Latest / Success Story with Scott Clary / Shane Neman - Serial Entrepreneur & Founder of Neman Ventures | The Business of Partying

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Shane Neman - Serial Entrepreneur & Founder of Neman Ventures | The Business of Partying · Success Story with Scott Clary

• 0:00
  There was no solution for texting, which was shocking. I built it, sent out the first text,
• 0:05
  and literally, I had every nightclub owner promoter of everyone call me and be like,
• 0:10
  how the hell did you just do that? Shane Neiman, CIO and General Partner of NAMM
• 0:15
  Inventures, has built his career on finding value where others dealt. From backing over 50
• 0:20
  startups like Impossible Foods, Flexport, and Kraken, to investing in real estate gems like Pacific
• 0:25
  Park and the Racket Lounge, Shane has a unique approach to seizing asymmetrical opportunities.
• 0:31
  We had an app store, he saved your stuff in the cloud, and we were a SaaS company,
• 0:36
  but none of those words existed. That was my first taste of building something,
• 0:41
  and then just getting punched in the face and falling down again.
• 0:44
  In this episode, Shane reveals how he's cultivated a keen eye for high growth investments
• 0:48
  across venture capital, real estate, and private equity. The better decision maker you are,
• 0:53
  the better you tend to do. It's very hard for a 20-year-old to understand how much can happen
• 1:00
  in 10 to 15 years, and how much money can compound. Welcome to Success Story. I'm your host,
• 1:06
  Scott Clary. The Success Story podcast is part of the HubSpot podcast network. I'm also a big
• 1:12
  user of HubSpot products. I've supported the show for over three years now, and for all entrepreneurs
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• 2:25
  Shane, I'm glad we finally got to sit down. This has been a lockdown. It's been, it's been a lot
• 2:41
  of fall starts, but yeah, listen, I was in the middle of a move. That's okay, congratulations on
• 2:46
  your move. Beautiful home, beautiful studio. I'm very happy for you and your family. Yeah,
• 2:52
  now we're getting more entrenched in Florida. Yeah, well, I mean, for LaRielle to Miami,
• 2:58
  it's like now you're a real Miami and a real Miami. Listen, like this was a lot of effort for
• 3:04
  the past two months, but it's worth it, so I'm happy. Well, anyways, it's beautiful. Not about me.
• 3:09
  Enjoy it. I will enjoy it. It's the first of many. I know I know we're only going to do like a
• 3:14
  little one this afternoon, but you'll have to come on again, and then when you don't,
• 3:17
  you don't have to go run off for your kids, you invite me. I'll come the old browns. Yeah,
• 3:23
  well, you do a lot of cool stuff. So I think it's going to be, there's going to be a lot of
• 3:26
  future stuff to talk about too. You're not done quite yet. No, I don't think so, but we'll see.
• 3:33
  Let's kick it off for people that don't know you. We'll talk a little bit about your background
• 3:38
  where you came from. I think you have an interesting story. So you were, well, your parents
• 3:42
  were immigrants from Iran, and they came over at the end or at during the revolution
• 3:47
  or right before I guess they came during in the in the late 70s. I guess right before it kind of
• 3:53
  really tipped, and I was born here in the United States. So I was lucky in that in that manner.
• 4:01
  And you know, kind of classic immigrant story, they're Jewish, so they definitely had to leave
• 4:08
  because at that time being Jewish in Iran was not, not that it's working now,
• 4:14
  was not much better than that, but it was definitely not a great place to be. And they came to New
• 4:20
  York and they started over. They had a great life in Iran, you know, probably upper middle class
• 4:29
  family. My dad was an architect. My mom was a teacher. And I was an only child at the first
• 4:37
  child, their first child. And so yeah, you know, I watched them go from zero. I mean, I was sleeping
• 4:46
  at the foot of their bed until I was, I don't know, 10. So when they came over, it was pure
• 4:54
  immigrant mentality, immigrant hustle. They had to start from scratch or absolutely. So my
• 4:59
  my dad couldn't be an architect. He'd have to go back to school again to get the licenses and
• 5:04
  everything, which just didn't make any sense. So he decided to go into clothing because he had
• 5:09
  design skills and you know, started very humbly selling clothes to boutiques and then open
• 5:18
  their own boutique and then open their own knitwear manufacturing company. And then about a
• 5:24
  decade later, finally, was able to buy their own house. And you know, kind of American immigrant
• 5:33
  story where I remember, I remember falling asleep in our basement at two o'clock in the morning,
• 5:40
  watching them work, literally making clothes on stop. Yeah. And I was in third grade, fourth grade.
• 5:48
  You know, and then if you look back like you, obviously you've built businesses now, you're
• 5:55
  an investor and you look back at your whole life and there's been lots of season, different seasons
• 5:59
  to your life. What was that? Was it was it them working exceptionally hard? There was a major
• 6:06
  influence on you. Was it because they were super entrepreneurial? They had the restart that like
• 6:10
  light the fire. Was it like, what was that inflection point in your life? I think the inflection
• 6:16
  point for me was actually there were there were many inflection points in my life. I had some
• 6:22
  pretty significant things happen to me earlier in my life. My father passed away when I was 13.
• 6:28
  So that taught me and he was 44. He was young. He was very young. He got stomach cancer, died
• 6:34
  within three months. And my mother was not the breadwinner, but had to learn and start over.
• 6:41
  So I learned that from my mother and she was actually perpetually ill. Her entire life, she
• 6:47
  had a lot of, she had renal disease and had a few kidney transplants and she had a lot of
• 6:53
  health issues. And despite that, despite that, she was a very successful businesswoman.
• 7:01
  Went into real estate after my dad passed and by against all odds made it really kind of
• 7:10
  pushed through, never had any excuses. So I saw these things. I understood how
• 7:19
  how fleeting and unfair life could be. Let's just say. And my dad passed when he was 44.
• 7:28
  So that was the measuring stick for me. I was like, I got to get everything done before 44.
• 7:34
  Because I don't know if I'm going to make it so it's actually very scary when you see that.
• 7:38
  When that's your reality. Yeah. Yeah. You're like, you're in high school, okay? You're
• 7:43
  15, 16, 17. You're going off to college, university, you're turning 20, like my life's half.
• 7:49
  Oh, absolutely. It actually, it sounds really messed up, but that's the way I thought about it.
• 7:56
  I didn't. I kind of really understood the value of hard work in the beginning of college.
• 8:04
  So I went to NYU and I was pre-med actually and I took my first chem exam and I thought I was smart
• 8:12
  until I took my first chem exam. And I got an F which literally was a punch in the face to me,
• 8:19
  ego wise and everything like that because I had kind of coasted by in high school without having
• 8:25
  to work too hard. And then I realized that that's not going to really work in the real world.
• 8:32
  Like, let's just put it that way. I actually had to save. I was like, university was like a slap
• 8:37
  to the face because in high school, I could do whatever I wanted and soak it. I was partying all
• 8:42
  the time hanging out with my friends doing my homework last minute, you know, studying right before
• 8:47
  the test and I thought that that would fly, you know, when there are 600 other kids in my class
• 8:53
  that are infinitely smarter and work a lot more than I do. And that actually was a tipping point
• 9:00
  and inflection point for me. I literally realized at that point that I can't do that and I went
• 9:06
  into this kind of like crazy work mode. I went into founder mode. Yeah, yeah. The Paul Graham
• 9:14
  founder and you like, but that was so just back up for a second. Why did you go into med school
• 9:20
  in the beginning? Um, well, because med school is not founder mode. Med
• 9:24
  med is like, no, but getting into med school is founder mode just to be honest because it's so
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  I don't know how it is now, but I'm talking about 25 years ago, almost, right?
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  And more, it's more than 25 years ago. So at that time, it was still kind of like respectable to
• 9:44
  want to be a doctor and there was prestige and there was honor in it, which actually, by the way,
• 9:51
  I think there is, I think that being a doctor is probably the most noble profession you can be in.
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  It's very important, but I think that people who do it now really have to love it because
• 10:04
  doctors are overpaid, I mean, underpaid, underpaid, overworked, right? And underappreciated.
• 10:11
  And I think that also what you're what you're saying is very true. So 25 years ago, I would say that
• 10:16
  entrepreneurship is not a thing the way it is now. No. So it was a glamorous is like doctor
• 10:23
  lawyer is pretty much the epitome of career success. Being an entrepreneur was not now.
• 10:29
  It's like popular. It's all over YouTube and everybody wants to be an entrepreneur of it.
• 10:32
  Yes, they don't realize how much it really sucks, but that's another conversation.
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  But yeah, I came from an immigrant family, doctor, lawyer, you know, I also had, you know,
• 10:44
  my father passed and my mom be sick her entire life. And so, you know, I was,
• 10:52
  I was motivated by that, let's just say. But, you know, to get into med school is very difficult,
• 10:59
  was very difficult. I don't know how it is right now. It was very competitive.
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  And you had to study a lot. You had to take pre-med classes and you had to take an MCAT,
• 11:13
  which was really crazy hard to and to get into a top medical school was not easy.
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  And so I made that my mission and that was my goal and to achieve that goal, I had to really work
• 11:25
  hard at it. But then you chose to not go down that path. So I actually went to med school.
• 11:32
  I studied computer sciences at back up in college. Like an undergrad or yeah, an undergrad. So you can,
• 11:40
  you can actually major in whatever you want, English, you know, span it, you could do anything,
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  actually, home economics or whatever you want to do, right? As long as you take the pre-med classes
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  and you take the pre, the MCAT, you can get into medical school. So I actually did computer science
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  because as a backup of like getting a job in case I didn't get into med school, right? It's
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  a lot of bad backup. 25 years ago was not as popular. Again, you were kind of out of the curve on
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  a lot of this stuff because the computer science now, it's like, yeah, you won't hear kids
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  to be able to code. But 25 years ago, I got, I don't even, well, kind of computers were you
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  coding on 25 years ago. I learned on Turbo Pascal, which was like just an IBM worked on like a regular
• 12:24
  IBM PC type. So I learned, I think it wasn't like still in the early, early days, but you know,
• 12:31
  there was, it was, it was pretty advanced at that time. And then Java came out. And so there
• 12:36
  was object oriented programming and stuff like that. But I, it was crazy because actually,
• 12:40
  you're right. Most of the classes I had to take were graduate level classes because they didn't
• 12:45
  have enough classes in undergrad to kind of constitute a computer science major. And anyway,
• 12:54
  so I learned, and I actually worked on the side. I got into med school early, like in my junior
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  year, I did early decision and I got into NYU. And so I ended up kind of having a relaxed time
• 13:07
  sort of for the last two years. And I worked as a web programmer. And at that time,
• 13:13
  that was really in demand. I was getting paid like a lawyer would get paid probably like 500
• 13:19
  an hour or whatever it was. Yeah, I was making a lot of money for my age, ended up saving a bunch
• 13:27
  of money. I also was a TA and that kind of stuff. So I had a little bit of the entrepreneurial spirit
• 13:34
  at that time. But then when I got into med school and I started med school, it was, I don't know,
• 13:41
  months and, you know, I was about four or five months into med school when my roommate at the time
• 13:48
  was working at Goldman. And he's like, what the hell are you doing, dude? We can make like millions
• 13:57
  of dollars and you're sitting here and reading biochemistry on a Sunday, you know, and he had been
• 14:03
  parting all night the night before. It's like, I know how to raise millions of, this is during the
• 14:08
  dot com boom, right? So he's seeing it everywhere. Oh, yeah. And I'm like in this apartment on park
• 14:15
  Avenue in 36th Street and literally like just studying all day long. And I don't know,
• 14:24
  something, when he said it to me that way, clicked. And I just called my mom and I said, listen,
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  I'm not going to go to med school on my day. She's like, why are you sure? And I'm like, yeah,
• 14:36
  and I said, I'm going to try this. I had saved up a little bit of money. He had saved up money too.
• 14:41
  And we tried a dot com. And someone, there were venture capitalists that were
• 14:49
  dumb enough to give 22 year olds, you know, a few million dollars to pursue something that was
• 14:56
  really actually, we basically tried to create Microsoft 365 through using Citrix. So at that
• 15:04
  time, apps were not web based. They were mostly like Windows based, but there was a way to use
• 15:09
  Citrix to kind of run your apps, look, you know, on a server. And we had an app store and we saved
• 15:17
  your stuff in the cloud. And we were a SaaS company, but none of those words existed. None of those
• 15:24
  words that I just said to you existed. You were making it with blue ocean. You were trying to build
• 15:30
  in a category that didn't exist. Yeah. And so sometimes you have a great idea. And this is
• 15:34
  obviously will lead into the VC portion of things, but you're just great idea, just really bad timing.
• 15:45
  And, you know, we built something that people actually use, but there were lots of reasons why
• 15:52
  we failed, not just because we were early. There wasn't enough broadband penetration. There was
• 15:58
  a lot of other issues. And then, you know, the dot com bubble bursts and people would not continue
• 16:03
  to fund us. And so anyway, that was my first taste of building something that I thought was amazing.
• 16:11
  And then just getting punched in the face and falling down again, right? But that must have been,
• 16:15
  so that that's probably raising venture money and then failing is probably the most stressful
• 16:21
  thing a 20 some year old can go through. Oh, absolutely. Because now all the investors want their
• 16:25
  money. They're asking you what's going on. And not even that. I mean, just the tension between founders.
• 16:31
  Also, because, you know, you end up kind of having disagreements of what should be done. If I
• 16:36
  wanted to just walk away, they didn't, you know, and there was another founder involved. And,
• 16:43
  you know, the dynamics of it is is is a lot more complicated than that. What what how did you get out
• 16:50
  of that? Because that that's I just gave I said, well, here are my shares. Have a nice day. You
• 16:55
  guys, if you want to continue to do it, do it. But I don't see a light at the end of this tunnel.
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  And so my options of that time was going back to med school or maybe starting something else.
• 17:08
  And I wasn't sure exactly what I would want it to do. And even if I wanted to go to
• 17:12
  back to med school, I had to wait until, you know, matriculating for the next year and that kind
• 17:16
  of stuff. So then when did and how did Junebug start? Because that was that was that's the one.
• 17:23
  I mean, you wrote book about it. Yeah, I wrote the book about it because I learned the most about
• 17:27
  it about about life and and business. It's just so funny because you were med school. You did a
• 17:34
  SaaS startup and then you go into night life. And you and the way you enter night life is
• 17:40
  I mean, eventually there was tech components built out. But at the beginning, it was like a very much
• 17:45
  like a non tech business. I think even from the so so let me kind of
• 17:51
  so so at the time I actually moved in with my girlfriend at the dorms. She was going to FIT.
• 17:56
  How old are you? No, I must have been 23 or 24 at that point. And and she, you know, she was
• 18:05
  still going to school. And then she worked at a couple of night clubs on the side
• 18:10
  to make extra money. And and so I would go and pick her up at three or four in the morning.
• 18:16
  And then you know, she got paid cash. And then I was looking around and I'm like, I don't understand.
