkey or whatever, you know, whatever new hotspot there is. But it's actually even funny because we've found figured out that you could do New Year's Eve parties at the worst thing places you could think of like we did like Dave and Busters and Times Square, right? And we would sell tickets at the highest price you could imagine. And there was really cheap to rent the place out because like who goes to David Busters. But what we realized because we were doing like data analytics is that there were a lot of people calling us being like, where can we go where we can bring our kids? Because we want to go out and we want to see the ball drop and we want a party. But we want to bring our 12 year old or 13 year old kids. Yeah, we're not going to go to a nightclub and get bottles service. Absolutely. And so we're like, wait, these guys will pay a thousand dollars to get for that. So, you know, we're $500 to ticket or whatever it was. And so, you know, we figured out a lot of things. We also did a lot of really advanced things like dynamic pricing. And you also collected the list of all the people that and then you use at the fill clubs. So if you had this list of a flywheel, yeah, it was a flywheel, right? And I remember I was reading, I read your book a while ago and before we moved. And I can't remember the number. Maybe you remember it off top of your head. But per club on New Year's Eve, the amount of revenue you could do was something was like some insane that we were making like half a million dollars of venue per venue. And you could do every venue in New York City. Well, that's the thing. Scaling that's really hard. Okay. But there was points when you did we did. We were doing like 20, 30 places a one night. And you know, it works very well in major metropolitan areas like New York, LA, Miami, those types of things. So the problem is logistically doing a lot of events in one night requires a lot of staffing, requires a lot of organization and and and a lot of free pre-planning. It also requires it also is a lot of risk because if you look at COVID, everyone who may have bought out a venue for an event was SOL at that point. So you could spend millions of dollars pre-booking a venue because that's the way we actually invented that we would pre-book a venue. So we would go to Marquis, we would go to Steve Ambusters, we would go to this nightclub and say we want to just basically rent out the place for all of New Year's. Here's a hundred thousand dollar deposit. How much is it to to have an open bar for six six hours and food and we'll bring the DJ and we'll bring the this and you know and we'd we'd have to guarantee that you know and that was also part of our six line is you have major metropolitan areas and you and you don't have COVID. It's fine to guarantee that but then you get in trouble when you don't. Yeah, but you're almost like reinventing your business every year if you think about it. So you have to really start over again. There's no there's no re you know other than human nature and wanting to go out on your years, right? It's not guaranteed that you're going to sell out. It's not guaranteed that that venue will stay in business too. There's a lot of risk involved in it. It's it's it's not crazy and and I think COVID's an outlier obviously but yes, you know, it's it's FOMO drives profits. I can tell you that and what what people don't realize is that every ticket you sell to an event like a New Year's event each ticket holder is a promoter because they're going to tell their friends and their friends are going to want to come with them and they buy tickets and then you know as it gets closer to the event you start increasing the prices and then people like freak out. You didn't raise for this. No, I did it literally I literally I didn't do it in my dorm room. I was in her dorm room like I'm holding this thing, right? So yeah, we really did a shoe string budget. Nothing. I didn't even have like I had no money at that point because I lost most of my money with the company. Yes, because I put like a hundred grand or 150 grand of my own money that I had saved up into the other business. That's what part of why I moved in with her. So when did you choose to sell it? What was the reason? So at that point I had started another company. There's easy texting. Easy texting. So we realized that we needed in 2004-ish, five-ish. We realized the texting was becoming you know really prevalent with blackberries and that kind of thing. And email was starting to become less effective. And you're seeing this from the data in in in Junebook. Absolutely because we were we were data first, right? And that's pretty normal now, but I think it was pretty advanced in 2004-2005 to look at your data and try and get insights from it. I don't think there were a lot of people who were doing that, right? Even even big tech companies weren't really even doing that. But I don't know we we we saw that and I was thinking of how can we cut through the clutter because at that point there was, you know, you were getting an email from the nightclub, you were getting one from the DJ, you were getting one from the door man, you were getting one from the grandmother, you know, you were getting one from everyone, right? And so like we were just another email and the efficacy of it was going down. So I'm like, oh, we need to start we're everyone's phone numbers. Let's start texting them. Easier said than done. I thought that there would be a solution like MailChimp out there that you know, by that time MailChimp was and in constant contact and all these other kind of ESPs, email service providers were out there, you know, and they were doing really well because everyone was building their email list, but there was no solution for texting, which was shocking actually. And so I was like, okay, we need to figure this out and then I figured it out. It took like six months and I figured it out. And because it's not, if you think about a texting goes through the phone systems, it's not the internet. It's different. So then there's the higher cost. There's higher cost. It's a closed system. It's not the same. It's text message is actually really considered phone call. It's not it's not it's not data. It's a little bit weird and it's too much for this podcast to go into it. But anyway, long story short, I built it, sent out the first text and literally I had every nightclub owner promoter DJ everyone call me and be like, how the hell did you just do that? And I was like, light bulb moment, which is wild because even in 2024 outside of like Twilio, still not a lot of companies focus on texting. It's still email. There are a few big ones that are like Shopify integrated that do this interesting thing where if you go to their text message list, they give you a coupon and then obviously texting someone is a lot more effective than then then. But even if there's people that even if there's companies that offer it, I get less texts and I get emails is my point. Yes, you do because it's actually highly regulated now. And so they never wanted it to become like, you know, you get like millions of text spam. And so actually companies like easy texting that started it, we would make sure that that our customers were in compliance and they're, you know, they're only sending to opt it in customers and that kind of thing. And we gave you tools that would help you build your list in a compliant way as well. And this is before the government had regulation because you were out of the curve like you were. Yes, we can do a whole podcast on regulations and stuff like that. We got slapped with a bunch of lawsuits that we got pulled into as well. And I learned a lot from that, learned all about probably it's like one of those things that if you knew that you had to go through that, maybe you would have never started it in the first place. But it doesn't matter. So anyway, the light bulb moment went off and I was like, this can be, you know, this could be MailChimp for text messaging. And so I didn't hesitate. I created that and I can't kind of ran both companies for a year until easy texting really started to become significant at that point. And I just really saw the opportunity with easy texting being a lot bigger than what I had already done in the previous 10 years with Junebug. And I was also ready for something new. The entrepreneur and me was ready for something new. This was the shiny new object. There was a competitor that was nipping at our heels all the time with Junebug. Yeah, with Junebug, that was trying to do what we were doing. And I just called them and I said, listen, this today's your lucky day. You know, we were, we were, we had already kind of like, we were the established company. I said, look, if you can figure out how to kind of make this acquisition work, I'm willing to do it. And so that ended up happening. And then I spent another eight years or so building easy texting. It also kind of coincided with what I wanted personally, because there was a lot of, you know, it's not easy. It's not easy to kind of want to get married and have kids and stuff and be in that type of business, even if you're just doing the tech for them. Let's just say like it's the old business like at odds with like a marriage and a stable family. Absolutely. And and and so what's really funny is that the entire time I was always in long-term relationships. So was it like I was going out in part of it? Probably why I could stay in the business and not kind of get caught up in it. A big shout out to HubSpot and the HubSpot podcast network for sponsoring success story. If you enjoy success story, you're going to enjoy a ton of podcasts brought to you by the HubSpot podcast network, including hustle and flow chart hosted by Joey Fier. The hustle and flow chart podcast with Joey is all about how to build a business. So it gives you the freedom and fuel for your life. You're going to join Joey as you discuss his systems, mindset tweaks, reframes and strategies for entrepreneurs and really anyone to enjoy the process of being in business and having fun. This isn't for entrepreneurs looking to build a billion dollar business. It's for somebody who wants to build a lifestyle, somebody who is looking to build systems that work. Listen to hustle and flow chart wherever you get your podcasts. But it's not, it's very, I know that business is tough. I was speaking to um uh Scott Harrison from charity watch. Yeah, I know him. And I was and yes, he was telling me his story. I'm like, for sure, he knows Shane. Yeah, yeah, I know him. Yeah, I mean, he realized it earlier on and understood that real purpose came through, you know, doing something significant. And by the way, he was like at the top of his game. I have no doubt. He said he left, uh, he left this beautiful condo with yeah, like this like grand piano and his panthouse and and he just left off and he just like never looked back. Yeah, good for him. And charity was big. They just, they just raised over a billion dollars just like last Thursday they hit like the billion dollar. How much, how much more fulfilling is that probably a lot? Absolutely, absolutely. So yeah, so you get, you get it like this is not going to be the business you're going to build for the rest of your life. Yes. Yeah. And and I also think that part of a lot of people get get caught up conflating themselves with their business, you know, they they almost see themselves in their business as one. I was very lucky that I never had that mentality. The business for me was always an ends to means and and and to to a degree, I have to like what I'm doing, but you tend to like things that are successful, right? So, uh, you know, uh, I never, you know, once I sold you and bug, it was like like turn that page, have a nice day, like that's in the past, right? I never really, I don't even really think about it ever. You know, it's not, it was never me, right? It was something I did, but it wasn't me. But that's a very healthy attitude. Yeah. I think a lot of entrepreneurs should probably have that attitude. It's easier said than done. And when you're in it and you're running it, it's hard not to move your room with yourself out of it. It's actually it's conflicting because you want as a VC, you want a founder that is all in, right? But you can be all in and still be detached from the outcome of what's going on. And that's that's that's either something that's innately in you or you have to work to kind of make yourself aware of that. That will, I mean, your mental health is going to be much better if you adopt that attitude versus the opposite, which I think is I think the less founders act like you act it. I think more founders just their whole identity as a business. It could be a detriment too because if you don't sell at the right time, you're also screwed. You could have sold and you could have done really well. And you you hold on too long and you burn yourself out or you