The Pomp Podcast - #1198 Anthony Pompliano Reveals His Investing Secrets

Episode Date: May 16, 2023

This episode is a special one. I went on a podcast called 'Under The Timfluence' hosted by Tim Luong. We talked about the financial economy, my life, creating content, building business, investing strategies, & much more. Anthony Pompliano shares his journey from army veteran to successful entrepreneur and investor. He emphasizes the importance of surrounding oneself with knowledgeable people and constantly learning new skills. He also discusses the impact of easy money on society and the need to constantly reinvent oneself and make connections across industries. ======================= Pomp writes a daily letter to over 235,000+ investors about business, technology, and finance. He breaks down complex topics into easy-to-understand language while sharing opinions on various aspects of each industry. You can subscribe at https://pomp.substack.com/

What's up everyone? This is Anthony Pompliano. Many of you know me as Pomp. You're listening to the Pomp Podcast, which is my effort to find the most interesting people in the world and sit with them for hours while I ask questions in an effort to learn. We have no advertisers on this podcast, so it would mean the world to me if you would subscribe to the show on your favorite audio platform, watch episodes on YouTube, and tell your friends and family about the podcast. My goal is to help millions learn from the world's most interesting people. So let's get into today's episode. What's up, guys? This episode is a special one. I went on a podcast called Under the Tim Fluence with Tim Lung. And in that conversation, Tim asked me all

sorts of interesting questions, and I thought that you all would appreciate it. We talked about things in the financial economy. We talked about my life. We talked about how I create so much content, how I think about the internet, building products, building businesses, and much, much more. Here is my appearance on Under the Tim Fluence. Learn more at Accenture.com slash Spotify. Anthony Pompliano runs Pomp Investments. All views of him and the guests on his podcast are solely their opinions and do not reflect the opinions of Pomp Investments.

You should not treat any opinion expressed by Pomp or his guests as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of his personal opinion. This podcast is for informational purposes only. Awesome. Well, welcome, Pomp. So nice to have you. You're super close here in Miami with us in Coconut Grove. So appreciate you coming on the show today. Absolutely. Thanks so much for having me. So I want to kind of jump

right into it. So I didn't even know you were in the army for how many, seven years? Six and a half years. Six and a half years. Yeah. What was kind of your story in terms of how'd you get into the army and then the big pivot into crypto? So I was in high school, graduated a semester early from high school was going to go to college in kind of the spring of my senior year. Ended up not doing that. Instead, enrolled in the Army, signed a contract that would let me go to school and have kind of Army reserve duty until I graduated. Then I would go active. And in hindsight, joining the Army was probably one of the best things I ever did, right? I was already pretty disciplined. I was pretty ambitious. All the things that kind of would make you either

want to sign up for the Army or be successful in the business world or whatever. But it really kind of hammered home I think two things for me uh one is like there's like this um understanding of mortality that comes especially if you get deployed and things like that and so uh at a very young age it was like oh shit I like I see the end right and so okay between now and the end uh I just want to enjoy my life and kind of do all this you know really fun cool stuff that's uh fulfilling for me but like I'm not confusing that I have forever and so it really set me on a path to like just do a lot of things um which I'm grateful for and then the second thing was uh it basically showed me just like how much stress you can endure how hard you can work um and kind of how to in my

mind like operate and so when you get pushed to the extreme uh in these situations like everything else seems pretty easy so one of the things that's always funny is like if you talk to uh you know combat veterans who went to iraq or afghanistan over the last you know 20 years or so uh in the business world people be like how why aren't you stressed and like a joke is almost like well no one's shooting at me right and so like it's kind of this weird thing where uh once you get to the extreme anything that doesn't actually put you in that extreme situation seems easier now it doesn't mean you make all the right decisions doesn't mean that you know you never are stressed it's just like you have this baseline of no real stress is something else and so i think that's been a great

thing for my career as well that's amazing so you you basically had a different you had a different understanding of what stress is for most people and so what what happened after college like how did you get to where you know where you are today I went back to school I tried not to go actually actually back to school my dad was like hey get your ass back here like do not try to go and sign a contractor you know contract and go back to Iraq or any of that stuff and so I started two businesses I started one when I was in school I didn't know what I was doing you know made a million mistakes we basically kind of barely got that across the finish line and

ultimately sold it second one was a little bit more successful and we're able to kind of really put ourselves in a position where i started okay like i'm picking this up right i'm understanding how do i recruit people how do i build products how do i do market research how do i actually uh convince people to give me money for uh you know as a customer things like that yeah but it was still clear to me that i didn't know how to scale right and so it was like okay now like i'm not an expert but at least i can go kind of zero to one and i can kind of get these things off the ground but how do you scale how do you build a big business and so i had this choice was to make, I could either go and, uh, you know, get an MBA and kind of like pay to, to get an

education, or I could go and have someone pay me. And so I ended up joining Facebook, uh, 2014. I was there for two years and it was like a crash course. It was, you know, again, probably one of the better decisions I made in my career because it just put me in the room with people who are world-class at what they did. And nobody like sat me down and was like, here's the curriculum, right? They were basically like, Hey man, you got to provide value around here. Right. And so at a, I think I was 25 when I joined at Facebook and they gave me way more responsibility than they probably should have. And so it was kind of like sink or swim, but because you're around these world-class people, you can kind of ask around, you know, the edges for advice on certain things

or, Hey, I'm dealing with the situation. How do you think I should handle it? And what you do is you pick up through osmosis. And so like, that was a lesson for me of like, okay, the rest of my career, I always want to be around people who have either done something I want to do, or I want to be around people who have knowledge that I want. And if I can just pick it up through osmosis by being around them that is like you know uh learning on steroids and so i've really been conscious over the years about how do i surround myself with those types of people uh because if you can continue to learn it's compounding right just like you can compound capital you can compound knowledge and you just pull away from everyone else because you just have more information

yeah yeah so would you say a lot of skills in terms of in the army i'm sure you had to build strong discipline like what you said and just be a sponge essentially that's that's what you did once you enter the workforce um and then what what was the decision for you in terms of like leaving facebook to start you know your own thing yeah so when i left uh facebook i mean basically uh i'd gotten advice early on in my career that was like you can stay somewhere for 10 years or you can stay somewhere and get two years of experience five times right and i was like oh that's interesting right so like even if you're somewhere 10 years you may actually only get like 80 90 percent of the knowledge in the first two years they just repeat that over and over again

that you don't actually keep learning. And so if you look at many of these kind of corporate jobs, usually that is about kind of the tipping point, right? Is if you stay past two years, you're probably staying for five, seven, 10 years. If you stay for two years or less, obviously you've moved on to something else. And so I just got to the point where I was kind of antsy and like, there's a fine balance between being a young person and constantly like grass is greener, you know, and having that antsy feeling just make you want to do something versus sticking with it. But again, in hindsight, I think it was probably the right decision. because I had learned probably, you know, 70, 80% of what I was going to learn from Facebook.

I went and I spent a little bit of time at Snapchat as the head of growth and then eventually started investing full time. And the investing was really like, I didn't have an idea of another company to start. And so I was like, well, maybe I can just like help other people with their companies. And then I'll get an idea over time and I'll start another business. And then, you know, here we are almost a decade later. And now I'm like, oh, okay. Yeah, sure. We have businesses and we kind of do all the operating stuff, but like, I really love investing. And so we keep doing that you know kind of uh in parallel to operating the businesses got it got it and so you started investing and did you you didn't start off with your own fund you you worked at a fund

we started a micro vc fund so myself and my buddy jason williams um you know i mean like match made in heaven we met up one day for uh for a beer uh somebody introduced us um i think it's supposed to be like a 45 minute you know 60 minute thing we were there for like three or four hours next thing you know like people are calling where are you guys you know the whole thing yeah um and we just hit it off because i think we both were very ambitious we both were worked really hard um we both had uh some pretty good common sense when it came to business but we weren't subscribed to like all the bureaucracy and all kind of the bullshit right and so um you know at the time jason had this like massive beard and all this stuff and so we

were like all right we can work together right yeah and um when we got started really it was uh about a three and a half million dollar fund maybe three point three three point five million dollars uh and we were going around in uh the mid-atlantic region which is basically like raleigh north carolina yeah right they call like dc to atlanta but it's like basically everyone that we could find in middle of north carolina and nobody invested more than like 50 or 100 thousand dollar check like these are all like super small lp checks they're like doctor lawyers like whatever and you just don't know what you don't know right so uh i was uh going back and forth between Raleigh and New York City at the time. And there's not a lot of entrepreneurs

that are building big companies in Raleigh, North Carolina. So what I would do is because I had the network from Silicon Valley, everything was remote. So like now this big rise of like all the remote work, I didn't do it because I thought it was cool or because I thought I was ahead of the curve. It was just like, if I want to invest in the best companies, I got to find them. Right. And so rather than go and try to find the founders, what I did was I knew some of the investors. And so I started calling investors and being like, Hey, here's the deals I'm seeing. What are you seeing. And so naturally, you call the right people, they have good deal flow, right, you start to get the deal flow yourself. And so in that first fund, we invested in a number of businesses

that absolutely exploded in value. And so that was kind of an initial start to building a track record. The critique of that fund was, it's a three and a half million dollar fund, you two have no infrastructure, you know, you basically are investors, you're not actually asset managers, which is kind of a nuance. And so that's when we then did a partnership with Morgan Creek Capital and mark yusko and they had real infrastructure right they had a big team they had kind of uh we used to joke all the time they have a compliance team the finance team right like all these things that go into actually building a business versus just managing uh kind of a single fund yeah um and you know got a crash course of education there as well that's amazing and so when did you

pivot from basically obviously you run your own family office now but pivot from that to like you know putting content online writing on twitter yeah you know your youtube so um you know when I was at Facebook, I was into this very kind of unique position where I started out, I was the product manager running the growth team for Facebook pages, which way to think about that is like the page product is the top of the funnel for advertisers. So you have to have a page to become an advertiser. Facebook wants advertisers, right? So naturally they want you to have a page because that's one step towards becoming an advertiser who gets a page, small businesses, uh, influencers, celebrities, uh, you know, corporations and brands. Right. And so what

would happen is I kept getting introduced because of being in that position to all these people who had audiences elsewhere. So one of the first people that I actually got introduced to was the Instagram account, fuck Jerry. And so, uh, Elliot, Ellie, um, they were building out fuck Jerry on Instagram and they were like, what should we be doing on Facebook? And so as I got to meet some of these people, it was like, Oh, you have to figure out how to use Facebook to build an audience yeah and so just seeing it over and over and over again having access to the data understanding how the algorithm works etc like you just build a base of knowledge when i left that team it was to go join uh kind of a very small team that worked directly with mark zuckerberg