• 18:22
  These guys operate this entire night club or this bar or whatever on paper and pen. It makes
• 18:31
  absolutely no sense. They don't even have they had no systems in place. And so also they would,
• 18:40
  I don't know if you remember this. I mean, it's pretty old school to do this. They would
• 18:43
  print out flyers and then there would be a person outside the club. Yeah, I mean,
• 18:48
  I was around for a minute when I had a long and they would give you a flyer. They would give
• 18:53
  you like a piece of paper and it would tell you about the next party that was next week or
• 18:58
  the New Year's party or whatever it is that they were trying to promote at that point.
• 19:03
  And so I was like, what 99% of those are on the floor because people just take it and throw it
• 19:10
  on the floor. And I'm like, these guys should be emailing people. They need to have systems in place.
• 19:18
  So we kind of, it started by us using tech to do an event and seeing if it if it makes
• 19:28
  certainly you are doing nightclub promotion, just nightclub promotion. I'll bet. No, so I was like,
• 19:33
  let me test this theory. Initially, we did a haul. I said to my girlfriend, look, let's do a
• 19:41
  Halloween party. I have an idea. We have email addresses. No one was doing e-vite. This is a
• 19:46
  pre-facebook, pre-camera phone, pre-my space, pre like event bribe, pre everything that you know
• 19:54
  today. None of that existed, okay? Not even like MailChimp, right? None of that existed. And so
• 20:03
  I'm like, I'm going to figure out we're going to do this website for an event. And that was like
• 20:08
  really, and then you're going to have a code to put it in. And you have to have the code to go in.
• 20:13
  And we're going to do this. And I had just moved at that point to the, to the, to, to
• 20:21
  sudden place, which is like near the Queensborough bridge. And there was a new place that a new restaurant
• 20:27
  that was built under the arches of the bridge that was beautiful. And it was like, it was like an
• 20:32
  ideal place to do a Halloween party. And so I'm going to, I'm going to give the whole book. But we
• 20:37
  do this event. And in one night, I make like 200 grand or something like that. Something crazy.
• 20:43
  And it was just, it was basically digital marketing. All through digital marketing. And that was
• 20:48
  novel. Yes, that was. Emails, emails. We made a credit card that had a Mac stripe on the back of it.
• 20:54
  People had to come and come and use that. And I figured out how to do sponsorships, which I had
• 21:00
  no idea how to do. And then I knew at that point, I had something. And so we ended up, it ended
• 21:07
  up becoming a lot more than that. So we ended up building the entire full tech stack that most of the
• 21:14
  night clubs and bars used. So they would use it internally. And then we, we became like a media
• 21:19
  arm for them. And just to give like an idea of some of like the numbers around the business. So
• 21:25
  that first event, what kind of money can running an event with a tech stack actually make you as
• 21:31
  an entrepreneur? Oh, well, I mean, it's mostly profit. Because if you sell tickets and then you
• 21:35
  guarantee a bar and you hit the bar numbers and then you get a piece of the bar. I mean, I don't
• 21:40
  know how it works now. This is like 25 years. I mean, sending emails costs nothing. I programmed it
• 21:47
  myself, right? And so, I mean, I don't know. We were selling tickets between 30 and 50 bucks and we
• 21:54
  had three or 4,000 people come. So you just do the math. It's not bad for one night. And you can
• 21:59
  do that at multiple and you did eventually do it at multiple venues, even some simultaneous. So
• 22:06
  we had the tech part of the business, where it was more like SaaS and media. So we sell media. We
• 22:11
  also built an email list that people would, you know, kind of pay to get on kind of like a daily
• 22:18
  can. I don't know if I remember daily candy, but at that time, there was a daily candy. But
• 22:22
  now there's like three lists and these other, these other ones that that kind of came out. We
• 22:27
  were the precursor to those types of things. And then we built a ticketing system. So if you can
• 22:34
  imagine, like ticket master was not, you know, selling tickets for a nightclub, which ended up
• 22:42
  becoming instead of like thousands of tickets. It's turned into millions of tickets because
• 22:48
  EDM really took hold and venues, you know, like Tau, Tau Group and bigger venues started to use
• 22:56
  this technology. And they wanted to pre-sell tickets because, you know, they were paying a lot
• 23:01
  to these DJs to come in. And so they wanted to make sure that they had their costs covered. And,
• 23:08
  you know, you just do the math. You sell millions of tickets and make two or three bucks on convenience fees.
• 23:13
  It's money out of threat thin air. And you basically built that. So all the tech that like
• 23:19
  the people would use now, including payment processing, would you do, would you build out your
• 23:23
  own payment processor? Yeah, well, that our systems, we didn't, we partnered with payment
• 23:27
  processing, but you'd still get a percentage. Absolutely. Because you're the one bringing in the
• 23:31
  business. And then we would sell ads. And then we were like, wow, these guys are making so much
• 23:34
  money on events. And we figured out that New Year's and Halloween are the two biggest money makers
• 23:40
  of every New Year's. I mean, everyone goes out on the years and people are willing to pay
• 23:45
  ridiculous prices for like the worst experience of their life. Okay. It's like, you know, just because
• 23:55
  like it's barkey or whatever, you know, whatever new hotspot there is. But it's actually even funny
• 24:01
  because we've found figured out that you could do New Year's Eve parties at the worst thing places
• 24:08
  you could think of like we did like Dave and Busters and Times Square, right? And we would sell tickets
• 24:15
  at the highest price you could imagine. And there was really cheap to rent the place out because like
• 24:22
  who goes to David Busters. But what we realized because we were doing like data analytics is that
• 24:28
  there were a lot of people calling us being like, where can we go where we can bring our kids?
• 24:33
  Because we want to go out and we want to see the ball drop and we want a party. But we want to bring
• 24:40
  our 12 year old or 13 year old kids. Yeah, we're not going to go to a nightclub and get bottles
• 24:44
  service. Absolutely. And so we're like, wait, these guys will pay a thousand dollars to get for that.
• 24:50
  So, you know, we're $500 to ticket or whatever it was. And so, you know, we figured out a lot of
• 24:57
  things. We also did a lot of really advanced things like dynamic pricing. And you also collected
• 25:02
  the list of all the people that and then you use at the fill clubs. So if you had this list of
• 25:08
  a flywheel, yeah, it was a flywheel, right? And I remember I was reading, I read your book a
• 25:13
  while ago and before we moved. And I can't remember the number. Maybe you remember it off top of your
• 25:18
  head. But per club on New Year's Eve, the amount of revenue you could do was something was like
• 25:23
  some insane that we were making like half a million dollars of venue per venue. And you could do
• 25:27
  every venue in New York City. Well, that's the thing. Scaling that's really hard. Okay. But
• 25:34
  there was points when you did we did. We were doing like 20, 30 places a one night. And you know,
• 25:41
  it works very well in major metropolitan areas like New York, LA, Miami, those types of things. So
• 25:49
  the problem is logistically doing a lot of events in one night requires a lot of staffing,
• 25:56
  requires a lot of organization and and and a lot of free pre-planning. It also requires
• 26:03
  it also is a lot of risk because if you look at COVID, everyone who may have bought out a venue
• 26:12
  for an event was SOL at that point. So you could spend millions of dollars pre-booking a venue
• 26:23
  because that's the way we actually invented that we would pre-book a venue. So we would go to
• 26:28
  Marquis, we would go to Steve Ambusters, we would go to this nightclub and say we want to just
• 26:34
  basically rent out the place for all of New Year's. Here's a hundred thousand dollar deposit.
• 26:40
  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
• 26:46
  bring the this and you know and we'd we'd have to guarantee that you know and that was also part
• 26:52
  of our six line is you have major metropolitan areas and you and you don't have COVID. It's fine to
• 26:57
  guarantee that but then you get in trouble when you don't. Yeah, but you're almost like reinventing
• 27:01
  your business every year if you think about it. So you have to really start over again. There's no
• 27:07
  there's no re you know other than human nature and wanting to go out on your years, right? It's
• 27:14
  not guaranteed that you're going to sell out. It's not guaranteed that that venue will stay in
• 27:18
  business too. There's a lot of risk involved in it. It's it's it's not crazy and and I think
• 27:25
  COVID's an outlier obviously but yes, you know, it's it's FOMO drives profits. I can tell you that
• 27:36
  and what what people don't realize is that every ticket you sell to an event like a New Year's
• 27:42
  event each ticket holder is a promoter because they're going to tell their friends and their friends
• 27:47
  are going to want to come with them and they buy tickets and then you know as it gets closer to the
• 27:52
  event you start increasing the prices and then people like freak out. You didn't raise for this.
• 27:58
  No, I did it literally I literally I didn't do it in my dorm room. I was in her dorm room like
• 28:05
  I'm holding this thing, right? So yeah, we really did a shoe string budget. Nothing. I didn't even
• 28:14
  have like I had no money at that point because I lost most of my money with the company. Yes,
• 28:19
  because I put like a hundred grand or 150 grand of my own money that I had saved up into the other
• 28:24
  business. That's what part of why I moved in with her. So when did you choose to sell it? What was
• 28:29
  the reason? So at that point I had started another company. There's easy texting. Easy texting.
• 28:36
  So we realized that we needed in 2004-ish, five-ish. We realized the texting was becoming you know
• 28:43
  really prevalent with blackberries and that kind of thing. And email was starting to become less
• 28:49
  effective. And you're seeing this from the data in in in Junebook. Absolutely because we were
• 28:55
  we were data first, right? And that's pretty normal now, but I think it was pretty advanced in 2004-2005
• 29:04
  to look at your data and try and get insights from it. I don't think there were a lot of people who
• 29:09
  were doing that, right? Even even big tech companies weren't really even doing that. But I don't know
• 29:16
  we we we saw that and I was thinking of how can we cut through the clutter because at that point
• 29:24
  there was, you know, you were getting an email from the nightclub, you were getting one from the
• 29:28
  DJ, you were getting one from the door man, you were getting one from the grandmother, you know,
• 29:32
  you were getting one from everyone, right? And so like we were just another email and the efficacy
• 29:37
  of it was going down. So I'm like, oh, we need to start we're everyone's phone numbers. Let's start
• 29:42
  texting them. Easier said than done. I thought that there would be a solution like MailChimp
• 29:49
  out there that you know, by that time MailChimp was and in constant contact and all these other
• 29:54
  kind of ESPs, email service providers were out there, you know, and they were doing really well
• 30:00
  because everyone was building their email list, but there was no solution for texting,
• 30:06
  which was shocking actually. And so I was like, okay, we need to figure this out and then I figured
• 30:14
  it out. It took like six months and I figured it out. And because it's not, if you think about a
• 30:20
  texting goes through the phone systems, it's not the internet. It's different. So then there's
• 30:24
  the higher cost. There's higher cost. It's a closed system. It's not the same. It's text message
• 30:29
  is actually really considered phone call. It's not it's not it's not data. It's a little bit weird
• 30:35
  and it's too much for this podcast to go into it. But anyway, long story short, I built it, sent
• 30:42
  out the first text and literally I had every nightclub owner promoter DJ everyone call me and be
• 30:49
  like, how the hell did you just do that? And I was like, light bulb moment, which is wild because
• 30:55
  even in 2024 outside of like Twilio, still not a lot of companies focus on texting. It's still
• 31:02
  email. There are a few big ones that are like Shopify integrated that do this interesting thing where
• 31:08
  if you go to their text message list, they give you a coupon and then obviously texting someone
• 31:15
  is a lot more effective than then then. But even if there's people that even if there's
• 31:20
  companies that offer it, I get less texts and I get emails is my point. Yes, you do because it's
• 31:26
  actually highly regulated now. And so they never wanted it to become like, you know, you get
• 31:32
  like millions of text spam. And so actually companies like easy texting that started it, we
• 31:39
  would make sure that that our customers were in compliance and they're, you know, they're
• 31:43
  only sending to opt it in customers and that kind of thing. And we gave you tools that would help
• 31:50
  you build your list in a compliant way as well. And this is before the government had regulation
• 31:54
  because you were out of the curve like you were. Yes, we can do a whole podcast on regulations and
• 32:00
  stuff like that. We got slapped with a bunch of lawsuits that we got pulled into as well. And I
• 32:04
  learned a lot from that, learned all about probably it's like one of those things that if you knew
• 32:11
  that you had to go through that, maybe you would have never started it in the first place. But it
• 32:16
  doesn't matter. So anyway, the light bulb moment went off and I was like, this can be, you know,
• 32:25
  this could be MailChimp for text messaging. And so I didn't hesitate. I created that and I
• 32:32
  can't kind of ran both companies for a year until easy texting really started to become
• 32:40
  significant at that point. And I just really saw the opportunity with easy texting being a lot
• 32:48
  bigger than what I had already done in the previous 10 years with Junebug. And I was also ready
• 32:55
  for something new. The entrepreneur and me was ready for something new. This was the shiny new
• 33:00
  object. There was a competitor that was nipping at our heels all the time with Junebug. Yeah,
• 33:07
  with Junebug, that was trying to do what we were doing. And I just called them and I said,
• 33:12
  listen, this today's your lucky day. You know, we were, we were, we had already kind of like,
• 33:19
  we were the established company. I said, look, if you can figure out how to kind of make this
• 33:25
  acquisition work, I'm willing to do it. And so that ended up happening. And then I spent another
• 33:33
  eight years or so building easy texting. It also kind of coincided with what I wanted personally,
• 33:40
  because there was a lot of, you know, it's not easy. It's not easy to kind of want to get married
• 33:47
  and have kids and stuff and be in that type of business, even if you're just doing the tech for them.
• 33:52
  Let's just say like it's the old business like at odds with like a marriage and a stable family.
• 33:58
  Absolutely. And and and so what's really funny is that the entire time I was always in long-term
• 34:06
  relationships. So was it like I was going out in part of it? Probably why I could stay in the business
• 34:11
  and not kind of get caught up in it. A big shout out to HubSpot and the HubSpot podcast network
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  for sponsoring success story. If you enjoy success story, you're going to enjoy a ton of podcasts
• 34:22
  brought to you by the HubSpot podcast network, including hustle and flow chart hosted by Joey Fier.
• 34:27
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• 34:32
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• 34:42
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• 34:47
  business. It's for somebody who wants to build a lifestyle, somebody who is looking to build
• 34:51
  systems that work. Listen to hustle and flow chart wherever you get your podcasts. But it's not,
• 34:57
  it's very, I know that business is tough. I was speaking to um uh Scott Harrison from charity
• 35:01
  watch. Yeah, I know him. And I was and yes, he was telling me his story. I'm like, for sure,
• 35:06
  he knows Shane. Yeah, yeah, I know him. Yeah, I mean, he realized it earlier on and
• 35:12
  understood that real purpose came through, you know, doing something significant. And by the way,
• 35:18
  he was like at the top of his game. I have no doubt. He said he left, uh, he left this beautiful
• 35:22
  condo with yeah, like this like grand piano and his panthouse and and he just left off and he
• 35:28
  just like never looked back. Yeah, good for him. And charity was big. They just, they just raised
• 35:34
  over a billion dollars just like last Thursday they hit like the billion dollar. How much,
• 35:38
  how much more fulfilling is that probably a lot? Absolutely, absolutely. So yeah, so you get,
• 35:44
  you get it like this is not going to be the business you're going to build for the rest of your life.