hold on in the market turns and what you were doing is no longer relevant, right? Did you raise for easy tax? I did not. I took all the majority of the money that I got from the sale and I pumped it into easy taxing. And then just that so that would be the third business. So Junbaugh considered a success easy taxing. How far did you take that? So I took that for another eight years and then it did very well. We grew it. It was have you have you been public about numbers or no? I can't say the actual number, but we were close to around 18 million in ARR at the time that we sold. But so I mean, you can kind of backtrack numbers if you wanted to. But what was interesting is that we were doing that with a team of 20-something people that's good at revenue per head. And you know, we were serving tens of thousands of customers. We were early to the kind of game. So we had a first mover advantage. And what was interesting was is that I wasn't even kind of looking to sell a strategic approach to me that wasn't doing taxing. They were doing calling. This is perfect. And so yeah. And then it's funny. That process taught me how to think about my business. Because all I knew before that. How do you say that? This is like your third business in. This is like, this is almost like 25 years of building your business. Why do you say that? This moment is when you thought about. Because I think I thought I knew because it was the first sale was a very friendly sale. It was when a choir who knew my business inside out because they were doing the same exact thing. And so there weren't many questions around what I was doing. It was kind of like a handshake deal. This was a little bit more different. They were asking me questions. And I'm like, I don't know. I never really thought of my LTV. I don't know. We never thought about what our cost of acquisition is. I just know I make a shit out of money. What was very interesting also is that at that time, they didn't really know what to do with us because I ran a very profitable business, which was weird for SaaS companies at the time. It was weird to be profitable. Absolutely. But I was licking it as a career, not like something that I'm building to sell. So I was like, I want to make something where I make a good living off of. And there are SaaS companies that do that. 37 is signals and other companies where they make millions of dollars a year and they have a great product and they have customers and they're never going to build, they're never going to sell. But I actually think that's again, all the things that you did, these are things that I think are just best practices for entrepreneurs. You shouldn't. I don't think most entrepreneurs should be building a company that's not profitable, that you're just looking for the next round and you're just burning through venture money and you're stressed out. I was actually looking at old posts, funny enough, just last night, old posts that I put out. And I'd done this little comment on a tweet this guy put out. And I can't remember the whole story. Basically, the tweet was, I sold my company for $237 million that I didn't get anything from it. And it was, it was a venture back and he was diluted or whatever happened. And he never took money out and he paid himself like this below average salary. And by the time that he raised whatever serious he was at, I don't know how it happened. Maybe they had to do a down-round. I don't know what happened. But basically, he sold the company to $237 million and walked away with zero money. I bet you, if you had a company that you own by yourself, they made $5 million a year and you sold that company, you wouldn't make as much as if you sold your venture back company for $150 million. The math probably works about the same. I bet you're right, actually. Right. So who's the better founder? I'll tell you, it gets the headlines. The guy with the 150 million gets the headlines and people actually give a shit about him because he's VC back. But no one gave a shit about me because I was a VC back to no one cared, no one cared to look. But maybe that was part of my successes that I went under the radar. Maybe if people knew how much money I was really making, they would have competitors like a $5 million, $10 million in pure profit. I think that's fucking phenomenal. That's absolutely phenomenal. I mean, try doing that right now. It's impossible. You have to have a lot of things work out for you to make that kind of money, right? A lot of hard work, a lot of luck, probably more luck than hard work. Right, right time, right place, right market, right product. Absolutely. And you have to be in the right mindset and the right experience levels to do something. And I also think that many people don't need as much money as they actually think they need. No. To actually live an insanely good life. No, they absolutely don't. They absolutely don't. And I live their great life without a lot of money for a long time. So okay, so easy tax thing. You went through a strategic. They approached you. They approached me. They were actually a customer of ours. And then and then you know, I learned a lot about my about my business through that process. Exited, had coincided with getting married and also having my first child. That was a busy year. Yeah, I was like within the first two years, let's just say, of doing that. I stayed on for like a year. And you know, I realized it wasn't going to, you know, like it wasn't my business anymore. And there was other, you know, like this happens to everyone. But I kind of made a cautious decision at that point, not just like what you said, you know, when is it when is enough enough? Right. And so I was a crazy workaholic. I would work all the time. I mean, my wife, I don't even know why my in-laws let me marry my wife. Because I would not, like I was never there, president, you know, like I was on my blackberry all the time. I remember I spent one new year as my poor wife at that time. She was my girlfriend. We were in Miami. We went to dinner at 10 o'clock. I had to leave because of a work emergency. I went to the basement of the Delano at that time, worked on the computers. Because they had a computer office computer system. Yeah, I lab. And I left it like three in the morning, you know, and I went and picked her up. And that was like my life. It was really like that all the time. I was never present on anything. I was only about the business mostly. Which I think, you know, coincides with how successful your business is. And there's nothing wrong with that in a season of your life that that that you may need to do that in order to get to a level of success that you may want personally, right? But anyway, I realized I wanted to be a present father. And I was like, what is this all for if you don't get to enjoy it a little bit. And so we moved to Miami about 10 years ago from New York City. I was always in New York City. So that hustle came from being in New York City. Also, the hustle came from trying to get into med school too. Like you never saw founder mode for like 25 years basically. Yeah. And by the way, I still have that in me. So now the founder mode comes into running investments, which I think I do differently than a lot of other investors. I want to unpack that because even now I find you busy. Like you're you're still very busy for somebody who is like quote unquote retired. Yeah, I'm very busy. I wish that people think it was some of my friends and family think I'm retired, but I'm not. I really work all the time. I know you work all the time. I work all the time because there's just so much exciting stuff happening. But it's interesting because I don't think I know too many other people because I don't. Do you consider yourself like a professional investor? I guess at this point. And I'll tell you why say that because the people that I know I know a lot of people that have exited companies and they all invest obviously, but they don't spend as much time investing as you do. No. So yes, I so so so I made it my mission. I realized afterwards that I didn't want to do a startup. And I'm like, I need to learn how to not suck at investing at least. Let's just put it that way because the one thing that people it's the ego when you sell a company, you think you know what you're doing. And then for some reason, people think that just because they can build a company, they can invest. It's actually diametrically opposed. Sometimes being a good investor and being a good founder are not necessarily some of the attributes are okay to have, but other attributes actually make you a worse investor because founders tend to want to do stuff to fix things if they see something wrong and they think they can outsmart everyone and they think they can maneuver. The problem with investing is that if you do too much, you actually end up screwing yourself over a lot of times. If you sell and buy and try and time things and do things like you try and control. Yes, yes, you just have to, you know, so people ask me like, so what is it that you really do now? My job is to consistently make good decisions. And that's very hard. It's very hard. It's very exhausting just to be honest because you know, I doubt myself all the time. How do you know the decision you're making is a good decision? You don't know until later on and you see the results of it, right? And sometimes what's even crazier is that the short term outcome of your decision may be bad, but the long term outcome might be amazing, right? Or the reverse. The short term is like, you're like, I'm the smartest guy in the world. And then like two years later, you're like, holy shit, what the hell was I thinking, right? So decision-making is a skill that no one teaches you. You're not taught like, were you taught in school? Of course not. In your story and in my story, the things that I learned in school were no longer applicable like in the first two days of what I did. Absolutely. Absolutely. So like, how do you learn how to make a good decision? You don't know. You did by doing by making decisions and by screwing up. Yeah, but you know what? Even even when you do that, people don't don't tend to learn because how many people do you know, sit down and be like, oh, let me review that really bad decision I did. And what were the problems with it? And why do how do I mess this up? Do you know what people do that? Because nobody wants to deal with it. No, but I actually do that. I do do that. I do a decision review every quarter. And I keep a journal. And I, and in my journal, it's like kind of like a daily journal of like what I did that would start when I do like a great, like one or two things I was grateful for. And then I, and then if I made any major decisions that day, I usually type it, type it out. And then I'm not just sitting in reverse to investing. No, because it's either you're either like constantly making good decisions and thinking about things in a rigorous way, or you're not. And that can permeate like, why wouldn't I want to do that for my children or my personal life or my health or my this or the other thing, right? So like, I think it's just an essential skill to have to have a good life, not just not just the business. Did you pick that up while you were actually building or was that more after? No, actually, I took, I learned this through a couple of people I was following, but the person who talks about this the most that I like, this the most clear about it is Shane Parish. He's in the knowledge project. He actually has a course called decisions, but I've taken that course. And I thought I was a good decision maker prior to the high. And then I was like, holy shit, like, I just learned something that I never thought of before. It's very difficult to take major decisions through a process. And you know, most people, most, most investors are bigger, bigger investors take it through investment committee and this kind of stuff. And you get everyone's feedback and even that can't can be not the best approach either. What's the decision making process that you'd make on anything from like personal health to investment to like, what's the, what's the framework? So the frameworks are, you know, are they consequential and consequential? Because, you know, if it's a reversible, you know, this is, this is kind of like what goes in Shane's. You know, I never really thought of it methodically until now until I took his course. So like, if it's reversible, then like, I don't know, just make the decision. And if it's not, you know, like, but if it's consequential and irreversible, you know, you want to kind of get information from the most pertinent people that have first hand knowledge of this, not second hand knowledge of it, whatever it may be like if you're making a health decision or, you know, that kind of stuff. And then at some point, having too much information actually hinders your decision making process, you have to also kind