and cheryl sandberg to help them do the same exact thing i didn't go to facebook and be like oh i'm gonna figure out how to help people build audiences on facebook or any of that stuff it's kind of you know you find your way there and so with uh mark and cheryl what they wanted to do was basically they were very very early they don't people don't give them enough credit but were early to going direct they realized hey we have a billion people on facebook mark had like nine million followers he's like they're like how do i reach my own users right and he didn't want to do like tom from myspace where he like forced everyone to become his friend yeah yeah like i mean tom's cool right but like but mark i think it was like hey i don't want to do that yeah um

he also didn't want to really like change the product too much like you know we now see kind of all these controversies around these platforms that are like boosting somebody's content or down ranking somebody's content, he didn't want to change the product. So he's like, I want to learn how as a user to reach more people, right? Now he's Mark Zuckerberg. So people see his content, they know who he is. Um, and so it was a lot of testing, right? It was like, Hey, if you post a photo, uh, what's in the photo versus what's not and how popular is that? So, you know, uh, I don't think I'm sharing anything that, that would be a controversial, but like, uh, if he has his dog in his photo, people like that photo. Right. And so like, okay, like how do we incorporate that into

the content just like any other brand or content team would do yeah this back 2014 though right so he's really doing it so when i got to um uh investing what i realized was two things one if you want deal flow people got to know who you are if you want to win deals people got to know who you are right like what do you stand for who are you like all that brand building type stuff and two was i had no audience i helped all these other people build an audience but i'd never done it for myself and so the easiest platform for me was twitter because i could basically just you type something on my phone and go. Um, and so in 2017, I literally just worked my ass off. Right. And it sounds weird to say like, Oh, on Twitter, you worked your ass off. But I literally was

tweeting like 20, 30 times a day. I was doing everything I possibly could to build that audience. And I went from about 2000 followers to a hundred thousand. And that's when I was like, all right, there's something here. And I kept, and I tweeted it multiple times throughout the year. Like I was very clear with people, audience is the new currency. If you have an audience, you have massive leverage in this kind of new world we're moving into. And so over a five-year period, I went Twitter, email, podcast, YouTube, et cetera. And what I learned was not only is audience the new currency, but also it's the fastest path to learning

because you can put an idea out there, and Twitter specifically, like it don't take a lot for some troll or critic or whatever to immediately say like, hey, that's wrong. Great, why? Explain. And so you get test ideas very, very quickly, in the feedback loop is kind of tight. And so what you can do is you can iterate closer and closer to the truth. So if you can do something that isn't really that big of a time investment,

you get the leverage from the audience and you get the learning. It's like a grand slam. And so I just started to do that kind of coinciding with the investing. And, you know, I never thought I would turn into what it is now, but happy that it did. That's amazing. And so you started off with Twitter, you moved on to email. So you write a daily email, right? And then on top of that, what made you want to start the podcast on YouTube? Was it just to expand your audience or? No, there's no master plan. Like the podcast is a great story.

There's two guys, Jason Yonowitz and Mike Ippolito. They run a company now called Blockworks. They came to me and they were like, hey, you should have a podcast. And this was after they had like literally harassed me to come speak at one of their events in New York City. And it was one of those things where like, do you ever have somebody who like reaches out to you

so many times? Like you don't even know how you met them or why or what. But I finally was like, if you got, if I come to one of your events, will you guys stop texting me yeah right i know i know jason by the way okay all right so like you already know right and so they were like yes of course like yeah that's what we want let's come to the event yeah so i went and then they like kept emailing me and all stuff and uh they actually sent it to me uh recently uh my first email back to them was what is this what do you guys do

like like they were putting on the events but i didn't understand the business whatever yeah and so long story short they were like you should have a podcast i was like i don't even know what a podcast says they're like don't worry we know how to do a podcast and so like you know A great lesson for young people was I didn't know this. They had no clue about a podcast, right? They just knew that if they could work with me somehow, that would be great for them and for me to be a win-win. And so when I was like, all right, fine, I'll do a podcast, but I don't want to do anything. I don't want to deal with equipment.

I don't want to deal with setup, takedown, like anything. I'll find a guest. I just want to show up in the room, talk, leave. That's it. They had gone, I think, to Gary Vaynerchuk's guy who was running all the podcasting stuff, and they basically DMed him and been like, hey, we're going to start a podcast. What equipment do we need? figuring it out on the go yeah so one figure it out on the go but also two like that's a pretty good person to ask right and that person probably wants to help other people figure it out and kind

of help young people etc so like that story i think is really uh kind of a great lesson of just you know one find people that you can kind of work together with and it's a win-win situation two is like you just got to kind of figure it out right and then if you go back and you watch the first podcast episodes it is cringeworthy right like we had um a microphone and there was basically like a spit cover or whatever, like whatever it is. And it's so big that the way that the camera shooting, you can't see my face. Like, it's like, I might as well just have like a curtain in front of me. Right. And so you watch it and you're like, man, how dumb were we? Right. And it's like funny to laugh at now. Cause you learn over time, all this stuff, but it was the willingness to basically

do it and just put it out there. Like who cares? Let's see what happens. Right. Um, and so very quickly you start to learn, Hey, how do you get better at this? You talk to people and stuff, And then, you know, it kind of takes a life of its own, but I actually don't think this would have been successful if I had approached it from like a top down, I am going to build this media business and here's, we're going to have a podcast. We're going to have the, like, that's just not how I work. And so I think the organic kind of bottoms up approach was much better and ended up actually building something that was valuable.

Gotcha. Gotcha. So you're, you're very, like, I'm just going to do a bunch of things, test it, see what works and, and keep, keep throwing stuff at the wall. And then when something works, you know, double down. most people who work very closely with me uh it is uh if you ask them they probably would say it's my gift and my curse right um over the weekend uh somebody was dming me uh about twitter subscriptions and so like my reaction is on saturday right was like literally within 20

minutes i had set up and then i was just like hey i'm starting a subscription thing i'm gonna do a 30-day test let's see what happens right yeah and so like the violence of action of like idea execute, uh, can be very, very powerful. It also sometimes can get you in situations where you're like, should I, maybe I should have thought through that more. Right. And so you've got to understand that it's like a positive and a negative. Um, but for me it is, uh, uh, I have learned to do it as experiments rather than like fully commit. So in maybe 10 years ago, I would have been like, Oh, Twitter subscriptions. Uh, I am going to launch Twitter subscriptions. Here's exactly what I'm going to do every single week. Here's exactly, you know, uh, what the value is

you like very rigid kind of approach and guess what would end up happening is it probably wouldn't end up being sustainable because i would sign up to do too much or whatever yeah instead i said i'm turning on subscriptions i'm going to do it for 30 days i'm not promising anything i'm just going to test and see kind of what works a couple people subscribe i start talking to them hey what would be valuable how does this work where uh what are you missing in you know content that you would rather have like all the stuff and like already in four or five days we've iterated our way to like oh people are like oh this is not only valuable but it's so valuable i'm gonna go tell my friends yeah something here right now how big can it get is it worth doing past the 30 days we'll

see but i think that's like a great example of you know there's the top down approach i call that like the boardroom approach is next year we are going to go do international expansion yeah i'm very much take what i call like the street approach which is no it's like we got to go get this product out into people's hands and so i'm a big fan of uh kind of 90s and 2000s hip-hop um and if you go back and you look at you know whether it's the jay-z's of the world the 50 cents whatever like they literally just flooded the streets with mixtapes like that was the beginning right and so like what like what is the mixtape strategy in the digital world today you have to flood the streets with content or product to be able to build hype and grab attention then you take that attention

you capture the value like that is what people have been doing for decades if not centuries yeah it's just that in the digital world you can't use all of the old analog playbooks but you can take the essence of what they did and apply it to the digital world and so no different than like burning your cd putting it in a you know plastic wrapper and then going out into the streets and handing it out to try to build hype well what's the version on the internet it's probably iterating quickly to try to find things that work and then try to scale those right yeah yeah so how big is your team right now yeah um the team is kind of split across a bunch of different things so we like the operating businesses um i would say there uh there's more than 50 employees across

all the different businesses um on the investing side uh it's just me and my brothers uh which you know for better or worse uh has been highly effective in terms of small team and able to kind of deploy uh capital cc fit two brothers or how i have four brothers oh wow yeah so not all of them are involved day to day but um there's me and one brother specifically that like every single day are doing stuff yeah uh the other ones uh if you were to ask them they'd tell you they invest only in the good deals. So we do the work and they invest in the good deals. But when you think about on the content specifically, we basically have three people, right? We have two people who do audio and video, and then we have one person who helps with like

partnerships, marketing, sponsorship events, things like that. So those three people plus me is like not a very big team, right? Now they are supplemented with, you know, we have a director of finance uh we have somebody on the team who handles all the operational stuff like we have all these other kind of roles that really are kind of my family office and they go across all of our companies but on content specifically to you know audio video and then that kind of partnerships person in today's day and age you could probably do this without anybody for me though just given how much you know i've got other things going on i need people who are fully dedicated and focused on it and so having a team makes sense got it so you have your content team operating businesses

and then investing side yeah when i was younger i would do everything myself like again blessing and a curse i got a lot of done but how long can you do that exactly right yes and so i think over time i've gotten much better about how do i go find people who are great at what they do and delegate right which is like a classic problem for a lot of entrepreneurs um but also how do i go find people that uh i'm able to work with where they actually may be better at it than i am right So for example, with video editing, a lot of people would be surprised. I don't actually see most of the videos, the final edit before they go out. Now, if you were to talk to, you know, a Mr. Beast or somebody like that, like they obsess

over every single little detail, right? But that is the core of their business. For me, the content is something we do, but it's not, you know, we're not hanging our hat on it. If the content was the biggest opportunity, then I would just shut everything else down, right? It's one thing that we do. And so I trust the people who edit the videos and they do that.

