The Iced Coffee Hour - Meet The Man Who Make Million From Twitter | Sahil Bloom

Episode Date: April 2, 2023

Start creating high-quality content easily with Streamyard: https://clickurl.ca/ICH-streamyard Use my code ICH to get $5 off your delicious, high protein Magic Spoon cereal by clicking this link: https://magicspoon.thld.co/ich_0423 Check out the Patreon! https://www.patreon.com/icedcoffeehour Add us on Instagram: https://www.instagram.com/jlsselby https://www.instagram.com/gpstephan https://www.instagram.com/alex_nava_photography Official Clips Channel: https://www.youtube.com/channel/UCeBQ24VfikOriqSdKtomh0w For sponsorships or business inquiries reach out to: [e-mail] GET YOUR FREE STOCK WORTH UP TO $1000 ON PUBLIC & SEE MY STOCK TRADES - USE CODE GRAHAM: http://www.public.com/graham Timestamps: INTRO: 00:00 Air Travel Etiquette: 02:58 Time Is Money | Flying First Class: 07:24 Sahil's Life Background: 08:38 Making Millions From His First Job: 10:03 How Scammers Make $$$ With Wire Fraud: 18:23 How To Climb The Corporate Ladder FAST: 25:00 The 4 Types Of Luck: 30:59 Starting A Newsletter: 40:19 Sahil's BIGGEST CONTROVERSY: 43:59 Sahil's Biggest Life Changes: 51:46 Is Hitting Rock Bottom A Requirement Of Success: 01:01:49 Does a "Cold Plunge" REALLY Do Anything?: 01:07:02 Sahil’s Day In The Life: 01:12:25 Will Tik Tok Become A Government Tool: 01:20:05 Life Comes In Seasons: 01:31:05 Is "The One" Real: 01:33:21 Life Advice For You Guys!: 01:38:26 Accidentally Meeting Tim Cook: 01:39:41 Life Lessons From Tim Cook: 01:43:28 How Sustainable Are The Biggest Companies?: 01:51:24 Should Apple Push More Into Banking: 01:55:45 Can/Will Amazon Take Over The Market?: 01:58:06 Is Tik Tok A Risk To National Security: 02:01:02 Career Politicians HAVE TO GO: 02:03:19 MY NEW COFFEE IS NOW FOR SALE: http://www.bankrollcoffee.com/ The Equipment used: https://tinyurl.com/y78py5g2 Audio Equipment Used In Podcast: Shure SM7B mics, cloud lifters, rodecaster pro audio interface The YouTube Creator Academy: Learn EXACTLY how to get your first 1000 subscribers on YouTube, rank videos on the front page of searches, grow your following, and turn that into another income source: https://bit.ly/2STxofv $100 OFF WITH CODE 100OFF For Podcast Inquiries, please contact [e-mail] *Some of the links and other products that appear on this video are from companies which Graham Stephan will earn an affiliate commission or referral bonus. Graham Stephan is part of an affiliate network and receives compensation for sending traffic to partner sites. The content in this video is accurate as of the posting date. Some of the offers mentioned may no longer be available. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Need a vehicle that isn't afraid to make a splash? That's the Volkswagen Taos. Capable and confident, the Volkswagen Taos is fit for everyday life, nimble in traffic, agile and tight spots, and still spacious enough for weekend getaways. While available 4-motion all-wheel drive gives confidence in rain and snow. The capable Taos, you deserve more confidence. Visit vw.ca to learn more.

SuvW, German engineered for all. Saw Hill Bloom was a former investment banker managing over $2.5 billion in his 20s. We went from half a billion dollars to managing $3.5 billion. Then he decided to quit. Being bored, having those periods of silence and quiet time is when you figure out what those nonlinear opportunities are. I follow his Twitter, and that's where I get most of my information from. And I have to say, he is a genius when it comes to all things business, personal finance, and investing strategies that we got to just dig deeper. So if you guys enjoy episodes like this, make sure to subscribe because we have episodes coming out every single Sunday here on the Ice Coffee Hour.

Thank you so much. And with that said, thank you so much StreamYard for sponsoring this episode. Streamyard is a live streaming platform that allows you to create high quality content with just the click of a button. All you need is a camera and an internet connection to be able to stream content right from your browser. One of my favorite things about Streamyard is the fact that you can multi-stream, which means that you can be live on YouTube, Facebook, LinkedIn, and more all at the same time through the platform, basically expanding your reach for free. I also really enjoy that Streamyard gives you really cool analytics tools

so that you could analyze the success of every single live stream that you do. Streamyard is the best way to start creating content without having to spend any money. I mean, you guys see the studio here. It was wildly expensive. It hurt our pockets very much. But you can get started creating high quality content on Streamyard for free today. Seriously, guys, Streamyard is fantastic. If you want a live stream at all, they make it so easy to do.

And if you're interested in doing that, we do have a link down below in the description where you could get started today for free once again guys the link is down below in the description it also helps support the podcast so it mean a lot to us thank you so much stream yard and back to the podcast why do you carry a notebook everywhere i write a lot man you know this this is like my my thing i mean you guys have your craftsmanship around video and everything you do for me writing is my thing and so i just try to like log interesting experiences ideas um struggles etc that i'm having during the course of the day and i end up going back and looking at the notebook, I don't know, maybe like 5% of the time, but something about the actual writing process of it,

it like just starts to register idea, like idea percolation in my mind. It's like, I think James clear said at one point, anything that you end up writing, like content you create is downstream from something you consume. And so for me, things I consume, sometimes it's things I'm reading or listening to or whatever, but a lot of times it's just things that I'm thinking on a daily basis. And if I don't write those things down, they never end up having the like time to kind of seep in my mind and work together. So the writing is big. How do you know it's worth it to write down what's not? Like if you're like, I'm hungry, I'm thinking of big Mac right now. I try to be judgmental about it. You know, it's like something, I'm sure if you went back and looked in the pages of this,

there would be some garbage like that that's just sitting around. Like, you know, I'm sitting on a plane. Actually, today, I'm sitting on a plane and the guy in front of me reclined his seat. And I was like in recliners, man, these like airplane recline. You're not a recliner? No, God, dude. It's only two inches. Dude, this is the most ridiculous thing. No. Oh, oh. Do you recline your I do not recline. Well, this is like my favorite Twitter debate, by the way, is like the whole recline. You know, there have been a few funny Twitter debates that have come up. Like, I don't know, do you know Cody Sanchez?

Yes. So Cody had the one recently that she set off about picking people up from the airport. Did you see this? So Cody tweeted, like, I will never be participating in this trend about, it was like a girl had said she was going to pick up a friend at the airport. And Cody was like, I'm never doing that. If you're my real friend, you'll just get an Uber. Like I shouldn't have to be called to pick up your friend at an airport. like if you're an adult.

And it's set off the most insane, like, viral, angry discourse about whether or not you should ask your friends to pick you up from their port. That's funny. What do you think? Okay, because I live in a house with four other dudes. Do you think, do you pick each other up? Unfortunately, yes. What's it called Alpha Sigma Pi, Jack?

Your house? No, he says it's a frat house. It's a normal house. We're very responsible, respectful men. But, uh, albeit, well, there's, they should be a brief letters. So you could be responsible. responsible and respectful in a frat by the way. Yeah, we do have a ping pong room. Okay. Yeah, with industrial. Okay. Okay. Okay. But anyways, uh, we have this debate within us. I'm the only person that airs on the side of I don't think that's worth it to go pick someone up for the airport and drop them off because I just time is money baby. I would Uber. I have no problem Ubering. Uh, especially and then, but of course, I'm, I get asked to pick people up. So I'm like, okay, if I get asked, I may as well ask them back, make it more transactional. Okay. So I air in the side. It's like a quid pro quo airport pickup thing. Exactly. I think it just makes more sense, especially like since you'd be. You'd be. You'd be. You'd be. You'd be. wasting their time and like then you have to make sure you get the timing right.

Yeah. You get off the plane and like, what do you think? Uh, I don't think it's really worth it, but if you care about a person, I think it's a good gesture. Yeah. Like if it was my, you know, if it was a woman that I was hoping to build a relationship with, I'm going and picking them up. But I would not, I mean, I would find it weird, I suppose if a friend of mine hit me up that

was like, hey, can you pick me up from the airport? It's one thing of I offer. Yeah. And I'm like totally cool. You know, like if a friend's coming that I haven't seen in a really long time, I might be like, hey, you swing by the airport if I don't have anything going on. But for someone to ask you, it's sort of like, dude, just get a cab. Like you're an adult.

Just get a get a Uber. I'm with you on that. Graham, every single time we land, he's always like, Jack, hit up one of your friends to come pick us up. Every, like, it happens. He's frugal, man. He's running a business. It's frugal. And then like, and then split an Uber.

So we could split in Uber. It's not bad. It's like 20 boxy. Yeah. Well, if someone is at the house, They're not doing anything anyway. Are you known for your frugality? Is this part of your brand? Probably, yeah.

Okay. But my point being, if they're not doing anything anyway. Because I use some dumb shit with Uber. I'm sure we'll talk about that soon. But if they're not doing anything anyway, then I think it makes sense. Okay. If they want to, obviously, if they say, no, I'm not going to be like. I would never text Graham for a ride back from the airport.

I would never, I wouldn't, I wouldn't, I wouldn't, I wouldn't pick you up. It would pick you up. Point being, though, that was one, like, wild Twitter, you know, argument that went off. The one before. that was airplane seat reclining and whether it's like immoral and whether you're a terrible person if you recline your seat on an airplane and i had honestly never known that that was a thing until i saw that people were popping off about it i had talked about like you know people that don't put their grocery carts away uh in shop you know in shopping centers things like that whatever

but people related it then to this airport airplane seat recline and i had no idea that that was a thing i was like baffled that people get that angry about it and then i sat on an airplane and i like started observing and watching people do this. And it is fucking annoying, man. It doesn't bother me. If someone reclines their seat in front of me, it does not, what,

it doesn't bother you? What bugs me is when they do it really quickly. Fast, dude, the dive bombers, man. The kamikaze. That was what the guy did to me. Your laptop's right there. Someone jams it down into your laptop. I do it really slowly.

I kind of look behind. Yeah. Okay, well, you're considered it. Yeah. Like, hey, is it cool if I recline, you're kind of like giving them

the benefit of the doubt why you go. I just give them notice. Yeah. Well, what if you have a drink on there, your laptop, it gets jammed up. But it's just like, does the two inches of recline really make your experience that much more comfortable?

Because you're basically saying that, like, my two inches of recline is worth more to me than your miserable experience on this flight. But they could then recline behind you and get that two inches back. It just sets off a chain reaction of pissing people off the entire plane. Right.

And then the very backseat, by the way, does not recline. It doesn't recline. Yeah. So they're stuck. And you're next to the bathroom, too. So you get both. You get cut on both ways. Anyway. Yeah. Well, that is interesting. All the more reason to fly first class, Graham.

Do you fly first class? Yeah. Every time? Yeah. Yeah. Why? It makes my experience so, so much better. I can get things done.

I get their refresh. Southwest first class? South West doesn't have first class, do they? I don't fly South West much, but. The priority season. No, no, no, no. No, like, I'll pay for first class on a flight. Like, you know, flying too.