of come to a conclusion after of when you have enough information to make it, to make a decision. Then, you know, you do things like probability scores of how certain you are of certain things. And then, and then you have to execute a decision. And, and, you know, when it comes to investing, you have to think of sizing. So sometimes this is the, this is a, so a problem that I've had personally is that I've made some really freaking amazing investments, but then I just didn't put in enough money in the investment. I was really convicted, but I didn't put in, I didn't size it correctly, right? And the reverse can happen too is like, you know, you make a decision, you size too big, and then you make a really big mistake in your out of the game. That's the other thing is that you, it's kind of like poker, right? Like you don't want to make a decision where you have one hand that takes you out of the game and then you can't play anymore, right? So there's a lot of that going on. You have to, you know, there's, there's a lot of different methodologies of making a good decision. But even that, even like a little bit of thought about it, I think is better than what most people do. Absolutely, blindly just thinking about things. You know, there's, there's, there's, there are more things that you can do. But, you know, I could spend the entire podcast telling you, but, but that's, you know, there are, there are books on this. There are people who are experts on this. I, I wish I had done this earlier, right? It would, it, not that I was a bad decision maker, particularly, but the better decision maker you are, the better you tend to do. Now, I mean, so I asked you if you're, if you consider yourself a professional investor, but at the very, at the very minimum, you are a professional decision maker. And that's what you, I think, but everybody is, I think that just, I think that actually it's all relative. I was going to say because there is more, there's more capital, there's more stakes, but it doesn't really matter because at any level, it's all relative. Really, he could be putting in like five grand into a company. And if you lose it all, it's still five grand on. If you're only making 70 grand a year or whatever, that's, that's significant to you. So it doesn't really make a difference. So being a good investor equates to being a good decision maker and also being able to remove your emotions from the investment. It's a very hard to do. It's a very, I am not particularly good at it, but I'm seasoned, and I'm hardened over that. So you sold easy texting. Yes. You started investing. I started investing. I made a lot of mistake. Okay. So, but even like the thought process, because again, I do see you being more active than a lot of the people that I know. A lot of people I know who sold the company, they only invest in the thing that they know. Yes. And all across the and or real estate, that's like the only like you could be like a SaaS founder and you just do like early stage, prop tech, SaaS, and then plus real estate or yeah, but you do everything. I do, because I and you have to talk about the stuff that you put money into. So I'll tell you my strategy is very different now than it was before, but I started. Yeah. But I think that being able to control, if you look at the best investors, like a buffet or those guys, they're all like all slightly on the spectrum. And so they don't experience emotion the same way that an quote unquote normal people do, right? Or you and I do, or we know. So they could see like a huge loss on their account and not flinch, because they're so certain about what they're they just did. And they're just like, I'm willing to wait, wait, be wrong for a long time until I'm right. Yeah, but for most people, if I thought hard attack, yeah, you go you go in and you see your account down 30%, 40%, 50%, you're going to have a hard attack. And you're going to make a bad decision. Okay. And so that's an acquired skill. And sometimes it's even when you acquire the skill, like even during COVID, like I was on the verge of making some really bad decisions that I'm thankful that I didn't make, but I was this close, you know, like I'm not immune to it, right? To making emotional decisions. And and so, you know, that's a that's a practice. It's it's really it's it's just like working out, right? Like the more you practice it, or you know, yoga or whatever it is, the more you practice it, the better you get at it. And you know, you can start small. I found, you know, a few few people who I respected, I I I I talked to them all the time. It's very hard to find those people. And in whatever you're looking for, but like for me, it was for investments, you know, for other people, it could be a health, you know, you know, you know, you and Gary are tight. Yeah, yeah. Now, right? And you know, you know, you as his own, like I mean, he's built a massive social media business with Valeria. So like he's one of the guys that I looked to for that. But there's not many people that that are killing it. Like the 0.001 percent is for a reason, right? Yeah. So so it's worth your time and effort to try and find those people that you want to surround yourself in. That's probably the 90% of the game. And the the amount that I learned from those people. And now I'm adding value to them because I learned their techniques. I learned from them. And now I'm like contributing, right? And so I think that that's that's an essential you really want to find those people that are experts in what you're trying to do and put yourself around them and put yourself into scenarios that give you high probability of meeting those people in situations. So yeah. So now my my my investment thesis is very different than them before. What was it when I don't even know you don't mean what I think I was trying to do a little bit of what you said. I know I didn't really state and I did sass and things I knew initially. But then, you know, when I put myself around other other investors that were really smart, they were opening up whole new worlds for me and showing me biotech and showing me, you know, deep tech and showing me CPG. Like we did in athletic greens, for example, we were one of the investments that I did with one of my friends. It's amazing investor as well. And then looking at late stage businesses, you know, like we did Pacific Park at the Santa Monica Pier, which we bought that business, which is one of the, it's a number one tourist destination in Los Angeles. I know. So you've literally bought a Santa Monica Pier. We didn't buy the pier itself. You can't own the pier, right? It sounds cool. We bought the business of the pier, so it's a little bit different. But there's, you know, there's a real estate component to it. But I think right now my tech, by the way, are those some of your biggest ones? So athletic greens? That's, yeah. So I think athletic greens, athletic greens, the pier is one of the biggest deals I've ever, I've ever been involved with. The, I did a company called Figure AI recently, which is a humanoid robot that Brett Adcock founded. I don't think I knew you when I first invested, we've invested, invested two years ago. It was a unique time because the markets were doing really poorly at that time. It was 2022, I think. And, you know, tech was down a lot. Inflation was raging and Brett comes out and he's like, I want to build a humanoid robot. And all he had was a few guys that he had hired from Boston Dynamics, a sample of a hand of a robot, and a bunch of, I don't know, like computerized prototypes. But he had a track record, though. He had a track record and he was putting in 20 million of his own money. So that's, see, that's the thing when you make decisions, you have to also kind of take into, because if you just look at it at the face of it, you, most 99.9% of people would never even, like, even consider it, because it's like, he's going to build a robot, a human robot that would, yeah, whatever, right? Like, but when you put your money where your mouth is, yeah, as a founder and going into details matter, right? So like those things matter, you know, he had a track record, he had two exits, he took archery aviation public. So he had a lot of hardware experience and scaling hardware. He was putting his money where his mouth was, he had done pretty far, even with very little money of actually making a functional hand, which is the hardest part of a robot mostly. Um, and so when I first did that investment, most people thought I was batch at crazy, because, you know, first of all, the markets were in turmoil at that time. So it's very hard under fear to make investments. That's where the removing your emotion peaked. Absolutely. Absolutely. Like, whether it's in the public markets or the private markets, it's irrelevant, right? People get disgusted and they don't want to look, right? They don't want to look, because they see their account down, right? And they're like, oh, yeah, now I'm going to make an investment and like take even more money out of there. But the thing is those two, those two things are completely separate from each other. Yet it is logically speaking, but it's very hard to separate it up. And so anyway, um, as luck would have it, which I think 90% of all this is luck, obviously. Uh, Brett was successful. He made a prototype that actually works. It's actually deployed in Amazon and BMW right now. It's probably the him, him and optimists from Tesla are probably the incumbents in the field, um, where they have a real viable product that can actually replace human labor. And if you think about a human labor, physical labor is a $3 trillion term, like, everything, like, it's all the work that no one really wants to do, right? Like this, you know, no one wants to go and pick and pack in a warehouse and go down aisles and pull things from boxes and, you know, take a piece of sheet metal and keep putting into a press a thousand times a day, um, which is where he's starting, which I think is the right thing. And also in the warehouse, uh, you know, robots in a controlled environment. So the safety issues are kind of much more manageable, mitigated a little. Yeah, they're much more manageable. It's also talking to a computer that's giving it directions, like a warehouse management system versus, you know, me, you know, robot being in my house and I'm saying, watch the dishes, right? It's a little bit different. It's almost like, um, well, robots exist in car manufacturing already. They do, but this is certain parts of it. So this is just like almost finishing or, or more parts of the, the factory is now going to. So Tesla, I think, you know, their, their idea is that the entire process will be done by a robot. And, and as a practical matter, all the other robots that work on, on anything are, you know, the environment is retrofitted for the robot so that the robot can work correctly in that environment. But the world is meant to interface with humans. It's meant to interface with hands, feet, you know, you know, stable, like a human it, like even an iPhone, if you go and actually look at how it's made, a lot of it's done by hand. You can't even imagine, right? It's done on a huge scale in China, but a lot of the pieces are being done by hand. And so, if you can really, truly replace that, the, the, the, the opportunity is huge. It's almost like bigger as big as cars were when cars were invented, right? The opportunity is, is huge in the entire physical labor. Uh, uh, so it's funny when, whenever an inventor or an entrepreneur is like cam, like total addressable market, and they say some ridiculous, outlandish number. And you're like, well, if I just captured like 1% of cam or whatever, then come any of these successful, but this is, this is, this is really truly a giant ham. I mean, like the payroll that's, I mean, first of all, Amazon and all these places, they, they can't even get enough workers. There's not enough workers that want to do this. So they have to constantly raise the price of, uh, of what they're willing to pay. I mean, the poor workers, you just saw what happened. It was just how to strike it. It is huge. Right. Yeah. No, it got resolved, but they're getting paid like $65 an hour now. That's, that's it. That's significant. That's, that's huge. Yeah. So like, why wouldn't you replace that person with a robot if you could? It makes no sense. What do you need a person to like move cargo from one side of the port to the other? And like, there's a lot of issues with that because they're safety issues. Like if, if a, if a, if a, you know, if a piece of cargo falls on a, on a robot, no one cares. But if they've that injuries a person, that's millions of dollars and yeah, the productivity gains the things that come with it. And so anyway, just recently, they raised 650 million from like Microsoft and open AI and Jeff Bezos put a hundred million dollars. And so, you know, I look smart. Yeah. And then