every once in a while they do something i'm like hey let's not do that anymore whatever but i think that uh understanding where to invest your time and energy is really important but also understanding like what's the roi on that investment and so if i were to spend three hours interview or uh reviewing every single you know kind of uh cut of every single video what are we going to do get an extra 10 000 views yep like what does that mean in terms of you know impact on the businesses impact on the investments in terms of revenue like it's immaterial compared to everything else. And so when I look at it that way, it's like, all right, the team put them in a position to be successful, give them, you know, kind of the green light and then just go and

focus on the areas where maybe you don't have somebody that you can kind of trust to do that stuff and go do that stuff. Yeah. Do you have an operator running your operating business on a day-to-day basis or is that you right now? Each business is different. So if you were to think through some of these, I also think that not only is the structure different. So there's some businesses. Like we have a, a recruiting business, uh, that we own that recruiting business. We purchased, um, there's two guys, they run it. They're the original, uh, kind of founder and his first hire. Who's now kind of come into, you know, his right hand man, uh, role. Uh, they're fantastic. Like we do a call once a week, uh, for 30 minutes, they ask when they need help,

right. I give them ideas if I've got ideas, but for the most part, like they run that business, they do a great job doing it. I don't really need to be involved. And like, I always joke with them. I say, Hey, if I was running the recruiting business, the recruiting business going to zero, right like i'm not the guy to be able to go and do that and so understanding that they're better at it than i am i can just kind of give them we have a business uh in the research space a business called reflexivity research where uh we basically create research and then we sell it to hedge funds family offices etc uh that business is fairly new it's less than a year old i've been very very involved in helping get it off the ground i'm not doing the research right the research analysts

know how to do the research well actually what we need is to go to market how do we actually get this into people's hands i have the connections people know who i am you know i understand how to structure the deals like i'll be very involved yeah if i'm still that involved a year from now something went wrong yeah right and so like where we are in the sequence of a business is really important and then on the media side like for better or worse this podcast doesn't get recorded if you don't do it right same same for me is if i don't do the content it doesn't get recorded and so it's actually a bad business from like a day-to-day uh um you know kind of operational standpoint because like being a doctor or lawyer you got to touch the patient you got to touch the

customer. If you don't do it, you don't. So if you go and Robert Kiyosaki has this, like something called a cashflow quadrant, I think, uh, which is like a really old book. Um, but he basically talks about like, you're, you can be an employee. You can basically be like a, a, a small business owner. Uh, you, or I'm sorry, you can be an employee. You can be self-employed. You can be a business owner. You can be an investor. And he's like, most people operate on the left side of that quadrant. Uh, but they think, Oh, I went from employee to a business owner, right? Like, like I'm killing it. He's like, no, you don't own a business. You are self-employed. You just got yourself a job, right? You have to touch every client. You have to do the work yourself. Really,

what you want to do is you want to move into either the business owner role where you're not running the business day to day or into the investor role, right? And so that's where kind of true wealth ends up getting built. It's just hard for people to do that because the easy things to do are the self-employed opportunities where they're like, oh, I'll just do it. It's great to get off the ground. It was zero to one. How do you scale? You got to get into those other areas. Yeah. Got it. So what other operating businesses do you have aside from, from the recruiting firm and then the research firm? Yeah. So we have all kinds of different businesses. I think minority positions, like over 200 businesses, right? Now those businesses are everything from

what I would consider like kind of small business stuff to you know, venture capital investments where we own like 1% of the business. Right. So it's like, that's from your fund that you've invest in? Okay. I had, uh, uh, the original fund then did the, uh, the bigger funds now out of the family office. We made a bunch of investments. Right. And so, um, those are, you know, yes, we own part of the business, but like we're not involved day to day in operating or anything like that. Um, in terms of the core operating businesses, I would say that there's really kind of three different things that, uh, we have. We've got the media business. We've got a holding company of various products and services in the crypto industry. Uh, there's a job marketplace,

there's training programs for corporations, there's research, there's the recruiting firm, et cetera. So like all the things that are not necessarily tech products, but are needed for an industry to thrive. We've been able to put them together in a really interesting way where we can go to a company and say, Hey, we can help you find people. We can train those people. We can form those people, right? We can kind of do all these things that you're going to need, but you want to outsource rather than build internally. So that holding company kind of houses all of that. And then we've got another one that we've recently just started where we're trying to go and actually acquire all sorts of different businesses outside of the tech industry.

We'll see how it goes. But I'm pretty excited about it. Because when you go and you look at a lot of these businesses, like take the industrial sector as an example, you are absolutely selling painkillers, not vitamins. People need these products, right? And they're going to buy the products whether you exist or you don't. And so really, it comes down to how do you execute? It's all about execution risk. And why I like that is because most of the competitors, you know, there's one business that we've been looking at that involves a call center. And now that call center is in the brokerage business. So when I see that business, I'm like, man, how antiquated is it that people are calling into a call center, people are looking things up on their computer,

and then they're calling the people back with pricing. Why don't you automate it? Right? And so that's a perfect example where like that execution has already built a pretty big business. But if you can upgrade with technology, can you execute even better? And then you can actually beat the competitors because you offer lower pricing etc so can you go into these sectors where most of the people i talk to about this in the tech industry they're like dude what are you doing right like why would you ever want to go play in a space where there's physical items right or dealing with uh you know people who don't understand technology or whatever it's like yes that is a challenge but part of it is like there's very little competition you know if you kind of

subscribe to the teal view of the world of like you know uh competitions for losers like maybe actually going to compete in these markets where nobody else is really looking or no one's excited is actually the opportunity that is kind of largest and so we're kind of putting that together now and trying to figure out how to do it in a sustainable scalable way but that's the one i'm probably the most excited about because if we get it right we can just run wild throughout you know that whole industry got it got it and so for your crypto holding firm i know you said that there's a lot of different pieces in that you know you have your crypto you know training program as well the job placement program who who runs and manages that that day-to-day and like how do you guys

get clients yeah so i run the kind of holding company if you will um and that entails a couple of different products and we have people who are like the person responsible for something right we've got uh somebody who's the director of education on the training program does a fantastic job he's involved day-to-day uh talking to potential customers he's actually helping to deliver the content etc um then some of the other businesses have you know like a gm or ceo or whatever um when you look at that product specifically or that kind of holding company what's interesting about it is it's all actually really focused on people so when you think about people in the non-crypto world there's tons of products out there right but actually if you look

at what we did is we basically just took the market and said well what if we just all specialize this stuff for this crypto industry and so we've helped over 2 000 people get a job right and so when i think about like what like what gets me up in the morning it's like do you know how impactful it is to get one person a job. They go from, maybe they had a job, but they don't like it. Or maybe they had a job and they weren't getting paid enough. Or for whatever reason, to get them a new job that they like and that they feel like they're getting paid the value that they deserve is incredibly impactful for one person's life. We've done that 2,000 times in about two and a half years. And so that's like two to three people a day that we're helping get these jobs. And so

when you look at that, you start looking at the average salary and it's meaningful. And so when you kind of take that approach, it's like, man, what else would be more fun to work on than having this impact on people's lives? Now, I tend to always look at this stuff from the perspective of like, I actually don't care that much about what are the financial results on a day-to-day basis. Like if we help people get these jobs, keep them informed, keep them trained, do all these things, the money will come, right? And so it's really, really focusing on just like, how do we help the companies and the people find each other and kind of make that match? And if we do that correctly everything takes care of itself so in terms of like your your week to week how do you

how do you find time to you know balance health your relationship work business i feel like that's that's uh that's quite a lot of just stuff you're you're involved in i have no hobbies like this is what i fucking love doing right and so um if you think about uh a single day um one of the one of the things to take great pride in is if you were to talk to most people who have ever worked with me they'll be like dude i thought i worked hard like that motherfucker is unstoppable right and it's just because over time i've built up this capacity uh for an immense amount of work in a single day and so to give you a kind of a glimpse at it i pretty much will go from eight to four back to back no breaks right and it's 30 minute meetings just back back back back whatever

now i don't necessarily want to do that but we have so much stuff going on and i'm needed in certain things until i can get them kind of delegated to other people that i'll do that multiple days a week right then i'll basically i'll go home i'll take like a little break or maybe an hour or so and then i'm just right back at it until about eight o'clock at night and so when you look at that like man that's a lot but it's like yeah but what else would i do like this is so much fun yeah right and it's like a lot of people are sitting in their corporate job and they're like man i can't wait to get out of here and go to the golf course i'm like dude i don't give a fuck about that right like i can't wait to get on this next call right i did a call yesterday

with somebody uh for an hour uh it's a friend of mine and i literally told him when i got on the call i was like dude i woke up this morning i was like i gotta fucking talk to him today right and it's just like like that to me was going to the golf course that was going to whatever and so if you just know that about yourself like double down on it and then the other thing uh that i do every single day is i make sure that i read and so at eight o'clock i pretty much shut whatever i'm doing down uh the team will laugh because every once in a while i'll sneak in a Slack message here or there, right? But I just fundamentally believe that like, I am happiest when I get to read every day. And so if I work out in the morning, do the work, and then I read at

night, it's the perfect day. So I just do that over and over and over again. And what you do is like, it's like building a muscle, right? I always joke that like, everyone's like, Oh, I want to work hard. Like cool practice. Yeah. Right? Like get started, actually do it. And so when you do that, it does two things. One, you do build the muscle memory, and you're able to just have a higher capacity for work than most people. But two is like, there's a lot of people that I work with that I think whether they work at our businesses or they work, you know, in the business we've invested in or whatever, they're just like, damn, like I can't complain. Right. How do you complain when the person who is leading an organization is willing to do so much work or willing to do

things that they're asking you to do? And so it goes back to like the military, right? Is if you're a nco or an officer you eat last right everyone else is is kind of taken care of first you're willing to always do the hard work right you're willing to always do the things that you're asking these other people to do and you probably have done it and so like one of the things in the military that you know kind of gets dramatized by the movies and stuff is like you know go clean the bathrooms in these war zones where there's everything that needs to be burnt people like why would i ever do that it's like well guess what like when other people were younger that's what they did right so they've been there they've done that stuff like they understand how it works

and so i think it's just like um we have a couple of crisis in america one is a financial education crisis one's a hard work crisis and one's a leadership crisis right and you can actually solve two of the three of those by simply just working hard and and actually leading by example and so what ends up being interesting about that is there's lots and lots of people who love to complain like we have absolutely become a nation of complainers right people just get on the internet, and they're just bitching about anything that possibly goes wrong in their life. I tend to think that actually, we need to shift back to being a nation of competitors. And if you think about, you know, think of like the people that came before us, right? I was reading a book recently

about the Macmillan family, which is the Macmillan and Cargill's created Cargill Inc. Cargill is, you know, one of the largest privately held companies in America today. They came from Ireland in like the early 1800s Macmillan family, and they literally showed up in Canada. and somebody was like you have 200 acres uh here is a map go out into the wilderness and go build your house like dude that's fucking hard yeah by the way don't get into any conflict and die don't get eaten by wild animals right like all this shit like dude we wake up and we fucking have a supercomputer in our hands within 10 seconds and we can press buttons and like breakfast could show up right like i mean it's like the most cake life of all time and so if

you think about that like the positive view is we live in the most prosperous safest time in human history the downside of that is damn is it easy to be lazy right and so if we just bring back this idea of like if you keep in context what the people before us had to do and you realize how fortunate we are like it is your responsibility to work hard it is your responsibility to do these things and if you do that not only will you be a good uh kind of i think example for the people you work with or people who look up to you but also you'll pass those traits on to your kids to your grandkids etc and we can kind of keep staying in the right path in life rather than you know once you become a nation of complainers complainers get fed like that's the other thing

and if you go back in history and you study it the uh kind of early warning sign of socialism is complaining because people complain they complain they complain they complain and then what ends up happening is the people in charge like dude we're tired of hearing people complain just give them shit right and when you give them shit it turns into socialism take away the incentive, you can completely screw up entire economies and nations by doing that. And so it's like, hey, we're at a fork in the road, stop complaining, start competing, and let's get on with it. Yeah. And I feel like it's tough to shift that, right? Because social media, like what you said, has made it so easy to complain that now you would have to rewire the whole... Culturally,

it has to become unpopular to complain. Spotify and Accenture are working together to reinvent the rhythm of ad sales, using automation, analytics, and smarter workflows to simplify campaign delivery and access better data across the business. The result? Less time spent on operations, more time connecting brands with the moments and fandoms that matter most. Learn more at Accenture.com slash Spotify. Right. And, you know, I have this saying I say in private, probably not politically correct, but whatever. But it's like if you think about cancel culture, cancel culture was a zero interest rate phenomenon. I don't see a lot of people getting canceled right now. All of a sudden, the economy gets a little rocky.