• 35:48
  Yes. Yeah. And and I also think that part of a lot of people get get caught up conflating
• 35:54
  themselves with their business, you know, they they almost see themselves in their business as one.
• 36:00
  I was very lucky that I never had that mentality. The business for me was always an ends to means
• 36:07
  and and and to to a degree, I have to like what I'm doing, but you tend to like things that are
• 36:12
  successful, right? So, uh, you know, uh, I never, you know, once I sold you and bug, it was like
• 36:20
  like turn that page, have a nice day, like that's in the past, right? I never really, I don't even
• 36:27
  really think about it ever. You know, it's not, it was never me, right? It was something I did,
• 36:33
  but it wasn't me. But that's a very healthy attitude. Yeah. I think a lot of entrepreneurs
• 36:38
  should probably have that attitude. It's easier said than done. And when you're in it and you're
• 36:43
  running it, it's hard not to move your room with yourself out of it. It's actually it's conflicting
• 36:50
  because you want as a VC, you want a founder that is all in, right? But you can be all in and still
• 37:00
  be detached from the outcome of what's going on. And that's that's that's either something that's
• 37:08
  innately in you or you have to work to kind of make yourself aware of that. That will, I mean,
• 37:16
  your mental health is going to be much better if you adopt that attitude versus the opposite,
• 37:21
  which I think is I think the less founders act like you act it. I think more founders just
• 37:26
  their whole identity as a business. It could be a detriment too because if you don't sell at the
• 37:31
  right time, you're also screwed. You could have sold and you could have done really well. And you
• 37:38
  you hold on too long and you burn yourself out or you hold on in the market turns and what you
• 37:45
  were doing is no longer relevant, right? Did you raise for easy tax? I did not. I took all the
• 37:50
  majority of the money that I got from the sale and I pumped it into easy taxing. And then just that
• 37:59
  so that would be the third business. So Junbaugh considered a success easy taxing. How far did you
• 38:04
  take that? So I took that for another eight years and then it did very well. We grew it.
• 38:12
  It was have you have you been public about numbers or no? I can't say the actual number, but we were
• 38:18
  close to around 18 million in ARR at the time that we sold. But so I mean, you can kind of backtrack
• 38:26
  numbers if you wanted to. But what was interesting is that we were doing that with a team of 20-something
• 38:32
  people that's good at revenue per head. And you know, we were serving tens of thousands of
• 38:38
  customers. We were early to the kind of game. So we had a first mover advantage. And what was
• 38:47
  interesting was is that I wasn't even kind of looking to sell a strategic approach to me that
• 38:53
  wasn't doing taxing. They were doing calling. This is perfect. And so yeah. And then it's funny.
• 39:00
  That process taught me how to think about my business. Because all I knew before that.
• 39:06
  How do you say that? This is like your third business in. This is like, this is almost like 25
• 39:11
  years of building your business. Why do you say that? This moment is when you thought about.
• 39:15
  Because I think I thought I knew because it was the first sale was a very friendly sale. It was
• 39:24
  when a choir who knew my business inside out because they were doing the same exact thing.
• 39:28
  And so there weren't many questions around what I was doing. It was kind of like a handshake deal.
• 39:37
  This was a little bit more different. They were asking me questions. And I'm like,
• 39:42
  I don't know. I never really thought of my LTV. I don't know. We never thought about
• 39:51
  what our cost of acquisition is. I just know I make a shit out of money.
• 39:57
  What was very interesting also is that at that time, they didn't really know what to do with us
• 40:02
  because I ran a very profitable business, which was weird for SaaS companies at the time.
• 40:08
  It was weird to be profitable. Absolutely. But I was licking it as a career, not like something
• 40:15
  that I'm building to sell. So I was like, I want to make something where I make a good living off
• 40:23
  of. And there are SaaS companies that do that. 37 is signals and other companies where they make
• 40:31
  millions of dollars a year and they have a great product and they have customers and they're never
• 40:36
  going to build, they're never going to sell. But I actually think that's again, all the things that
• 40:40
  you did, these are things that I think are just best practices for entrepreneurs. You shouldn't.
• 40:44
  I don't think most entrepreneurs should be building a company that's not profitable,
• 40:49
  that you're just looking for the next round and you're just burning through venture money and
• 40:53
  you're stressed out. I was actually looking at old posts, funny enough, just last night, old posts
• 40:59
  that I put out. And I'd done this little comment on a tweet this guy put out. And I can't remember
• 41:03
  the whole story. Basically, the tweet was, I sold my company for $237 million that I didn't get
• 41:09
  anything from it. And it was, it was a venture back and he was diluted or whatever happened.
• 41:13
  And he never took money out and he paid himself like this below average salary. And by the time
• 41:18
  that he raised whatever serious he was at, I don't know how it happened. Maybe they had to do a
• 41:23
  down-round. I don't know what happened. But basically, he sold the company to $237 million and
• 41:28
  walked away with zero money. I bet you, if you had a company that you own by yourself,
• 41:33
  they made $5 million a year and you sold that company, you wouldn't make as much as if you sold
• 41:39
  your venture back company for $150 million. The math probably works about the same.
• 41:45
  I bet you're right, actually. Right. So who's the better founder?
• 41:49
  I'll tell you, it gets the headlines. The guy with the 150 million gets the headlines and
• 41:55
  people actually give a shit about him because he's VC back. But no one gave a shit about me because
• 42:01
  I was a VC back to no one cared, no one cared to look. But maybe that was part of my successes that
• 42:08
  I went under the radar. Maybe if people knew how much money I was really making, they would have
• 42:15
  competitors like a $5 million, $10 million in pure profit. I think that's fucking phenomenal.
• 42:22
  That's absolutely phenomenal. I mean, try doing that right now. It's impossible. You have to have a
• 42:26
  lot of things work out for you to make that kind of money, right? A lot of hard work, a lot of
• 42:31
  luck, probably more luck than hard work. Right, right time, right place, right market, right product.
• 42:37
  Absolutely. And you have to be in the right mindset and the right experience levels to do something.
• 42:43
  And I also think that many people don't need as much money as they actually think they need.
• 42:47
  No. To actually live an insanely good life. No, they absolutely don't. They absolutely don't.
• 42:54
  And I live their great life without a lot of money for a long time.
• 42:57
  So okay, so easy tax thing. You went through a strategic. They approached you.
• 43:01
  They approached me. They were actually a customer of ours. And then and then
• 43:05
  you know, I learned a lot about my about my business through that process.
• 43:11
  Exited, had coincided with getting married and also having my first child.
• 43:16
  That was a busy year. Yeah, I was like within the first two years, let's just say, of doing that.
• 43:22
  I stayed on for like a year. And you know, I realized it wasn't going to, you know, like it wasn't
• 43:29
  my business anymore. And there was other, you know, like this happens to everyone.
• 43:34
  But I kind of made a cautious decision at that point, not just like what you said, you know,
• 43:40
  when is it when is enough enough? Right. And so I was a crazy workaholic. I would work all the time.
• 43:48
  I mean, my wife, I don't even know why my in-laws let me marry my wife. Because I would not,
• 43:53
  like I was never there, president, you know, like I was on my blackberry all the time.
• 43:58
  I remember I spent one new year as my poor wife at that time. She was my girlfriend.
• 44:02
  We were in Miami. We went to dinner at 10 o'clock. I had to leave because of a work emergency.
• 44:08
  I went to the basement of the Delano at that time, worked on the computers.
• 44:13
  Because they had a computer office computer system. Yeah, I lab. And I left it like three in the
• 44:18
  morning, you know, and I went and picked her up. And that was like my life. It was really like that
• 44:24
  all the time. I was never present on anything. I was only about the business mostly.
• 44:29
  Which I think, you know, coincides with how successful your business is. And there's nothing wrong
• 44:35
  with that in a season of your life that that that you may need to do that in order to get to a level
• 44:44
  of success that you may want personally, right? But anyway, I realized I wanted to be a present
• 44:50
  father. And I was like, what is this all for if you don't get to enjoy it a little bit. And so
• 44:57
  we moved to Miami about 10 years ago from New York City. I was always in New York City. So that
• 45:05
  hustle came from being in New York City. Also, the hustle came from trying to get into med school too.
• 45:11
  Like you never saw founder mode for like 25 years basically. Yeah. And by the way, I still have
• 45:18
  that in me. So now the founder mode comes into running investments, which I think I do
• 45:26
  differently than a lot of other investors. I want to unpack that because even now I find you
• 45:32
  busy. Like you're you're still very busy for somebody who is like quote unquote retired. Yeah,
• 45:38
  I'm very busy. I wish that people think it was some of my friends and family think I'm retired,
• 45:43
  but I'm not. I really work all the time. I know you work all the time. I work all the time
• 45:48
  because there's just so much exciting stuff happening. But it's interesting because I don't think
• 45:53
  I know too many other people because I don't. Do you consider yourself like a professional investor?
• 45:59
  I guess at this point. And I'll tell you why say that because the people that I know I know a lot
• 46:04
  of people that have exited companies and they all invest obviously, but they don't spend as much time
• 46:09
  investing as you do. No. So yes, I so so so I made it my mission. I realized afterwards that I
• 46:18
  didn't want to do a startup. And I'm like, I need to learn how to not suck at investing at least.
• 46:23
  Let's just put it that way because the one thing that people it's the ego when you sell a company,
• 46:28
  you think you know what you're doing. And then for some reason, people think that just because
• 46:32
  they can build a company, they can invest. It's actually diametrically opposed. Sometimes
• 46:38
  being a good investor and being a good founder are not necessarily some of the attributes are okay
• 46:45
  to have, but other attributes actually make you a worse investor because founders tend to want
• 46:54
  to do stuff to fix things if they see something wrong and they think they can outsmart everyone
• 47:02
  and they think they can maneuver. The problem with investing is that if you do too much,
• 47:08
  you actually end up screwing yourself over a lot of times. If you sell and buy and try and time
• 47:15
  things and do things like you try and control. Yes, yes, you just have to, you know, so people ask
• 47:22
  me like, so what is it that you really do now? My job is to consistently make good decisions.
• 47:30
  And that's very hard. It's very hard. It's very exhausting just to be honest because you know,
• 47:39
  I doubt myself all the time. How do you know the decision you're making is a good decision?
• 47:44
  You don't know until later on and you see the results of it, right? And sometimes what's even
• 47:49
  crazier is that the short term outcome of your decision may be bad, but the long term outcome
• 47:56
  might be amazing, right? Or the reverse. The short term is like, you're like, I'm the smartest
• 48:02
  guy in the world. And then like two years later, you're like, holy shit, what the hell was I thinking,
• 48:07
  right? So decision-making is a skill that no one teaches you. You're not taught like, were you taught
• 48:16
  in school? Of course not. In your story and in my story, the things that I learned in school
• 48:22
  were no longer applicable like in the first two days of what I did. Absolutely. Absolutely.
• 48:28
  So like, how do you learn how to make a good decision? You don't know. You did by doing by making
• 48:32
  decisions and by screwing up. Yeah, but you know what? Even even when you do that, people don't
• 48:38
  don't tend to learn because how many people do you know, sit down and be like, oh, let me review
• 48:43
  that really bad decision I did. And what were the problems with it? And why do how do I mess this up?
• 48:49
  Do you know what people do that? Because nobody wants to deal with it. No, but I actually do that.
• 48:55
  I do do that. I do a decision review every quarter. And I keep a journal. And I, and in my journal,
• 49:02
  it's like kind of like a daily journal of like what I did that would start when I do like a great,
• 49:06
  like one or two things I was grateful for. And then I, and then if I made any major decisions
• 49:11
  that day, I usually type it, type it out. And then I'm not just sitting in reverse to investing.
• 49:17
  No, because it's either you're either like constantly making good decisions and thinking about
• 49:24
  things in a rigorous way, or you're not. And that can permeate like, why wouldn't I want to do that
• 49:31
  for my children or my personal life or my health or my this or the other thing, right? So like,
• 49:40
  I think it's just an essential skill to have to have a good life, not just not just the business.
• 49:46
  Did you pick that up while you were actually building or was that more after?
• 49:49
  No, actually, I took, I learned this through a couple of people I was following, but the person
• 49:56
  who talks about this the most that I like, this the most clear about it is Shane Parish.
• 50:02
  He's in the knowledge project. He actually has a course called decisions, but I've taken that course.
• 50:07
  And I thought I was a good decision maker prior to the high. And then I was like, holy shit, like,
• 50:13
  I just learned something that I never thought of before. It's very difficult to take major
• 50:21
  decisions through a process. And you know, most people, most, most investors are bigger,
• 50:28
  bigger investors take it through investment committee and this kind of stuff. And you get everyone's
• 50:33
  feedback and even that can't can be not the best approach either.
• 50:40
  What's the decision making process that you'd make on anything from like personal health to
• 50:45
  investment to like, what's the, what's the framework? So the frameworks are, you know,
• 50:50
  are they consequential and consequential? Because, you know, if it's a reversible, you know,
• 50:54
  this is, this is kind of like what goes in Shane's. You know, I never really thought of it methodically
• 51:00
  until now until I took his course. So like, if it's reversible, then like, I don't know,
• 51:05
  just make the decision. And if it's not, you know, like, but if it's consequential and irreversible,
• 51:10
  you know, you want to kind of get information from the most pertinent people that have first hand
• 51:17
  knowledge of this, not second hand knowledge of it, whatever it may be like if you're making a
• 51:22
  health decision or, you know, that kind of stuff. And then at some point, having too much information
• 51:28
  actually hinders your decision making process, you have to also kind of come to a conclusion
• 51:34
  after of when you have enough information to make it, to make a decision. Then, you know,
• 51:40
  you do things like probability scores of how certain you are of certain things. And then,
• 51:48
  and then you have to execute a decision. And, and, you know, when it comes to investing,
• 51:53
  you have to think of sizing. So sometimes this is the, this is a, so a problem that I've had
• 52:00
  personally is that I've made some really freaking amazing investments, but then I just didn't put
• 52:06
  in enough money in the investment. I was really convicted, but I didn't put in, I didn't size it
• 52:14
  correctly, right? And the reverse can happen too is like, you know, you make a decision, you size
• 52:20
  too big, and then you make a really big mistake in your out of the game. That's the other thing
• 52:25
  is that you, it's kind of like poker, right? Like you don't want to make a decision where you have
• 52:30
  one hand that takes you out of the game and then you can't play anymore, right? So there's a lot
• 52:37
  of that going on. You have to, you know, there's, there's a lot of different methodologies of making
• 52:43
  a good decision. But even that, even like a little bit of thought about it, I think is better than
• 52:49
  what most people do. Absolutely, blindly just thinking about things. You know, there's, there's,
• 52:56
  there's, there are more things that you can do. But, you know, I could spend the entire podcast
• 53:01
  telling you, but, but that's, you know, there are, there are books on this. There are people who
• 53:06
  are experts on this. I, I wish I had done this earlier, right? It would, it, not that I was a bad
• 53:15
  decision maker, particularly, but the better decision maker you are, the better you tend to do.