now, now, and then let's see what happens in two years yet. All right. Like, it could be zero, right? What when you look at companies like that where it's, because of different types of companies, you can invest and you can invest in a company that's building almost like a copycat product that would already exist. And you know, for a fact, it's going to get snatched up the second to get big enough. Absolutely. When you look at a company like this, like, what's the end game? Because the exit horizon or the ability for you to take cash out could be 15 years from that. It could. It's more likely a five to 10 year one. And like, as you know, yeah, I think for this particular one, but, you know, I think that I do both. Just my style is I just outside, now I outsize my investments and things where I think can give me outsize returns, right? And so, you know, when you invest in a company like that, you're looking to get like a hundred X on your money, right? And, you know, you have to size appropriately and it's high risk, high reward. But the other one that's a copycat, you know, you know, you can maybe two or three extra money in like four or five years, possibly. And you, you know, it's like, like, I'll, I'll go out and make a really big investment in real estate, because I know the likelihood of that piece of real estate going to zero is very low. Plus you have the land is glideral to it. And so, and so you have to kind of, you have to have a methodology of how you're, how you're looking at stuff. It's, it's not easy for me to tell you my methodology, because it's a little bit unconventional. I'm not as a structure, as like a, let's say a blackstone is or something like that. The only person I have to answer to is myself and not like, you know, I have people who, who, you know, who invest alongside me and I show stuff to as well. But I'm not like a fund manager, for example, or something like that, right? So it's a little bit different. I can take risks and do things that a lot of other people can't because it's, yeah, I owe money. It's your own money. It's your own money. But so even if you were just going to like, I know you said your framework is a little bit difficult. But if you look that so between, between cash flowing businesses like private equity or funds or real estate or early stage or late stage venture capital, you have like a mix that you aim for, like a loose may. Yeah. So I have personally, I have the most allocated to public equities because I think, I think that it's very hard to replicate US equities and the, the amount of value creation that there that is done there. Probably for me, is that through a fund or just through picking? No, I do it. Yeah. Good. Good. I do it. I mean, like one hedge fund, one hedge fund, but that's because I know the person very well. But I've done, you know, like I do funds for early stage stuff, like crypto and like biotech where I don't see, like, and I'm not an expert in the field. So I tend to pick managers that are really good at that. But I like to do individual deals. And I'm probably more than normal in venture than than a lot of people are. And I would probably say that my venture and my real estate and my private equity are probably equal onto onto that thing. I also have a, I have a barbell strategy now, right? So the way I'm thinking about things is I'm trying to invest in deep tech, like quantum AI robotics. I did a company called Luma field recently that that invested in a company called Luma field recently that has a CAT scan machine that can look at any object and then find the defects in it through AI. So even like a Nike sneaker, it can, but they do a lot of electronics too. So like you could put a battery in there and then they can figure out the defects without having to take it apart. I did a company called sandbox a invested in a company called sandbox a queue, which is the leading quantum cyber security company in the world. It actually spun out of Google. So I did an investment in that two years ago. And people thought we were crazy like like figure AI too, because like there was no chat GPT at that time, right? Like so this was bleeding edge. Yeah, yeah, it was, it was, it's our Schmidt. It's, you know, it's, and quantum and this and the other thing. And people really didn't understand what it did. And it was a little early for its time, because, you know, you're, you're protecting against a quantum computer that doesn't exist yet, right? See? Just in case someone does it, right? So anyway, so now that, that business has done very, very, very well. It has a lot of government contracts and they just got to contract with the Air Force and this, this type of stuff. So doing follow-ons on, on those or I'm trying to find businesses where I don't have a good enough imagination to think about how AI or deep tech or quantum can really disrupt that company. And you're looking for businesses that, that you do not have, you do not have the understanding of and explain. I don't have the imagination, a good enough imagination to contemplate how AI or deep tech can disrupt that company and put them out of business. I understand. Okay. And so I'm not doing a lot of SaaS at all, because I think that eventually computers will be coding. Like I mean, they're coding mostly right now. And it's just, it's going a lot faster than people think. Um, I actually, I was, I was able to go to SpaceX and get a tourist. I saw that last week. Yeah. Yeah. And so I mean, I really saw first hand how crazy things are going to get and I see the magic that's happening there. I saw them actually putting together the components of the rockets. I saw how they're using AI. I saw, I actually touched a Starlink satellite, which was amazing. I went on the launch pad. Um, very cool. I drove a Plaid X at 165 miles an hour down where the shuttle used to land. Um, anyway, that's I digress. But, that part of that was like, holy shit, they're really going to get to Mars because I saw it. I saw what was happening there. And I know that they're going to get to a place where they're going to do multiple launches a day. And Boeing can never do what they do. So you see the tech, you see that you see what people are, you see people are capable of. No, it's just in the scribe. I wasn't able to take pictures. So I wish I was, but I understand why. But like, it's so much further along than you can imagine. It's just hard to, to, to human brains are not meant to understand change this rapidly, but it's happening. And so I think that with the robots and with AI and those types of things, a lot of things, and this, this might sound psycho to a lot of people because it might, it might sound like an exaggeration. But I don't, I personally, my opinion is not, like, oh, in 10 years things are going to be changing. I think in is like, in one year, two years, three years, you're going to see some really crazy changes. Um, of how rapidly things are going to become. So when you, when things change that quickly, and you're investing in them, like, there's a really good chance you're going to screw it up or miss it or, or, or pick the wrong thing. So when you look at something like a quantum computing company that is protecting against malicious quantum computing attacks that have not, quantum computers are not even, like, commercially available yet. Like, who do you talk to to make sure the founder is not full of shit? How do you go to like, so for me, I'm lucky that there were a lot of really big, but this doesn't work all the time because like, Theranos is a good, good, good, good example of this. But, you know, typically you, you know, I, I rely, I read to the degree that other investors have investment memos or experts in the field that I can talk to. Um, that, that's leveraging your network, right? So a lot of the deal flow that I get is from other fun guys that I've given stuff to, or I've personally gone into their fund just so I could see their deal flow, right? And, and, and, and, and get to pick their brain and talk to them. You know, that's, that's worth every penny. If you think about it, right? The smartest guys, you know, have been in this for a long time, run their own funds. You know, you put a little bit, or you could put a lot, you know, and get to, get to, get to talk to these people find a way to get around those tables. Exactly. And so to that degree, I have a degree in computer science. So to the degree that I can diligence things, I'm pretty technical. So I'm, I'm cutting unique in that way. Um, so I leverage that, right? Like, uh, by the way, like, if they, if someone tells you they understand quantum, I mean, they don't understand quantum. So that's a, that's the number one rule in quantum. It's like, so like, I don't understand it, but I have enough interest in it and enough background to get the concepts on a high level. And that's, I think, probably one of the most important lessons. Like, there has to be some data point where some person or some, some thing that allows you to understand it just, uh, like, just so you're not ignorant going into it. So you're not just dumb money going into it. Yeah. So, but also if you think you're, think, think about it, you know, you're also 90% of the time betting on the horse. So Jack Hittery who's a CEO is literally considered to be the foremost expert in quantum. He wrote the, he wrote the textbook on quantum computing that's taught. And Eric Schmidt was the CEO and chairman of, uh, of Google for 12 years. So like, what better horse can I bet on, right? Just like how people bet on Elon, right? It's the same, same, same concept there. Um, yes, you know, the tech is important and everything like that's important. But I would argue to you, like, in those cases, 90% of it is who you're betting on, right? Who you're betting on, not just what you're betting on. So, um, so, and then, and then, so like, let's talk about the other end of the spectrum, right? What, what can't be, uh, you know, disrupted by all this stuff that's happening, right? Santa Monica Pier. People are going to still be going on the weekends on, you know, they're going to be still challenging, you know, these are, these are, yeah. Um, you know, experiences, although, although some, what some people can argue that, you know, you can virtually do with some of these things. Um, and that might ever replace by virtual reality. But, um, but not yet. I mean, that's, I mean, it could be, but not yet. And there's also, if you think about like the, so can a row, who can a robot replace a person in a warehouse tomorrow? Yes. But if you're going to talk about replacing a, a tourist destination, you have to replace like the, the smells and the feeling of the wind on your face and the taste of the hot dog or the pretzel you go eat. Like, that's it. I can, I can argue the neural ink will do that for you because it'll, it'll go into your brain. And the precursor technology is not already there, right? The precursor, yes, you're right. Yeah. But when that happens, so it's like, it depends on like, what are you investing in the technology that's directly applicable? Or are you investing in the technology that's going to create another category or another industry? I think, I think for those things, those are a little bit, uh, we don't, you're going to have regulation issues also. And they're regular. Yeah, regulatory issues. So the things that could stop this and stop, you know, AI from advancing is government intervention, regulation, one of the robots accidentally kill someone, shoot someone, gets, gets hijacked through cyber security. You know, there's a lot of scenarios that you can come up with that can really kind of put us back as well. So you can't have all your eggs in one basket thinking that only the future, the things in the future. Um, but like again, I'm looking at a hemorrhoid cream that's like trying to disrupt preparation agents. It's been the incumbent for like 657 here. What was the one that you sent me? I didn't look at it yet. You just sent me one like last week or this week. I think it was something for creators. It was a creator. It was a creator. I see a lot of things. So I, uh, the one thing I, I, uh, the one thing I haven't done much of is anything that's like social media related. Um, it's just way too difficult and competitive, I think for me to a lot of people that build in the space. Yes. It's too, it's too hard to know the the winners of that. That's so interesting because I think that it's almost so if you look at investing in blue ocean versus red ocean or red ocean, you know, there's a market for sure, blue ocean with the things that you're talking about. The market should be created in the future. But it's not like really here yet. But you feel more comfortable doing that because it's just less crowded. I think I'm, I'm doing that on that barbell. The other thing where I'm doing where I think they can't be disrupted. It's already, it's red ocean. Like, you know, yeah, the