Like, if I'm doing cross-country, like JetBlue Mint is actually pretty reasonably priced for what it is, but you get a full, you know, experience and space. Like my whole life, I never did that, obviously. I have the means fortunately to be able to now. And for me, I get, like if I'm doing a one day trip, like I'm here for a day, I want to be able to do a bunch of writing on the flight, because otherwise I'm losing an entire day of writing on the, you know, eight hours, 10 hours of flying. Me doing that in economy with some, you know, jerk reclining into me while I'm doing that, it's basically going to be impossible. And so for me, I'm like, the calculation of me just spending the money on doing it versus the time that I would be losing on the

writing, it's actually probably worth it. Sometimes it's not, like flying first class to, you know, India on Emirates where you're playing, like paying a whole lot to go do that. Yeah. And if you're running it through your business, it's like, you know, 50% off when you take off the taxes and stuff. So you can figure out a way to justify it, but it's expensive nonetheless. But yeah, I do now. In order to fly first class, you must be doing pretty well for yourself, right? That's why you're here because you've built up some incredible businesses. How exactly did you get to where you are today? Could you give us a little synopsis. Yeah. So look, I mean, I started my, I started my career in like a pretty mainstream track. So I went to Stanford. I played baseball in Stanford. I thought I was going to play

professionally. I had like these big hopes and dreams like most kids when they go and, you know, going to collegiate athletics. Everyone tells you the whole thing of like 99% of, you know, NCAA athletes will never do this professionally, but you never believe that. You always think you're going to be the one. I got hurt my last year. And so I kind of derailed whatever aspirations I had had to figure out what I was doing next. I ended up stumbling into a role at a private equity fund that was just getting started in the Bay Area in 2014. And I took it over a job at McKinsey in New York. And from like, you know, Indian mother, right? So like name brand things are big in Indian culture. And so the idea of me going to some like no name private equity fund that

she, you know, she didn't even know what private equity was. Neither did I. Over McKinsey. Like my mom, I don't know, to this day, I think she's like, what the fuck were you thinking? That's crazy. The whole idea of that. I mean, she still wants me to go to medical school. She's still asked me every year. Yeah, I mean, she's like, Are you sure you don't want to be a doctor, Sahel?

I'm like, mom, I mean, that's kind of far. I don't think I can do this. So anyway, I took this job. Didn't really know what I was getting into, but I happened to be one of the first, I don't know, 10 employees at this private equity fund that was managing a half a billion dollars at the time. Over the course of seven years that I stayed there full time,

we went from half a billion dollars to managing three and a half billion dollars. I was co-leading all. consumer investing for the fund, sitting on a bunch of boards, had an amazing experience. Did the like finance grind, right? What was that like? Because I hear it's a ton of hours. Yeah. Like 16 hours a day. You're sleeping under your desk. Yeah, I didn't do the sleeping under my desk, fortunately. I did, yeah, I did a couple all-nighters in the office, but never slept there. But yeah, I mean, it's, look, it's part of the learning experience. It's like anything. Like when you're diving into it,

I'm sure you guys have done this with what you're building your careers around. It's like, if you want to learn a lot, you have to work hard. I'm not one of these people that'll come out and say, oh, yeah, working hard's overrated. It's, you know, just work smart and that's what matters. Like my big belief, frankly, is, did you play video games in your kid? Yeah,

using a video game analogy. Did you do? Okay. So there are these games in your kid where, like, you start on a map, and the whole map is black. You can't see anything. And you're in the one spot.

You can see where you are. And as you start exploring around, it lights the map up. Like you went and you kind of uncovered the different regions. And then, you can kind of see the whole map and you see where all the resources are and you know where you should be building and doing all your you know building your army or whatever. I think that that same thing applies to your career where like when you start you just are in one little spot. That's

where you started. Everything else is black out there. And by working hard and by saying yes to things early on and taking on these different opportunities, you like spread light around the map. And then you can see everything and you can decide like where do I want to deploy my effort and get leverage out of it. Like, where is the gold that I can go deeper down and figure out? But without that first part, you're just going to try to go deep in an area you have no idea what's there. It can be a total show. And so, like, I'm a big, big believer that early on that hard work just pays off in a big, big way. Jack, what are you doing? I'm getting gazed, ma'am. Shouldn't you be eating something with more protein than cereal? Oh, silly old graham. This ain't just any old cereal. It's

Magic Spoon. Do you just carry that with you? Everywhere. Magic Spoon is cereal reinvented. Not only is it delicious, but it's also wholesome and satiating. All right, let me try that. It's made with high quality ingredients and zero grams of sugar. Their variety pack comes in four different flavors. Again, you carry this all with you. Everywhere. So one, we have peanut butter, then we have frosted, and then we also have, oh, this

looks pretty good. Coco. Wait a second, Jack. I'm looking at this. One serving is only 140 calories, 13 grams of protein, and only 14 grams of carbs. Magic spoon is perfect for those who are carb conscious and trying to live a low-carb lifestyle. So click the link of the description to try out their variety pack. Jack, stop that.

I can't help it. It is good, isn't it? Anyway, so click the link below to try a variety pack today. Just make sure to use the promo code ICH to get $5 off of any order. Or you could just go to magic spoon.com slash ICH. And MagicSpoon is so confident in their product, they're backed by a 100% happiness guarantee. So if you're not fully satisfied, they'll give you a full refund. Again, click the link down below in the description or scan this QR code that's appearing on the screen right now and use code ICH to get $5 off.

And now what that said, let's get back to the podcast. What would you be doing in those days, though? Like, what would that involve? It depended on what level you were. So analysts, the hours are largely like, you know, cranking through analysis. It's like modeling, right? Like you're building financial models. In private equity, it's like, you know, you're doing leverage buyouts. So you're taking on debt to buy companies. And so the whole model there is you're like looking at the cash flows of the business and seeing if it can service the debt that you're going to put on the business and pressure testing it in a variety of scenarios. And that always just takes a whole bunch of time and energy. Eventually, it probably should be

done by AI. Like those models should probably be getting automated, but it wasn't at the time. And so it was very manual and you're having to crank through it. Is it just like a formula or some sort of algorithm that you put on all the data in and it like, I mean, it's like a multi-tab spreadsheet. It's like a three statement financial model. So you're looking at a financial model and you have to take the numbers from the company. The problem, if you're investing in a sophisticated public company, and you're going to go buy a public company, like Blackstone's a big private equity fund. They're going to go buy some big public company and take it private. That company has tons of like really clean, nice, beautiful financial statements that they can take

and very easily drop into a model. And it's super easy to kind of have a template. For the companies we were investing in, like middle market, a lot of family-owned businesses, you're talking about like poorly kept QuickBooks financials for the last several years. So you can't just like grab numbers out of a spreadsheet and put them into your spreadsheet. It's not that easy. Like, you know, someone's going to be running their like country club membership through the financials and you need to figure out should that stay, should that go.

Like, there's all these things that you need to be asking questions about. That end up taking a lot of time because you're having to kind of like dig through the weeds of these businesses. So what types of businesses where you buy? Like would you just find like some hat store down the street and they're like doing all right? But could be doing better and you buy it? I mean, these had to be big because we were investing, you know, we were investing in 10 to like 50 million EBITDA businesses.

So they were doing 100 plus million of revenue. So, I mean, we looked at everything. Like, I spent some time in oil field services in, like, Midland, Texas. You know, going down there and, like, going and looking at pump jack businesses, like those things that are kind of coming in and out of the ground. How would you know what you're looking at?

Like, why would they send you down there? I mean, you go, these private equity funds are very good about, like, finding an operator who has been there, done that with that industry. And then pair them with horsepower, i.e., the analysts, who can, like, crank through the shit. So that person is, like, your field guide. you go down and they're the one telling you like this is interesting or not and then if it is yes interesting

and we're going to spend time on it pass it over to the like cogs in the machine who are going to do the actual grunt work to figure out how to make the numbers work to do a deal um and that's the model that has worked for the private equity industry for a long time um but man it's it's a grind when you're early in your career was there ever any pressure that like you were worried about being wrong on some of that so like how many people review that before it goes up to the point of actually purchasing something. Yeah, I mean, I think that happens. And you hear funny stories of it now and then, like there's some model that's wrong and someone loses $80 million or there's like a wire that gets sent that's wrong. The scariest thing, which is a funny thing that no one talks about or writes about, are these things called funds flows. So when a deal gets done, the last step of the deal getting done is like wires need to get sent to all the different people. And so in one of these companies, like, you know, there's not just one owner of the company. There's like a cap table that has tons of different shareholders and they own different percentages. And

they get, you know, different thresholds where they get paid out different amounts. There's all the, like, banks that lend money, all these different wires. And so when you're looking at a deal, there's this document called a funds flow that usually the analyst manages that literally has all of the different wires that have to get sent to all the different places, the exact amounts that have to get sent, and the wiring details of all the different people that are having the wires sent, where they're coming from, where they're going. One letter being off in one of those documents sends like tens of millions of dollars to the wrong freaking place. And so there was always this joke of like, oh yeah, did you add in that,

you know, that one that sends it to the Cayman Islands bank account for me or whatever. Like, you know, send off like 250K. No one will know like in this, you know, a billion dollars is flowing. Maybe no one will notice. And it was always like this hilarious thing because literally there's some analyst that's managing the fly. I mean, I did one deal where I was the only one that knew where like two billion dollars of funds were flowing one morning. Like we said, yes, all the wires get sent and two billion dollars are flowing and everyone's assuming that I'm right. that like this thing actually works. There's no checks.

Yeah, manually into an Excel spreadsheet. And by the way, Excel, if something has a leading like zero in an Excel document, it automatically eliminates it. So if you don't put like a apostrophe before the zero, you can actually miss a zero. And so like there are actually things that can happen that can like screw up the entire deal. I always just thought that was so, so funny because you would hear stories every now. And then I'm like someone screwing up and you're like, oh, that's the nightmare. fired for something like that.

That's crazy. Had that ever happened at your firm? Never at our firm. But you'd hear, I mean, like, you'd hear about it. Like in, you know, the great find of stuff. Like, oh, some deal got, had to get like redone at the last second because a wire went to the wrong place because someone got the wrong amount or like whatever. That was common in real estate.

But for wire fraud used to be a huge thing. What would happen? So like between 2012 and 2016, wire fraud. was beginning to ramp up. And what they would do, they'd usually crack into like an escrow account's email address, find the buyer, but then send them fake wiring instructions.

They look legitimate. Like the same thing just with the numbers changed around. So the buyer would see this and think, oh, I'm safe to wire my money here at closing. They'd have no idea. And so they wire the money there. And then escrow calls a day later, we never got your wire.

Well, I sent it. We never received it. Who did you send it to? I sent it to this. That's not our bank account. And so I've seen instances happen before Of people wiring millions of dollars To the wrong place to scammers

And thankfully in every scenario that I've like seen I've never been a party to it But like just I've heard of these things The FBI and the police get involved And they're usually able to get it back If they catch it within like 24, 48 hours They could trace it back and send it Yeah

But they're like hours from someone like just getting a money order Yeah And then like leaving the country with millions of dollars The other one I always found funny was ransomware attacks. We used to get ransomware attacked a lot. Like, you know, this became a big thing, especially with middle market companies,

the type of companies we had because sophisticated public companies have these like incredible cybersecurity infrastructure that they've paid for tons of money. A random like middle market company, you know, somewhere in the country, doesn't have all the money to spend on cybersecurity infrastructure.

And so you would get hacked. And basically these attackers would come in, it would be a ransomware attack, which locks all of your access to data. and it's encrypted. And so the only way you can unencrypt it is with a key that they're going to give you. And their whole thing was like, you can't do business. Like we had a business that was doing $250 million in one year, completely shut down.

Like could not sell, buy, do anything until we got this key to unlock all of our data. And their whole thing is like, okay, if you pass $5 million in Bitcoin, we'll give you the key. Otherwise, you don't get it back and you're not allowed to do business. And it became this like efficient market almost. where we would just pay. And you had to get insurance that would cover the payment. And the insurance company would negotiate with the hackers. Yeah.

And it was like an efficient market because the hacker knew that they actually had to deliver the key because otherwise the next time they did it, people would just say, no, I'm not paying you. I know you're not going to deliver the key. And so like this one company, it happened to us. And they asked for five and we negotiated it down to a million. And we sent them a million dollars of Bitcoin. And then they unlocked our data. And like two days later, we had back access.