People are like, oh, shit, I need to make sure I got a job. I got to take care of my family. What's on my balance sheet? It's back to serious time. And so when you have easy money flowing around, people are bored. It's literally a product of boredom. People are on the internet. They're arguing with each other.

They're acting like idiots all across the economy. they're literally just like throwing money out the window right because it's easy money and so when you return back to tighter financial conditions all that nonsense goes away and so i do think that the pendulum is kind of swinging back i don't know if we'll fully swing from complaining to competing but if we can even get to equilibrium and reduce some of the complaining great right and so then we can kind of get back into it and like nothing will refocus someone more than a threat to their economic status. So if you own a business and easy money's happening, what do you do? You get distracted. You start doing all kinds of crazy stuff, right? The second you think a

recession's coming, people are like, oh shit, take that golf session off my calendar. I got to make sure I got customers, right? And so I think that's kind of, as a society, we're getting back into that a little bit. And you see politicians kind of changing their language a little bit. You see the large banks and asset managers, but you also see individuals. All of a sudden now it's a lot about, you know, hey, let's focus, let's get more serious again, because the tighter financial conditions, you know, kind of force them to do that. Yeah, people just get too comfortable when it's when money's easy, right? So yeah, and this is not a new thing, right? I mean, it's been a lesson throughout history that we've seen over and over and over again. But it's also a thing

where you confuse being smart for being, you know, fortunate with good timing. And it's like, you know, in 2021, if you got rich, I put that in air quotes, because like, whatever that is, means for you? Was it because you did anything? Or is it literally just because you happen to just live through 2021? Right? And so if it is the latter, then you just got to very quickly become comfortable with the fact that like, oh, maybe I'm not actually some genius. And I should just stick to the fundamental principles, right? There's a lot of people running around, they thought they had all kinds of, you know, really unique investing strategies, only to lose a bunch of money in 2022. And so it's like, yeah, you can press out on the risk curve, you can, you know,

become distracted you can do all this stuff but the end of the day it's not about how much money can you make in a short period of time it's how much money can you make and keep over decades right and and i think that there's a whole generation of people who are just relearning that lesson so what are your thoughts right now on the economy in terms of 2023 and what's going to happen in 2024 i think long term like the writing's on the wall right um regardless what anyone does in the short term like we have too much debt uh we're going to continue to debase the currency it will financially ruin the bottom 50 of the population uh taxes will continue to increase to try to feed the beast of the national uh kind of government and uh i think that america

unfortunately um has continued over this you know 250 275 year run uh built this amazing thing but we now have become a nation of complainers right like tiktok is the best example in my opinion right uh i subscribe to the view that tiktok is a massive threat and is being used in a way that has the potential to program kids and do all this kind of stuff right how we got there though is very heavily debated and i think there's a part of that conversation that's missing tiktok was successful because they built a better product nobody held a gun to the 14 year old kids head and said you have to use tiktok correct no they downloaded an app because their friend told them and they were like this is fucking awesome right look at these dumb videos i'm addicted and

i'm gonna keep opening this app right now why did tiktok do that and facebook or google or twitter or whoever not do it we got out competed in the market and so a from my view of the world the way to correct that problem in the future is we have to win from an innovation standpoint we cannot let other countries or other companies from other countries out-compete us. We need to be a nation of competitors. And so if you take that view, you then can kind of go all throughout society and realize competition is a huge, huge part of this. And so another example that's kind of more tangible for most people is the Brightline here in South Florida. So for those that don't know, Brightline, it's not exactly a high-speed rail, but it's probably the closest thing we have to

high-speed rail in the United States. It was bought by a bunch of investors in 2007, 2008, maybe, I think. And in March of 2023, it was the first month in the history of the Bright Line that they basically turned a profit. Now, if you think of a train, there's not a goddamn train in America that's profitable without subsidies from the government and all the things that have to happen. At one point during 2020, the MTA thought they were going to go bankrupt in New York City with the subway because they had bonds that they had to pay out and there was no fairs because everyone's locked at home right like these are not great businesses historically and they've really struggled financially because they're just big projects that are expensive they use a lot of

debt all this stuff now why is the bright line profitable in march of 2022 they had 70 000 rides in march of 2023 they had 170 000 rides now some of that is just demographic tailwinds right uh in terms of more people are comfortable using a train than they used to be uh some of that is a migration to south florida so you get more people just coming here some of that actually has to do with the miami heat are good right so people from these other places they're coming down they're coming to whether it's marlins games whether it is uh miami heat games whatever right some of it is because it's freaking nice so i wrote it the other day for the first time and i literally texted my wife and i was like oh this is like a subway above ground that's nice and on time wow like it's

every new yorker's dream right it's like the train's on time and it's nice there's not like crazy people screaming at you right and like whatever and you can sit down and like you know it's like a nice experience they have like a little food card wi-fi right wi-fi free like i mean it's like amazing you walk into the train station you could eat off the floor right i mean it's like so clean like all this stuff and so you're like okay this is a better product right that ends up actually being put out there it has all these tailwinds uh along it and it's working that is competition right and so when you look at something like that it's like man why can't I bring this to the rest of the United States right we can and so what is it going to take

it's going to take people to do it and I think that I forget who tweeted this one time but they were like look around you somebody had a dream for every single one of those things right the building we're in right now somebody was like I think I should build that building and they when they did it yeah and it's like weird to think about whenever that happened that could have been two years ago or 200 years ago right or 20 years ago yeah and somebody went and they got the plans they went and they got the approvals they then went and they literally poured the foundation and they built the actual building and like all this stuff and you look around you the whole entire world that's true and so like miami is probably one of the best examples if you look

at pictures of brickle 10 years ago to now so yeah it's like a different video on tiktok actually okay and it was education content transformation is crazy there was no high-rise buildings for the this part now all of a sudden 10 years later it looks like a mini new york city right now again i'm not going to say that brickle is manhattan right yeah but like it's definitely headed in the direction of more high rises more dense urban area more restaurants walkable like all these things and so that's in 10 years extrapolate that out over 30 40 50 years if that continues it probably only compounds faster right because now more people are paying attention more capital pours in all this stuff and so like that area will look completely different in one person's

lifetime right and so i just always go back to this idea of whether we're talking about tiktok we're talking about the bright line competition is the ultimate uh kind of game and it's this free market and the more we get back to that and people realize if i want the world to look a certain way i can do it i can go compete and create that world i think that's really uh one of the great advantages that we have in america because a lot of countries you can't do that yeah right and so if you can do that here and you want something to change go do it it's your responsibility to go do that. And it'll make everything around your life and other people's life better. A hundred percent. And I think I even saw something the other day in terms of

downtown Miami, where it's like the second largest development in the United States. And the first one was Hudson yards recently for that. And now it's my world center. Yeah. I think that's like a, what is it? Art Falcone and Mark Roberts, a couple of those guys. Yeah. Yeah. So that's a, that's going to be huge as well. I mentioned them. Yeah, exactly so i i think miami for sure is on the come up and i think as long as the policies here are good and it's you know it's the taxes right the weather i think it's there is a huge migration right now even even still coming to florida when you are a nation of complainers that is the first step towards socialism right and one of the things that i

continuously go back to over and over and over again is the reason why miami i think is so attractive to so many people in south florida in general is uh the joke is that miami is the capital of uh south and central america right or latin america um and if you think about what do all of those people have in common for the most part most of those countries have experimented with some form of socialism and those people wanted out and they moved right and so what ends up happening is if you've seen the experiment before you vehemently reject those ideas when you see them again. And so I tell all my friends, I'm like the last place in the United States of America that socialism will take hold is in Miami, Florida. Why? Because all of these people already

saw the experiment and they ain't down for it. They're the people who moved with their feet and went somewhere else because they realized this is not the world I want to live in. And so like, that's one key piece to it. I think taxes is a big one. The weather's obviously nice. But also there's this like a magnetism that happens with density, right? And so like all of a sudden, you start getting a couple people to move. And then people are like, well, if they're all moving, and I want to be around those people, then maybe I should move. And then you start to kind of compound that over time. I have a friend who actually moved from New York to Miami. And he said, Miami is the Monaco of America. And I was like, why? And he was like, well, it's a lot of

wealth, tax situation, it's near water. And there's this element of kind of as people want to move there and continue to move there, it becomes a thing, right? And so like, I think that's actually a great way to look at it is if you look in California, New York, et cetera, some people are moving to Texas or Colorado or some of these places, but Miami has been a big winner in terms of flow of capital and a flow of people. And I don't think that it's going to reverse, but also I'm actually of the belief that it's going to accelerate. So if you look at like Ken Griffin moving Citadel to Miami, like people don't realize that's hundreds, if not thousands of people that are high income earners that are going to move to a single city, he's going to build a high rise

tower like all this stuff where are those people going to live they're going to go into the community where they can spend their money in the community right like like that one decision by that one person has this massive tailwind effect and so when you think about it from that perspective you're like okay how many more of those do you need to completely revitalize an area that wasn't necessarily destitute right it was already pretty good but you inject some capital inject some people game on and you know i think that miami could easily become uh the city of the 2020 decade um i saw somebody tweet and they said every single decade has a city so if you go back and you look at like uh the 90s and 2000s it was uh new york if you look at kind of like 2005 to like 2020 it