hemorrhoid cream hemorrhoid cream. Right. Yeah. Yeah. Yeah. Yeah. I mean, if you think about it, no one's done like man-scaped, for example, is a big brand and they do a lot of money and they took what, what a lot of people wouldn't talk about men's grooming and made it into a hip cool brand and they make a lot of money doing it. And no one's done that in that, in that space or, you know, there's the female hygiene space. So I invested in a company called ant flow, which is doing that. Um, so, so I think a lot of it is, um, really kind of thinking deeply about things and also who you're investing in. Yeah. It's a person because they're going to eventually, just like I did, you know, they're going to eventually hit these roadblocks that everybody eventually gets to and you have to feel comfortable that that person has the wits in them to figure it out. However, they do it, they have to be able to figure it out or pivot or do whatever it is that needs to be done to continue on. Um, and that's, that's really, that's really what you, the best you can hope for. What was the biggest, the biggest loss that you would be willing to talk about, the biggest failure? Yeah. Oh, so many of them. It's hard to take one. Well, I mean, my first one was the biggest failure. The Offix, which I told you about when I did investing, but yeah, oh, yeah, investing. Oh, man, I can, if you, maybe you haven't, we do him another hour. I can tell you about all of them. Uh, probably more, we'd probably need a day than an hour. Um, probably the one that kind of, there was a company called Convoy, uh, which was kind of doing what Uber Freight does, but it did it first. Uh, we were the early and early, I was an early investor in that company. And then a few years later, it got like a three billion dollar valuation. We had an, we had an offer of the sell. We didn't. We're like, this is going to be the next thing. And then COVID came in and my god, zero, zero, are you serious? Please zero. Yeah, shut down, shut down this past year. Yeah. A lot. No, no, we got zero. They had ventured that, the ventured guys took it over. Yeah. So, uh, yeah, I thought I was maybe going to retire on that, maybe that, maybe that's not going to happen. Maybe it's, maybe it's one of the ones that you're in now. Yeah. Maybe, you know, you can only, listen, I've, uh, learned one thing. Don't ever, don't ever, uh, counterchickens because it doesn't, you know, even to the last minute, um, um, I actually, in the public markets, I had made not even a year ago. I thought, I thought that, um, Moderna was a good investment. And I've gotten really crushed on that investment. You've had 60% down, something like that. Shit on that investment. I haven't been watching it. Yeah. It's, it's, it was, I was wrong. Man, well, I'm wrong until now. It might be brought right later and things might change. But that's the thing you're removing the, the emotion out of it because if you sold when it was down 60%. I haven't sold, but, you know, it, so, so that's, that's another one I, I, I did. Um, it's interesting. So, you know, real estate, I, I ended up selling a lot of the real estate that I owned in Miami. I bought when I first moved because there were no tech people here in Miami. It was a lot of real estate people. So I just did what everyone else did, but it turned out just to be a good thing to do because COVID pulled everything forward. So I was over the mindset when New York and LA people came here and started paying ridiculous prices for, I, I don't do multi-family or houses. I did, I do commercial real estate, um, like shopping centers and industrial and that kind of stuff. And so, um, I sold a lot of it into this market that was like two years ago right, right after COVID was like kind of dying down. Mark rates were still low. People were paying insane prices. What, for what I had paid, you know, because no one was looking at Miami 10 years ago. Really? No, it's changed a lot. Yes, changed. And I haven't, I've only been here four years, three and a half years, whatever. But the, what, the few things that I chose to keep. And I'm like, oh, this is going to become like a triple from where it is now. Uh, yeah, I was wrong. It's not doing bad. Let's just put it that way. But I could have done much better if I sold it at that time. And I actually, it's, it's people tell you that you can't lose on real estate. I've lost plenty on real estate. Like I bought my apartment in New York City, um, in 2013. And it turned out that I bought it at the exact high that you could possibly buy it. I held on to it for 10 years and never recovered back to the price that I paid for it. I luckily sold it right after COVID when interest rates were still. And then the market for New York got hot again. And I sold it losing 25% on that, on that, on that after 10 years, after 10 years, it depends on the market that you invest. And I think, like, I, people will tell you, New York City, yeah, best area in New York City, Chelsea. I know Chelsea. Yeah. Yeah. Yeah. Like, were you like looking at the Empire State Building? Was it like literally? Yeah. I was a pen, it was a pen house. I think I know, I know some of the, a genius sister was living in Chelsea. I can't remember the name of the building, but she was looking right at the Empire. It wasn't a bad house, but it was a nice building. And reds, reds are really good if you read it out. She was paying, oh, I think like seven or eight grand a month just for something. Yes. It's, I mean, the reds are insane, but the problem is is that, you know, uh, when you have an apartment that's 10 years old, the, the upkeep of it is very high. And so your rents don't cover that because you got to replace all of the everything inside of it. So whoever, also whoever tells you real estate is passive is absolutely lying to you, right? These YouTubers that tell you this is the passive and, you know, yeah, wait until you get a call at four in the morning that there's a flood in your, in your thing, and you have to find the someone to fix it. And then that, that caused us 10 other secondary and tertiary problems for you. How do you keep track of all of your, your stuff? Like, I mean, you have real estate, you have venture companies, uh, and, and you mentioned something before, like you were, you wanted to talk about like family offices, and then you, you built a family office. But what's the infrastructure around you that allows you to sort of manage all of this without dropping the ball on anything or not paying attention to something that you should be paying attention to? Because there's a point where you should have a team that eventually supports. So I'm taking the AI approach to that, actually. So we've, um, through software and automations, the past few years have really automated a lot of the functionality that goes along with that of keeping track of things, of making sure that there, nothing gets slips through the cracks and, uh, marking things to market and, you know, doing a lot of other things that go, go along with just the mechanics of, uh, of a family office and an investment firm. So, um, I've always been really good at that, kind of taking what can be automated and automating it through software. Um, we, you know, either through programming it ourselves or create it using different software and conjunction with each other. I think, um, I'm, I don't think I know because I, I speak to a lot of other family offices. I'm probably a lot more technologically advanced than a lot of them are. So you have like reporting and whatnot on all your port calls. Absolutely. Absolutely. And, and we keep track of everything. And it's refreshed daily, actually, even like to a degree. Really? Yeah. And funds and all these other things that we're in. So you have like you, like, I mean, it doesn't have to be like a custom dashboard, but you have some way of checking all the portfolio. Yeah. It is a custom dashboard. Actually, yeah. Oh, shit. I didn't know you guys. It's like, we have business intelligence. Yeah. We, we know like where we're losing, where we're, where we're winning, you know, those types of things. But, but there are people that work, I still have an operations person and that kind of thing. But you'd, you'd be, you'd be surprised how much one person can really do. So the one really good person can do the work of 25 people, but an automation can do, you know, a lot more. So we really can't, we, we turned everything into standard operating procedures. And then most of these standard operating procedures, you can automate most of the steps of it. If you really think about it and really know how to do it. So that, that's, that's an interesting way of approaching it. The other thing I think is that if you look at family offices these days and you look at just like exited founders and stuff like that, there are a lot more sophisticated than they were before. And they're want to be involved, right? Like they, they want to underwrite and learn about the investors that they're not just giving them money, they're money to like a wealth manager to do it for them or to a fund where they don't know what the fund is going to invest in. They'd rather do individual deals where they can actually use their brain, use their expertise, use their network, use their, I don't know, whatever it may be that gives them the edge to make a decision about an investment. And I think you, you're seeing that they're, they're, they're acting a lot more like endowments that like, and that, you know, like, and also allocating like that too. So they're, they're doing a lot more venture, they're doing a lot more sophisticated things that, that, that really bigger investors do. And they may not be anywhere near as big as, but they're trying to modernize and they're trying to act like, yes. And they're also taking the same kind of investment approaches and allocation approaches. What were they doing? Like what was the, so explain what family offices are doing, for example, like 10 years ago compared to. I don't even think there really were, you know, most, most of the time you were going to like UBS City Group or JP Morgan or whatever. And then they would just manage your money for you. And then they would put you into like a bunch of funds. They would make fees on. Yeah. Yeah. And then, and then put your money into a bunch of stocks that they have analysts were. And they charge your fees on that too. And then, you know, they make you use your, your, their, their bank accounts. And then, you know, that didn't make, and they put you in some bonds. And then they, you know, like they kind of like would advise you in that. And that. So the cause of the family office started. It ended up being almost like a very basic investment vehicle. And then it's just now it's evolving to the point where it can be its own fun. Yeah. It's almost like a business. You're running it like an investment firm. Yeah. Right. Yeah. So, so you're doing a lot more sophisticated things. There are things that are called multi-family offices where many family offices come in under one roof and they share resources like a CFO, like a CIO, like an investment officer, like reporting systems because they can get skill and not, and not, and not paying soap. And you're doing that. I mean, I would assume that if you have your systems in place and your automations, it's, they're like one person can manage a very large portfolio or a small team can manage a huge portfolio. And do you do it? Like, I mean, you, I know, I know some guys that have like billions of dollars on their management and have like five people working. Do you have you built out a team yet? Or is it mostly you? It's just me and just a few other people. Okay. So do you think you'd ever do you think you'd ever as like you'd turn like more into professional investment? Part of part of the reason why I didn't want to start another company is because at the end of the day, I really did not. I was the worst at employees. So I did, I never, that was like my weak spot. Oh, it's so funny. Because you've built even, I mean, you actually, you actually built businesses without lots of employees, even though you had great revenue. Yes. So that, that's my, that was my hardest thing to overcome. And so I compensated for it through this other method. And so I just, I suck at it, just to be honest with you, like, and, and I have to work on it. And it was all, I did it because I had no other choice to do it. But, um, I actually don't want it. Like, I don't want something where I have to go in and, um, you know, I have like 20 people or 50 people working for me. And then like, all these people are like, you know, it's just the stress level on that is just like, it's not worth it for me. It's so funny how different people perceive stress. How you like that to you is like a lot of stress. It is because I feel, I feel obliged to those people. So you will never raise a fund. I don't think, no, the worst