• 53:21
  Now, I mean, so I asked you if you're, if you consider yourself a professional investor, but at
• 53:26
  the very, at the very minimum, you are a professional decision maker. And that's what you, I think,
• 53:31
  but everybody is, I think that just, I think that actually it's all relative. I was going to say
• 53:36
  because there is more, there's more capital, there's more stakes, but it doesn't really matter because
• 53:40
  at any level, it's all relative. Really, he could be putting in like five grand into a company.
• 53:45
  And if you lose it all, it's still five grand on. If you're only making 70 grand a year or whatever,
• 53:50
  that's, that's significant to you. So it doesn't really make a difference. So being a good investor equates
• 53:56
  to being a good decision maker and also being able to remove your emotions from the investment.
• 54:04
  It's a very hard to do. It's a very, I am not particularly good at it, but I'm seasoned,
• 54:12
  and I'm hardened over that. So you sold easy texting. Yes. You started investing.
• 54:18
  I started investing. I made a lot of mistake. Okay. So, but even like the thought process,
• 54:23
  because again, I do see you being more active than a lot of the people that I know. A lot of people
• 54:26
  I know who sold the company, they only invest in the thing that they know. Yes. And all across the
• 54:32
  and or real estate, that's like the only like you could be like a SaaS founder and you just do like
• 54:37
  early stage, prop tech, SaaS, and then plus real estate or yeah, but you do everything.
• 54:44
  I do, because I and you have to talk about the stuff that you put money into.
• 54:49
  So I'll tell you my strategy is very different now than it was before, but I started.
• 54:54
  Yeah. But I think that being able to control, if you look at the best investors, like a buffet or
• 55:02
  those guys, they're all like all slightly on the spectrum. And so they don't experience emotion
• 55:09
  the same way that an quote unquote normal people do, right? Or you and I do, or we know. So they
• 55:18
  could see like a huge loss on their account and not flinch, because they're so certain about what
• 55:24
  they're they just did. And they're just like, I'm willing to wait, wait, be wrong for a long time
• 55:29
  until I'm right. Yeah, but for most people, if I thought hard attack, yeah, you go you go in and
• 55:36
  you see your account down 30%, 40%, 50%, you're going to have a hard attack. And you're going to make
• 55:42
  a bad decision. Okay. And so that's an acquired skill. And sometimes it's even when you acquire
• 55:52
  the skill, like even during COVID, like I was on the verge of making some really bad decisions
• 55:59
  that I'm thankful that I didn't make, but I was this close, you know, like I'm not immune to it,
• 56:05
  right? To making emotional decisions. And and so, you know, that's a that's a practice. It's
• 56:13
  it's really it's it's just like working out, right? Like the more you practice it, or you know,
• 56:19
  yoga or whatever it is, the more you practice it, the better you get at it. And you know, you can
• 56:24
  start small. I found, you know, a few few people who I respected, I I I I talked to them all the
• 56:36
  time. It's very hard to find those people. And in whatever you're looking for, but like for me,
• 56:42
  it was for investments, you know, for other people, it could be a health, you know, you know, you
• 56:47
  know, you and Gary are tight. Yeah, yeah. Now, right? And you know, you know, you as his own,
• 56:51
  like I mean, he's built a massive social media business with Valeria. So like he's one of the
• 56:56
  guys that I looked to for that. But there's not many people that that are killing it. Like the 0.001
• 57:02
  percent is for a reason, right? Yeah. So so it's worth your time and effort to try and find those
• 57:08
  people that you want to surround yourself in. That's probably the 90% of the game. And the the amount
• 57:14
  that I learned from those people. And now I'm adding value to them because I learned their
• 57:20
  techniques. I learned from them. And now I'm like contributing, right? And so I think that that's
• 57:29
  that's an essential you really want to find those people that are experts in what you're trying
• 57:38
  to do and put yourself around them and put yourself into scenarios that give you high probability
• 57:44
  of meeting those people in situations. So yeah. So now my my my investment thesis is very
• 57:55
  different than them before. What was it when I don't even know you don't mean what I think I was
• 57:59
  trying to do a little bit of what you said. I know I didn't really state and I did
• 58:03
  sass and things I knew initially. But then, you know, when I put myself around other other
• 58:11
  investors that were really smart, they were opening up whole new worlds for me and showing me biotech
• 58:17
  and showing me, you know, deep tech and showing me CPG. Like we did in athletic greens, for example,
• 58:25
  we were one of the investments that I did with one of my friends. It's amazing investor as well.
• 58:33
  And then looking at late stage businesses, you know, like we did Pacific Park at the Santa
• 58:39
  Monica Pier, which we bought that business, which is one of the, it's a number one tourist destination
• 58:45
  in Los Angeles. I know. So you've literally bought a Santa Monica Pier. We didn't buy the
• 58:50
  pier itself. You can't own the pier, right? It sounds cool. We bought the business of the pier,
• 58:58
  so it's a little bit different. But there's, you know, there's a real estate component to it.
• 59:02
  But I think right now my tech, by the way, are those some of your biggest ones? So athletic greens?
• 59:07
  That's, yeah. So I think athletic greens, athletic greens, the pier is one of the biggest
• 59:13
  deals I've ever, I've ever been involved with. The, I did a company called Figure AI recently,
• 59:21
  which is a humanoid robot that Brett Adcock founded. I don't think I knew you when I first invested,
• 59:29
  we've invested, invested two years ago. It was a unique time because the markets were doing
• 59:35
  really poorly at that time. It was 2022, I think. And, you know, tech was down a lot.
• 59:46
  Inflation was raging and Brett comes out and he's like, I want to build a humanoid robot. And
• 59:54
  all he had was a few guys that he had hired from Boston Dynamics, a sample of a hand of a robot,
• 1:00:05
  and a bunch of, I don't know, like computerized prototypes. But he had a track record, though.
• 1:00:11
  He had a track record and he was putting in 20 million of his own money. So that's, see,
• 1:00:16
  that's the thing when you make decisions, you have to also kind of take into, because if you just
• 1:00:22
  look at it at the face of it, you, most 99.9% of people would never even, like, even consider it,
• 1:00:32
  because it's like, he's going to build a robot, a human robot that would, yeah, whatever, right?
• 1:00:37
  Like, but when you put your money where your mouth is, yeah, as a founder and going into details
• 1:00:42
  matter, right? So like those things matter, you know, he had a track record, he had two exits,
• 1:00:48
  he took archery aviation public. So he had a lot of hardware experience and scaling hardware.
• 1:00:56
  He was putting his money where his mouth was, he had done pretty far, even with very little
• 1:01:06
  money of actually making a functional hand, which is the hardest part of a robot mostly.
• 1:01:13
  Um, and so when I first did that investment, most people thought I was batch at crazy,
• 1:01:20
  because, you know, first of all, the markets were in turmoil at that time. So it's very hard
• 1:01:26
  under fear to make investments. That's where the removing your emotion peaked. Absolutely.
• 1:01:32
  Absolutely. Like, whether it's in the public markets or the private markets, it's irrelevant,
• 1:01:36
  right? People get disgusted and they don't want to look, right? They don't want to look,
• 1:01:41
  because they see their account down, right? And they're like, oh, yeah, now I'm going to make
• 1:01:47
  an investment and like take even more money out of there. But the thing is those two, those two
• 1:01:52
  things are completely separate from each other. Yet it is logically speaking, but it's very
• 1:01:58
  hard to separate it up. And so anyway, um, as luck would have it, which I think 90% of all this
• 1:02:05
  is luck, obviously. Uh, Brett was successful. He made a prototype that actually works.
• 1:02:11
  It's actually deployed in Amazon and BMW right now. It's probably the him, him and optimists
• 1:02:17
  from Tesla are probably the incumbents in the field, um, where they have a real viable product that
• 1:02:24
  can actually replace human labor. And if you think about a human labor, physical labor is a
• 1:02:32
  $3 trillion term, like, everything, like, it's all the work that no one really wants to do,
• 1:02:39
  right? Like this, you know, no one wants to go and pick and pack in a warehouse and go down
• 1:02:45
  aisles and pull things from boxes and, you know, take a piece of sheet metal and keep putting
• 1:02:51
  into a press a thousand times a day, um, which is where he's starting, which I think is the right
• 1:02:57
  thing. And also in the warehouse, uh, you know, robots in a controlled environment. So the safety
• 1:03:04
  issues are kind of much more manageable, mitigated a little. Yeah, they're much more manageable.
• 1:03:10
  It's also talking to a computer that's giving it directions, like a warehouse management system
• 1:03:16
  versus, you know, me, you know, robot being in my house and I'm saying, watch the dishes, right?
• 1:03:21
  It's a little bit different. It's almost like, um, well, robots exist in car manufacturing
• 1:03:27
  already. They do, but this is certain parts of it. So this is just like almost finishing or,
• 1:03:33
  or more parts of the, the factory is now going to. So Tesla, I think, you know, their,
• 1:03:39
  their idea is that the entire process will be done by a robot. And, and as a practical matter,
• 1:03:46
  all the other robots that work on, on anything are, you know, the environment is retrofitted
• 1:03:52
  for the robot so that the robot can work correctly in that environment. But the world is meant to
• 1:03:57
  interface with humans. It's meant to interface with hands, feet, you know, you know, stable,
• 1:04:05
  like a human it, like even an iPhone, if you go and actually look at how it's made,
• 1:04:11
  a lot of it's done by hand. You can't even imagine, right? It's done on a huge scale in China,
• 1:04:17
  but a lot of the pieces are being done by hand. And so,
• 1:04:23
  if you can really, truly replace that, the, the, the, the opportunity is huge. It's almost like
• 1:04:31
  bigger as big as cars were when cars were invented, right? The opportunity is, is huge in the
• 1:04:38
  entire physical labor. Uh, uh, so it's funny when, whenever an inventor or an entrepreneur is like
• 1:04:44
  cam, like total addressable market, and they say some ridiculous, outlandish number. And you're like,
• 1:04:49
  well, if I just captured like 1% of cam or whatever, then come any of these successful, but this is,
• 1:04:55
  this is, this is really truly a giant ham. I mean, like the payroll that's, I mean, first of all,
• 1:05:01
  Amazon and all these places, they, they can't even get enough workers. There's not enough workers
• 1:05:06
  that want to do this. So they have to constantly raise the price of, uh, of what they're willing to
• 1:05:11
  pay. I mean, the poor workers, you just saw what happened. It was just how to strike it. It is
• 1:05:15
  huge. Right. Yeah. No, it got resolved, but they're getting paid like $65 an hour now. That's,
• 1:05:20
  that's it. That's significant. That's, that's huge. Yeah. So like, why wouldn't you replace that
• 1:05:25
  person with a robot if you could? It makes no sense. What do you need a person to like move cargo
• 1:05:32
  from one side of the port to the other? And like, there's a lot of issues with that because they're
• 1:05:38
  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
• 1:05:45
  cares. But if they've that injuries a person, that's millions of dollars and yeah, the productivity
• 1:05:51
  gains the things that come with it. And so anyway, just recently, they raised 650 million from like
• 1:05:58
  Microsoft and open AI and Jeff Bezos put a hundred million dollars. And so, you know, I look smart.
• 1:06:06
  Yeah. And then now, now, and then let's see what happens in two years yet. All right. Like,
• 1:06:11
  it could be zero, right? What when you look at companies like that where it's, because of different
• 1:06:16
  types of companies, you can invest and you can invest in a company that's building almost like a
• 1:06:20
  copycat product that would already exist. And you know, for a fact, it's going to get snatched up
• 1:06:25
  the second to get big enough. Absolutely. When you look at a company like this, like, what's the end
• 1:06:31
  game? Because the exit horizon or the ability for you to take cash out could be 15 years from that.
• 1:06:37
  It could. It's more likely a five to 10 year one. And like, as you know, yeah, I think for this
• 1:06:44
  particular one, but, you know, I think that I do both. Just my style is I just outside, now I
• 1:06:52
  outsize my investments and things where I think can give me outsize returns, right? And so, you know,
• 1:07:00
  when you invest in a company like that, you're looking to get like a hundred X on your money,
• 1:07:05
  right? And, you know, you have to size appropriately and it's high risk, high reward. But the other
• 1:07:12
  one that's a copycat, you know, you know, you can maybe two or three extra money in like four or
• 1:07:17
  five years, possibly. And you, you know, it's like, like, I'll, I'll go out and make a really big
• 1:07:24
  investment in real estate, because I know the likelihood of that piece of real estate going to zero
• 1:07:29
  is very low. Plus you have the land is glideral to it. And so, and so you have to kind of,
• 1:07:37
  you have to have a methodology of how you're, how you're looking at stuff. It's, it's not easy for me
• 1:07:42
  to tell you my methodology, because it's a little bit unconventional. I'm not as a structure,
• 1:07:50
  as like a, let's say a blackstone is or something like that. The only person I have to answer to
• 1:07:59
  is myself and not like, you know, I have people who, who, you know, who invest alongside me and I
• 1:08:07
  show stuff to as well. But I'm not like a fund manager, for example, or something like that, right?
• 1:08:12
  So it's a little bit different. I can take risks and do things that a lot of other people can't
• 1:08:19
  because it's, yeah, I owe money. It's your own money. It's your own money. But so even if you were
• 1:08:24
  just going to like, I know you said your framework is a little bit difficult. But if you look that
• 1:08:29
  so between, between cash flowing businesses like private equity or funds or real estate or
• 1:08:38
  early stage or late stage venture capital, you have like a mix that you aim for, like a loose
• 1:08:45
  may. Yeah. So I have personally, I have the most allocated to public equities because I think,
• 1:08:51
  I think that it's very hard to replicate US equities and the, the amount of value creation
• 1:09:00
  that there that is done there. Probably for me, is that through a fund or just through picking?
• 1:09:05
  No, I do it. Yeah. Good. Good. I do it. I mean, like one hedge fund, one hedge fund, but
• 1:09:13
  that's because I know the person very well. But I've done, you know, like I do funds for
• 1:09:20
  early stage stuff, like crypto and like biotech where I don't see, like, and I'm not an expert in
• 1:09:27
  the field. So I tend to pick managers that are really good at that. But I like to do individual
• 1:09:33
  deals. And I'm probably more than normal in venture than than a lot of people are.
• 1:09:41
  And I would probably say that my venture and my real estate and my private equity are probably
• 1:09:46
  equal onto onto that thing. I also have a, I have a barbell strategy now, right? So the way I'm
• 1:09:56
  thinking about things is I'm trying to invest in deep tech, like quantum AI robotics. I did a
• 1:10:05
  company called Luma field recently that that invested in a company called Luma field recently that
• 1:10:10
  has a CAT scan machine that can look at any object and then find the defects in it through AI.