But that was happening. Did they ever catch the guys? Did they know where they are? No, there was like North Korean rings, Russian rings. It was like a big, big. And a lot of people thought it was state sanctioned stuff that was happening. But there was like the Wall Street Journal did a big expose on it. It was fascinating actually seeing it happen in real time.

Because you're like, you know, this random, this was like, you know, a random company that had to like acquire and then send Bitcoin to these hackers in order to get access back. How much would insurance be on something like that? I actually don't know what the premiums were. I'm guessing it's got to be 30 grand a lot. Oh, yeah, yeah, they were ramping up, especially as it became more prevalent. And the insurance premiums were all reliant on what your infrastructure actually is.

And so if you had great cybersecurity infrastructure and tech infrastructure, it was cheaper. But for most of these companies, it wasn't great. So you were paying a lot. Yeah, I mean, it was probably $50,000 plus in cyber insurance premiums. Okay. So when you were working at this company, can you say what you were earning throughout the time? Yeah.

I mean, I was making, like, by the time I was a vice president, which was like, you know, six, seven years in, you're making like seven figures of all-in compensation across cash and equity, you know, carry in the funds. Your cash comp is like, you know, mid to high, six figures, and then you have carried interest. So equity, profit share in the funds. So your late 20s at that time. Yeah, so I was 27 when I became a vice president.

How did you get to vice president of 27th? I mean, the whole, like, vice president thing is hilarious in finance because it's like, oh, I'm a vice president. Yeah, I'm a vice president. Like it's a meme now because like literally it's a bunch of 27 year old kids that are like I'm a vice president and like you know I was sitting on my first board because when you become a vice president that's when you can sit on boards usually Because it sounds official enough but you're like a 27 year old kid what are you doing sitting on a board of a company? I still thought it was ridiculous But yeah I became so I did two years as an analyst two years as an associate and then like a year as a senior associate and then became a vice president and you know we were a small firm so like if you were doing well and the funds were growing and we were raising bigger funds funds were performing well, you kind of got on an accelerated track.

And we, I mean, I wouldn't even say we were like paying in the like top 10%. Like private equity is a very, very lucrative track for kids out of school. Because right away, you're making north of, you know, 150, up to 200 maybe in your like analyst years, associate years. And then by the time your VP, you're making at least, you know, 500K of cash comp. Plus you have interest, you know, profit share in the funds. How many years does it usually take to become an associate? Um,

associates after two years as an analyst or two years in banking or consulting. That's like the first thing when you come into it. And like the, you know, the reason that people go, they go into banking for two years. They go to like Goldman Sachs and go to investment bank for two years and they put up with 100 hour work weeks and the misery of it is because they're hoping to get this like

lucrative private equity or hedge fund gig as soon as they come out of that. A lot of them now are recruiting. You're locking in your private equity or hedge fund job before starting your banking job. So you start your banking job. banking job knowing that you're leaving and that you're going to be going to this other place in two years. Why do they set it up like that? Are they that hungry for people to work with them? I mean, how does... They're basically, the private equity funds and hedge funds are basically outsourcing their training to the banks and consulting firms. And the banks and consulting firms, the banks in

particular, don't really care because they're happy to get two years of like crazy hard work from some young, smart kid and then have them leave. And the reality for the banks is like, they only need one out of every like 10, you know, good analysts to rise up and become a partner because they don't have room. They can't have 100 partners sitting at the top. They need a bunch of people cold. And so they're happy to have like a lineage that goes to these great firms. It improves their brand. It's kind of like a symbiotic relationship. But it's crazy. I mean, you're making a lot of money at a young age. Working really hard. Your hourly rate sucks. Your hourly rate really sucks. But you sound, you know, the status of it feels good. You're like, you know, you're flying first class

for work. Like it feels good. Wow. So how did you justify quitting that then? Hold up. Before we go to that, I'm curious how you leveled up so fast. What do you feel set yourself apart? Yeah, I mean, look, part of it is a track.

Like you get on the track by doing well your first, you know, year, year and a half. I mean, honestly, first impressions are everything. Like, if you do well, your first, like three months and people like you and you say yes to everything and you're, you know, setting the standard that you work really hard and that you're, you know, a good, frankly, team member. and that you're not weird, like, that they can bring you to a meeting and you're not going to be weird. I'd played baseball my whole life. I'd been in locker rooms.

All these middle market businesses are run by a bunch of people that like to talk about sports. So, like, I could go to a meeting and shoot the shit with some guys that like baseball and talk to them about my glory years. And they loved that. And so, like, being able to be normal. So what's a lot? What would be weird, though, if they ask about like a baseball and you're like, I don't know what that is? Honestly, no. No, I mean, honestly, the weirdest.

No, no, no. That is weird. But, but. What's a baseball? weirdest thing you can do in a meeting, in my opinion, is present yourself as like better than them in some way. And this is a big, big risk in private equity and in the finance world in general is because, you know, like I went to Stanford, right? Like we were hiring kids that went to Princeton, Stanford, Harvard, like all these like elite pedigreed kids. And if you took one of them to a meeting

in, you know, middle of Kansas and into a guy's company who's running, you know, a playset business that's doing 300 million of revenue, 50 million of EBITDA. The guy has an airplane hanger in his back. But he's from Kansas. He grew up there. He hasn't, you know, gone to some fancy school, but he's unbelievably successful. And you bring in an analyst that is almost like talking down to him in a certain way because like they feel like they're so smart that they went to a school. That's really bad. You can't have that be like the type of relationship that gets set. And I saw that a bunch. You'd see, you know, analysts all the way up through directors that would like give off an air of superiority. And it's like a coastal thing that I think is just,

a bad thing in general. We've seen it societally as a country. Um, but that, that is weird. And that's really hard to accelerate if you're that and if you're, if you're, if you're creating that vibe. So what do you do if you see that? Do you pull them aside? You like, hey, you got to cool it? Or do you just let them do their thing and they'll kind of fall into place on their own? It depends who you are as the senior person. We, I mean, we had people that would give that feedback very directly. And that was great. I, I've always been big on like, give me the feedback right away because I want to be able to improve on whatever the thing is. That's from an athlete background, like it's what I believed in. Um, Some people didn't do that.

And so then, you know, you'd get a year in and you'd get your first review. And it was like, hey, you're not doing so great here. And you'd wonder why because you hadn't been giving that feedback along the way. But I think you have to tell the person right away. Because usually they don't mean anything negative by it. It's not like they're trying to be condescending or trying to give out that vibe. It's just they've always been around. Like they went to a fancy private school in New York.

And then they went to Harvard. And then they, you know, got this fancy private equity job. And so they've only been around that type of culture. And you get put into a different environment. you have to learn how to adapt. Now, I think saying yes is so important. I think that's one of the huge quality that people don't really pick up on.

What are some of the weird requests that you've gotten? I'm sure there's got to be some like off stuff. It's like, you know, I'm going to say yes to it. I mean, yes, man. But it's kind of strange. I had to go to a catfish farm in Louisiana to go like see how the catfish were going on a conveyor belt once. That was a pretty weird request.

We were looking at investing in this catfish farm. and people wanted to see it actually in action. Now, like, this catfish farm was real. And look, I'm like, I'm 23, you know, I'm like 23, 24 getting out of school. I thought that was the coolest thing in the freaking world. I was like, this is amazing that I could do this. I was like down in Midland, Texas, you know, like going and driving through the fields to go, like, make sure that these like pump jacks are working.

It was like an amazing experience that when you say yes to, you get to like go see all these things. My first actually, my first like month working, you know, I thought private equity was going to be like sitting at a desk and cranking out numbers on an Excel spreadsheet. And I literally was in Fargo, North Dakota, uh, helping one of our like, um, retail, uh, salespeople at one of the companies we owned, uh, like, fix, uh, store signage at one of our, at one of our stores in the place. Like, I was like climbing up a ladder and like fixing this store signage at the top of the store because it was looking kind of janky. And I was just sitting there like, wow, this is not

what I expected my finance gig to be. Gosh. But it was fun, man. I totally agree with you on saying yes. I think especially early on, saying yes to things just kind of expands your like surface area of luck. You know, you just get exposed to new things. People start looking to you for opportunities when they have something cool come up. They then are like, oh yeah, Graham said, you know, was around doing that thing. He did that one thing. Well, let me call them in to like sit in and just listen to this call that I'm about to do. And that's when you end up learning. In a world with rampant ads, not enough confidence.

content and uncomfortable YouTuber merch. Two men brave against the standards and create something more community oriented, more robust, and wait for it, ad free. This is Jack and Graham, starring in the iced coffee hour club, linked below. That's because dot com was taken. If you want an extra in-house episode every single month, if you want ad-free, uninterrupted content and early access to every episode, then the iced coffee hour club is for you. Starting at just $5 and completely free for the first month, you can have access to all of that and more at iced coffee hour. dot club.

Linked down below. Seriously, guys. Enough of the voice, man. Guys, check it out with the link down below in the description. It would mean a ton. And the first month is free for a limited time. So check it out before it expires

with the link down below. Thank you so much. And let's get back to the episode. Now, you mentioned before there are four types of luck out there. Could you explain that? I thought that was so insightful. It makes a lot of sense.

Yeah. I mean, the first type is blind luck. Yeah. This is just like what we think of as luck, frankly. It's like, you know. Right place, right time. Just happen to,

things like that. It's like, you know, acts of God. It's like where you were born, who you were born to. You know, the second one is luck from motion. This is like hustle luck. This is kind of what we're talking about. It's like you're hustling. And this is, you know, you're creating motion and ecosystem. So where you're like literally driving connections where people are bumping into each other. You're like connecting people. And so then all of a sudden you're brought into stuff that you otherwise wouldn't have been. The third type is luck from awareness. This is like you are so deep with. knowledge in a given area that you're able to spot luck. You see it from a mile away. You're like, man, I've been in this, you know, in the YouTube space for so long that I can see where the ball is going before it's there. So we can position ourselves out in front of that. Yeah, it's kind of lucky that you were there before it, but not really because you've been doing all the work. And then the last type is luck from uniqueness. And this is kind of the weirdest and like most esoteric type, which is just like your weird quirky habits and quirky hobbies and quirky loves and dislikes

and all those things lead to luck actually being attracted to you. So like, you know, the example that Naval gives around this is like someone that's really into weird, like treasure diving. And they're like super into this. They've been doing this for 20 years. And so then there's this rare deep sea find in the ocean and they're the first person that everyone calls. And so it's kind of lucky that they got the call.

But really, it's because they were so unique and they had this esoteric set of interests and skills that they actually get the luck brought to them. Yeah. I just think having an awareness of those different types and how you kind of approach things over the course of your life is interesting because your life starts with all blind luck. You're like where you're born, who you're born to, the situations you come into. That's all blind luck. You can't control that. But then as you start moving, you start building into that second type of luck of hustling. You're trying to create motion. You're trying to do things. As you start going deeper in your life and into your career, it's more luck from awareness. It's more like, hey, how can I spot these opportunities that are out there? And then there's the fourth type, which is like it requires you. years of weird interest, experience, hobby, etc. For that to even ever come to you and into your life. So I've always thought that the progression of that over the course of your life is a really, really interesting concept.

I like that. How did you, going back to Jack's question now, justify quitting? Because making seven figures, late 20s, that's really, really, really hard to walk away from. Because you could very easily justify if I just do this another 10 years and save, I'll be set. Yeah. So this is a, this is an inch. This opens a can of worms, so I hope you're ready. So I, COVID hit May or March of 2020.

I was marching down the path to become a partner at this fund. I was honestly, like, loving it. I had a great experience. The group of people was incredible. I was learning a ton. But in the back of my mind, I was always like, is this what I'm going to really do the rest of my life? Part of that was just because I was never that motivated by money.