thing is other people's money. You do not want other people's money. But you know that, you know that, like, I agree with you because it's very stressful. But you know, that's, that's opposite advice from what people give. They say, don't use your own money. Use other people's money. Use OPM. Go invest, go raise a fine. Listen, I've had, I've done it a couple of times. It's not, and I've only done it for very unique situations where the people who are coming in with me are very sophisticated and they're grown-ups and they know if they lose their money. Like, like, I don't feel bad for them if they did because they're big boys, right? But at the end of the day, you know, you can, you can either become their best friend if they make a lot of money or if they lose their money, you can lose friends. And you often understand that that might, you know, is that worth it for you? And I don't know, I feel like if you're a good investor, why would you want other people's money other than to leverage it, I guess, you know, like, but, you know, again, it goes to when's enough enough, right? If, you know, like, even if you look at like Renaissance technologies or these other guys, like, their best fund is their medallion fund. They're only, they're the only ones that are in that fund. It's only their money. I didn't know that. Yes. Yes. So they use other money, other people for their, for their shitty or other funds, which is right. But like, you know, if you look at, if you want to know what fund to go into, see how much money of the principle is in that fund. And that'll probably give you a good indication of whether that's a good fund to go into. That's good advice. Yeah. That's very good advice. Yeah. What do we not talk about? You went to a lot of different things. Oh, man. Went through the whole, you went through the whole June bug journey, easy texting journey, investment. I think you and I have a lot of, you know, kind of synergies in the, in the health and wellness portion of things. Try it. You got to, got you into a, got you into sauna. Yeah. Through Gary and cold. You have like, you have like a routine that's worked well for you, like for just, just, I guess, just operating at your best self highest level. Yeah. I mean, I'm 47. So the thing that had the most thing for me is TRT actually. I did TRT and it really changed everything for me. I think very, very low dose. But it really, at my age, it makes a huge difference in, in the way you feel and your energy levels and getting results from your workouts and that kind of thing. I think men don't pay attention enough to their hormones and their health. And they think they're just like feeling shitty as you get older is normal. Yeah. Listen, I mean, I've aches and pains in places I never had before. You know, I've tried some things like peptide therapies and stuff. Didn't really work for me and I did NAD. I've done it, tried a lot of stuff. TRT's had the most significant real world impact for me. And it was like not even a significant though, because as men, like your testosterone does decline, like the epicotally, it's not like a small increase makes a huge difference in the way you feel, the way you function, your sleep. I started taking magnesium pills before I go to sleep and I changed my sleep a lot. That's another thing that had a big, big effect on me. Hot cold therapy, definitely. Although I haven't been doing it as much. You told me to get a sauna in here, so we can do the podcast. We'll do a sauna podcast. You should do that at Gary's place. Yeah. He would be so dappy. I would love it. He loves that sauna, man. I have one in indoors in my apartment that I use. It's like an infrared one. I got it right before COVID, so I got lucky. No, I'm trying to think. Did you start taking care of yourself after you sold? Were you so focused into the business that you were letting your health help laps? Yeah. I mean, I never knew you back then, so I don't know. No, yeah, I did. And then even after I was so used to that, and then for me, actually, this is interesting. I think this might be valuable to the people who were really saying. At 40, I was, and by the way, I've never been really overweight. I've been pretty inshate. I would work out maybe not so often, but I would work out. At 40, my doctor took my blood, and my doctor was like, you're pre-diabetic, and I'm like, what? I'm a pre-diabetic. I'm not fat. I mean, I didn't even really eat that much. Like, re-salear sizes, you are right now? Maybe, like, 10 pounds out here. Not, yeah, not huge. You know, I'm six, one, so 10 pounds isn't there. He's so crazy. And so, I got scared, because he's like, oh, you got to go on diabetes medicine. And I didn't know, by the way, met for a man. It's like, it's a longevity thing now. So people take it regardless of whether having diabetes or not, but I was really scared of it. And I was like, holy, why were you pre-diabetic if you weren't overweight? He, there was no good answer to that. Maybe because of the food, I was eating too much process food. I was also not working out as much. I wasn't taking care of myself. You know, I was, were you, I was the RT that? No. So your testosterone is going down, and then yeah, but I don't think TRT actually does anything for me. No, but if you lose weight or whatever, then absolutely. Yeah, if you lose weight, you gain muscle. It helps with your, with your, with, with your blood sugar levels. So then I was like, I got a reverse this. He's like, there's no way to reverse it. That's what the doctor told me. You have to take medicine and you have to kind of lower the amount of carbs and sugar that you eat and also work out more often. So I did a lot of research and I found this thing called mastering diabetes, which is actually a program. And I went on the program and the program was counterintuitive to anything you could imagine. It was low protein, low fat, high carbs, whole foods, no oil. Okay. Okay. And by the way, you know, like rice and potatoes all day, like what were you eating? I was eating pasta with tomato sauce that had no oil. It would make the tomatoes. I would, I'd buy strained tomatoes and I'd put herbs and spices in it. I was eating commute bread with peanut butter in the morning. I would have salads, obviously. Rice, brown rice, potatoes, whole wheat tortillas. They have the single force over knives so you can they had all these recipes that you could like but like it was it was it was also vegan. So they didn't want you to eat animal protein because it's it's it's a little counterintuitive, but it was developed by type one diabetics that are biochemists and type one diabetics they don't produce insulin. So it's a different kind of diabetes type two is like what I had where you know um I was what's called insulin resistant. And so my body made the insulin but it wasn't updating the insulin. And so they came they they understood that that what happens is when you have too much fat and to a degree protein but by different mechanism it goes into your cells and it denatures the cell membrane to to a way that where insulin binds to the cell membranes it can't buy it by and properly and so you become insulin resistant when your your your your cells are full of fat. And so there I they're saying like oil for example any kind of oil I'm not talking about just olive oil or any any kind of oil is actually considered a process food because as a practical matter you're not supposed to sit down and have 25 olives with each meal. You think about it. Yeah right. Yeah you know when you say it a lot it makes sense. Yeah like like what that's what you're doing you you coat your food with oil you add oil on your on your salad or olive tree right behind you. Yeah you dip your bread in oil yeah you know and and all this stuff and so and also half your calories come from that. It's the most condensed amount of calories you can imagine and so if you can even if you can simply just do that part it makes a big difference. I got down to like 7% body fat in six months I was ripped. I never I'd never been that ripped even in high school and I was really ripped in high school and this was no protein though so what are you very low protein I would have plant protein shakes so you could have plant protein shakes and were you working out. Yeah I worked out every day I was lifting of four times a week but I got crazy and I wasn't on TRT by the way at that time and I got crazy crazy hard to get ripped if you had low testosterone. So then as as I got those results I started looking into other things that I was doing and then I started by the way I'm not at 7% body fat right now I can't it's hard to really it's hard it's very hard to eat out and not have oil you if you try and do it you'll see how much oil goes into every food that restaurants give yeah that will they make it they make a taste with they the vegetables are cooked in butter and butter butter it while the cake is injected with butter and yes so so unless you're bringing your own food or preparing it at home which is also a big pan in the ass which I did but I also brought my blood sugar down my A1C down that my doctor was baffles he's like how did you reverse here it was this diet and I was a high carb by the way high carb a whole carbs whole foods whole carbs um and that you know and I and I take I still do mostly that kind of diet but I can't do it to the same extreme as I did before I had low back problems and some other issues but still I mean so this was like kind of like the start of your health journey which is which is awesome and then you then you went on TRT after that so now you're feeling like I mean and you don't have to be walking around a 7% like who who needs that I mean go I'm married with three kids yeah like I'm not like I'm not like a Calvin Klein model or anything like that dude you still look good I saw you posted a picture of a store on Instagram a while back and you're still pretty ripped like yeah I still have well TRT does that so yeah you get like you're still you know you can enjoy life yes yes it's also I have a very young baby baby so it takes up a lot of my time right now but like in terms of like energy levels what diet do you feel work because now you do TRT you work out you have a good diet you do hot and cold like sauna and whatnot and cold plunge I guess what's like the energy levels that you feel right now is you're I pretty much wake up around like 5 30 in the morning and I go to sleep on average between 9 and 10 yeah it's just early yeah I do but like I need try and get the eight eight hours I put my kids to sleep and then I go to sleep pretty much I try to so I think that's a full day do you still keep the same diet or slightly modified it slightly modified I do eat animal protein I actually the thing that got me off of it is that I got COVID and I just couldn't recover without that animal protein for real I need I was craving it that's so interesting when your body's like super sick what it's looking for yeah and so I don't really read meat that often although I'll have a steak here in there I like chicken but I eat chicken you have fish and that kind of stuff and I eat out more often than I did before but what I was doing before that I'm trying to do now is that worked really well is I would look at the menu of where I'm going beforehand for like five minutes and I would pick what I wanted to eat before I was starving and so I would make better choices usually and like healthier choices and and I would I'd always end up modifying whatever it is that they have and making making a better choice because if you do it in the moment again it's emotional you're hungry it's all comes back to the decision making how to make better decisions yeah well this is this is where you're talking about right we were talking about so for your health and that kind of stuff I think you could do the eating out portion just as long as you're you know you're you're you're conscious of it right and you make deliberate choices yeah I think that I mean I've done that too like where I look at the the menu before I go out and I think it's just like I always try and like I try not be too severe with my diet well I mean like I'll focus on like eating healthy for 90% of the day or what or even like 90% of the week and then like one or two days that won't mind or one or two meals I don't care as much it just makes it a little bit it just makes it a little bit easier to live and be social and and go out and have fun and have friends and whatnot I mean especially Miami yeah it's very hard out all it's hot so I tried intermittent fasting I've done that it didn't do very much for me the benefits didn't outweigh the cost I think it's more of a psychological thing like if you just if you just don't focus on eating and you're drinking coffee or whatever and just going about your day and then you just have less time to eat well yeah of course you're gonna eat less calories unless you just try to force