• 1:10:16
  So even like a Nike sneaker, it can, but they do a lot of electronics too. So like you could put
• 1:10:22
  a battery in there and then they can figure out the defects without having to take it apart.
• 1:10:28
  I did a company called sandbox a invested in a company called sandbox a queue, which is the
• 1:10:32
  leading quantum cyber security company in the world. It actually spun out of Google. So I did
• 1:10:38
  an investment in that two years ago. And people thought we were crazy like like figure AI too,
• 1:10:44
  because like there was no chat GPT at that time, right? Like so this was bleeding edge. Yeah,
• 1:10:49
  yeah, it was, it was, it's our Schmidt. It's, you know, it's, and quantum and this and the other
• 1:10:55
  thing. And people really didn't understand what it did. And it was a little early for its time,
• 1:11:00
  because, you know, you're, you're protecting against a quantum computer that doesn't exist yet,
• 1:11:06
  right? See? Just in case someone does it, right? So anyway, so now that, that business has done very,
• 1:11:13
  very, very well. It has a lot of government contracts and they just got to contract with the
• 1:11:18
  Air Force and this, this type of stuff. So doing follow-ons on, on those or I'm trying to find
• 1:11:27
  businesses where I don't have a good enough imagination to think about how AI or deep tech
• 1:11:37
  or quantum can really disrupt that company. And you're looking for businesses that, that you do
• 1:11:44
  not have, you do not have the understanding of and explain. I don't have the imagination,
• 1:11:49
  a good enough imagination to contemplate how AI or deep tech can disrupt that company and put
• 1:11:57
  them out of business. I understand. Okay. And so I'm not doing a lot of SaaS at all, because I think that
• 1:12:05
  eventually computers will be coding. Like I mean, they're coding mostly right now. And it's just,
• 1:12:12
  it's going a lot faster than people think. Um, I actually, I was, I was able to go to SpaceX
• 1:12:19
  and get a tourist. I saw that last week. Yeah. Yeah. And so I mean, I really saw first hand
• 1:12:25
  how crazy things are going to get and I see the magic that's happening there. I saw them actually
• 1:12:30
  putting together the components of the rockets. I saw how they're using AI. I saw, I actually
• 1:12:35
  touched a Starlink satellite, which was amazing. I went on the launch pad. Um, very cool. I drove
• 1:12:42
  a Plaid X at 165 miles an hour down where the shuttle used to land. Um, anyway, that's I digress. But,
• 1:12:51
  that part of that was like, holy shit, they're really going to get to Mars because I saw it. I saw
• 1:12:59
  what was happening there. And I know that they're going to get to a place where they're going to
• 1:13:05
  do multiple launches a day. And Boeing can never do what they do. So you see the tech, you see
• 1:13:13
  that you see what people are, you see people are capable of. No, it's just in the scribe. I wasn't
• 1:13:18
  able to take pictures. So I wish I was, but I understand why. But like, it's so much further
• 1:13:26
  along than you can imagine. It's just hard to, to, to human brains are not meant to understand
• 1:13:35
  change this rapidly, but it's happening. And so I think that with the robots and with AI and
• 1:13:43
  those types of things, a lot of things, and this, this might sound psycho to a lot of people
• 1:13:48
  because it might, it might sound like an exaggeration. But I don't, I personally, my opinion is not,
• 1:13:54
  like, oh, in 10 years things are going to be changing. I think in is like, in one year, two
• 1:14:02
  years, three years, you're going to see some really crazy changes. Um, of how rapidly things are
• 1:14:09
  going to become. So when you, when things change that quickly, and you're investing in them,
• 1:14:15
  like, there's a really good chance you're going to screw it up or miss it or, or, or pick the wrong
• 1:14:18
  thing. So when you look at something like a quantum computing company that is protecting against
• 1:14:27
  malicious quantum computing attacks that have not, quantum computers are not even, like,
• 1:14:31
  commercially available yet. Like, who do you talk to to make sure the founder is not full of shit?
• 1:14:37
  How do you go to like, so for me, I'm lucky that there were a lot of really big, but this doesn't
• 1:14:43
  work all the time because like, Theranos is a good, good, good, good example of this. But, you
• 1:14:48
  know, typically you, you know, I, I rely, I read to the degree that other investors have investment
• 1:14:55
  memos or experts in the field that I can talk to. Um, that, that's leveraging your network, right? So
• 1:15:02
  a lot of the deal flow that I get is from other fun guys that I've given stuff to, or I've
• 1:15:08
  personally gone into their fund just so I could see their deal flow, right? And, and, and, and,
• 1:15:16
  and get to pick their brain and talk to them. You know, that's, that's worth every penny. If you
• 1:15:21
  think about it, right? The smartest guys, you know, have been in this for a long time, run their
• 1:15:26
  own funds. You know, you put a little bit, or you could put a lot, you know, and get to, get to,
• 1:15:31
  get to talk to these people find a way to get around those tables. Exactly. And so to that degree,
• 1:15:36
  I have a degree in computer science. So to the degree that I can diligence things, I'm pretty
• 1:15:43
  technical. So I'm, I'm cutting unique in that way. Um, so I leverage that, right? Like, uh, by the
• 1:15:51
  way, like, if they, if someone tells you they understand quantum, I mean, they don't understand quantum.
• 1:15:56
  So that's a, that's the number one rule in quantum. It's like, so like, I don't understand it,
• 1:16:03
  but I have enough interest in it and enough background to get the concepts on a high level.
• 1:16:10
  And that's, I think, probably one of the most important lessons. Like, there has to be some data
• 1:16:13
  point where some person or some, some thing that allows you to understand it just, uh, like,
• 1:16:20
  just so you're not ignorant going into it. So you're not just dumb money going into it. Yeah. So,
• 1:16:24
  but also if you think you're, think, think about it, you know, you're also 90% of the time betting on
• 1:16:29
  the horse. So Jack Hittery who's a CEO is literally considered to be the foremost expert in quantum.
• 1:16:37
  He wrote the, he wrote the textbook on quantum computing that's taught. And Eric Schmidt was the CEO
• 1:16:44
  and chairman of, uh, of Google for 12 years. So like, what better horse can I bet on, right? Just
• 1:16:52
  like how people bet on Elon, right? It's the same, same, same concept there. Um, yes, you know,
• 1:17:00
  the tech is important and everything like that's important. But I would argue to you, like, in those
• 1:17:06
  cases, 90% of it is who you're betting on, right? Who you're betting on, not just what you're betting on.
• 1:17:14
  So, um, so, and then, and then, so like, let's talk about the other end of the spectrum, right?
• 1:17:21
  What, what can't be, uh, you know, disrupted by all this stuff that's happening, right?
• 1:17:27
  Santa Monica Pier. People are going to still be going on the weekends on, you know,
• 1:17:31
  they're going to be still challenging, you know, these are, these are, yeah. Um, you know, experiences,
• 1:17:37
  although, although some, what some people can argue that, you know, you can virtually do with some
• 1:17:42
  of these things. Um, and that might ever replace by virtual reality. But, um, but not yet. I mean,
• 1:17:49
  that's, I mean, it could be, but not yet. And there's also, if you think about like the,
• 1:17:54
  so can a row, who can a robot replace a person in a warehouse tomorrow? Yes. But if you're
• 1:18:02
  going to talk about replacing a, a tourist destination, you have to replace like the, the smells and
• 1:18:07
  the feeling of the wind on your face and the taste of the hot dog or the pretzel you go eat. Like,
• 1:18:13
  that's it. I can, I can argue the neural ink will do that for you because it'll, it'll go into your
• 1:18:18
  brain. And the precursor technology is not already there, right? The precursor, yes, you're right.
• 1:18:22
  Yeah. But when that happens, so it's like, it depends on like, what are you investing in the
• 1:18:27
  technology that's directly applicable? Or are you investing in the technology that's going to
• 1:18:32
  create another category or another industry? I think, I think for those things, those are a little
• 1:18:37
  bit, uh, we don't, you're going to have regulation issues also. And they're regular. Yeah,
• 1:18:42
  regulatory issues. So the things that could stop this and stop, you know, AI from advancing is
• 1:18:49
  government intervention, regulation, one of the robots accidentally kill someone, shoot someone,
• 1:18:56
  gets, gets hijacked through cyber security. You know, there's a lot of scenarios that you can come
• 1:19:02
  up with that can really kind of put us back as well. So you can't have all your eggs in one basket
• 1:19:08
  thinking that only the future, the things in the future. Um, but like again, I'm looking at a
• 1:19:13
  hemorrhoid cream that's like trying to disrupt preparation agents. It's been the incumbent for like
• 1:19:19
  657 here. What was the one that you sent me? I didn't look at it yet. You just sent me one like
• 1:19:23
  last week or this week. I think it was something for creators. It was a creator. It was a creator.
• 1:19:29
  I see a lot of things. So I, uh, the one thing I, I, uh, the one thing I haven't done much of
• 1:19:38
  is anything that's like social media related. Um, it's just way too difficult and competitive,
• 1:19:45
  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
• 1:19:50
  the winners of that. That's so interesting because I think that it's almost so if you look at
• 1:19:56
  investing in blue ocean versus red ocean or red ocean, you know, there's a market for sure,
• 1:20:01
  blue ocean with the things that you're talking about. The market should be created in the future.
• 1:20:05
  But it's not like really here yet. But you feel more comfortable doing that because it's just
• 1:20:10
  less crowded. I think I'm, I'm doing that on that barbell. The other thing where I'm doing where I
• 1:20:16
  think they can't be disrupted. It's already, it's red ocean. Like, you know, yeah, the hemorrhoid cream
• 1:20:22
  hemorrhoid cream. Right. Yeah. Yeah. Yeah. Yeah. I mean, if you think about it, no one's done like
• 1:20:27
  man-scaped, for example, is a big brand and they do a lot of money and they took what, what a lot
• 1:20:34
  of people wouldn't talk about men's grooming and made it into a hip cool brand and they make a lot
• 1:20:39
  of money doing it. And no one's done that in that, in that space or, you know, there's the female
• 1:20:45
  hygiene space. So I invested in a company called ant flow, which is doing that. Um, so, so
• 1:20:53
  I think a lot of it is, um, really kind of thinking deeply about things and also
• 1:21:04
  who you're investing in. Yeah. It's a person because they're going to eventually, just like I did,
• 1:21:09
  you know, they're going to eventually hit these roadblocks that everybody eventually gets to
• 1:21:15
  and you have to feel comfortable that that person has the wits in them to figure it out.
• 1:21:24
  However, they do it, they have to be able to figure it out or pivot or do whatever it is that
• 1:21:30
  needs to be done to continue on. Um, and that's, that's really, that's really what you, the best
• 1:21:40
  you can hope for. What was the biggest, the biggest loss that you would be willing to talk about,
• 1:21:47
  the biggest failure? Yeah. Oh, so many of them. It's hard to take one.
• 1:21:53
  Well, I mean, my first one was the biggest failure. The
• 1:21:57
  Offix, which I told you about when I did investing, but yeah, oh, yeah, investing. Oh, man,
• 1:22:02
  I can, if you, maybe you haven't, we do him another hour. I can tell you about all of them.
• 1:22:08
  Uh, probably more, we'd probably need a day than an hour. Um, probably the one that kind of,
• 1:22:16
  there was a company called Convoy, uh, which was kind of doing what Uber Freight does,
• 1:22:21
  but it did it first. Uh, we were the early and early, I was an early investor in that company.
• 1:22:27
  And then a few years later, it got like a three billion dollar valuation.
• 1:22:32
  We had an, we had an offer of the sell. We didn't. We're like, this is going to be the next thing.
• 1:22:38
  And then COVID came in and my god, zero, zero, are you serious? Please zero. Yeah, shut down,
• 1:22:44
  shut down this past year. Yeah. A lot. No, no, we got zero. They had ventured that, the ventured
• 1:22:54
  guys took it over. Yeah. So, uh, yeah, I thought I was maybe going to retire on that, maybe
• 1:23:00
  that, maybe that's not going to happen. Maybe it's, maybe it's one of the ones that you're in now.
• 1:23:06
  Yeah. Maybe, you know, you can only, listen, I've, uh, learned one thing. Don't ever,
• 1:23:12
  don't ever, uh, counterchickens because it doesn't, you know, even to the last minute, um,
• 1:23:19
  um, I actually, in the public markets, I had made not even a year ago. I thought, I thought that,
• 1:23:25
  um, Moderna was a good investment. And I've gotten really crushed on that investment.
• 1:23:32
  You've had 60% down, something like that. Shit on that investment. I haven't been watching it.
• 1:23:37
  Yeah. It's, it's, it was, I was wrong. Man, well, I'm wrong until now. It might be
• 1:23:42
  brought right later and things might change. But that's the thing you're removing the,
• 1:23:45
  the emotion out of it because if you sold when it was down 60%. I haven't sold, but, you know,
• 1:23:50
  it, so, so that's, that's another one I, I, I did. Um, it's interesting. So, you know,
• 1:24:01
  real estate, I, I ended up selling a lot of the real estate that I owned in Miami. I bought
• 1:24:07
  when I first moved because there were no tech people here in Miami. It was a lot of real estate
• 1:24:12
  people. So I just did what everyone else did, but it turned out just to be a good thing to do
• 1:24:17
  because COVID pulled everything forward. So I was over the mindset when New York and LA people
• 1:24:23
  came here and started paying ridiculous prices for, I, I don't do multi-family or houses. I did,
• 1:24:29
  I do commercial real estate, um, like shopping centers and industrial and that kind of stuff. And
• 1:24:37
  so, um, I sold a lot of it into this market that was like two years ago right, right after COVID
• 1:24:45
  was like kind of dying down. Mark rates were still low. People were paying insane prices. What,
• 1:24:52
  for what I had paid, you know, because no one was looking at Miami 10 years ago. Really? No,
• 1:24:58
  it's changed a lot. Yes, changed. And I haven't, I've only been here four years, three and a half
• 1:25:02
  years, whatever. But the, what, the few things that I chose to keep. And I'm like, oh, this is going
• 1:25:08
  to become like a triple from where it is now. Uh, yeah, I was wrong. It's not doing bad. Let's just
• 1:25:19
  put it that way. But I could have done much better if I sold it at that time. And I actually,
• 1:25:25
  it's, it's people tell you that you can't lose on real estate. I've lost plenty on real estate.
• 1:25:30
  Like I bought my apartment in New York City, um, in 2013. And it turned out that I bought it at
• 1:25:37
  the exact high that you could possibly buy it. I held on to it for 10 years and never recovered
• 1:25:45
  back to the price that I paid for it. I luckily sold it right after COVID when interest rates were
• 1:25:53
  still. And then the market for New York got hot again. And I sold it losing 25% on that, on that,
• 1:26:01
  on that after 10 years, after 10 years, it depends on the market that you invest. And I think,
• 1:26:05
  like, I, people will tell you, New York City, yeah, best area in New York City, Chelsea.
• 1:26:10
  I know Chelsea. Yeah. Yeah. Yeah. Like, were you like looking at the Empire State Building?