Like the whole industry, if you're going to be great at private equity, if you're going to be the best at private equity, you have to fucking love money. Like, you have to just want to make money. Like, you know, one of the most successful private equity funds in the world is led by this guy who, I don't want to say his name because people will know him, but he during fundraising told this, like LPs asked him,

what type of people do you want to hire? And his response was, I want to hire the type of kid who he's sitting at his grandmother's house on the couch and he's digging between the sofas. looking for pennies. That's the type of kid I want to hire. And like that's what you have to do to be the best at private equity. That's like a perfect microcosm. And I'm not that. I like money. Don't get me wrong. I like I like doing nice things. I like being able to fly first class. I like being able to take care of my kids. I'm never going to care about a $10,000 bottle of wine. Just not.

I don't have a watch. Like I'm wearing a woop band. I'm not into fancy things. I like being able to have, you know, a nice place, take care of my family, et cetera. But it's just not what drives me on a daily basis. And I started to think about that. I was like, hmm, you know, I don't know that I'm ever going to be the best at this simply because what motivates me is not what needs to motivate me to become the best. I'm not nerding out on this stuff enough. That coincided with me discovering my talent and love of writing. I all of a sudden wasn't working 80 to 100 hours a week. I was stuck at home. I couldn't travel. We were traveling three to four days a week for work. I couldn't do that. I wasn't commuting. So I had all this time on my hands. What were they having you do in the meantime,

by the way. The Port Equity World was kind of dead. Really? I mean March. For I guess a month or two. March to like March April 2020 was like total chaos because our companies, some of them were just shut down. You were like, do we have any money?

Are we going to get PPP loans? Like there was just chaos. No one knew what was going on. May things kind of settled into like there's not much new deal activity because people don't know what interest rates are going to be and it's hard to get someone to loan you money at that time. And so you can't really do a buyout. So there wasn't much new deal activity.

And your companies were kind of stable because we had figured out that like consumers were still spending money. PPP loans were getting, you know, our bad companies through the tough time. And so you were kind of in this like weird limbo of there wasn't a ton of new stuff and your companies weren't in chaos. And so there wasn't a whole ton of work actually. And so on the weekends, I was like, I have time. I don't have a social life because you can't go out.

I was living in the Bay Area. So you really couldn't go out. And I wasn't like in Texas or in Florida where you were fine. Unless you're the governor. Yeah, exactly. Then I could go to the French laundry. And I can go to my, you know, yeah, exactly, go to a wedding, whatever. No, I was not the governor.

I didn't hang out with Newsom. But look, so I had time on my hands. And I was sitting around and I started writing. And this is like before Twitter threads were the meme that they are today. I kind of discovered them and started building them as like a format for writing slightly longer form content on the platform. At the time, I had like 500 Twitter followers. This is like May 12th.

when I posted my first thread. And I very quickly realized there was product market fit to it. And it was originally around sort of personal finance, similar stuff to what you were originally kind of doing around YouTube. Personal finance, you know, markets, things that were happening in the world, a little bit of explainers, simplifying complex topics. And there was a big demand for that. And it started growing.

It started scaling. By the end of that year 2020, it had grown to about 75,000 or so followers on Twitter. And I had spun up a little side business, like an agency business, helping other people to build their personal brand. So like startups I had invested in things I had done personally on the side, I was starting to help those founders with growing their personal brands, kind of leveraging the playbooks I had used. That was starting to cash flow and generate income on the side in this like little weekend hobby. By early 2021, that plus the newsletter I had just launched was making me more money than what I was making at my lucrative finance job. It's crazy. One year?

Yeah, not even a year. I mean, it had been, at that point, it had been like six months. What was it, what was the percentage of the money? What do you mean? Like, where did the money come from? Was it mostly the course business?

No, no. So agency was the primary chunk of it, which it was like, look, it was helping startup founders build their personal brands. And so it was like, you know, I could get them a ghost writer if they needed one.

But a lot of it was just like helping them with strategy, with the playbooks, with, you know, the cadence, like the things I was doing. Because at the time, there was like a real arbitrage opportunity on Twitter too. And so you could really grow quickly by leveraging this format and leveraging this structure. And those were, you know, it was like

highly recurring business. It was like $5,000 to $10,000 a month from someone, you know, and you would just get a set of clients. And it was pure cash. I didn't have costs. It was just cash to me. And I had a bunch of clients. And so I was like helping people on the weekends and like I would, you know, help them with all the structure stuff. And it was just generating a whole ton of cash in. With those people drop off, though, once they feel like they get good enough traction, wouldn't they feel like, well, I kind of get this now. I'm going to do it on my own. I mean, there was so much more demand than supply of my time, though, that any time someone would churn, which it was always because of success, actually. Like, there was never a case study where it just didn't work because

the format just worked. You would have some churn, but you'd have like three people that you just had waiting, basically on a waiting list. You're like, hey, I know you were interested in this, and you could just pull someone in. So that, I mean, that business, to this day, I mean, I still run it as like a side agency. Now it has an operator. There's, you know, people involved. And it's a lot more systematized. It was pretty janky at the time. That business has never declined in revenue since those early days. Yeah, every single month has been flat or up. And a month over a month? Yeah, it's never declined because there's always just been a backlog of, I mean, there's infinite demand. Like even just today, like I saw Alex Lieberman, the morning brew guy tweeted about this like,

hey, would anyone be interested? And he said, like, I texted him. I was like, oh, what did people say? And he was like, dude, I got like 20 DMs. And so then I ended up, I mean, that sparked me thinking about like, oh, is there a bigger business play with this that's disjointed from my time? And so we ended up, I co-founded a broader play to do this that's in stealth right now, but scaling up. And we'll be, you know, 100K MRR within three months of launch. So these businesses are like, there's a big, big pie to doing stuff like that. And what about the newsletter? What gave you the inspiration for that? Newsletter originally was just, I want to go a little bit deeper. So the way I always thought

about it was like Twitter is super surface level, you know, the format in and of itself. At the time when I first started, it was 140 characters per tweet. It obviously expanded since then, but it was 140 characters. And people wanted, A, people wanted a better format to read my threads. So that was the first thing is I was like, oh, I'll just send them to you in your email inbox. So sign up for this, and I'll just send them to you. And if you don't like reading them on Twitter, just read them in your email. It'll look nicer, it'll flow better, et cetera. So originally it was that. And then I was like, okay, I want to create a deeper connection with these people than just on Twitter. I want to be able to, own them in a deeper way and build a better community here.

And so writing in a more deep construct around the same topics became what I started writing about in my newsletter. And that was like May 2021 was when I really started putting effort into that. And it started with, I don't know, 10,000 subscribers that were on the list at the time. Now it's grown to, I don't know, 300,000 today. And it's growing fast. I mean, it should be at a million, I would say, within the next year based on the current. most of the growth coming from?

Now it's a combination of top of funnel from Twitter, LinkedIn, and Instagram. LinkedIn is probably the highest source right now. LinkedIn's like the new Twitter in terms of arbitrage. That's what I'm trying for. We can talk about that. I can definitely give you some ideas on that front. But LinkedIn is incredible arbitrage in it. LinkedIn has a lot of characteristics that look like what Twitter was to me in early

2020 in terms of audience growth capabilities and a very high value audience growth because people are professional and they're there to grow. They want to learn. They want to grow. And it's not like, on Twitter, if you post something, you get like 10 people reply, you know, three of them are telling you're the devil and you should kill yourself. You know, five of them like you and then a couple are indifferent. Why do you think Twitter's so toxic? It's only Twitter.

It's so easy. It's anonymous. It's like so. I mean, YouTube comments have to get pretty toxic too, right? They're nowhere near Twitter. Yeah, YouTube, I believe that like 95% of YouTube is very positive. Interesting. Five percent of people are going to hate no matter what you do.

But I would say like 90, 95% of people are supportive in some way or want to add something. Twitter. And I'll spend like an hour going through Twitter and just reading whatever I see. And no matter what, it seems more like 25% is just people like just hating on whatever this person has to say. I agree with that. I agree with that number too. I mean, Twitter's interesting. It's, uh, you know, I basically only post positive things.

Like I, I'm in general. I'm just a very positive guy. I'm like a happy guy. And so I, I, I avoid. controversial things for two reasons. One, I don't think about particularly controversial things. I like posting positive things. And two, I just like don't want to invite that into my life. And so it's just not, not part of my brand. But I still get a bunch of that. And so it's amazing. Like if I'm getting that, imagine if you post things that are even borderline. So we've tried going, not like controversial, but like riding the line a little bit. And you see the engagement go up. So it like it makes sense. The more controversial you get. We'll see 10 times more growth, comments, shares, whatever, the more extreme. you are. Yes, the Donald Trump playbook. Right.

Works really well. Right. Joe Rogan did it. I mean, like, it's a tried and true playbook for content creators is you like, you say something that is controversial. 50% of people are going to like it. 50% of people are going to hate it so much that they share it saying how much they hate it, which actually just drives your growth more, which it's great.

It's actually really, really smart as a content creation strategy. I just don't want that in my life. I have no desire. Like, I've gotten death threats for things that I posted that I didn't think were remotely controversial. Like, I wrote this thing about, A kid came and knocked on my door. This is like, when is this?

2022, like May. Knock on my door on a Saturday morning. Go to the door. Young Hispanic kid. He's like, hey, you know, I live in the Bronx nearby or live in Harlem. And I'm, you know, trying to make it in the music industry. Curious if you have any like, you know, business. I just want to chat about business.

And I was like, you come to my house in particular? He's like, no, I just came to the neighborhood. and I'm just like going and knocking on some doors. I live in a nice neighborhood, like a nice residential street in a, in Westchester. And I was like, sure, yeah, let's chat. So I sat on my deck, we chatted for a little while. He seemed like a nice, like, earnest kid.

And I had him back the next day, and he, like, I had him back the next day. I was like, yeah, he's like, the hustle to do that, yeah, to go into a nice neighborhood, knock on people's door and talk business. That's what I thought. Man, that's, yeah, that's what I thought. So what I wrote about, that was my kind of point.

It was like, rather, like, if he had sent me an email, 99% chance I wouldn't have seen it or I would have ignored it because I get a million emails of people asking me for different things. But he came to my door and he was like very earnest, polite, had interesting ideas, thoughts, et cetera. And it was very hard to say no to someone to their face. Honestly, it was just difficult because I consider myself a nice person. And so him saying like, hey, would you be willing to chat for five minutes? I was just like, huh, that was interesting. He did something different. And so could you sit in a coffee shop?

a nice area and ask people for business advice. Maybe could you go do things like that? Like just take a different approach, finesse the system a little bit. So I wrote something quickly about that. And it turned into this like viral, actually like the first 24 hours, not much happened. And then all of a sudden it got taken over by this like dark side of Twitter that turned it into this like viral outrage that I was going to put people in danger that like kids were going to get shot. Amazon presents Jeff versus Taco Truck Salsa. Whether it's Verde, Roja or the orange one. For Jeff, trying any salsa is like playing Russian roulette with a flamethrower.

Luckily, Jeff saved with Amazon and stocked up on antacids, ginger tea, and milk. Habaniero? More like habanier, yes. Save the everyday with Amazon. They were going to go to someone's house and knock on their door, and, you know, a young Hispanic kid goes to someone's door in the wrong part of the country and gets shot. And obviously that wasn't my intention.