was san francisco like are we going to be you know 2021 to 2030 or 2035 miami unclear but it's got a damn good shot to do that yeah definitely so when did when did you move to miami at the end of 2020 gotcha gotcha i wrote out the whole thing in new york and then decided to leave and you're like i can't take it anymore no to be completely honest like uh i think my wife and i both like we heavily identify with new york um and like our mentality the way we work a lot of our friends are still there like like i don't think it was like we're running from new york yeah i think it was very much like we love new york we go back quite often um and uh if there's only the only other place i think we would live other than miami is in new york right um and so i think miami was more of

just like at first let's go just for a weekend and like see what's up um then we realized a lot of our friends had moved all the stuff and so we're like well let's just try it for a couple months and that turned into now you know whatever two and a half years um and i think that we look at it as like basically it is as close to new york as you can get without it being new york with better weather better taxes and kind of density of people exactly and so if you're fortunate enough to live in miami and then maybe just go back you know four to six times a year for you know a week or two kind of get best of both worlds like to me that is um you know ultimate freedom like the ultimate wealth is like that stuff not some number in a bank account or

anything so it's like we know that that's something that's important to us it's like let's just go build that life yeah so how's your travel schedule right now do you travel looking about? I've been traveling drastically less. So in 2019, uh, I took 120 flights. Um, I was running around the world. I was fundraising. I was doing all this kind of crazy stuff. Um, 2020 obviously, uh, took very few flights. Um, in 21, I basically made the decision. I want to try to keep the 2020 schedule, but go back to, uh, kind of the work velocity and kind of capacity as the world opens up that I had in 2019. Um, it was much more successful than I thought. And so I've pretty much said to myself, look, I will travel for certain things if I need

to. Um, but now I'm much more intentional about it. Like when, uh, I was single for sure. And then even, uh, when, uh, Flynn and I were just, um, uh, dating, I didn't like really no responsibilities. I could, you know, get a phone call tonight and be on a plane. Literally I would drive to the airport right now. Right. And like, go, go fly somewhere if I needed to. It's different now. Right. And so, um, I think that by being more intentional, like we will go, um, there's a couple of trips we have to make over the summer uh for work stuff but we're gonna go for like a week right and try to enjoy it and do all this stuff and so like yeah i think it's less about like are you traveling or not traveling and now it's more like we travel in a different way um

and by being more intentional about it actually it's more enjoyable like you know i don't know how many planes i slept on you know red eyes and in airports and cancel flights like it's just a chaotic life right chaotic fine when you know you don't really have a lot of responsibility and you're kind of really focused on you know achieving something in the professional world but how long can you really do that some people do the whole career i don't know how some people do it like because i know some people like what you said they'll they'll fly out on on like sunday night or super early monday morning and then come back you know by like friday morning or you know late thursday night and that's just that's this good i'll tell you two stories of things i used

to do so i used to drive to the airport on in a morning fly to chicago go do like two or three meetings and then fly back that night wow right then there was another time um i flew to chicago i don't know why chicago's both of these but i flew to chicago we did a meeting we got a rental car uh then we drove to i think it was like detroit or somewhere michigan maybe yeah i forget uh and then we like took a flight back right and it was like what are we doing but like it was important right there was things that we were doing whatever part of it also was like i always want to try to get home yeah like i know a lot of people who you know they'll like plan these business trips and like i'll have a meeting on tuesday at noon and then uh i'm gonna meet a

friend at 5 p.m uh and i could you know rush to the airport and try to catch the last flight but i just stay overnight and i'll come back the next day i always try to get back and so when you try to get back what you do is you kind of try to be more efficient try to cram things in uh but now you got two flights in a single day yeah that's right and so yeah i mean it's tough but if again if you can just be more intentional about what you're going to do, it's a more enjoyable life. So how did you, how'd you meet your wife? We met through work. She was a reporter at Fortune magazine. She used to write articles about, you know, tech industry and venture investing. And eventually she became

the writer behind term sheet, which is like Fortune's big daily email about the tech industry. And it was kind of this weird thing where, you know, we met and I don't think that I'd ever like dated or even got on a date or anything with anyone from work i was very much like hey this is different you know the kind of different part of my life um and in in the first meeting it was kind of like all right we're gonna have to like this is a professional relationship or like are we interested in each other personally um and i don't know it's kind of like this weird thing i never believed the like oh you know as soon as you meet someone type i was like that's bullshit right like whatever um but yeah it was just like very obvious right out of the gate uh where it was like i want

spend more time with that person, but you don't know what they think. Right. So you're kind of like, uh, all right. And so we were just talking and like, it became obvious, I think pretty quickly, like, all right, we want to spend more time together. Um, and, uh, I joke with her all the time. Like that was it. Like, it was like, literally I went from absolute maniac, you know, partying all the time. Like, you know, had what most people would consider like the life in terms of like being a single guy, um, run around the world doing all kinds of crazy shit. This was when what year 20 this is in 2016 at the end of 2016 yeah and then like literally overnight i was like that's my girlfriend and she was like wait hold on wow that's like that's my girlfriend

and this is back when you were you know you said you're single going out you were working a ton on business as well it's like a fucking i used to have a saying anything worth doing anything worth doing is worth overdoing yeah right like that pretty much Like that one sentence summarizes my life before I met my wife, right? It was just like, oh, we wanna work? Cool, let's work 12 hours, right? Oh, we wanna go out?

Let's go out till four o'clock in the morning, right? Like, oh, we wanna drink? How about we drink 10 beers, right? Like just anything worth doing was worth overdoing. And like, to be honest, I like squeezed every ounce of juice out of my life. I possibly could. And so I always joke, and she hates when I say this,

but I'm like, if I literally die tomorrow, I won, right? Like I've had an amazing life. I literally have accomplished so many things that i wanted to accomplish and i had fun right like i'm happy and so uh i hope that doesn't happen right you know knock on wood right but like uh when you get to that point i look back i'm like why did that happen and it's because when i was 20 years old right and i was sitting in the desert in iraq and you see a bunch of shit all of a sudden you're like you know what actually i know what the end of this story is and so let me go and do this now when you're

really young that's like reckless stuff right yeah motorcycle you're going fucking 120 miles an hour down the highway like all the crazy stuff that people uh kind of know and as well documented of young guys who you know feel like they're invincible right but now all of a sudden it's like all right what am i optimizing for and when i ask a lot of people that i work with or companies i invest in or whatever almost always they answer with a professional answer right and i always ask them i say is that what you are optimizing for in your life or in your work and a lot of people they never thought about what am i actually optimizing for in my life and so for me like it is this really stupid thing but like my goal is to be happy and it feels so

fluffy and all this stuff but like all that means is i took okay what makes me happy how do i structure my days to do as much as possible just do that like that's fine and so like there's a lot of people who probably look at my life now and they're like dude this is boring as shit like what you have no hobbies you have no i'm like no you don't understand i get to do my hobby all day long. Right. You know, on the ride over here, uh, there's nothing on my calendar. Two people called me and I'm sitting there talking to them. I have no interest in their business. I have no benefit like any of this stuff. It's just fun. Right. I'm like, Oh, you could do this. What about this? Did you ask this person this, if you structured it this way, what would be the

ramifications? Like, Oh, whatever. Last night at eight 30 at night, a founder called me and it's like, hair's on fire. Right. He's got a problem that he's dealing with. And my wife's like, come on. But I'm like, Hey, you know, it's like a guy who sneaks out in the backyard and he built a little putting green, right? I'm like, Hey, like, you know, like the addict is going to get here. It's only five minutes, five minutes, 12 minutes later, she's like, let's go. And so like a lot of the founders that I've invested in, like they kind of know now, right. They're like, all right, look, I can call him and he'll answer, but like, I ain't got an hour. And so, but it is kind of like that, right. Is some people, you know, they literally can't wait for the basketball

game and they're like dude my friends are gonna come over i'm gonna drink some beer and watch a basketball game i played three sports in high school i played football in college like i love sports right it's really hard for me to sit down and watch entire seasons of sports now like if you asked me at the age of 18 to name nba players i could name a very high percentage of people at least the starting five on like half the teams right like i like knew a ton yeah um i wasn't an expert but i was very interested now i don't think i could name the starting five on a single team wow and so it's like is that because i got more mature is that because like my life interest changed is that just because like i realized hey this is fun to like watch one game but i don't

really don't care about the season i don't know but it's probably one of the biggest differences because i have a brother who has doubled and tripled and quadrupled down on sports right and he could actually sit here and he probably could name starting five on every single nba team right And so it's kind of this weird thing where maybe through life you kind of get really interested in some things and then at other times you're interested in other things. I'm not sure. But I'm happier today than I've ever been, which is like a very weird thing because it's doing things that previously I didn't like to do. Like I used to hate to read. Right?

Like teachers would be like, will you read? I don't think I read a single book in high school. Right? Like a signed book. Yeah, yeah. I just – I got through high school, but I don't think I read a single one they told us to read. and so like i was a power user of cliff notes and like i probably spent more time trying to figure out what the was in the book than just if i had sat down and read the book right

but like now i'm like man if i went to high school right now i'd sit in front of the class i'd ask all the questions i'd read i would be like the model student back then i was the exact opposite i was a complete class clown yeah and so it's just like i don't know maturity life you know interest change whatever but like it's interesting yeah it's interesting to see just the progression and and how your things but like what you said the biggest thing is just figuring out what you really enjoy doing what makes you happy and only doing that that's it so that's literally uh again it goes back what are you optimizing for yeah and some people are optimizing for a number in their bank account some people are optimizing for an accomplishment right they want to achieve

something whether it's in their personal professional life or whatever uh i've just chosen like i want to be happy and the way that i define happy uh with my wife is uh we want to live an extraordinary life doing the things we want to do when we want to do them. Right. And if you can do that every day, like you win. And so it's the old joke of people saying, you know, Hey, uh, once I get rich, then I'll like become a writer or, you know, once I get rich, I'll do this. Or once I retire, I'll do this. And it's like, cool. You really going to work till you're 65 years old and then try to do it. Yeah. Like just do shit now. Yeah. Right. And once you start to kind of think that way it scared people because like maybe that job you thought you

wanted at work is actually just a further investment in a bad deal right are you is this bad money chasing uh you know even worse money maybe and so if you get the promotion does that just mean you're going to be here for another two or three years but you already hate the job so why are you trying to achieve something that you know you hate yep it's hard right it's hard to be intellectually honest with yourself. Yeah. And I think when, especially when emotions get involved, especially when time gets involved, like people, it's very tough to cut ties for anything. All of that is true. And then you add in responsibility, right? Like I always, I talked to a lot of small business owners over the last couple of months. And one of the things I was

asking them is I say, Hey, what's your responsibility? And most of them will immediately, cause we're talking to business sense. They'll start talking about, you know, well, we have a rent payment. We have this. What's your responsibilities, right? Oh, I got a significant other. I got kids. My neighbor's kid has a medical bill and I'm helping them out with that. I got a car payment. I got a mortgage. I got like all this stuff, right? And so you like total it up and you're like, dude, you can't do anything else. Like financially, you are not in a position to make a different decision because the second you make a different decision, this tsunami of responsibilities debt whatever will consume you yeah and so you're trapped and so the only way

to get in a position to kind of make a move on a chessboard you got to deal with the responsibility stuff now you can't get rid of your kids please don't get rid of your significant other right so there's like some non-negotiables but there's a lot of things that actually you can address right and some of it is like uh financial stuff some of it's social stuff right you'd be shocked how many people are like oh well every uh thursday night i i go and i do this why well i've been doing it for you know 10 years yeah do you enjoy doing it no i hate it stop going yeah well i'm gonna they're gonna judge me or this or my you know this in the community whatever it's like do you really care yeah do people really pay that much attention don't go next thursday and see if

anyone calls you if they call okay then you're gonna have to address it if they don't call just never show up again. Maybe six months and they're like, Hey, where's Andy? I haven't seen him in a while. You just don't know. And so I tend to think a lot about the responsibilities you sign up for. Are they reversible or irreversible? A kid's irreversible. But a lot of responsibilities are reversible. And so which ones should you be reversing and which ones do you want to keep doubling, shuffling down on? You're investing your time. It's your most valuable asset. Think about it as a capital allocator, your time allocator, where do you, where you put your time is ultimately where your focus goes, your energy goes, your happiness goes, et cetera.