• 1:26:15
  Was it like literally? Yeah. I was a pen, it was a pen house. I think I know, I know some of the,
• 1:26:20
  a genius sister was living in Chelsea. I can't remember the name of the building, but she was
• 1:26:23
  looking right at the Empire. It wasn't a bad house, but it was a nice building. And reds,
• 1:26:27
  reds are really good if you read it out. She was paying, oh, I think like seven or eight grand
• 1:26:32
  a month just for something. Yes. It's, I mean, the reds are insane, but the problem is is that,
• 1:26:38
  you know, uh, when you have an apartment that's 10 years old, the, the upkeep of it is very high.
• 1:26:44
  And so your rents don't cover that because you got to replace all of the everything inside of it.
• 1:26:50
  So whoever, also whoever tells you real estate is passive is absolutely lying to you, right?
• 1:26:57
  These YouTubers that tell you this is the passive and, you know, yeah, wait until you get a call
• 1:27:04
  at four in the morning that there's a flood in your, in your thing, and you have to find the
• 1:27:08
  someone to fix it. And then that, that caused us 10 other secondary and tertiary problems for you.
• 1:27:16
  How do you keep track of all of your, your stuff? Like, I mean, you have real estate,
• 1:27:20
  you have venture companies, uh, and, and you mentioned something before, like you were,
• 1:27:25
  you wanted to talk about like family offices, and then you, you built a family office. But
• 1:27:30
  what's the infrastructure around you that allows you to sort of manage all of this without
• 1:27:35
  dropping the ball on anything or not paying attention to something that you should be paying
• 1:27:39
  attention to? Because there's a point where you should have a team that eventually supports.
• 1:27:43
  So I'm taking the AI approach to that, actually. So we've, um,
• 1:27:48
  through software and automations, the past few years have really automated a lot of
• 1:27:55
  the functionality that goes along with that of keeping track of things, of making sure that there,
• 1:28:03
  nothing gets slips through the cracks and, uh,
• 1:28:07
  marking things to market and, you know, doing a lot of other things that go,
• 1:28:12
  go along with just the mechanics of, uh, of a family office and an investment firm. So, um,
• 1:28:21
  I've always been really good at that, kind of taking what can be automated
• 1:28:27
  and automating it through software. Um, we, you know, either through programming it ourselves or
• 1:28:34
  create it using different software and conjunction with each other. I think, um,
• 1:28:40
  I'm, I don't think I know because I, I speak to a lot of other family offices. I'm probably a lot
• 1:28:47
  more technologically advanced than a lot of them are. So you have like reporting and whatnot
• 1:28:53
  on all your port calls. Absolutely. Absolutely. And, and we keep track of everything. And it's
• 1:28:59
  refreshed daily, actually, even like to a degree. Really? Yeah. And funds and all these other things
• 1:29:05
  that we're in. So you have like you, like, I mean, it doesn't have to be like a custom dashboard,
• 1:29:09
  but you have some way of checking all the portfolio. Yeah. It is a custom dashboard. Actually,
• 1:29:14
  yeah. Oh, shit. I didn't know you guys. It's like, we have business intelligence. Yeah. We,
• 1:29:18
  we know like where we're losing, where we're, where we're winning, you know, those types of things.
• 1:29:24
  But, but there are people that work, I still have an operations person and that kind of thing.
• 1:29:31
  But you'd, you'd be, you'd be surprised how much one person can really do.
• 1:29:36
  So the one really good person can do the work of 25 people, but an automation can do, you know,
• 1:29:43
  a lot more. So we really can't, we, we turned everything into standard operating procedures.
• 1:29:49
  And then most of these standard operating procedures, you can automate most of the steps of it.
• 1:29:55
  If you really think about it and really know how to do it. So that, that's, that's an interesting way
• 1:30:03
  of approaching it. The other thing I think is that if you look at family offices these days and
• 1:30:12
  you look at just like exited founders and stuff like that, there are a lot more sophisticated
• 1:30:20
  than they were before. And they're want to be involved, right? Like they, they want to underwrite
• 1:30:27
  and learn about the investors that they're not just giving them money, they're money to like a
• 1:30:31
  wealth manager to do it for them or to a fund where they don't know what the fund is going to invest in.
• 1:30:38
  They'd rather do individual deals where they can actually use their brain, use their expertise,
• 1:30:45
  use their network, use their, I don't know, whatever it may be that gives them the edge
• 1:30:52
  to make a decision about an investment. And I think you, you're seeing that they're,
• 1:31:00
  they're, they're acting a lot more like endowments that like, and that, you know, like,
• 1:31:06
  and also allocating like that too. So they're, they're doing a lot more venture, they're doing a lot
• 1:31:12
  more sophisticated things that, that, that really bigger investors do. And they may not be anywhere
• 1:31:18
  near as big as, but they're trying to modernize and they're trying to act like, yes. And they're
• 1:31:24
  also taking the same kind of investment approaches and allocation approaches. What were they doing? Like
• 1:31:28
  what was the, so explain what family offices are doing, for example, like 10 years ago compared to.
• 1:31:34
  I don't even think there really were, you know, most, most of the time you were going to like UBS
• 1:31:41
  City Group or JP Morgan or whatever. And then they would just manage your money for you.
• 1:31:46
  And then they would put you into like a bunch of funds. They would make fees on. Yeah. Yeah.
• 1:31:50
  And then, and then put your money into a bunch of stocks that they have analysts were. And they
• 1:31:56
  charge your fees on that too. And then, you know, they make you use your, your, their, their
• 1:32:00
  bank accounts. And then, you know, that didn't make, and they put you in some bonds. And then they,
• 1:32:07
  you know, like they kind of like would advise you in that. And that. So the cause of the family
• 1:32:12
  office started. It ended up being almost like a very basic investment vehicle. And then it's just
• 1:32:18
  now it's evolving to the point where it can be its own fun. Yeah. It's almost like a business.
• 1:32:22
  You're running it like an investment firm. Yeah. Right. Yeah. So, so you're doing a lot more
• 1:32:27
  sophisticated things. There are things that are called multi-family offices where many family
• 1:32:33
  offices come in under one roof and they share resources like a CFO, like a CIO, like an investment
• 1:32:40
  officer, like reporting systems because they can get skill and not, and not, and not paying soap.
• 1:32:47
  And you're doing that. I mean, I would assume that if you have your systems in place and your
• 1:32:51
  automations, it's, they're like one person can manage a very large portfolio or a small team
• 1:32:57
  can manage a huge portfolio. And do you do it? Like, I mean, you, I know, I know some guys that have
• 1:33:06
  like billions of dollars on their management and have like five people working.
• 1:33:10
  Do you have you built out a team yet? Or is it mostly you? It's just me and just a few other people.
• 1:33:15
  Okay. So do you think you'd ever do you think you'd ever as like you'd turn like more into
• 1:33:18
  professional investment? Part of part of the reason why I didn't want to start another company
• 1:33:23
  is because at the end of the day, I really did not. I was the worst at employees.
• 1:33:30
  So I did, I never, that was like my weak spot. Oh, it's so funny.
• 1:33:35
  Because you've built even, I mean, you actually, you actually built businesses without lots of
• 1:33:41
  employees, even though you had great revenue. Yes. So that, that's my, that was my hardest thing
• 1:33:49
  to overcome. And so I compensated for it through this other method. And so I just, I suck at it,
• 1:33:58
  just to be honest with you, like, and, and I have to work on it. And it was all, I did it because
• 1:34:03
  I had no other choice to do it. But, um, I actually don't want it. Like, I don't want something where
• 1:34:11
  I have to go in and, um, you know, I have like 20 people or 50 people working for me. And then
• 1:34:18
  like, all these people are like, you know, it's just the stress level on that is just like,
• 1:34:22
  it's not worth it for me. It's so funny how different people perceive stress.
• 1:34:26
  How you like that to you is like a lot of stress. It is because I feel, I feel obliged to those
• 1:34:31
  people. So you will never raise a fund. I don't think, no, the worst thing is other people's money.
• 1:34:38
  You do not want other people's money. But you know that, you know that, like, I agree with you
• 1:34:42
  because it's very stressful. But you know, that's, that's opposite advice from what people give.
• 1:34:47
  They say, don't use your own money. Use other people's money. Use OPM. Go invest, go raise a fine.
• 1:34:53
  Listen, I've had, I've done it a couple of times. It's not, and I've only done it for very unique
• 1:35:00
  situations where the people who are coming in with me are very sophisticated and they're grown-ups
• 1:35:06
  and they know if they lose their money. Like, like, I don't feel bad for them if they did because
• 1:35:12
  they're big boys, right? But at the end of the day, you know, you can, you can either become
• 1:35:21
  their best friend if they make a lot of money or if they lose their money, you can lose friends.
• 1:35:26
  And you often understand that that might, you know, is that worth it for you? And I don't know,
• 1:35:33
  I feel like if you're a good investor, why would you want other people's money other than
• 1:35:38
  to leverage it, I guess, you know, like, but, you know, again, it goes to when's enough enough,
• 1:35:46
  right? If, you know, like, even if you look at like Renaissance technologies or these other guys,
• 1:35:52
  like, their best fund is their medallion fund. They're only, they're the only ones that are in
• 1:35:57
  that fund. It's only their money. I didn't know that. Yes. Yes. So they use other money, other people
• 1:36:03
  for their, for their shitty or other funds, which is right. But like, you know, if you look at,
• 1:36:11
  if you want to know what fund to go into, see how much money of the principle is in that fund.
• 1:36:19
  And that'll probably give you a good indication of whether that's a good fund to go into.
• 1:36:23
  That's good advice. Yeah. That's very good advice. Yeah. What do we not talk about? You went to a
• 1:36:28
  lot of different things. Oh, man. Went through the whole, you went through the whole June bug
• 1:36:32
  journey, easy texting journey, investment. I think you and I have a lot of, you know, kind of
• 1:36:39
  synergies in the, in the health and wellness portion of things. Try it. You got to, got you into
• 1:36:45
  a, got you into sauna. Yeah. Through Gary and cold. You have like, you have like a routine that's
• 1:36:51
  worked well for you, like for just, just, I guess, just operating at your best self highest level.
• 1:36:58
  Yeah. I mean, I'm 47. So the thing that had the most thing for me is TRT actually. I did TRT
• 1:37:09
  and it really changed everything for me. I think very, very low dose. But it really, at my age,
• 1:37:16
  it makes a huge difference in, in the way you feel and your energy levels and getting results
• 1:37:24
  from your workouts and that kind of thing. I think men don't pay attention enough to their hormones
• 1:37:28
  and their health. And they think they're just like feeling shitty as you get older is normal.
• 1:37:32
  Yeah. Listen, I mean, I've aches and pains in places I never had before. You know, I've tried
• 1:37:40
  some things like peptide therapies and stuff. Didn't really work for me and I did NAD. I've done
• 1:37:45
  it, tried a lot of stuff. TRT's had the most significant real world impact for me. And it was
• 1:37:54
  like not even a significant though, because as men, like your testosterone does decline, like
• 1:37:59
  the epicotally, it's not like a small increase makes a huge difference in the way you feel,
• 1:38:05
  the way you function, your sleep. I started taking magnesium pills before I go to sleep and I changed
• 1:38:12
  my sleep a lot. That's another thing that had a big, big effect on me. Hot cold therapy,
• 1:38:22
  definitely. Although I haven't been doing it as much. You told me to get a sauna in here,
• 1:38:25
  so we can do the podcast. We'll do a sauna podcast. You should do that at Gary's place.
• 1:38:30
  Yeah. He would be so dappy. I would love it. He loves that sauna, man. I have one in indoors in
• 1:38:38
  my apartment that I use. It's like an infrared one. I got it right before COVID, so I got lucky.
• 1:38:45
  No, I'm trying to think. Did you start taking care of yourself after you sold?
• 1:38:51
  Were you so focused into the business that you were letting your health help laps?
• 1:38:54
  Yeah. I mean, I never knew you back then, so I don't know.
• 1:38:57
  No, yeah, I did. And then even after I was so used to that, and then for me, actually,
• 1:39:05
  this is interesting. I think this might be valuable to the people who were really saying.
• 1:39:12
  At 40, I was, and by the way, I've never been really overweight. I've been pretty
• 1:39:18
  inshate. I would work out maybe not so often, but I would work out. At 40, my doctor took my blood,
• 1:39:28
  and my doctor was like, you're pre-diabetic, and I'm like, what? I'm a pre-diabetic. I'm not fat.
• 1:39:34
  I mean, I didn't even really eat that much.
• 1:39:36
  Like, re-salear sizes, you are right now?
• 1:39:38
  Maybe, like, 10 pounds out here.
• 1:39:41
  Not, yeah, not huge. You know, I'm six, one, so 10 pounds isn't there.
• 1:39:46
  He's so crazy. And so, I got scared, because he's like, oh, you got to go on diabetes medicine.
• 1:39:54
  And I didn't know, by the way, met for a man. It's like, it's a longevity thing now.
• 1:39:59
  So people take it regardless of whether having diabetes or not, but I was really scared of it.
• 1:40:04
  And I was like, holy, why were you pre-diabetic if you weren't overweight?
• 1:40:10
  He, there was no good answer to that. Maybe because of the food, I was eating too much process food.
• 1:40:16
  I was also not working out as much. I wasn't taking care of myself. You know, I was,
• 1:40:21
  were you, I was the RT that?
• 1:40:22
  No. So your testosterone is going down, and then yeah, but I don't think TRT actually does
• 1:40:27
  anything for me.
• 1:40:28
  No, but if you lose weight or whatever, then absolutely. Yeah, if you lose weight,
• 1:40:32
  you gain muscle. It helps with your, with your, with, with your blood sugar levels.
• 1:40:39
  So then I was like, I got a reverse this. He's like, there's no way to reverse it.
• 1:40:43
  That's what the doctor told me. You have to take medicine and you have to
• 1:40:47
  kind of lower the amount of carbs and sugar that you eat and also work out more often.
• 1:40:54
  So I did a lot of research and I found this thing called mastering diabetes,
• 1:40:58
  which is actually a program. And I went on the program and the program was
• 1:41:05
  counterintuitive to anything you could imagine. It was low protein, low fat, high carbs,
• 1:41:12
  whole foods, no oil. Okay. Okay. And by the way, you know, like rice and potatoes all day,
• 1:41:19
  like what were you eating? I was eating pasta with tomato sauce that had no oil. It would make
• 1:41:22
  the tomatoes. I would, I'd buy strained tomatoes and I'd put herbs and spices in it.
• 1:41:28
  I was eating commute bread with peanut butter in the morning. I would have salads, obviously.
• 1:41:37
  Rice, brown rice, potatoes, whole wheat tortillas. They have the single force over knives so you
• 1:41:45
  can they had all these recipes that you could like but like it was it was it was also vegan.