And, you know, that scary to me that, like, people took it that way. That would have been a further thing from my mind. Partially, like, I understand. It was just, it was something that I didn't think of and, you know, kind of had a blind spot around and missed. But clearly it wasn't my intention. And it turned into this, like, crazy, you know, I was getting death threats. You know, like, Fortune and Business Insider decided to write, like, hit pieces on it,

told, like, said that I declined comment when they never reached out to me. It, like, turned into this whole thing. thing. Wow. And that moment for me, we had just had our first kid. He had been born like a month before. And I'm getting death threats over something that I tried to write in a positive vein. And I just realized like, yeah, the same for me. I'm never, I'm not even touching anything that's like borderline. Like I'm not going anywhere near that kind of thing. But the thing is you didn't even know it was borderline. I didn't know. So it's like sometimes the things you say or post you don't even think are controversial. But someone can interpret it in a way like you never even thought. Yeah, it got taken in a direction that I did not anticipate. But, but. But it was a crazy experience of like, okay, this is the type of thing that can happen when you have a platform and when you have reach. And you need to be cognizant, frankly, of like, I don't want to endanger anyone. That's obviously not my intention. I don't want that to happen.

You know what I am thinking. Why Twitter attracts more so those people is because maybe it's showing more people your post who maybe don't want to see it. Like on YouTube, the search recommendations are very catered to what you've previously watched. It's probably more in line with what you enjoy watching. Yeah. Whereas on Twitter, you're kind of. exposed to a bit of everything. So you see things that may be more prerogative. Yeah, there's a bit of mob mentality that comes out on Twitter where, um, with like quote retweets in particular. Um, I mean,

you see this like when, when Cody posted her thing and it went crazy viral in a negative way, it's like the quote retweet army comes out. And when it gets picked up in like these little micro communities that exist on Twitter, like if you get picked up in the like anti work Reddit community that exists on Twitter, that was what happened to me. That was what happened with this is like the anti-work people took it as like, I'm promoting hustle. I'm like not a big hustle culture guy, but they took it as like this hustle culture bro is endangering kids by telling them to go knock on doors.

And like that wasn't the point of what I said, but it was taken that way. And I wasn't going to comment further on it because then you're just like digging your, you know, I'm a big believer in the Warren Buffett quote. Like when you find yourself at the bottom of a hole, just stop digging.

And so I just did that. I just muted it like went underground. And it was just like a fascinating. few days and an interesting story to me to say like, hey, I'm not touching anything that's borderline anymore. But man, crazy. Was that tough for you to deal with personally? Like getting all of those hate comments and everything? Yeah. It was just scary with a newborn. It was mostly just scary because I had the newborn where I was just like, yeah, I don't need this in my life. Like I have a newborn kid. I'm not trying. Like I, it'd be one thing if I was trying to be controversial and then a bunch

of hate came my way. And I was like, yeah, I asked for this. I did this. I just didn't mean to. I clearly wasn't trying to get anyone in trouble or do anything. And so it was like just Dicey. My wife was pissed. Did you ever question your initial tweet once you started getting all of those poorly received comments? You're like, oh, maybe I shouldn't have said that. Or were you always still just like, no. No, I mean, I completely stand by what the principle of the idea was, which is that like doing things differently and finessing a system, like figuring out a different way to get in the door with people to network and do these things is smart. Like I completely stand by that.

You know, should I have like sat down and spent more time thinking about, you know, the exact idea, of knocking on doors, maybe, but that wasn't really the point. It's just that Twitter as a platform doesn't have room for nuance. And so if you just read it directly, you would take it in one way when if you actually just read it

with like an open mind, you'd take it in the way I wanted people to take it. So I don't know. I mean, more than anything else, I think it just showed that like you have to assume that people are going to read the thing and experience it like by the letter of exactly what you wrote,

that they're not going to be like flexible in the way that they experience it. And if that's the case, and they're going to take it negatively, I'm just not going to post it. Is there anything else you've posted that got a totally different response than you were expecting,

like to that degree? Or was that like... No, that was like far in a way, the main one. I've had a few things that people have like gotten outraged by, you know, in like a stupid way, but that was the only one that got like really dark. But I'm pretty flowery, man. Yeah.

So how do you approach it now to make sure there aren't any misinterpretations of what you have this stuff? I mean, most of my content now, since my son was born, frankly, most of my content is sort of about my own personal journey of experiences, struggles, and wrestling with the like changes that come in your life as you're starting to kind of get older and experiencing these things. My content. Lower back pain.

Yeah, lower back pain. Next dip. Next dip. Just getting old. No, I mean, my life has changed a lot in the course of the last three, four years, right? I went from like being like hustle hustle hustle finance. I want to make, you know, this amount of money in this many years, et cetera, to experiencing a really incredible and profound kind of new happiness and

comprehensively wealthy existence. That is very different for me. It's what I'm writing my book about. It's like this whole idea that you can experience wealth in a number of different ways beyond money and figuring out how to balance that wealth and build it across the different seasons of your life is what I'm sort of committing to as my life's work. I have experienced more happiness and moments of happiness and also just durable happiness over the course of the last year and a half, two years since I've made these life changes than I had experienced in the 15, 20 years prior to

it combined. And I want to be able to actually kind of take and bottle up some of what I've learned from that journey and help other people experience that in the same way. Can you say some of the life changes that you made? Yeah. What is that evolution for you? I mean, the biggest thing has been figuring out the points of leverage that exist in the systems that I'm building. Like, you know, working in finance, everything is one to one. It's like everything about your life is like, I'm going to put in one unit of input, and it's going to create one unit of output. That unit actually might be pretty large.

I'm going to work 90 or 100 hours a week, and I'm going to make a million dollars. You know, on the surface, you're like, oh, that's great. I made a million dollars. Well, you know, if it's 600K that's cash and you're living in New York City or you're living in the Bay Area and 50% goes out the door to taxes and your apartment's $6,000 a month to live in a nice place, you're actually not rich. Like, no matter what anyone says and everyone's like,

oh, that's a privileged perspective to live in a city and say you're not rich on 500K a year, it's just true. Like in New York City, if you are making $500,000 a year and you have a family, you are not rich. You're just not. I mean, it's crazy to think,

but it's just the case. And that's just the way that that whole career path works. It's one to one. Until you become like a super senior partner when maybe you're starting to get more leverage on your time, although the partners worked freaking hard and were stressed all the time. Everything about my life was that.

And because my finances and my career was one-to-one, nothing else in my life could really thrive because all my time was sucked up trying to feed the money machine. Everything was like, you know, the Sisyphus, like from Greek lore where you're like pushing the boulder up the mountain. And as soon as it gets near the top, it rolls back down to the bottom. Everything is that. And so my physical health suffered.

I was like pretty overweight at the time. I can show you guys a before and after picture. I was like pretty overweight. I was stressed. My like skin was bad. relationships suffer. You know what? I don't know if it was you that tweeted this about Goldman Sachs.

It might have been you, but I spent too much time on Twitter. There was a post that I saw about someone going into investment banking and wanting to go to Goldman Sachs. And they said they looked at the people who worked there. And like 95% of the people who worked there were overweight, bald, divorced, stressed. and they thought, why would I want to go into a career where that's my most likely outcome? Yeah, and that's the successful outcome, by the way. Those guys made money.

Like, they were doing well. They were thriving. That's winning. I'm a big believer in that. I don't think I tweeted that specifically, but I do believe that. It's basically, I mean, the heuristic is, what is the game I'm playing?

What is the prize that I'm going to win if I win that game? And do I actually want that fucking prize? And if you see that prize, and you get a glimpse at that by looking at the people that are ahead of you that have won it. And you're like, damn, that's not a pretty prize. I don't necessarily want that life. You know, you see the person that's climbed the mountain,

and they're sitting up there and they're like stressed about stupid shit. And, you know, they're not happy because they're traveling all the time. And they're, you know, their relationship with their wife or husband has suffered because they're not around and they don't have relationship with their kids. I mean, for me, I was like, my one single heuristic in life was that I want to coach my son's little league team. And it seems like a stupid small thing. But for me, that bleeds out into everything.

in my life because coaching my son's little league team means I have control over my time to be able to do something like that. It means that I'm the type of father that he wants to have around to be there in coaching his teams. It means that I'm a type of husband that is present and able to go do those things. And so that to me was like, am I going to be able to do that in the life that I'm currently living and in the trajectory I'm currently on? And if the answer is no, then what am I waiting for? I was like, I shouldn't be on this trajectory. I shouldn't keep going on this climb. What happens to so many people is, I love the like climbing analogy because I think it applies to so many things in life. What happens to a lot of people is that you climb and you're like halfway up that climb of whatever

your first mountain is that you're climbing in life and you realize it's not the right mountain. You're like, oh crap, I don't want that price. But it's so scary to think about climbing back down and starting on a new mountain that people just stay at that halfway point and it sucks there. And they're never going to excel because they don't really want that thing and they're not going put in the effort to get to the top of it. And so they're just in this limbo, their entire lives, and they sit there. Because the reality is what it takes to go to the next one is you have to go down.

Like you have to go backwards. And that's terrifying in life to go backwards and go to the next thing. So most people don't do it, even when they should. And so for me, it was like, I'm going to just do that. And it took having a full-on, like, panic attack, kind of borderline nervous breakdown in order to experience that and realize I needed to make that change. And that happened for me in May of 2021. I mean, I woke up one morning on the floor of my house and I couldn't move.

And I was just like, couldn't breathe. Chest was constricted. Didn't know what, you know, I was like, didn't know what was going on. I had never experienced a panic attack before. And, you know, it was the cumulative. It was kind of like, how did you go bankrupt gradually, then suddenly? That was kind of how this happened to me. It was like, gradually, I just had spent years kind of doing this thing and assuming that it was

the right thing and then suddenly was like I had a conversation with a friend who basically said you're living someone else's life why are you doing this and it kind of hit me like a ton of bricks and I woke up and I literally couldn't move and kind of came out of that and told my wife I wanted to move back to the east coast and within 45 days of that happening I had quit my job we'd sold our house in California that we had just built like a year prior and bought a new place on the east coast and moved yeah now what about for her how How was it for your wife thinking, all right, this is a huge life change to get on board? Yeah.

She, to her credit. Yeah, I mean, it's pretty crazy because I, so that was one of my biggest fears. I was most scared of not, you know, I'm kind of a traditionalist. Like, I believe that, you know, my duty as the husband is to provide for the family. I just, I sort of believe that. I take that on myself. That doesn't mean anything about what her role is, by the way. But that's how I feel about my role.

that my job is to protect. And my biggest fear was that she was going to like not accept that I wanted to make this change. It's like because I'm providing while I'm making good money, high prestige status. Like it sounds impressive what I'm doing. I'm on these boards. Everything.

Things are good. Why do you want to change that? When I told her this, she was like, yeah, I don't know why you haven't done that already. That's stupid. And I was like, what do you mean? She said, well, you don't really like this thing you're doing.

And you're making a bunch of money doing this thing you really like doing. So, and you're doing that on the weekend. Like, what if you did that with all your time? Imagine how much money you could make. And I had just never thought of it that way. I was like, sometimes it just takes that one person giving you the, like, new perspective to unlock how you think about it. Do you know Sean Puri?

He's a host of My First Million, another podcast. Yeah, I actually had a conversation with him right around that same time. And he was like, I was like, I'm thinking of making a big life change. And he's like, well, what are the two paths? I was like, well, one path is I go and, you know, I just apply to jobs at an investment fund on the East Coast. We move back closer to family, but I go take another job at investing. The other path is that I kind of go like out of my own and keep building these things I'm building, start these different businesses, go double down on myself. And he looked at me and he was like, it sounds like you're choosing between something that sounds like it sucks and something that sounds really fun and interesting.

So why is there a decision here? And the way he said it, it became so blindingly obvious to me. But I had never thought about it that way until he just phrased it in those words. And so it, I mean, it just shows you the power of someone giving you like a different lens through which to see something. Because we're looking at our own lives so zoomed in every single day. You're like, I mean, you're the ultimate zoomed in version of your life. You're seeing everything like on the ground in the weeds, et cetera. And until you can zoom out, either you have to force yourself to or someone else gives you the zoomed out perspective, you just miss.