So invest it wisely. Yeah. And it's, it's so tricky in today's day and age because of lifestyle creep, right? It's, you know, especially early on in your career, as you start to get momentum in your career, right? And you start making money, you start making better money. You want nicer things. It's just a natural part of life for most people. And I think When you were younger, do you, did you have a number in your head of how much money you needed to make? I did. Yeah. Okay. Was it like a, a net worth number? Was it like cash in a bank or was it like monthly income? It was a network number. Okay. I was a kid. What was the number? Uh, at least a hundred mil. Okay. So that's a really big number for a young kid to think about, right?

For me, when I was in college, this is going to sound absurd. I literally was trying to back into how could i make two thousand dollars a month because then i could live forever yes right like right now like that sounds absurd now right you're like dude what now this is you know a decade ago 15 years ago whatever right um but like when you think about that for a second that was the goal was like five hundred dollars a week i'm good yeah right now you get into the real world and you get like slapped in the face you're like okay hold on maybe i need to make five thousand dollars a month right but like you lifestyle creep happens yeah i actually think a lot of people don't realize and that when they stop and kind of look back like dude i accomplished

every goal i've ever had financially until the goals i have now right yeah that's not because i'm some genius or whatever but it was like the goals weren't really that big right so like a hundred million dollar uh net worth i don't think i would have had the confidence or like the courage to have that as a goal. Mine was like $2,000. I got $2,000. How did I get $5,000, right? You kind of just move up.

And so it goes back to this idea of like if you could choose any point in history to live, you would choose tomorrow. The next best time to live is today, right? Like the world is only getting better, safer, more prosperous, all this stuff. If you think about your financial life, for most people, if things are going well,

the single greatest time to be alive in your financial life is tomorrow. next best time is today right now some people get in bad situations so it's all about the compounding and like the direction of change but if you are in a if you're making good decisions you do go from you know hey i want to make five hundred dollars for the summer right then it's i want to make a two thousand dollars a month five thousand dollars a month whatever and you kind of slowly build up and as you check off each goal it's kind of like natural right like what's the next goal because you already achieved the thing that came before and so in some ways like lifestyle

creep can be uh negative obviously but maybe it's like you don't want lifestyle creep but you want goal creep yeah right so your goals get bigger but your responsibilities stay the same and that delta is really like the true wealth that you're generating yeah i agree i agree and i think especially when i when i first started out in business it's obviously i had that big goal in mind but it's like okay how can i make you know 10k a month from this business how can i make 50k month then 100k a month then you know x amount so when you look at those goals too what i think is so funny is business people they always come with a plan and so many people outside the business world they have like the goal but there's no plan right and so um one of my favorite things to do

with young people is like what do you want to do right and i was talking to a kid recently he's in college trying to figure out a summer internship or whatever he was like i want to break into investing i was like okay what's the plan and he was talking all about uh how he was trying to like get introductions to people and do all this stuff and everything and i said that is a path you could you could do that but what if you flip it how do you get them to come seek you out he's like what do you mean i was like if you want to meet people who you deem of high value the best way to do it is to be of high value yourself right like be interesting yeah and so he was like well what do you mean? And I started talking to him. I was like, well, what happens if you had a niche that

you got on Twitter and all of a sudden you became known as the person who had the expertise on X, right? A lot of people would want to talk to you. And so, you know, for a college kid, like maybe your thing is you run surveys at all these colleges and you get all the technology trends and then you package it up and you send it to all the, you know, billionaires and VCs and all these people you want to meet and everything. And then you say, hey, by the way, I'm happy to jump on a call for 20 minutes and explain this to you, right? And you send it to 400 of them. five of them say yes we just met five of you know your heroes like you know like these games of just like how do you provide value rather than try to extract it yeah um i think ultimately comes

back to this idea of uh a plan not just some wishy-washy like oh i hope that i could meet you know whatever and so to me uh you know the story of the guy who stood outside of uh tesla or spacex uh to meet elon yeah this episode is brought to you by accenture when you're advertising Using operations fall out of sync, everything else follows. Spotify and Accenture are working together to reinvent the rhythm of ad sales, using automation, analytics, and smarter workflows to simplify campaign delivery and access better data across the business. The result? Less time spent on operations,

more time connecting brands with the moments and fandoms that matter most. Learn more at Accenture.com slash Spotify. He was live streaming and posting videos on the internet for 40 days. i forget all the details right yeah but like i mean that's insane yeah right he met elon like like imagine telling your grandkids like i one time hung out with the world's richest man like how'd you do it grandpa i was a psychopath i stepped in my car outside his office and i literally harassed the shit out of him until he met me right like respect yeah right now please please do not go do this right but like that's a perfect example of like he had a plan that

seems insane to everyone but like eventually it's like okay dude this guy's been out here for 45 days like how do we get him to go away yeah right just come come in here and i'll talk to him for five minutes right and then he'll leave and so like there is kind of this weird world uh of just like what are you trying to accomplish what's the plan then go execute yeah and i almost feel a lot of people do that there's there used to be a big trend on tiktok where it's like it's like someone's like day one of slapping myself every single day until X person responds to this TikTok. And like that used to be a thing.

That is literally the Chinese Communist Party trying to make America dumb. Hey kids, how cool would it be if you slapped yourself? Right, but like, I mean, but yes, right. A perfect example of like trying to use the leverage of a platform to do something to get somebody's attention. At the end of the day, whether you send a cold email or you slap yourself on Twitter every single day until someone responds to your DM, you're trying to get their attention. And the question is, what is the best path, right?

And how do you get them to respond and do it in the context that you want them to know you as? But those two things are much more similar than they are different. Exactly. I want to talk a bit about your podcast. How often do you film episodes? How have you systemized that and how has that grown since the beginning? started out there was no system i mean it literally was just i just did whatever i wanted um which was fun but not sustainable um then we became highly highly systematized we did all

kinds of different shows all this stuff uh and now i've kind of found like a sweet middle ground right where uh we did two to three episodes a week uh they're usually just the people i want to talk to uh they tend to lean much more towards business finance economics uh bitcoin things like that. And I just sit down and I talk to them like I do almost no prep, right? And it's just me trying to learn. And some people build podcasts because they want to build a business. I built a podcast because I wanted to learn and the business just happened to come along with it. But you know, we've done many times we've made decisions that are financially disastrous for the business. But I don't care, right? Like my goal is to just meet people learn from them,

and then be able to share that information with other people. And so, again, what are you optimizing for? I'm not optimizing for the money. I'm optimizing for the learning. And so as we've done that, what we've come to the conclusion of is like we want to have kind of a very loose structure in terms of how many episodes a week, who are the types of people, that type of stuff. But actually we don't obsess over did we grow 3% day over day.

Did we grow 10% week over week? We just don't do that stuff. And it would be bigger if we did. But again, that's not my focus, right? My focus is the learning component of it. And it'll kind of organically grow over time just from high-quality content. Gotcha, gotcha. And so are you interviewing people two, three times a week?

Or is it just you have some episodes where you talk alone? How do you balance that? It's all interviews on the podcast. YouTube, every once in a while, I'll do a video where I just kind of talk to the camera. They're way easier to do, frankly, than the two-hour interview. Um, and, uh, usually the interviews, what's fascinating about it is, uh, I try to pull out information that isn't just about what they do, right? So same way that we're talking about goals or, you know, daily routines or whatever,

like anyone who you meet, you can learn something from, but it's not only about the thing that they're an expert in, because actually I would argue that you and I are more experts in our daily routine than we are in business or finance or whatever, right? because it's the thing that we do every single day like we could talk with you know immense detail you know do you put your left or right shoe on first like you got a system right like we can say whatever we want but like you got a system even if it's one that you don't intentionally create right when you brush your teeth like do you start on the left side or right side of your mouth like we're humans we're we're uh built with this nature and so how do you take something that like i don't

give a shit how you brush your teeth right yeah but then how do you look at well how do you read and so like one of the funny things about as I've read so many books is I'll meet people and they're fascinated with quote-unquote the system that I use to read right and then I'll ask them well how do you read and some people will say oh I do audiobooks right and I don't take any notes and I just kind of listen when I'm out on a run or driving or whatever other people are like oh no I read on my kindle I highlight I pull it into you know read wise I do like all this stuff and everything and then what you start to learn is not only what the system is but who the person is based on the system they use, right? If you take tons and tons of notes,

that says something about you. If you take no notes, it says something about you, right? And neither one's good or bad, but you start to build kind of this like profile of someone and kind of who they are and what makes them tick. And so I love to do that in the podcast where you can talk about their area of expertise, but then you start to really understand them. And one of the things that gets lost in social media is the context around the conversation, right? So all you see, you see a profile picture and somebody you think is yelling and screaming at you but then if you knew well wait a second here hold on this person's having a bad day or this person you know has a certain viewpoint because of a b and c experience they have or

whatever become more understanding and so i just try really really hard on the podcast like how do i extract that information so that it puts more emphasis on certain parts of what they're saying around their area of expertise i don't know if anyone everyone gets that out of it but for me like that's super super valuable yeah i agree 100 and i think it's it's seeing a lot of these core fundamental like it's almost like you have your business operating principles and you have your life operating principles right and i think if you if you have a good idea on both you'll understand how someone got his results that they got essentially so it's um it's it's very interesting to see if you go back and you look at many of the most successful people in the world