• 1:41:52
  So they didn't want you to eat animal protein because it's it's it's a little counterintuitive,
• 1:41:57
  but it was developed by type one diabetics that are biochemists and type one diabetics they don't
• 1:42:04
  produce insulin. So it's a different kind of diabetes type two is like what I had where you know
• 1:42:10
  um I was what's called insulin resistant. And so my body made the insulin but it wasn't
• 1:42:17
  updating the insulin. And so they came they they understood that that what happens is when you
• 1:42:25
  have too much fat and to a degree protein but by different mechanism it goes into your cells
• 1:42:33
  and it denatures the cell membrane to to a way that where insulin binds to the cell
• 1:42:40
  membranes it can't buy it by and properly and so you become insulin resistant when your
• 1:42:47
  your your your cells are full of fat. And so there I they're saying like oil for example
• 1:42:54
  any kind of oil I'm not talking about just olive oil or any any kind of oil is actually
• 1:42:59
  considered a process food because as a practical matter you're not supposed to sit down and have
• 1:43:04
  25 olives with each meal. You think about it. Yeah right. Yeah you know when you say it a lot
• 1:43:11
  it makes sense. Yeah like like what that's what you're doing you you coat your food with oil
• 1:43:15
  you add oil on your on your salad or olive tree right behind you. Yeah you dip your bread in oil
• 1:43:21
  yeah you know and and all this stuff and so and also half your calories come from that.
• 1:43:26
  It's the most condensed amount of calories you can imagine and so if you can even if you can
• 1:43:32
  simply just do that part it makes a big difference. I got down to like 7% body fat in six months
• 1:43:40
  I was ripped. I never I'd never been that ripped even in high school and I was really ripped in
• 1:43:46
  high school and this was no protein though so what are you very low protein I would have plant
• 1:43:52
  protein shakes so you could have plant protein shakes and were you working out. Yeah I worked
• 1:43:57
  out every day I was lifting of four times a week but I got crazy and I wasn't on TRT by the way
• 1:44:06
  at that time and I got crazy crazy hard to get ripped if you had low testosterone. So then as
• 1:44:13
  as I got those results I started looking into other things that I was doing and then I started
• 1:44:19
  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
• 1:44:25
  to eat out and not have oil you if you try and do it you'll see how much oil goes into every food
• 1:44:34
  that restaurants give yeah that will they make it they make a taste with they the vegetables are cooked
• 1:44:39
  in butter and butter butter it while the cake is injected with butter and yes so so unless you're
• 1:44:45
  bringing your own food or preparing it at home which is also a big pan in the ass which I did
• 1:44:53
  but I also brought my blood sugar down my A1C down that my doctor was baffles he's like how did
• 1:45:01
  you reverse here it was this diet and I was a high carb by the way high carb a whole carbs
• 1:45:07
  whole foods whole carbs um and that you know and I and I take I still do mostly that kind of diet
• 1:45:17
  but I can't do it to the same extreme as I did before I had low back problems and some other issues
• 1:45:23
  but still I mean so this was like kind of like the start of your health journey which is
• 1:45:27
  which is awesome and then you then you went on TRT after that so now you're feeling like I mean
• 1:45:32
  and you don't have to be walking around a 7% like who who needs that I mean go
• 1:45:36
  I'm married with three kids yeah like I'm not like I'm not like a Calvin Klein model or anything like
• 1:45:42
  that dude you still look good I saw you posted a picture of a store on Instagram a while back
• 1:45:47
  and you're still pretty ripped like yeah I still have well TRT does that so yeah you get like
• 1:45:52
  you're still you know you can enjoy life yes yes it's also I have a very young baby baby so
• 1:45:58
  it takes up a lot of my time right now but like in terms of like energy levels what diet do you feel
• 1:46:03
  work because now you do TRT you work out you have a good diet you do hot and cold like
• 1:46:09
  sauna and whatnot and cold plunge I guess what's like the energy levels that you feel right now is
• 1:46:15
  you're I pretty much wake up around like 5 30 in the morning and I go to sleep on average between
• 1:46:22
  9 and 10 yeah it's just early yeah I do but like I need try and get the eight eight hours I put
• 1:46:29
  my kids to sleep and then I go to sleep pretty much I try to so I think that's a full day
• 1:46:37
  do you still keep the same diet or slightly modified it slightly modified I do eat animal protein
• 1:46:44
  I actually the thing that got me off of it is that I got COVID and I just couldn't recover
• 1:46:50
  without that animal protein for real I need I was craving it that's so interesting when your
• 1:46:56
  body's like super sick what it's looking for yeah and so I don't really read meat that often
• 1:47:02
  although I'll have a steak here in there I like chicken but I eat chicken you have fish and
• 1:47:06
  that kind of stuff and I eat out more often than I did before but what I was doing before that I'm
• 1:47:14
  trying to do now is that worked really well is I would look at the menu of where I'm going
• 1:47:21
  beforehand for like five minutes and I would pick what I wanted to eat before I was starving
• 1:47:30
  and so I would make better choices usually and like healthier choices and and I would
• 1:47:39
  I'd always end up modifying whatever it is that they have and making making a better choice
• 1:47:47
  because if you do it in the moment again it's emotional you're hungry it's all comes back to
• 1:47:51
  the decision making how to make better decisions yeah well this is this is where you're talking about
• 1:47:57
  right we were talking about so for your health and that kind of stuff I think you could do the
• 1:48:02
  eating out portion just as long as you're you know you're you're you're conscious of it right and you
• 1:48:11
  make deliberate choices yeah I think that I mean I've done that too like where I look at the
• 1:48:17
  the menu before I go out and I think it's just like I always try and like I try not be too severe
• 1:48:24
  with my diet well I mean like I'll focus on like eating healthy for 90% of the day or what or
• 1:48:30
  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
• 1:48:35
  care as much it just makes it a little bit it just makes it a little bit easier to live and be
• 1:48:39
  social and and go out and have fun and have friends and whatnot I mean especially Miami yeah
• 1:48:44
  it's very hard out all it's hot so I tried intermittent fasting I've done that it didn't do very much
• 1:48:50
  for me the benefits didn't outweigh the cost I think it's more of a psychological thing like if you
• 1:48:56
  just if you just don't focus on eating and you're drinking coffee or whatever and just going about
• 1:49:00
  your day and then you just have less time to eat well yeah of course you're gonna eat less calories
• 1:49:05
  unless you just try to force feed yourself which is I mean that's avoiding the whole point of it right
• 1:49:12
  absolutely but but you know I did I did some crazy things right any for three days or whatever
• 1:49:18
  we tried every diet I tried I tried what's the ritual that you is there like a piece of the ritual
• 1:49:23
  or the morning routine that really is like a little bit different or that you think people would
• 1:49:28
  benefit from outside it is waking up early working out is there anything else I reserve a certain
• 1:49:35
  part of my morning for my kids and and so um I mean I don't know if that's unusual because I think
• 1:49:43
  a lot of people love their kids and want to spend time with Lauren though yeah it really is and
• 1:49:50
  and I purposefully drive them to school so that they're like a captured audience I love that
• 1:49:56
  and I love and I don't like sometimes as a treat I let them listen to music for a little bit of it
• 1:50:03
  but I talk to them and and I listen to them and um it does it does a lot for them I think
• 1:50:13
  you know I talk to them about real things I tell them about you know my parents that are in
• 1:50:18
  alive I tell them about stories of things that happen to me when I was younger the they're interested
• 1:50:25
  in that I learned about um you know some of them are old enough that they're learning about money
• 1:50:31
  a little bit right now like they're getting their first debit card or you know yeah but mostly
• 1:50:38
  it's like talking about Harry Potter this is the other thing you know but it's like I mean it sounds
• 1:50:43
  so simple but you're just creating like this like this dedicated time for them yes yeah it also
• 1:50:50
  kind of centers you and makes you realize you know that this is what you're doing at all for
• 1:50:56
  because you know you're not going to be here at the end of the day and I think yeah and I think
• 1:51:01
  it's easy to lose sight of what you do it for yeah because all you have um is you know you really
• 1:51:08
  you really all you have is now I'm a very big I don't believe in legacy and those types of things
• 1:51:14
  I think like everyone's going to be forgotten they will I mean it's true they will be yes
• 1:51:19
  everyone's lean of England is already being forgotten so yes I mean there's nothing special
• 1:51:25
  about you or me um and you know you're special in this moment that you're on the earth to yourself
• 1:51:32
  and to the people immediately around you so you might as well make the best of it um but like to
• 1:51:38
  think of legacy and like you know all these other things I think that's um that's a lot of ego
• 1:51:43
  in this good advice if people want to connect with you and just like what like what do you want people
• 1:51:48
  to like where where are you going in the future I mean I guess if people want to look at the
• 1:51:53
  portfolio you're building but I think we're portfolio public yeah yeah I put on my website
• 1:51:58
  okay so if people want to connect you where did they go I actually have a contact page that I
• 1:52:02
  read every single email and I respond to every what's your website is it is chain name and chain
• 1:52:07
  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
• 1:52:15
  of emails and most of them are startups that are pitching me um and you know 95% of them
• 1:52:23
  is like I can tell immediately that they're not doing but I have a methodology that I think is
• 1:52:29
  different than a lot of other um people is that um I give them resources that I've built over the years
• 1:52:38
  of what to do to better themselves in terms of and I also give them uh resources in terms of
• 1:52:45
  list of other VCs that would be appropriate for them good that's super nice yeah and I mean
• 1:52:51
  it's better than the no response no yeah no well if someone has just taking the time to do it I
• 1:52:58
  might take me a week or two to respond to them but I respond to them um I respond to everybody
• 1:53:04
  really honestly because I was in their shoes uh and you know I think it's you know if you took
• 1:53:12
  the time to obviously unless a spam right I love it right but you know I'll take I'll take a few
• 1:53:18
  moments to respond to you and then it's funny because there have been some cold emails that I've
• 1:53:24
  gone where I've done major investments what would entrepreneur have to say to stand out or to be
• 1:53:30
  impressive outside of like right I can tell you whoever tells you it's this is not true if there's
• 1:53:36
  a way that you can find someone who knows me to recommend you to me that makes a big difference
• 1:53:42
  and that always makes a difference to everyone and if someone tells you that otherwise they're lying
• 1:53:46
  to you because everyone's looking through a filter of signal so if you know someone that I know
• 1:53:54
  and it's coming from them it's already passed some signal for me um the other thing is um
• 1:54:03
  I think if you you know you have to learn marketing and if you can in two three sentences
• 1:54:11
  get your point across and be impactful that grabs my attention I mean I'm human just like
• 1:54:18
  everyone else is right if I I'm going to skimming through these emails right and if I see something
• 1:54:24
  that catches my eye I'm going to be like do a double take right and that's that's you know
• 1:54:30
  a girl Shawnee did that to me a couple years ago um what was her company a learned a
• 1:54:36
  allergy which is a custom compounded nasal nasal allergy spray that's prescription so it's
• 1:54:44
  a telemedicine she had she had done her research she saw that we had invested in her posture
• 1:54:49
  fee that got bought by him which is um did the same thing for dermatology for like acne and latisse
• 1:54:56
  and that kind of stuff and she wrote this really amazing you know three sentence email to me
• 1:55:04
  and I replied to her and then she replied to me something very thoughtful back and I got on a call
• 1:55:12
  with her and I didn't invest initially I said listen you I really like you but this is a way to
• 1:55:18
  do thing let me introduce you to a couple other guys that I know very very very well I introduced
• 1:55:24
  them introduced her she was coachable she did and exactly what they said and then we ended up
• 1:55:32
  taking her entire seed round which is like a three million dollar round and doing it and now she's
• 1:55:38
  this super successful business super successful with all from a cold email all from a cold email
• 1:55:44
  and I also helped her get her a round done I introduced her to a bunch of vcs
• 1:55:49
  origin being one of them that that that did it which is one of the like top vcs and you know
• 1:55:56
  it's a it's a very it's a it's a very significant company you know two years later that's amazing
• 1:56:03
  so just I mean I don't get as many pitches as you do because I mean I don't put myself out there
• 1:56:08
  as an investor but I see it from the lens of people trying to get on the podcast and I must
• 1:56:14
  probably get 50 emails a day it's just insane but dude it's like walls of text it's just like
• 1:56:22
  four paragraphs no one's gonna read them no one can read this no one and and there's it sucks
• 1:56:28
  because I mean usually it's the founder reaching out themselves but for me it's these agencies
• 1:56:33
  that I know people are paying these huge retainers to to get them on podcasts and they're just
• 1:56:37
  doing the shittiest job so I I learned this and you must have dealt with this when you were trying
• 1:56:43
  to do a book tour couple years ago so actually I didn't end up doing it I sold a good amount of
• 1:56:49
  the book but this book was never meant to to be like I know it's a money loser it was never a
• 1:56:54
  money maker for me it was a passion project I actually the reason why I built the even wrote
• 1:57:01
  it is because I dealt with so many founders and I was giving them the same advice over and over
• 1:57:07
  again and I'm like hey I could just write a book on this and how do I write a non cliche book where
• 1:57:14
  you're not hearing the same shit that you hear from everyone else so I was like hey I I think it's
• 1:57:20
  kind of interesting to take this nightlife approach have some interesting stories in it and then
• 1:57:27
  and then kind of give you how I learned those lessons and how I used it in easy texting and then
• 1:57:33
  how I use it in venture now so at the end of each each each chapter is a lesson at the end of each
• 1:57:42
  chapter I actually show you how I used it again so you know it's it's pretty practical in that in
• 1:57:48
  that manner um but you know I learned in easy texting when I first tried to sell this to people
• 1:57:59
  I did the same thing I wrote I made these like white papers and I you know like how to chart
• 1:58:06
  and I would send this like two page email to people and it was crickets and and then I was like
• 1:58:15
  wait I had a conversation with the guy this Israeli guy actually on the phone and I started
• 1:58:22
  trying to explain to him what easy texting is he's like he's like don't talk to me like that
• 1:58:28
  just tell me what it is you have you have one minute to tell one second to tell me what it is
• 1:58:34
  Israeli yeah and then I was like how do I tell this guy in one sentence how can I pull
• 1:58:41
  boiler down to one I was like it's impossible but then I was just like I just blittered out I was like
• 1:58:46
  I have a way that you can automatically get everyone's phone numbers and then text them the next day
• 1:58:50
  or the next week about your next event or your next sale he's like really and I was like he
• 1:58:58
  thought it was like some automagical machine yeah but you put it in like here you're you're
• 1:59:03
  thinking it like sucks everyone's cell phone number you're like this guy like I I had like
• 1:59:09
  hit a nerve with this guy and I'm like holy shit if I could I was like yeah do I'm gonna show
• 1:59:15
  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
• 1:59:20
  so I got you know at that at that time you have to it's 2005 there wasn't even zoom
• 1:59:25
  so I was just like log in use these credentials you know I had a demo account he sent himself a
• 1:59:32
  text message and the light bulb went off and then I was like I'm doing this all wrong I'm doing
• 1:59:40
  this all wrong so I changed it to two sentence email exactly what I said you know with a catchy two
• 1:59:48
  sentence two word you know subject and I was getting demos left and right and the minute I would
• 1:59:58
  demo someone it was a 90 percent close rate people over complicate business absolutely absolutely
• 2:00:05
  and it wasn't like I was doing anything special you know it was text messages stuffy
• 2:00:11