You like miss all of those things. difficult is it to get back into investment banking, finance. Is that one of those careers where you take like a year or two off and come back in? You're kind of like the black sheep. I'm sure people think it is. My perspective on that in general is like it's always worse in your mind than you actually think it is. There's this tendency in those tracks to be like, oh, I have to hit this by this age, like vice president by 27, principal by 30, partner by 32, start my own fund by 35. And if I'm not on that track, I'm not. you know, doing the thing I'm supposed to be doing. The reality is when you go look at successful people when they're 60 and you go ask them about their career. You're like, hey, how'd you get here?

They're like, well, I spent, you know, seven years here and then that didn't work. So then I joined the military and I got deployed for four and then I came back and went to business school and then I started at this one company for two and then they went under. And so then I ended up here and I've been here for 17 years and now I'm the CEO. And like there was nothing trajectory, you know, driven or timeline driven. And who cares if like the game is to get to where you want to get to by the time you're 50 and like be in a place where you're excited about your work on a daily basis, why do those timelines of like hitting Forbes 30 under 30 matter? I cared so freaking much about that. Like I wanted Forbes 30 under 30 more than anything else in the world. I was so upset when I didn't

get it. I wanted the realtor 30 under 30. So the step below, you know, you get the Forbes. The amount of, I mean, that thing was swimming in my head rent free for a while that I didn't get that. I heard by the way a lot of it's paid. It's definitely paid. I mean all these venture funds. It's like random associates at venture funds are getting on this list and you're like bro i like you're like cold calling people how are you like for 30s 30 under 30 it's just the funds are paying to get them on there i get it it's a business it is what it is but i mean the point is these timelines that you create around all this stuff are just bullshit and then i think it applies to the idea of getting back my general opinion when people are like oh i want to go you know try this thing that i'm thinking about

for two years or go try it for a year i'm like yeah go fucking try it like you can always go back to job at Deloitte. Deloitte's always going to be hiring smart people that have done interesting things. McKinsey's always going to be hiring smart people, whatever. Go back. If you're two years behind the people that you were previously in line with, who cares? Doesn't matter. You think a lot of the best chains and biggest changes in life comes out of like a rock bottom type thing? Or do you think some people need to hit rock bottom in order to find a different avenue and flourish? Yes. I mean, I think there's this concept in, so I'm half Indian. There's this concept in ancient Indian culture called the Wheel of Life, which basically says that time and your life goes through these

cycles of creation, destruction, and then rebirth. And it's this endless cycle. And it's supposed to be on cosmic time. But I think that in our lives, we experience that same thing where like creation is those periods of growth. Then you end up kind of getting high on yourself and you have these periods of destruction when things crumble down. It's really dark and really challenging. And when you're in those moments of destruction, the most powerful thing is to be able to have an awareness that after every destruction comes some rebirth. So it's like this whole idea that when you're in the darkness, a lot of people, I saw this quote somewhere. When you're in the darkness, a lot of people think they've been buried when the reality is they've just been planted. And there's something really,

really powerful about that to being able to outlast those dark periods to just say like, oh, this is actually a precursor to whatever is next for me. It's not the end. It's a precursor to whatever's coming next. I don't think it's necessary to hit rock bottom to make a big change, but it's not shocking that a lot of people do have that experience before coming to whatever the new thing is. It's just hard to make a big change unless you're forced into it sometimes because it's so scary. I mean, like, I remember the fear associated with like leaving this safe thing that I was good at, that people were telling me I was good at to go do this like weird creator thing that didn't sound impressive to anybody. I mean, still, like, I don't know when I was leaving my firm,

my bosses must have thought I was nuts. When I told them I was leaving, it was originally going to be that I was going to go join another firm on the East Coast to be closer to home and that it made sense. And then I was like, actually, I'm just going to, you know, do this thing that I'm like social media stuff that I'm doing and see what happens. And I hadn't talked to them about, you know, I didn't talk to them about this holding company, like the businesses, the cash flowing things that I had built on the side or like some of the things I was working on that front. I hadn't talked to them about, you know, potentially raising a venture fund and things I was doing there. And so their view of what I was doing was literally like tweeting. and they were like, wait, so you're going to quit a private equity job to tweet? That doesn't make any sense.

And so, I don't know. I mean, it felt very scary on the surface. But, I don't know. Big, big changes. It's like sometimes you just got to take the leap. How do you remain so positive and optimistic? What is it in you? Is this like a change, or have you always been like this?

I'd say I've always been, had a disposition towards optimism. Um, like in my baseball days, I was always big on the idea that you were always just like one pitch away from getting out of any bad situation. There were like two types of baseball players. I was a pitcher. There were two types of pitchers. There was people who like would be in a bad situation and be like, oh my God, this is a bad situation. I'm going to give up this many runs. This is going to happen. And then there were pitchers who would be in a bad situation and be like, if I just do one good thing right now, I'm out of this. Like this is going to be much better. I get a double play, whatever it is. And you're out of the situation.

And I always viewed baseball that way, and now I always kind of view life that way, where like, if you just make one good decision in the moment, and then you make another one, you can get out of basically anything and you can start stacking things in a positive direction. And so my bias has always been in that direction of just like nothing good comes from being pessimistic about whatever your situation is. A lot of good comes from being optimistic and kind of seeing your path to actually driving out of it. I'm also just really happy, man. I'm like, my life is very, very good right now. I'm like very, very blessed with, you know, our son and the experiences it's brought me and my relationship with my wife and being close to family for the first time in 12 years. There's just a lot of good that is coming to my life from the changes that I've made. And so I am just personally extremely grateful on a daily basis.

And that manifests as positivity and happiness, I think. It's interesting that you mentioned only, like you didn't mention any monetary things. It was just like, like being close to the family, the kids. kids, wife, stuff like that. Yeah, I mean, I like, I'm making a lot more money than I was when I was working in finance. And frankly, a lot more than I would have made for like the probably five to 10 years after if I just stayed on that trajectory. I mean, like, the way things have accelerated, the like businesses that have stood up, the opportunities that have come because of like, you know, some uniqueness luck, some awareness luck,

I would say, some of the things that we've kind of opened up and doors we've opened up. I just, you know, the financial side has sort of started to comment. compound in a way that it wouldn't have and at an earlier date than it that it would have without my time actually be involved in it. And so I'm not like spending all of my days thinking about ways to make money and yet I'm making more than I was. And so that to me, I'm like, I'm kind of just separated from it in a certain way where I'm not thinking about making money every day, which is a nice feeling. How many hours a day do you work now? What does the average day look like? We were having this discussion earlier and he was laughing about this. So I, my average day,

I wake up at 4.30 every single morning. I'm a morning person. I go to bed at like 8.30. I'm like a grandpa. Sure. I wake up at 4.30. I get my cold plunge, which I know we can have a debate about.

You want to go now or you want me to go after? Geez, well, you know, we could go. We could go now. I think it's silly. I think this is going to be something we look back on in 30 years and think. What were we thinking? Like in what? Like, you think it's bad for people?

I don't see the bad. Yeah. I don't see how shocking your body with really absurd, cold temperatures would do anything other than just a quick adrenaline adrenaline rush maybe something that a cold shower couldn't do so I mean it's similar to a cold shower right like it's but you're submerged your whole body ice water but do you do like do not believe the science is true like this stuff huberman has put out around like not familiar okay so like 200% dopamine increase that

lasts for several hours after you get out is like a pretty big impact sure that I personally feel on a daily basis. Like the the feeling I feel when I get out of it and then go start my first kind of like work stream of the day and the feeling of energy, happiness, kind of just like euphoria that comes from having done that thing, I think is very real. This might

sound stupid, but that dopamine release is there a sense that maybe you could use up all of it in the morning and then you have to like produce more? No, I don't think so. I mean, so the thing with dopamine is it's like the tradeoffs of like pleasure and pain. Right. It's like kind of the swings of it. And so

The idea with this dopamine release is that it's associated with going through something challenging or painful. Similar to like doing a really hard workout and then you feel this feeling of euphoria. Like go for a long run, runners high. And that versus the dopamine you get from like a bunch of likes on social media and you're scrolling and you're refreshing and you're seeing a bunch of likes is maybe an unhealthy type. Or doing drugs is maybe an unhealthy type. There was no pain associated with it. You just get the spike.

And so then you get this massive collapse. This is a more sustained and kind of long duration and sort of gradual up and down, I think. it's associated with a painful, challenging experience. I think personally, the reason I do it is because it's doing one tiny, very hard thing to start the day that makes everything else feel much easier. I don't like, even if none of the science is true, if there's no impact on like brown fat or my metabolism, if there's no impact on dopamine, you know, if there's no impact on like my mood, any of those things, I would still do it because I just start the day with this feeling that I can

like tackle anything because it's doing one thing that I really don't. want to do that I find really challenging and just conquering my mind around doing it. I don't like proselytize from the mountains saying like, hey, you don't do this gram. You're a loser. You're not, you're never going to make it. Like that's ridiculous. I don't think that that's true at all. But it has positively impacted my life. And so I talk about it because I think it's, you know, some people might really like it. So do you walk me through here? So you get, you get out of the bed. And then what, in your backyard, you probably have this tub or something. I have. So our master bedroom has a deck that overlooks our backyard. And it has a cold plunge and a son.

on it. And so I will, like, I mean, I wake up at 4.30 and I go outside onto the deck. And right now, it's in New York. And so it's cold. So I go outside and open up the thing and get into the water. Sit there for three to seven minutes, depending on the day. Seven minutes? Yeah.

Isn't that a really long time? That's pretty long. Seven minutes is long. I mean, seven minutes is tough. Hasn't it gotten easier, though, as time is going on? It doesn't, it gets easier to do during the day. Like if you went in when there's sunlight out, sun's on your face, even on a cold day and the birds are chirping. It's rather pleasant, actually. Like, I would enjoy doing that. Getting in at

4.30 in the morning when it's pitch blackout and you're tired and you just got out of bed will never get easy for me. Like, I hate, I mean, every single morning, this morning I did it before flying out here, fought it. Like, just standing at the door to go out onto the deck being like, shit, I don't want to do this. And it's just like open the door, go out and do the thing. So what makes you do it? I like the feeling of being able to like control my mind. Sure. And say that I did the thing that was challenging. And if I do nothing else during the course of the day, productive, but I know that I, like, challenged myself in that way, I feel like there's a win. I also, my stress response, my ability to manage stress is so, so much better now than it was before I started doing this,

because that's what it is. You're putting yourself into this, like, extreme stressful environment and having to control your breathing and control yourself. And life is pretty stressful. You're going to have, like, a bunch of involuntary stress and struggle that comes into your life. And so my opinion is that by embracing and getting better, like training yourself with voluntary stress, you can actually be better and more well equipped for when the involuntary stress comes. Just my opinion. Do you meditate? I've never been able to get into meditation. I do like breathwork.

Sure. And while I'm in the cold plunge especially, because you really have to. But I've never been able to get into a real like meditation habit. When you're in the cold plunge, do you focus on the sensation of the cold or do you just try to bring your mind elsewhere? Breathing, try to focus on breathing. And then after the cold plunge, do you get in the sauna? No, I do sauna at night before bed. You're supposed to like do sauna like later in the day.

So I get out, do like, you know, a few minutes of jumping jacks to try to like warm myself up naturally. And then depending on how cold it was outside, I will either like take a shower to get back to baseline so that I'm not like miserable during my first working. Yeah. During my first like working stint. Or if it's summer and it's just warm out, then I'll just. put on clothes and start my day.

But we got sidetracked. My, uh, after that, about at 5 a.m., I get a Dunkin' Donuts, cold brew. That's like my go-to.

Why Dunkin' Donuts? Best coffee in the world, man. Really? Best coffee in the world. Founded by Benjamin Franklin. No, that's not true. Abraham.

Yeah. Um, no, there's a Dunkin' Donuts right near our house. And, um, I just like, Duncan has become my thing that I go to.