feed yourself which is I mean that's avoiding the whole point of it right absolutely but but you know I did I did some crazy things right any for three days or whatever we tried every diet I tried I tried what's the ritual that you is there like a piece of the ritual or the morning routine that really is like a little bit different or that you think people would benefit from outside it is waking up early working out is there anything else I reserve a certain part of my morning for my kids and and so um I mean I don't know if that's unusual because I think a lot of people love their kids and want to spend time with Lauren though yeah it really is and and I purposefully drive them to school so that they're like a captured audience I love that and I love and I don't like sometimes as a treat I let them listen to music for a little bit of it but I talk to them and and I listen to them and um it does it does a lot for them I think you know I talk to them about real things I tell them about you know my parents that are in alive I tell them about stories of things that happen to me when I was younger the they're interested in that I learned about um you know some of them are old enough that they're learning about money a little bit right now like they're getting their first debit card or you know yeah but mostly it's like talking about Harry Potter this is the other thing you know but it's like I mean it sounds so simple but you're just creating like this like this dedicated time for them yes yeah it also kind of centers you and makes you realize you know that this is what you're doing at all for because you know you're not going to be here at the end of the day and I think yeah and I think it's easy to lose sight of what you do it for yeah because all you have um is you know you really you really all you have is now I'm a very big I don't believe in legacy and those types of things I think like everyone's going to be forgotten they will I mean it's true they will be yes everyone's lean of England is already being forgotten so yes I mean there's nothing special about you or me um and you know you're special in this moment that you're on the earth to yourself and to the people immediately around you so you might as well make the best of it um but like to think of legacy and like you know all these other things I think that's um that's a lot of ego in this good advice if people want to connect with you and just like what like what do you want people to like where where are you going in the future I mean I guess if people want to look at the portfolio you're building but I think we're portfolio public yeah yeah I put on my website okay so if people want to connect you where did they go I actually have a contact page that I read every single email and I respond to every what's your website is it is chain name and chain even dot com good domain yeah I and I got I get a lot like I don't get a little bit I get a lot of emails and most of them are startups that are pitching me um and you know 95% of them is like I can tell immediately that they're not doing but I have a methodology that I think is different than a lot of other um people is that um I give them resources that I've built over the years of what to do to better themselves in terms of and I also give them uh resources in terms of list of other VCs that would be appropriate for them good that's super nice yeah and I mean it's better than the no response no yeah no well if someone has just taking the time to do it I might take me a week or two to respond to them but I respond to them um I respond to everybody really honestly because I was in their shoes uh and you know I think it's you know if you took the time to obviously unless a spam right I love it right but you know I'll take I'll take a few moments to respond to you and then it's funny because there have been some cold emails that I've gone where I've done major investments what would entrepreneur have to say to stand out or to be impressive outside of like right I can tell you whoever tells you it's this is not true if there's a way that you can find someone who knows me to recommend you to me that makes a big difference and that always makes a difference to everyone and if someone tells you that otherwise they're lying to you because everyone's looking through a filter of signal so if you know someone that I know and it's coming from them it's already passed some signal for me um the other thing is um I think if you you know you have to learn marketing and if you can in two three sentences get your point across and be impactful that grabs my attention I mean I'm human just like everyone else is right if I I'm going to skimming through these emails right and if I see something that catches my eye I'm going to be like do a double take right and that's that's you know a girl Shawnee did that to me a couple years ago um what was her company a learned a allergy which is a custom compounded nasal nasal allergy spray that's prescription so it's a telemedicine she had she had done her research she saw that we had invested in her posture fee that got bought by him which is um did the same thing for dermatology for like acne and latisse and that kind of stuff and she wrote this really amazing you know three sentence email to me and I replied to her and then she replied to me something very thoughtful back and I got on a call with her and I didn't invest initially I said listen you I really like you but this is a way to do thing let me introduce you to a couple other guys that I know very very very well I introduced them introduced her she was coachable she did and exactly what they said and then we ended up taking her entire seed round which is like a three million dollar round and doing it and now she's this super successful business super successful with all from a cold email all from a cold email and I also helped her get her a round done I introduced her to a bunch of vcs origin being one of them that that that did it which is one of the like top vcs and you know it's a it's a very it's a it's a very significant company you know two years later that's amazing so just I mean I don't get as many pitches as you do because I mean I don't put myself out there as an investor but I see it from the lens of people trying to get on the podcast and I must probably get 50 emails a day it's just insane but dude it's like walls of text it's just like four paragraphs no one's gonna read them no one can read this no one and and there's it sucks because I mean usually it's the founder reaching out themselves but for me it's these agencies that I know people are paying these huge retainers to to get them on podcasts and they're just doing the shittiest job so I I learned this and you must have dealt with this when you were trying to do a book tour couple years ago so actually I didn't end up doing it I sold a good amount of the book but this book was never meant to to be like I know it's a money loser it was never a money maker for me it was a passion project I actually the reason why I built the even wrote it is because I dealt with so many founders and I was giving them the same advice over and over again and I'm like hey I could just write a book on this and how do I write a non cliche book where you're not hearing the same shit that you hear from everyone else so I was like hey I I think it's kind of interesting to take this nightlife approach have some interesting stories in it and then and then kind of give you how I learned those lessons and how I used it in easy texting and then how I use it in venture now so at the end of each each each chapter is a lesson at the end of each chapter I actually show you how I used it again so you know it's it's pretty practical in that in that manner um but you know I learned in easy texting when I first tried to sell this to people I did the same thing I wrote I made these like white papers and I you know like how to chart and I would send this like two page email to people and it was crickets and and then I was like wait I had a conversation with the guy this Israeli guy actually on the phone and I started trying to explain to him what easy texting is he's like he's like don't talk to me like that just tell me what it is you have you have one minute to tell one second to tell me what it is Israeli yeah and then I was like how do I tell this guy in one sentence how can I pull boiler down to one I was like it's impossible but then I was just like I just blittered out I was like I have a way that you can automatically get everyone's phone numbers and then text them the next day or the next week about your next event or your next sale he's like really and I was like he thought it was like some automagical machine yeah but you put it in like here you're you're thinking it like sucks everyone's cell phone number you're like this guy like I I had like hit a nerve with this guy and I'm like holy shit if I could I was like yeah do I'm gonna show you all demo it to you he's like do you have time right now I was like yes let's do it right now so I got you know at that at that time you have to it's 2005 there wasn't even zoom so I was just like log in use these credentials you know I had a demo account he sent himself a text message and the light bulb went off and then I was like I'm doing this all wrong I'm doing this all wrong so I changed it to two sentence email exactly what I said you know with a catchy two sentence two word you know subject and I was getting demos left and right and the minute I would demo someone it was a 90 percent close rate people over complicate business absolutely absolutely and it wasn't like I was doing anything special you know it was text messages stuffy social for real yeah I know but it's it's it's like the it's like just simplifying it just a simplified simplified yeah no one's gonna read it they you're busy look at how busy you are no one's gonna read it you you literally have to think in 160 characters like Twitter in this day and age I think always I mean I still don't get how people because I get I get hit up on LinkedIn with these paragraphs I get hit up with email with these paragraphs and it's just like it's too much it's too much but but when somebody says something like hey this is what I've done this is what I can talk about oh and by the way I left you like a review rating your podcast five star like literally three sentences and it would stand out from everything else I'd be like oh shit thanks for the review thanks for the rating and thank you for telling me exactly what you've done in one sentence that's it and it may be maybe the only other thing that you could add would be like a link to a show that you've done before so I can watch absolutely so simple absolutely and you should make sure your profile is well done yeah because I will click on your profile and if I see this like you haven't sat down made your LinkedIn the like look to the holistic yeah possibly be yeah then what you know if you're not you're not you're not spending time on yourself why would I spend time on you yeah so funny yeah just some of the and I don't understand why people still try and do pull that reach the way that they do with these walls of text and it's so it's so ineffective it it is it is but it's it's you know it's an acquired skill is that how you I was actually going to ask you isn't I forgot to ask you before sorry what were you gonna say I said you know that's that's probably one of the most important skills the founder needs to have being able to sell in market of sell themselves thousand percent I was gonna say um the lot one of the questions that about easy texting because you grew it so large without um that a big team was there like a lesson for entrepreneurs about how you grew it because you didn't jump on demos of 10,000 people you probably did a lot of another Paul Graham I did it through I did it through product I was like I got a sage stay true to the name of this thing easy texting and if it's not easy that like my grandma can log in and know how to send the text message then we're doing something wrong and the although I couldn't do demos for people we made itself sign up like mail mail chimp like itself serve like like yourself sign up yeah yeah yeah yeah yeah you put your credit card in and then you can you can you can use it we give you we're like a free trial and then just like any other sass business right um but we made the product at that time and you have to realize this 2005 like we had when you would come in you'd get a product tour like a demo like that's pretty commonplace now but it wasn't done before and I would end up doing a lot of the support tickets myself because I wanted to know what's wrong with the system that someone couldn't figure out how to do something and how I fixed that through the software so that we would get less support tickets so you were actually you were looking through and you were just looking at the biggest problems