  social for real yeah I know but it's it's it's like the it's like just simplifying it just
• 2:00:17
  a simplified simplified yeah no one's gonna read it they you're busy look at how busy you are
• 2:00:23
  no one's gonna read it you you literally have to think in 160 characters like Twitter
• 2:00:29
  in this day and age I think always I mean I still don't get how people because I get I get hit
• 2:00:35
  up on LinkedIn with these paragraphs I get hit up with email with these paragraphs and it's just like
• 2:00:40
  it's too much it's too much but but when somebody says something like hey this is what I've done
• 2:00:49
  this is what I can talk about oh and by the way I left you like a review rating your podcast five
• 2:00:55
  star like literally three sentences and it would stand out from everything else I'd be like oh
• 2:00:59
  shit thanks for the review thanks for the rating and thank you for telling me exactly what you've
• 2:01:03
  done in one sentence that's it and it may be maybe the only other thing that you could add would be
• 2:01:08
  like a link to a show that you've done before so I can watch absolutely so simple absolutely
• 2:01:13
  and you should make sure your profile is well done yeah because I will click on your profile and if
• 2:01:18
  I see this like you haven't sat down made your LinkedIn the like look to the holistic yeah possibly
• 2:01:25
  be yeah then what you know if you're not you're not you're not spending time on yourself why would I
• 2:01:30
  spend time on you yeah so funny yeah just some of the and I don't understand why people still
• 2:01:37
  try and do pull that reach the way that they do with these walls of text and it's so it's so
• 2:01:42
  ineffective it it is it is but it's it's you know it's an acquired skill is that how you I was
• 2:01:50
  actually going to ask you isn't I forgot to ask you before sorry what were you gonna say I said
• 2:01:54
  you know that's that's probably one of the most important skills the founder needs to have being
• 2:01:57
  able to sell in market of sell themselves thousand percent I was gonna say um the lot one of the
• 2:02:03
  questions that about easy texting because you grew it so large without um that a big team
• 2:02:08
  was there like a lesson for entrepreneurs about how you grew it because you didn't jump on
• 2:02:13
  demos of 10,000 people you probably did a lot of another Paul Graham I did it through I did it
• 2:02:18
  through product I was like I got a sage stay true to the name of this thing easy texting and if
• 2:02:25
  it's not easy that like my grandma can log in and know how to send the text message then we're
• 2:02:32
  doing something wrong and the although I couldn't do demos for people we made itself sign up like
• 2:02:38
  mail mail chimp like itself serve like like yourself sign up yeah yeah yeah yeah yeah you put your
• 2:02:43
  credit card in and then you can you can you can use it we give you we're like a free trial and then
• 2:02:48
  just like any other sass business right um but we made the product at that time and you have to
• 2:02:56
  realize this 2005 like we had when you would come in you'd get a product tour like a demo like
• 2:03:02
  that's pretty commonplace now but it wasn't done before and I would end up doing a lot of the support
• 2:03:09
  tickets myself because I wanted to know what's wrong with the system that someone couldn't figure
• 2:03:17
  out how to do something and how I fixed that through the software so that we would get less support
• 2:03:25
  tickets so you were actually you were looking through and you were just looking at the biggest problems
• 2:03:29
  people had and then you were you putting down the product roadmap I did I spent hot like at least two
• 2:03:37
  days a week doing tickets and picking up the phone really listening to the yes you find that you
• 2:03:43
  find a lot of founders don't like doing the hard work yes that's a shitty job dude no one wants to
• 2:03:48
  do it but you don't you what you what you have to what you well it depends on what stage you're in
• 2:03:55
  you know a lot of founders are doing every job right when they're very very young but in order to
• 2:04:02
  kind of I think to keep the magic going you have to stay as low to the ground as possible you
• 2:04:09
  know you can't lose sight of what made you successful um and you'll have to constantly be in fear
• 2:04:17
  of losing it and and improving for real you do I I did something even more interesting I was
• 2:04:26
  afraid that people were going to realize how good of a business this is I white labeled the software
• 2:04:32
  and created six or nine other websites like club texting church texting this texting that were
• 2:04:42
  like front-facing websites and then I rebranded the software to that and then I read ads
• 2:04:48
  against myself so that when you would text search for text messaging software there wouldn't
• 2:04:54
  just be easy texting because that's what was happening like I wanted people to think that this
• 2:05:00
  is like a real market and there are competitors but so they wouldn't enter the market so funny
• 2:05:06
  I've never heard that before I've never heard anyone do that before so you created your own
• 2:05:11
  fake competition it didn't make a lot of sense to people but it made sense to me I actually do
• 2:05:16
  think it makes sense at the time it didn't make sense a lot of people because I was ending up
• 2:05:21
  paying double or triple for the clicks because someone would click on like three of them instead of one
• 2:05:26
  especially for paid paid clicks and at that time you know there wasn't so much social media advertising
• 2:05:32
  there it was mainly through Google AdWords right and so but I'm like you know what I'd rather
• 2:05:37
  pay triple for that person and then you know like no and no competitors come into the market yeah
• 2:05:45
  I even like made all different kinds of things like I made a version of the software that was
• 2:05:51
  like had limited functionality and we called it like cheap texting so it was like half the price
• 2:05:58
  you know so look like there was real competition that's really funny what are other like
• 2:06:06
  what's like another way that you like growth hacked it because you growth you you hacked your
• 2:06:10
  competition what's another way that you like because obviously okay so like boots on the ground
• 2:06:15
  you're a founder your answering calls you're doing support tickets cool you understand what's
• 2:06:19
  that working you build into your product you made it see it as a whole market when there wasn't
• 2:06:25
  what are some other like growth hack things that you did they were really good because I know you
• 2:06:30
  did a lot with Junebook but I think I know less about easy text we decided to do
• 2:06:34
  were you you know you don't really need to read reinvent the wheel we realized was like if you
• 2:06:41
  look at MailChimp or you look at like uh constant contact how would you find out about MailChimp
• 2:06:47
  or constant contact you you get an email oh yeah at the bottom it would send sent by MailChimp on it
• 2:06:53
  you know how mail did that how mail did that it said like made with love uh yes and that's how they
• 2:06:59
  so what we did is we couldn't like really we tried this thing where we gave a free version that
• 2:07:06
  would say easy text thing on the bottom or discounted that didn't really work out really well
• 2:07:11
  but what we did figure out is is that people were looking up the phone number that it was being sent
• 2:07:17
  by they were googling it so then we created landing pages for anybody and and and it adds for
• 2:07:26
  anybody searching for that phone number how did that so when they search that phone on google
• 2:07:32
  they would what would the landing page say it would say start texting through you know easy text
• 2:07:37
  thing and build and then that's how you brought them in that was your funnel correct so like we
• 2:07:41
  realized that that you know because so so so people would look to see what that phone number was or
• 2:07:46
  how to reverse engineer how someone sent it that's so funny so I mean like you have to know like
• 2:07:53
  you were so in the weeds though you understood the customer's behavior like I was the customer
• 2:07:59
  initially if you think about it for June bug right so so I I was we were we were like we took the best
• 2:08:08
  we we literally just took the playbook of what the ESPs did and just learned from the best of what
• 2:08:13
  they did really good customer service a phone number date people could call like constant contact
• 2:08:21
  was different than MailChimp because you could call them and they would help you on the phone
• 2:08:25
  MailChimp would only do email um cost effective easy to use you know like the three things for us
• 2:08:37
  was like you have to be the three things of the software that had to always be working
• 2:08:43
  and 24 hours a day was sending receiving text and paying if those if those three things work
• 2:08:53
  everything else it's like secondary tertiary to it's like there's the bells that we called
• 2:08:58
  the bells and whistle yeah yeah that they're just extra people want to send and receive text and
• 2:09:03
  pay for it and that's it there were you ever were you ever I mean like looking back obviously
• 2:09:09
  there's tons of opportunity and you could have taken this and put it into any industry but
• 2:09:12
  did you ever think about taking like June bug and just putting it into any other industry like
• 2:09:18
  as you had this whole little like business at a box no I think that it was so evergreen at that time
• 2:09:24
  I mean we could have done more and more events and we could have done more and more stuff you know
• 2:09:29
  that that it would have for easy texting I really um well initially we had called the club
• 2:09:34
  texting and then we changed it to easy texting because because I realized that this is not just
• 2:09:39
  for nightclubs right and so I kind of I had the vision that developers would integrate texting
• 2:09:49
  into all their stuff um into all their software and so we created an API initially but Twilio
• 2:09:56
  did it much better than we did um they they only went after the developer I'm thinking of Twilio
• 2:10:01
  and Twilio is like a huge huge company now yeah it is well so is easy texting it's a really big
• 2:10:06
  company now very big company are you happy that you saw when you did absolutely I mean would I
• 2:10:12
  have made more money who knows probably yes I don't know or I might have died I mean like when
• 2:10:21
  when the options they die or make more money I don't know maybe I would have had a hard attack
• 2:10:25
  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
• 2:10:34
  experience my daughter growing up my son growing up that's important uh no no uh I don't regret it
• 2:10:41
  and and in part of you know part of making good decisions is knowing when to to to to to to to leave
• 2:10:48
  the party which is the last actually the last chapter of my book you know it's it's it's knowing
• 2:10:56
  when to leave the party right um it's a hard thing to engage when is the right time to leave
• 2:11:04
  when you're on top when you're sending to the top when you're starting to descend from the top
• 2:11:09
  how do you know that you're at the top you know did you think about that as you were building
• 2:11:14
  this seems like your exits actually just sort of came out you fast like yeah yeah I think I think
• 2:11:20
  for me it was more practical approach to things but when you talk to founders or you invest and
• 2:11:25
  do you tell them to think about that life cycle of the company you had to absolutely because at the
• 2:11:30
  end of the day I'm investing to make money I'm not investing to support someone's lifestyle
• 2:11:35
  aside charity no I know I know I know so like you know like I'm trying to make money just like
• 2:11:42
  they are to my when you invest in them do you agree on like okay so this is how long we're going
• 2:11:48
  to be in this together well yeah obviously if it's early everyone knows no one knows one knows
• 2:11:54
  what the hell is going to happen if you want to the founders should still be the founders should
• 2:11:57
  still be they should know if they're going to look at a strategic or they want to sell the private
• 2:12:02
  equity or if they're going to take it to IPO well they should know I think it's hard to tell in the
• 2:12:06
  very early stages to be honest but if you look at the companies at the early stages that are getting
• 2:12:13
  the highest valuations they are typically the post-exited founders so they've either had one or two
• 2:12:22
  exits before and so they've built a track record and so as an investor you feel you're willing
• 2:12:30
  to pay a premium for that because you know they know how to and I guess you trust the you trust
• 2:12:36
  them a little bit more to figure it out absolutely and they know that an exit needs to happen
• 2:12:43
  right eventually eventually all right last thing I always like to ask is you know you've had great
• 2:12:52
  career built several companies one not so successful two very successful now you invest you know
• 2:13:00
  now you're focused on family if you go back and tell your 20 year old self one lesson what would
• 2:13:05
  it be I would learn how to have invested earlier I wish I knew how the mechanics of investing
• 2:13:13
  the importance of investing what compounding is because I never did that
• 2:13:19
  during dream bug and easy texting I invested in my business but you never took off the money
• 2:13:24
  of the table and put it into other investment no and had I done that I like by the way I'm not
• 2:13:30
  complaining in any I'm very fortunate person in my life despite some really bad things that
• 2:13:37
  happen to me but if I had done that I would have been in like whole other level and it's very hard
• 2:13:47
  for a 20 year old to understand how much can happen in 10 to 15 years and how much money can compound
• 2:13:58
  and I just not even done anything that's sophisticated just bought SPY maybe even just you know
• 2:14:07
  bought a piece of real estate or you know anything and just let it be and just did it consistently
• 2:14:15
  um I wish I had done that because I build profitable businesses and I could have done it but I
• 2:14:24
  didn't I always saw my business as my source of wealth so you just got very good at making money
• 2:14:32
  correct I thought that that was the way that you make wealth not investing absolutely yeah that's
• 2:14:38
  a good lesson too and that's also why again it's like just because you're a good business owner
• 2:14:42
  entrepreneur doesn't mean you're a good investor no because because it's so counter to what
• 2:14:47
  business owners do investing you just it's hard to make that first leap of putting the money in
• 2:14:55
  but the more you do after you put that money in the worse your outcome exactly so it's and in business
• 2:15:00
  you gotta do you gotta keep yes or you dead yeah so it's the opposite it's like just stop
• 2:15:08
  yes put it in and shut off yeah that's it just put it in an sdf you and like
• 2:15:16
  and like just keep doing it and then wake up in 15 years and be like holy shit I'm glad I did that
• 2:15:24
  you know so um it's not a regret obviously but if I could give myself a piece of advice
• 2:15:33
  that's a piece of advice um and and I don't know maybe have a little bit more fun
• 2:15:40
  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
• 2:15:48
  didn't have the kind of fun that people would think that you uh I think that kind of fun is
• 2:15:52
  overrated yeah I think that that kind of fun gets Scott Harrison had a lot of that kind of fun
• 2:15:58
  and I think and I think that it gets old pretty quickly yeah absolutely I get a little pretty quick
• 2:16:05
  I think that what you've optimized for in your life which is business success but then
• 2:16:10
  ultimately family I think that's the most fulfilling thing you can ever optimize for well that's
• 2:16:16
  that was the thing I actually got married and had kids latest out of all my close friends from
• 2:16:21
  growing up you were still young you were still young um I had my first child when I was 37
• 2:16:28
  that's pretty late I think um and I got married just a few years before that
• 2:16:33
  so um I was like seeing my like cousins or whatever my friends had kids and I'm like all right
• 2:16:41
  you have fun going out tonight you know like their kids were cute and stuff but like I didn't get it
• 2:16:46
  but like having a kid is experiential it's impossible to explain it to someone
• 2:16:53
  and so I get it now obviously but what you're going into clubs every night you were even doing
• 2:16:58
  clubs the way a lot of people do clubs because you had these long-term girlfriends but if you're
• 2:17:02
  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
• 2:17:07
  out late anymore for like oh no and you also you also when you're in work mode and founder mode
• 2:17:13
  you're very selfish you're very selfish I was very selfish absolutely and that's why I think
• 2:17:19
  it's important that I mean okay so fine you're not going out you're not partying but as an
• 2:17:23
  entrepreneur you're going to have kids you have to realize that something else is going to take
• 2:17:26
  all your attention and I actually I'm like actively even like for myself like I'm actively
• 2:17:31
  understanding that okay I work a lot now but I'm trying to architect something it doesn't take
• 2:17:36
  so much of my time so I can be present yes so now I actually give up a lot of my opportunities
• 2:17:44
  because yes I mean there are opportunities that I have lost that I could have made an incredible
• 2:17:50
  a return on but at the cost of you know not having time to do the other things that I want to do
• 2:17:59
  and spend time with my kids.