So I get a Dunkin' Donuts and then I sit down at my desk. And so from five to, 730, which is like before my son has woken up. Yeah. I do my first kind of stint of deep work. And for me, that's writing always. So right now I'm really working on my book. And so it's either newsletter or book, really,

for like a two and a half hour stint. And then basically like, I'll take my son for a walk for an hour when he gets up. I'll go work out. I'll do, you know, all my personal stuff that I like, spend some time with my wife. And then in afternoon, I have like one more two and a half hour stint of deep work. And that's pretty much it. Hmm.

So maybe like. day. Yeah. It's like five hours of like deep focused work and then all my walks, like I'll walk my son for about three hours a day. That's all my like thinking time. So I don't consider that work, but walking is when I do my best kind of creative thinking. You listening to music and stuff like that? No, silent walks or while I work. You ask him while I walk. No, silent. You found that to be more beneficial. Yeah, I just like being able to like hear myself think. So I've experimented with everything. Like classical music. I tried. I tried those. I tried those. like binoral beats things for your brainwaves. I just like the sound of just being able to hear things around me.

And what about when you write? When I write in the morning, I've been using those binoral beats. There's like this app called Brainwaves that I like. Huberman recommended it on his podcast. And so I started trying it and found that it actually really helped my like flow state writing. And what is that? It's like a, it's supposed to be something that like kind of optimizes how you're like the sound actually like optimizes your brainwaves for different mental states that you

want to get into. And that sound, you know, you can play like a soothing track over it. So like you don't actually hear like the waves. You can play like forest sounds or rain pattering or whatever, something like that. But it has a whole bunch of different focus states. You can do like focus. You can do creative. There's like a bunch of different things. And I've actually found it helps. I'm, I've never been like a big believer in those kind of things. But it helps me right. Do you know the science behind that? No. I'd be so curious to try that. Yeah. I'll send you that. It's cool. It was like three or something like that. Okay.

It's great. I always write to Philip Glass or Danny Elthman. Hmm. That's good. I mean, it's like figuring out what gets you into your state is what works. I used to be a huge believer in classical music. I would love writing with classical music.

Now I like reading with classical music on, like a light in the background. But it just depends. It just depends on the day. But yeah, I mean, I try to like, I'm really trying to optimize for time with my son right now, candidly, like in terms of like what really matters to me. in the world. There's this 10-year period with your kids when you're like their favorite person in the

world. It's the first 10 years of their life. After that, they have best friends, they have girlfriends, boyfriends, they get married, and you're like no longer the most important person in their life. And we live in a culture where those 10 years, where you are, typically is like your hardest working years. And you're gone most of the time and you're not spending time with them. And I am in a fortunate state where I can actually flip that on its head and really take advantage of the fact that I have a, you know, life and a kind of like business structure where I can really be around and really embrace this time with him. And it's special. I see that thing circulating online of time spent with other people. That was me. That was you. Yeah. Yeah, where it's in the beginning, it's like family.

And then it, you know, dissipates off spouse spikes around 20 through, you know, 60 or whatever. And then the time spent alone was something where I think from 30 to 35, you spend the least amount of time alone. And then every year after that just creeps back. It's really interesting to see it. Yeah, those charts were fascinating. I mean, I stumbled upon the combined chart, which had been out for years, because it was like a 2019 American Time Use survey, I think, that they used the data around. And I had seen the combined chart a few times, but it's so, like, clumsy with all the lines on it.

It's, like, very hard to actually see what it's saying, and you kind of just look at it, and you're like, oh, okay, interesting. And the data was available to download. So I just downloaded it and was like, oh, let me look at what each of these lines looks like. So I just put it into an Excel spreadsheet. Like brought back my analyst hat, like opened Excel for the first time in three years and separated it out.

And I was sitting, it was like a Saturday morning. I was sitting there and I was like, showed it to my wife. I was like, hey, this is kind of cool, right? I should post these graphs. This is like pretty interesting. And she was like, yeah, that is actually pretty interesting. I posted it and it went, I mean, pretty mega viral. Like really, really blew up.

But yeah, I thought it was fascinating. I mean, the couple that really jumped out to me were the children one, which is what I just talked about. Like, you get very, very short period of time. And then the alone one is like. Yeah, that's the one for me that really good. Wow. Yeah. I mean, you got to get comfortable with yourself because you're going to be spending a lot of time alone over the course of your life.

And most people are terrified of being alone. The idea of being bored in 2023 is, why? I mean, it's like impossible. When's the last time you were really bored? Like, you have your phone with you. And so you just, like, pop it. open. If your phone dies and you're like on a plane and your phone's dead and you don't have your laptop and there's no TV in front of you, it's like, what am I going to take SkyMall? There's not even

SkyMall anymore because everyone has their phone. They got rid of it. They got rid of it. I mean, being bored is like, I actually sat on a cross-country flight next to a guy like a few years ago that for six hours didn't take out his phone, didn't read a book, didn't watch anything on TV, literally just stared straight ahead for six hours. And I thought about calling the FBI. I, I was like, bro, this guy is gonna kill us. Like, this is terrified. I imagine like an old man. No, yeah, like 45, 50.

I don't know. Like, did you say anything to him? No, I was terrified. I'm actually not kidding. I was terrified. Like, looking straight ahead? Like with a pleasant look on his face, just stared straight ahead.

Not eyes closed, didn't sleep. Like, literally just stared. And we were in the exit row in the like bulkhead. And so it was literally a wall. Like, it wasn't like there was people watching. Like, there was interesting things. He literally just looked straight ahead. And like, shift.

a few times, didn't go to the bathroom. I mean, crazy, crazy. I don't know if he must have been meditating or something. To be able to do that for six hours. Or maybe he had, like, been in jail and spent time in solitary until he just knew how to do that. But we're really bad at being bored humans right now. I mean, I'm terrible at it.

So, like, when I go on these walks, that's kind of my way of, like, finding that boredom in my life. So, you know what? It's interesting. I deleted TikTok because it was sick for the full day and I was in bed. And so I would kill time by watching TikToks. Yeah. And one day of doing that, I found myself the next day.

Instinctively, every time there's a spare moment, pulling up my phone and opening it up every time. So I deleted the app. It took me a few days to like come off of that. Yeah. I'm just constantly needing to grab my phone for any spare moment that I'm not like engaged in something. Yeah.

I mean, it's kind of scary. Like you look at your screen time and it's part of your job. Yeah. So like part of me justifies the amount of time I spent on Twitter or these things as like, I kind of have to do this. It's part of my job. But it's kind of scary. And the amount of.

impact it has on our life and on our behaviors. Like the fact that when something is going by, I mean, you probably have this with videos, but like when you post a tweet and it's going viral and you're like, oh, let me just check. Let me just check. Let me just check. What's going to go? Let me just check what's happened. Like, it's controlling your mind. You don't need to check. Nothing new has happened. It's just going to have another 100 likes or whatever the number is. But we've let it come to that. I mean, I don't have TikTok on my phone because I don't want the Chinese influencing my brain. But that's a separate, you know, national security risk and everything. that'll eventually get gotten rid of, I think.

I know, I just get a whole bunch of dumb crap, though. It's like, on TikTok? On TikTok? I just, my issue with TikTok, frankly, was like when I first opened it for the first time, they must have patterned me, you know, like 32 year old male. I don't know what, like, it would have patterned me as whatever the algorithm was. But it was literally just like half naked women on there, every single swipe. Yeah.

And I was like, I can't open this at home because my wife is going to like, She's gonna like, I'm gonna like open it on the couch to like look at TikTok and it's just gonna be a bunch of like girls dancing And I'm gonna be like I didn't look at a bunch of like I don't follow these people. I don't know what to tell you And it's just gonna lead to like a bunch of you know I don't I don't need that so I also don't have TikTok on my phone the one I found very interesting I started getting recommended You wouldn't know this but jack I think you've seen this the North Korea videos Where they're going through and showing just how like great it is Oh really? Yeah

So you are patterned as like a North Korea sympathizer? I don't know what it was trying to put that information out there. Maybe, but it was pivoted. It's like someone who took, someone who took like a camera in there, like the iPhone started like just posting it. And showing like great streets and like everything is calm and like people walking around and like it looked so peaceful.

Like a really nice New York city with no trash. Everyone is friendly. And it was weird that those kept getting like recommended over and over and over again. And then I didn't think much of it I thought, oh, yeah, this is weird. Until I went online and there was a YouTube video that was also like getting pushed alongside with that, people were like, are you getting these recommended too?

And they're like, yeah, I am. It's weird. That is weird. Yeah, no, I hadn't gotten that in weeks. Was this a while ago or when was this? A month ago? Oh, that's weird, man. I mean, the thing that scares me about TikTok

just in all seriousness is like, right now we're in the midst of a pretty chaotic banking situation in the United States. I'm sure you've talked about this in different videos. What terrifies me is a lot of these crises are propagated by fear with people and human behavior actually leads to these things, right? Silicon Valley Bank, like I almost got cut up in it, right? My venture fund was banked at Silicon Valley Bank. We had to get money out at the last second to escape it. It's driven by like people panicking and pulling money from these things. In addition to all the interest rate stuff that has happen in the changes and, you know, unrealized losses, et cetera.

If China, like, TikTok is a state-owned business, effectively, like all Chinese businesses are, whether they say they are or not. And in a situation where, like, they are one of our main adversaries and they can during a period of already people being on edge, make a tiny tweak to the algorithm that starts surfacing for 100 million Americans, a bunch of fear-inducing content about the banking situation that further leads to economic challenges in the country or to a banking collapse, that's a cyber attack. I mean, that's like a full, that's war that is propagated through an app that is controlled by one of our main adversaries. And that to me is like, that's scary.

Couldn't you say the same thing about Twitter? Because I've heard a lot of things that the bank run started on Twitter. But Twitter is not controlled by anybody. So Twitter is people. But it could be their algorithms. But Twitter's owned by, yeah, I mean, maybe Elon Musk doesn't have incentives for the US bank system to collapse. And Twitter's banned in China. So, like, China has banned all of the American apps from having influence in their country. I'm more so saying that it makes it very easy for information to spread very quickly. I totally agree with that.

I totally agree with that. And it did. It did happen on Twitter. You saw it with Silicon Valley Bank stuff. But it's not controlled by one of our main geopolitical adversaries. Did you see that video that went pretty viral of the Twitter owner or sorry, the TikTok owner or CEO? that was asked if their kid has TikTok. And they're like, no, my kid doesn't have TikTok.

Oh, no, I didn't see that. There was a clip that went super viral of that. I think it depends how old the kid is. I think the kid's 11. 11's too young. What age would you give your kid a phone? A phone, probably 8 to 10, to be honest. Because I feel like they would need to have a means of communication.

It's always on them. TikTok. What's the age that they put on it? 13. So why would the TikTok owner say like, oh yeah, my 11-year-old to get tick. I think 13 He's 10's young for a phone

You think so? I think if they're out because he's very Lazai fair as far as like parenting goes So he was lazai fair until he has kids man He'll be like yeah go ahead Go start working this job when he's five years old And then his kid's gonna get picked up or something No I'm not gonna get picked up

You're not gonna fly first class on your own You gotta I don't know Like TikTok Preferably not at all But they're gonna be exposed to it in one way whether it be, you know, reels or shorts. I mean, it's there.

Yeah. I was vague on the wise I fair parenting. 13. You were. Until you had a kid. Until I had a kid. And then I was like so nervous. You get everything.

I'm just like, oh, oh, shit. Oh. Really? Dude, I mean, it's scary. You like, you put a kid out into the world. And, uh, I mean, it's, it's basically like whatever they feel, you feel 10x. Like, if they experience joy, you feel it even more. It's like amplified in you.