people had and then you were you putting down the product roadmap I did I spent hot like at least two days a week doing tickets and picking up the phone really listening to the yes you find that you find a lot of founders don't like doing the hard work yes that's a shitty job dude no one wants to do it but you don't you what you what you have to what you well it depends on what stage you're in you know a lot of founders are doing every job right when they're very very young but in order to kind of I think to keep the magic going you have to stay as low to the ground as possible you know you can't lose sight of what made you successful um and you'll have to constantly be in fear of losing it and and improving for real you do I I did something even more interesting I was afraid that people were going to realize how good of a business this is I white labeled the software and created six or nine other websites like club texting church texting this texting that were like front-facing websites and then I rebranded the software to that and then I read ads against myself so that when you would text search for text messaging software there wouldn't just be easy texting because that's what was happening like I wanted people to think that this is like a real market and there are competitors but so they wouldn't enter the market so funny I've never heard that before I've never heard anyone do that before so you created your own fake competition it didn't make a lot of sense to people but it made sense to me I actually do think it makes sense at the time it didn't make sense a lot of people because I was ending up paying double or triple for the clicks because someone would click on like three of them instead of one especially for paid paid clicks and at that time you know there wasn't so much social media advertising there it was mainly through Google AdWords right and so but I'm like you know what I'd rather pay triple for that person and then you know like no and no competitors come into the market yeah I even like made all different kinds of things like I made a version of the software that was like had limited functionality and we called it like cheap texting so it was like half the price you know so look like there was real competition that's really funny what are other like what's like another way that you like growth hacked it because you growth you you hacked your competition what's another way that you like because obviously okay so like boots on the ground you're a founder your answering calls you're doing support tickets cool you understand what's that working you build into your product you made it see it as a whole market when there wasn't what are some other like growth hack things that you did they were really good because I know you did a lot with Junebook but I think I know less about easy text we decided to do were you you know you don't really need to read reinvent the wheel we realized was like if you look at MailChimp or you look at like uh constant contact how would you find out about MailChimp or constant contact you you get an email oh yeah at the bottom it would send sent by MailChimp on it you know how mail did that how mail did that it said like made with love uh yes and that's how they so what we did is we couldn't like really we tried this thing where we gave a free version that would say easy text thing on the bottom or discounted that didn't really work out really well but what we did figure out is is that people were looking up the phone number that it was being sent by they were googling it so then we created landing pages for anybody and and and it adds for anybody searching for that phone number how did that so when they search that phone on google they would what would the landing page say it would say start texting through you know easy text thing and build and then that's how you brought them in that was your funnel correct so like we realized that that you know because so so so people would look to see what that phone number was or how to reverse engineer how someone sent it that's so funny so I mean like you have to know like you were so in the weeds though you understood the customer's behavior like I was the customer initially if you think about it for June bug right so so I I was we were we were like we took the best we we literally just took the playbook of what the ESPs did and just learned from the best of what they did really good customer service a phone number date people could call like constant contact was different than MailChimp because you could call them and they would help you on the phone MailChimp would only do email um cost effective easy to use you know like the three things for us was like you have to be the three things of the software that had to always be working and 24 hours a day was sending receiving text and paying if those if those three things work everything else it's like secondary tertiary to it's like there's the bells that we called the bells and whistle yeah yeah that they're just extra people want to send and receive text and pay for it and that's it there were you ever were you ever I mean like looking back obviously there's tons of opportunity and you could have taken this and put it into any industry but did you ever think about taking like June bug and just putting it into any other industry like as you had this whole little like business at a box no I think that it was so evergreen at that time I mean we could have done more and more events and we could have done more and more stuff you know that that it would have for easy texting I really um well initially we had called the club texting and then we changed it to easy texting because because I realized that this is not just for nightclubs right and so I kind of I had the vision that developers would integrate texting into all their stuff um into all their software and so we created an API initially but Twilio did it much better than we did um they they only went after the developer I'm thinking of Twilio and Twilio is like a huge huge company now yeah it is well so is easy texting it's a really big company now very big company are you happy that you saw when you did absolutely I mean would I have made more money who knows probably yes I don't know or I might have died I mean like when when the options they die or make more money I don't know maybe I would have had a hard attack because I was working so much but um no I got to like oh my god I got to move to Miami I got to experience my daughter growing up my son growing up that's important uh no no uh I don't regret it and and in part of you know part of making good decisions is knowing when to to to to to to to leave the party which is the last actually the last chapter of my book you know it's it's it's knowing when to leave the party right um it's a hard thing to engage when is the right time to leave when you're on top when you're sending to the top when you're starting to descend from the top how do you know that you're at the top you know did you think about that as you were building this seems like your exits actually just sort of came out you fast like yeah yeah I think I think for me it was more practical approach to things but when you talk to founders or you invest and do you tell them to think about that life cycle of the company you had to absolutely because at the end of the day I'm investing to make money I'm not investing to support someone's lifestyle aside charity no I know I know I know so like you know like I'm trying to make money just like they are to my when you invest in them do you agree on like okay so this is how long we're going to be in this together well yeah obviously if it's early everyone knows no one knows one knows what the hell is going to happen if you want to the founders should still be the founders should still be they should know if they're going to look at a strategic or they want to sell the private equity or if they're going to take it to IPO well they should know I think it's hard to tell in the very early stages to be honest but if you look at the companies at the early stages that are getting the highest valuations they are typically the post-exited founders so they've either had one or two exits before and so they've built a track record and so as an investor you feel you're willing to pay a premium for that because you know they know how to and I guess you trust the you trust them a little bit more to figure it out absolutely and they know that an exit needs to happen right eventually eventually all right last thing I always like to ask is you know you've had great career built several companies one not so successful two very successful now you invest you know now you're focused on family if you go back and tell your 20 year old self one lesson what would it be I would learn how to have invested earlier I wish I knew how the mechanics of investing the importance of investing what compounding is because I never did that during dream bug and easy texting I invested in my business but you never took off the money of the table and put it into other investment no and had I done that I like by the way I'm not complaining in any I'm very fortunate person in my life despite some really bad things that happen to me but if I had done that I would have been in like whole other level and it's very hard for a 20 year old to understand how much can happen in 10 to 15 years and how much money can compound and I just not even done anything that's sophisticated just bought SPY maybe even just you know bought a piece of real estate or you know anything and just let it be and just did it consistently um I wish I had done that because I build profitable businesses and I could have done it but I didn't I always saw my business as my source of wealth so you just got very good at making money correct I thought that that was the way that you make wealth not investing absolutely yeah that's a good lesson too and that's also why again it's like just because you're a good business owner entrepreneur doesn't mean you're a good investor no because because it's so counter to what business owners do investing you just it's hard to make that first leap of putting the money in but the more you do after you put that money in the worse your outcome exactly so it's and in business you gotta do you gotta keep yes or you dead yeah so it's the opposite it's like just stop yes put it in and shut off yeah that's it just put it in an sdf you and like and like just keep doing it and then wake up in 15 years and be like holy shit I'm glad I did that you know so um it's not a regret obviously but if I could give myself a piece of advice that's a piece of advice um and and I don't know maybe have a little bit more fun I could have had a lot of fun than I didn't have that's it oh whatever I had fun I had fun I didn't have the kind of fun that people would think that you uh I think that kind of fun is overrated yeah I think that that kind of fun gets Scott Harrison had a lot of that kind of fun and I think and I think that it gets old pretty quickly yeah absolutely I get a little pretty quick I think that what you've optimized for in your life which is business success but then ultimately family I think that's the most fulfilling thing you can ever optimize for well that's that was the thing I actually got married and had kids latest out of all my close friends from growing up you were still young you were still young um I had my first child when I was 37 that's pretty late I think um and I got married just a few years before that so um I was like seeing my like cousins or whatever my friends had kids and I'm like all right you have fun going out tonight you know like their kids were cute and stuff but like I didn't get it but like having a kid is experiential it's impossible to explain it to someone and so I get it now obviously but what you're going into clubs every night you were even doing clubs the way a lot of people do clubs because you had these long-term girlfriends but if you're going to clubs every night it's still you're like okay well the one I if I have a kid I can't be out late anymore for like oh no and you also you also when you're in work mode and founder mode you're very selfish you're very selfish I was very selfish absolutely and that's why I think it's important that I mean okay so fine you're not going out you're not partying but as an entrepreneur you're going to have kids you have to realize that something else is going to take all your attention and I actually I'm like actively even like for myself like I'm actively understanding that okay I work a lot now but I'm trying to architect something it doesn't take so much of my time so I can be present yes so now I actually give up a lot of my opportunities because yes I mean there are opportunities that I have lost that I could have made an incredible a return on but at the cost of you know not having time to do the other things that I want to do and spend time with my kids.