today it will blow your mind that shit they did in their 20s 30s right um i was just listening to um uh the acquired podcast whenever you're listening out um but they do kind of these breakdowns of companies and stuff and they did one on lvmh and uh it's like three three and a half hours fantastic work right and i'm listening to it and all of a sudden uh i'm literally working out and they say and then bernard arnault moved to palm beach to build like shitty 20 unit uh multi-family like uh apartment buildings in like you know early 20s or 20s 30s whatever he does you know like wait a minute you're telling me the guy who literally owns you know louis vuitton and dior and like all these like super luxury brands was literally building like affordable housing in

palm beach uh at one point and it's like well yeah his family was in the construction business they got out of like kind of the construction they were doing to get into like vacation rental type stuff then he was like let's go to america right and he did it there then he ended up going back like all this stuff and you're like dude that guy was just trying to figure it out man right and like he figured it out he's you know second richest guy in the world like he really figured it out yeah but like when you when you start to understand that you're like maybe it's okay that i'm trying a or b or c in my life and you can go through all these people right and it's fascinating and so like um you know warren buffett is a great example right where like warren buffett

early on with some of like the partnerships and some of the things that he did if you go back and you look it's like not exactly what warren buff is known for today right but that's because he was trying to figure it out right if you go um and you read uh uh jimmy um uh sony i think his last name uh he wrote uh a book called uh i think the founders was all about the paypal mafia and one of the stats in there is like four of the five paypal founders had created bombs in high school okay well like they weren't terrorists right like they were doing science experiments and they were trying to figure out they were tinkering and like it was like an inquisitive curious mind type thing right at least the way that's presented and so when you see that you're like okay i don't think

people should go do that right but like maybe it is okay to try a bunch of different things when you're younger and as you kind of build up uh the muscle memory and the experience and the connections and all this stuff, then you can start to find success. And so I tweeted this morning, the average age of a successful founder is 42 years old. Wow. 42. Why? Maybe the first 20 years of their career is just practice. They learn, they try to build a little base of financial security, they get experience, they build connections, they do all this stuff. only 42 that's the average age of a successful founder so if you think about that everything that happened in my 20s and 30s now my wife and i we always talk about like or practicing

there's a lot of people who look at the shit that we do and they're like that's not practice right but i'm like no there's some bigger opportunity that will come in my 40s or in my 50s maybe my 60s or 70s and this is all practice leading up to that and so when you make a mistake it's practice right learn from it yeah when you make a good decision it's practice it doesn't count right and so by presenting it to yourself as practice you never believe your own bullshit and you never get too down when you make a mistake and you realize that this is a lesson that i'm learning right that i then will apply in the future and so it's been like this great kind of framework to constantly be serious right if you want to be a professional athlete

you're serious in practice but also understanding it's practice and so hey when the real game comes whenever it comes be ready yeah and i think especially at that's so true in business too like every five years could be less it could be more you you're reinventing yourself right it's like you have a new business opportunity like first business you start might be some you know cleaning company in your local neighborhood or something that gets to a million dollars a year but next thing you know, you automate that and it's your next business that takes you to 10 mil or 50 mil, right?

And then it's the next business after that, that's the nine figure opportunity, so. 100%, and it's also something where you start to make connections across industries, right? I mentioned earlier these industrial brokerage businesses. The second I saw them, I was like, oh, that's Uber. What's Uber? It's a brokerage business, right?

I'm brokering riders and drivers. The only reason why I knew that was because I had looked at Uber and studied it. right? And started to connect. So like, what is this super high tech, you know, fast flying kind of tech company got to do with an industrial company, same business model, right? Then there's businesses that you'll look at, and you'll say, the makeup of this team matches exactly this other industry. Why? They're actually in the same business. Right? And so like, one of the things I always love to talk to people is,

you know, if you run a restaurant, you're in the restaurant business, people think you're in the food business, but in the restaurant business, right? Why is that different? Well, what are all these DTC food companies. They're not in the restaurant business. They're in the e-commerce business, right? And so understanding what game you're playing is really important because that determines capital, structure, team, marketing, like all these different things. But then what you start to realize is that restaurant, what do they really care about? How do we efficiently at low cost make great food? That DTC food company cares about the same thing, right? So there's similarities, but there's also differences. And so being able to identify, hey, what can you learn

from the other but also what are the things that you shouldn't take away right and being able to do that i think just again it's like being informed having that like a lot of people call like a prepared mind so when you see an opportunity you're ready to go and you can pounce on it so for your podcast are you i'm sure you have someone helping you reach out and get guests as well so is it kind of like a mix of nobody wow it's just you yeah because the people i want to talk to yeah right and you're reaching out yourself yeah just like dm on twitter or email them whatever every once in a while somebody introduced me to someone or something like that yeah but i would say for the most part it is uh uh just me reaching out to them saying hey you know i'd love to talk

to you um and you know i'm incredibly unfortunate that a lot of people say yes right every once in a while somebody says no or timing doesn't work or whatever um but yeah it's just me reaching out and i think it's it's more that is in line with kind of how i like to operate is you know i don't want uh people to have to like go and talk to somebody else on our team or whatever now for scheduling and that type of stuff sure yeah but uh if i want to talk to them you'll reach out i'll i'll ask you right you'll talk to me um and then you know our team their team whatever can kind of work together on all the details but at least they know like hey he wants me to come on this isn't just like a mass email blast to you know 20 different people to see who will say yes yeah

Got it. And so you talk to people in finance and business. What have you learned, I guess? Because I know you've interviewed tons of guests at this point. What are some of your top things you've learned? The biggest lesson is the best investors don't follow the average financial advice, right? The average financial advice is basically buy index funds, dollar cost average, hold them for a really long time, and kind of diversify. Name a big investor that's ever done that right literally like a world-class investor they do the exact opposite right heavily concentrated heavy big bets uh there's very little dollar cost averaging it's like i'm gonna execute now um there's almost no diversification like all you know they're super specialized like whatever

and so there's this barbell where actually uh if you know nothing the kind of like generic advice is probably pretty good yeah right it's like just get invested get into the market uh uh have the index and you're good to go if you know a lot the specialization the concentration you know all that stuff is pretty good the people that get in trouble i think are actually people in the middle the people who think that they know a lot but don't right or the people who uh um kind of are like oh i don't really know that much i know i don't know that much but like i'm gonna try to do it myself yep and so it's like this like weird barbell and so um you know a great example is like diversification uh is the anti-thesis to what warren buffett does it's all about concentration

right um if you look at george soros who you know now a lot of people like to yell and scream about all the political stuff but like still one of the best investors in the world like immense leverage super heavily concentrated investments and when the odds were in his favor would bet real big again you're kind of playing you know high risk high reward game there right and so um another one is a high risk high reward uh if you look at uh monish pabrai who's kind of like a he'll just come out and say like, Hey, I just copied Warren Buffett. Right. His whole thing is like, no, I'm a value investor. I actually want low risk, high reward. How do you get that? It's like the definition of value investing, right? It's things that like basically for sure you're going to make

money and there's a potential that goes up a lot. And so like all this, you know, kind of generic financial advice ends up actually not being what the best people in the world follow. Now what's interesting is then if you go to the other side, well, what's the positive argument for the generic financial advice. It works, right? If you just dollar cost average into the S and P 500 for 40 years, you're going to have more money, right? I don't know how much, or, you know, how often you dollar cost average. Like there's a lot of details in there, but like you will have more money at the end than you do today. It's holding cash. And so it then goes back to like, well, what do you want to do? If you want to be an investor, you got to quote unquote, turn pro. You're going to give

another job. When you turn pros, the idea that Steven Pressfield has, Steven Pressfield talks about turning pro as a writer. If you want to write books, you want to do this, I've got to turn pro. What does a professional athlete do? They show up every day, whether they're sick, injured,

you know, tired, whatever, and they do the work. And they do it all day long. They're pro, right? They are a professional athlete of whatever. Okay, if he says that for writing, what about investing? How many people turn pro as an investor?

Right? Now a lot of people think, oh, I've got to quit my job. I'm like, no, no, no. You have to approach it as a professional. Do the work. Put in the time. study talk to people like do all the stuff yeah once you do that then you have a chance not a

guarantee but a chance to be a good investor but you know we all know i mean i have a young brother my youngest brother who in 2021 he told me one time uh i was like hey man what are all your friends doing he's like 24 25 years old at the time what are all your friends doing investing wise he's like ah man you don't want to know and i was like why and he's like i mean they just invested in all kinds of crazy stuff right now and i was like like what he goes they won't invest in anything unless they think it can go up 10x and i remember being like oh shit right because it's just like like that is such an insane thought process uh because as a response to the economic environment now if you're saying no i'm gonna make heavy bets like like it's more of like a

calculated investment strategy okay fine yeah but this was just like money is free and you know it's flowing everywhere and so like i basically only want things that are super asymmetrical and so i think that's like a perfect example where you had people who weren't that educated but you know wanted to be professional investors that's not what i'm talking about yeah talking about actually turning pro um so that's one big lesson a second big lesson is people are all trying to figure it out i have some of the world's most successful people come onto the podcast and i talk to them after the podcast about different things and they sound like they are fucking confused interesting because they're just like yeah like everyone knows me for this thing yeah

And I got this thing figured out in the eyes of the public. But like, dude, let me pull back this curtain. Look at this fire that's going on over here, right? And everything's on fire, and I'm trying to figure it out. And I just had an employee quit, and I had this happen. And you're like, oh, shit, my problems ain't that bad, right? Correct. So I think that's another one.

One of the things that I think is really interesting is some of the best investment ideas don't come from traditional sources. So you can read research. You can do all this stuff, whatever. um their story after story after story of you know uh how teal invested in facebook how um some of the uh lightspeed guys invested in uh snapchat uh how um you know somebody invested in google because the google founders were working out of their garage like like all this like weird shit right it's like nobody was like sitting there reading a wall street you know research report being like oh the company google has a seven percent chance of disrupting the 20 search

just to come before it yeah no it's like somebody went to a party right like a barbecue at someone's house and they were like oh well that guy larry over there starting a company where do you start i'm a stanford genius yeah well here's 50k let's see what happens kid bam google yeah it's not like hundreds of page of research where it's like super like linear right it's not so so like one is like people are in financial position where a 25 or 50k check didn't it didn't warrant the research right so like they're fortunate to be in that position but also it goes back to like maybe if they'd done a bunch of research they would talk themselves out of it right so like you get into kind of that that kind of uh uh weird you know analysis but also the google founders didn't even

think they were going to build what they were going to build right as well they were that they wanted to sell it for like a million bucks or something and 10 million whatever it was right yeah like imagine if they had sold for a million dollars it's like comical yeah and so now here is where you get you put reading learning all this stuff together the story of google trying to sell for a million dollars no one wants the business and so they are forced to go build it and they end up building google is the exact same story as jay-z jay-z tried to get a record contract no one would give it to him so what do you do he said shit i gotta flood the streets with my mixtape i gotta build my own record label right i gotta bet on myself and they say no bam jay-z

happens those two stories are the exact same thing where nobody wanted them and they were forced not by choice they were forced to go do it themselves and ended up working out for every one of those good stories there's a thousand bad ones yeah but those two stories are the exact same story yeah so how do you balance like you know the research linear logical side with this you know non-routine like going to just some networking party saying yes doing these things where you you can basically make that connection right like how do you balance the the chaos and and the routine to become a better investor do you decide with your gut or with your brain you got to decide who you are i'm gut right and there's a lot of people who say don't decide with your gut i look

at my gut right as it is the culmination of all the information i have in my head can't explain it sometimes i'm like yep i should do it sometimes i shouldn't i'm wrong yeah all time but given the type of investing that we do it's all about power loss you gotta be right one time right and so actually going with your gut where you're like this could be big it's all about how big could it get not how much could we lose yeah in venture investing and so going with my gut nine times out of ten is a much better thing than if i sit down i start calculating shit right i i have this like standing rule i don't look at financial models in terms of early stage startups people that's insane why would you do that no it's literally fiction they're fucking making it up yeah they're

guessing right like it's like okay you guys made one let me make one right like i don't think you're gonna do 10 million i think you're doing 2 million why i don't know i fucking made it up right like like there it's just complete fiction and so yeah maybe i'll do like a little like googling you know like oh how big's the market right or like like very loose type stuff but at the end of the day I'm investing in this person. And so I've invested in, I don't know how many, 10, 12, 13 different unicorns at this point where I was an early investor in them. And if I go back and I look at most of them, most of them are still doing something that is tangentially related to what they originally pitched, but very few of them are doing exactly what they originally pitched.

And so if you go and you study like a Clayton Christensen and kind of the disruption theory and all this kind of stuff, or innovators dilemma, what you find is that there are like kind of defined strategies and then there's something he calls like an emergent strategy and so defined strategy means like i am going to build this table and here's the exact specifications here's the material i'm going to use and all this stuff right and i go and i build it like i follow the defined strategy and i did exactly what i said i was going to do that's great when you're building one single unit of a product right but if you want to build a company what you do is like i'm going to build 50 tables and then i'm going to sell them to this person i'm just for

this price whatever and then you go talk to the customer they're like dude i'm not buying it for that shit right yeah okay so like either i'm it's over or well how much would you pay what type of materials are interesting to you what are you going to use it for so learning oh well rather than sell them the 50 tables for that price i thought what if i actually built it with a different material i could lower the price and then rather than them use it inside of their really fancy you know uh commercial real estate building actually what they're going to do is going to use it out back in the recreation area and the cheaper material make it you know affordable whatever great you'll buy that awesome okay i'm gonna go follow that strategy now right that's

the emergent strategy it's because the defined strategy ended up not working and so when you go and you look through all these companies most of them did not actually end up building what they thought they were going to build right amazon jeff bezos never thought about aws yeah right he was he's going to sell books on the internet and maybe he could sell some things past that. He did. We got some pretty good business, right?

Facebook was called hot or not. Right. And they were basically, or face smash, whatever the hell it was called. Right. Like they were basically like, are you hot or are you not turned into Facebook?

Right. And so like you start to like see some of this stuff and you're like, man, you want to have a defined strategy, but you got to be open to the, the kind of emergent strategy and be willing to jump on that. And then one other thing I would say that I think is pretty interesting, um, is the more successful and older someone is, the more obsessive they are with

surrounding themselves with young, intelligent, hardworking people. So, um, I've been fortunate to go to a bunch of, uh, these folks offices and like, so this isn't like, you know, social, right? This is work, right? They are in an office and literally the richer they are, the more young people there are and it's because they're getting older and they know i have to disrupt myself but i'm old right interesting and so you know we have a we have somebody who works for us who he texts me sometimes and it's like uh i'm uh deciphering like you know the magna carta right he'll be like uh uh something something fr you know words words words i'm like the fuck is f oh for real right like i gotta think right yeah and then the other day i asked him how something

he he did he's like an event thing and i was like how'd it go and he hit me with p good pretty good right like like i literally felt like i was like a detective like under covering what he was saying yeah and so i thought for a second to be like hey dude can you write the words out yeah and i was like no actually i want him to text like this because guess what that's how he's texting his friends right and so i didn't know what p good meant or fr but as i was realizing i was like one shit i'm getting old right but two is man how do i learn more things from him he probably thinks he's learning a lot from me but i'm learning just as much from him about how you know a 21 year old and kind of his uh friend group operate that's

gonna tell me a lot about how the world's gonna play out over the next you know 20 years and i think that what you're saying uh it goes back right because i the the light speed venture uh partner who invested in snapchat it was his daughter who basically was like look at this app that all my friends are using yes right so i mean that's how a lot of these things end up uh getting discovered right if you have a product or service that is targeted to a kid right how's an adult supposed to find it they're not maybe they buy it for their kid or something right but like no and so um you know my wife uh we joke all the time she's better investor than me she has told me about four different companies that ended up going on to be billion dollar

businesses that she told me very early on and i was like i don't know whatever right like i don't know anything about that type thing and i asked her i was like okay time out like how where's the deal flow coming from basically right and she was like no you don't understand she's like i am the perfect demographic for these products and services right because she was in her late 20s uh as a woman with a friend group where word of mouth goes viral like all this stuff she's like and a lot of times i would just look and see who's spending a ton of money on on uh facebook and instagram ads to target me they have money they're spending a lot if i see my friends then posting about it like like you just you can very quickly figure out oh shit this is becoming big yep right so like

is it better to read the wall street research report is it better to talk to other like you know uh you know old dude vcs or is it better to talk to my wife who literally is like getting bombarded with instagram ads yep like actually she had the advantage on that specific market right now she's gonna have zero clue uh for a business that's targeting you know 30 year old dudes right it's just yeah she's not in the demographic and so a lot of times it's like go and find the people who are organic to that community and they know right and so like one of my favorite things dude i'm talking about a lot it's like the small businesses but we talked to like the number two or three in charge like hey if joe wasn't here for a month what would

you do to grow the business and the things they tell you are like completely different than the plan right yeah and you're like why this and they have like very good well this and this and this and why aren't you guys doing that yeah joe's got his plan you know we're gonna do joe's plan and so you're like okay right like hey let's have a conversation about this yeah why is these people who are usually younger you know kind of more involved in the day-to-day have a different type of plan or a variation of the plan that the business has right then you go to like a tech company and if you go and you talk to all the employees like hey if um uh if you wanted to grow the business, you know, you want to grow the user base by 2x, what would you do? Sometimes

there's overlap, right? They're providing the ideas to the company. Sometimes there's ideas and you're like, that's actually a good idea. Like, why aren't they doing that? Like, I haven't told them. Go tell them, right? Go try it, go experiment. And so I think that it's just, again, like ideas can come from anywhere, right? You just got to kind of really pay attention. Just double down on the good ones. Final question I have for you is how much weight do you put, you know obviously i know you said you're more you're more of a gut instinct type of person how much weight is it for you in terms of like hey i'm i'm placing my bet on the founder itself versus the idea and the market and how big it can potentially be every mistake i've ever made

uh in investing like big mistakes i fell in love with the idea every great investment i've ever made i invested in a person got it so i still make mistakes right all the time um and i'm human get excited about you know oh look at this massive market whatever right um but this person gotcha it's really the person um and it's because uh everything is going to change especially in the early stage right uh when somebody comes to say i got an idea like that's really where uh i spent a lot of my time the product that they're talking about is going to change right the emergent strategy stuff the market is going to change the competitors are going to change the funding environment, the economy, the talent market, all that stuff's going to change. The one thing that's

not going to change in this business is who's running it. And really what you're trying to get at is how good of a decision maker are they? If they make good decisions, they got a shot, right? Good decision doesn't mean a sane decision maker though, right? A sane decision maker doesn't build Tesla, doesn't build, you know, Facebook, right? No, you need someone who is a good decision maker, but has a unique view of the world. And so you start trying to pull out some of these, you know, kind of insights or things from people. And it goes back, it's not like I got like a scoreboard, right? Where I'm like, okay, decision making, that's seven. Oh, unique perspective on the world. That's a three, right? I need a 12 to be able to invest. That's

only 10. So I'm out, right? Like, no, it's just, it's kind of gut. And, you know, it's easier for me to say gut, because I've invested in so many companies now, and I've seen enough of them kind over time end up uh you know which one's working which ones don't um but also it's a probability game and so if you go into it trying to avoid mistakes you'll be a horrible investor in venture if you go into it and you're like i'm just looking for the grand slams and like i know i'm gonna waste a bunch of money that's okay right because the way the portfolio is constructed that's that's what you're supposed to be doing awesome well that's basically all i have on my list so i appreciate you taking the time to to talk about can i ask you one question before we

end of course what's the one thing you've learned so far i think i'm episode eight what what's one thing that you've learned uh so far the first eight conversations the the thing i've learned the most so far i love learning about um people's decision making skills or just thought process and then i love correlating that to basically where where they are so like you know when i ask questions like i'm genuinely interested in terms of like you know for you when i was asking like you know what do you do outside of work and stuff you said you had no hobbies funny enough i don't have other hobbies as well right and so like i i love learning about these little things in terms of how someone got to a decision because it gives me context in terms of okay that makes sense

i'm on board why am i not applying that or it's like oh that makes sense i personally don't want that but but i love knowing the decisions in terms of how someone got there and so every time i talk to someone you know i interviewed um you know a couple other people before you who had their own podcast and it's interesting because everyone has their own view of like why they're starting the podcast how they get guests and things like that um but it's less about like who's right and who's wrong versus, you know, the why and the decision to get there. I think that's exactly right. Advice is only helpful if it's actually applies to your life. Correct. Right. And so if I told you, you know what you should do, you should go build out a whole TV studio and like all this

stuff. That's not what we're trying to accomplish here. Exactly. And so I think that just knowing who you are and being comfortable with what you're trying to accomplish is a great advantage in life. Awesome. Well, thanks for coming on the show, Pomp. We're happy to have you and I'm sure we'll stay in touch. So absolutely. Thanks so much for having me. We'll be right back.