You feel so happy for them. but if they feel pain, it's way worse for you. You're just like, your heart just brain. I mean, I can't imagine like my kid getting bullied at school and coming home and being upset. Like, I would want to go kill whoever that kid was. And that's like a terrifying thing about being a parent. But it also makes you, I mean, like for me, you know, like my kid falls and like hits his face on a coffee table. Because he's trying to learn how to walk and, you know, he's not stable.

And so he just like fell and hit his face. And he like had a little cut on his lip. And he was upset for a minute and then was done. And now I'm like, oh shit, like I got grab him every time. But the falling is actually part of him learning how to walk. He needs to experience the pain in order to like learn that if he crosses his feet, he's probably going to fall flat on his face and it's going to hurt. And that's part of it.

But for me, I'm just like, now I don't want him to experience that pain again because it was really sad. I felt really bad. And what if he hits his head harder than that or he like hits a step and it cracks his head open? Like that is terrifying. So I think that the whole you become like a much stricter parent in a certain way and like less laissez-faire. from just having a kid and becoming more nervous naturally, I think. Would you agree with this quote? I heard it.

I thought it was kind of interesting that humans experience emotions on a range of zero to 10. Then you get married and then the range goes from negative 10 to 20. And then you have a kid and then the range just gets completely obliterated and it's negative infinity to infinity. Yeah, I think so, actually. It's a good quote. I like that. I'm going to start using that. I mean, I, everyone has their own range.

Everyone has their own like point on the spectrum that their baseline is too. Like my, um, my mom is a highly emotional person. My mom, like if there's a scale of one to ten, my mom's probably like a nine on the emotion scale of where like her baseline is. Like she's highly prone to,

not in like a weird way, but she's, um, she experiences emotion very deeply and like she'll be very sad about something, you know, for years afterwards and we'll continue to talk about it and feel real emotions around it. I am like much more of a stoic. Like I'm probably like a two.

And our relationship, um, has had challenges at times because she is experiencing something as a very emotion-inducing event. And my natural disposition is to be stoic about it. And so when we're trying to communicate around that thing, it's very challenging. And so like in a relationship, in a loving relationship and an intimate one, if your wife is an eight or nine and you're at a two, you're going to have to really communicate around that gap because it's going to be a struggle. And when you have kids and they get added to that mix, if you're going to be on different ends of the spectrum, it's really, really hard.

my wife and I are both pretty low on the emotion scale actually naturally and so with our kid while maybe our like the amplitude of the wave has expanded we're able to manage it because we're sort of aligned on our general baseline what role does your wife play in your business your life how does she massive role I mean she I mean I would argue like none of this is possible without her in it both indirectly indirectly I mean my wife is she's a fashion design designer. She worked for the first eight years, I guess it was 10 years, 10 years of her career at different companies under the gap umbrella. So she was at Athleta, I'd been in a republic, at this new brand they launched. She worked on some of the Yeezy stuff when Kanye West was with them, like done a bunch of

different things. When our son was born, she decided she wanted to spend the first year, like take time off to spend the first year and really focus on being a mom. And now she's going back and working with a startup brand kind of part time in the time that she can balance around, around being a mom. But if not for her being like as actively involved and as amazing as a mother as she is, I would never have the freedom to be able to pursue these different things that I am pursuing right now, especially around like my own kind of like health and wellness journey, which has become a big part of the things I write about. You know, like my book has a big component around physical wealth, like building wealth in your life in different ways. And so part of that is guinea pigging all this

stuff on myself and experiencing it and being able to storytell around it. And without her, you know, willingness to kind of allow me to kind of go on these journeys and really like, you know, help me go on these journeys and be able to do it, travel to things like this, et cetera, none of it would be possible. So she's a huge part of it. She's not directly involved in any of my business stuff, which is a cognitive, cognizant, you know, like an active decision that we've made that we didn't want to like work together because we like to be able to like separate church and state, if you will. I think it's personally, it's just like works better for us. But I mean, she's like the CEO of our household in a big, big way.

When you got married, did you guys do a pre-up? No. No. My wife comes from a wealthy background. I don't think she would be mad at me saying that. Her father was a successful entrepreneur, had sold a couple of companies in the biotech space. If we were to have had a pre-up at the time of our marriage, it would have been pro her. Because we were high school sweethearts. We'd been dating since she was a freshman in high school. I was a sophomore in high school when we met. and had dated all the way through, gotten married. You know, I was like an analyst or associated at my fund.

I don't think we wouldn't have entertained a pre-nup. I have tons of friends who have now gone and gotten pre-ups and are pretty, you know, emotionless about it. I don't think it would have been an easy conversation for us to have personally. Yeah, especially as high school sweet arts. Yeah, after that long. Yeah, I think at that point. Yeah.

What do you attribute to the success of that? Because very few high school sweethearts really last this long. I think part of it is luck. And I don't say that there wasn't work along the way, but there are people who are really only fit for like one season of your life. If you take that your life kind of comes and goes in seasons, you have different experiences, you change, you're different from one season and next.

There are people that are only really meant for one season of that. You have friends that are like that. You have friends who were like a great friend in high school and you really needed them in that fun, kind of effervescent stage of your life. Now that you're building or you're doing something different, they're not maybe the right friend for that. And that's okay. You have these friends that come and go.

There are relationships that come and go like that. There are marriages for some people that come and go like that. We've been very fortunate in that we met when she was 14, I was 15. And for whatever reason, cosmically or individually, emotionally, we've somehow matched and grown together through all of the different seasons that we've gone through. The first season of that was me being a high school douchebag and just like, you know, thinking way too highly of myself

and being kind of like an arrogant prick at the time at age 16 and not being the type of person I'm proud of today, but her really like sticking with me through that and helping me grow as an individual. And then, you know, the next season was like, we were in college and we were far apart from one another. She was in New York City. I was in the Bay Area.

we kind of were doing our own thing and really like struggling through long distance. Then we got engaged and she moved out to the Bay Area and we had our first season of like living together and that was this new exciting thing. And now we're in the next season of that, which is like raising a child together. And so I feel like at every stage we've sort of grown closer and gotten to know each other better in a different context and in a different way and experience new challenges together. But a lot of it is just luck that we've been fortunate that we have grown together in that way. I think it's pretty intentional.

I would say most people are more compatible than they think. I think there's kind of just a threshold that needs to be met as far as compatibility goes for a lifelong partner. And it's not that high. Like for the most part, if two intentional people care enough about the relationship to make it work, they can make anything work. So I would say you're probably not giving yourself enough credit. But both people have to equally want to make it work. That's true. One wants to make it work more than the other.

Well, of course. Both people have to be intentional. So you don't believe in the idea of the one. I want to. But you don't think I do. No. I don't either. for what it's worth. And my wife, like, maybe would punch me in the face for saying, you know,

like saying it on air. But I don't believe that that's true. I think that it, basically, I think a lot of people are miserable through life because they believe in that idea, because they're looking, they're spending their entire life, like waiting for that perfect thing to just show up and plop itself onto their lap when the reality is what actually makes a great relationship is taking the imperfect thing and working at it to make it as perfect as you possibly can. And if you're so blinded by looking for the perfect, you just ignore all the things that are imperfect that come along. It's like, you know, you see the like, you're looking for a perfect shell on the beach or whatever and you never find one. Well, there were these other shells that were pretty damn good that you could have polished and cut a little bit.

Yeah, exactly. And that's part of what makes these things interesting, frankly, is the like the growth and the learning that comes from dealing with those. I mean, like I said, like I spent many years of our relationship as a person that I'm not proud of today. But part of what makes us so strong today is that we've got through. that and that I had to change and that she changed with me and that she like taught me to grow up. And those, those experiences are a big part of who we are today as a relationship and as a, as a unit. So I mean, I also don't believe in the whole idea of the one. And I, I agree with you. Like, I do think a lot of people would be much better off by like going a layer deeper on some

of the people that they don't think are the perfect fit for them right away. So our average viewer demographic is, let's say, like a 24, 23 year old guy. what advice would you give to the average person listening? On relationships? No, in general. Oh, in general. It could be relationships, sure. Yeah.

Sure, it could be relationships. Just something that you think would really help them out. Yeah, I mean, on relationships, expand your definition of attraction. I think that at 24, at 25, everyone I know that's that age, their definition of attraction is entirely physical. And I get it.

Like, I love, you know, my wife is extremely attractive. I love that. I think that's an amazing feature. But if you don't expand your definition of attraction, you're going to be living a life that is really unfulfilling in the long run. If you find a partner that's purely based on physical attraction. Because the reality is, you know,

you might find that super exciting for a few weeks, for a few months, maybe for a year. But eventually, it's not going to be the most exciting thing in the world. And you need to have, layers of attraction with an individual as you're building a relationship that go well beyond the physical attraction. There needs to be spiritual attraction. There needs to be emotional attraction with a person. Things that just go well beyond that physical attraction. And if you're not looking for that, if you're not thinking about that when you're on the dating circuit, when you're going out and

meeting people, you're just going to go down the path of dating the person that you think other people will think is impressive. So many of my friends that are like 24, 25, these guys I've played baseball with whatever. They're like, the people that are dating, it's not because they really care about the person. It's because they think their friends will think it's impressive that they're dating this person. And that's just a recipe for disaster and longer. I've had some friends marry that person eventually and quickly realize that it's not a good, not a good move. So I've experienced that too. I never dated that person, mostly because it was unattainable while I was in high school. But back in the day, I remember everyone would be like, oh my God, this girl is so attractive.

This edge, she plays soccer. She's really good to talker or something like that. Like, this is the girl, right? And I would find myself attracted to this person. My medic desire, man. And then, like, a couple years later, I'm like, what am I, I didn't find them attractive, nothing about them I found attractive. It was just the fact that I just heard that they're so great. And I'm like, yeah, sure, they're great. Yeah. And you, you wanted to be able to tell your friends that you were getting that person because it would sound so cool. I had a crush on that. Yeah, yeah. Yeah. Yeah. And look, I get it. Like, part of it is, um, everything is status signaling, right? Like we're monkeys at the end of the day. And so status signaling matters and like my medic desire, like that desire to want

things because other people want them is a real thing. It's like an actual social, psychological phenomenon. But I think that that like expanding your definition of what you were attracted to about someone and really thinking more deeply about that at a young age is is an important thing. Because if you find the right life partner, I mean, your life's success or misery is so driven by the person that you choose to marry and the person that you choose to partner with. Whether you marry them or not, like if marriage is something you don't believe in, okay. But whoever you choose to partner with, that can be your best friend. You know, the person you spend all your time with, your partner, whatever it is. Your success or misery is so driven by that person. It's unbelievable.

And people don't understand. I mean, it can be a 10x, like massive unlock for your life like it is for me. I mean, my wife is like all of my success. Anything that we accomplish as a family is because of her, or it can be a huge drag and it can lead to a ton of misery and a ton of heartache that holds you back from achieving anything that you want to achieve. So I think just being deliberate about that is a huge piece of advice I would have. So what piece of advice would you have philosophically for the average 20 to 24 year old? Philosophically. Because you said you kind of err on the side of being a stoic. Yeah. Which is actually really interesting. Yeah. Learn to embrace boredom at a young age. Learn to embrace silence and being in your own mind at a young age. Go for more

I mean, I like go, if you can learn to and train yourself to just go for like a 30 minute walk every day without feeling like you need to listen to a podcast or like do some self-improvement activity during it, I really think you're going to start unlocking more creative and non-linear outcomes in your life. That's like the big goal of life is to have non-linear outcomes and anything you're doing. If you were to like take a step back and break it down, nonlinear outcomes are what we're all looking for. Like linear outcomes are fine, right? I'm working an hour. I'm making. this much money. I'm like working out. I'm getting this much benefit from it. I'm eating this. I'm getting this much benefit. Those are all linear outcomes. Great. What I really want is for me to like work that five hours and I'm making more money than I was making before, way more. Or I want to be able to work out for 15 minutes and get the hours benefit. Like I want those nonlinear outcomes. And I personally think that being bored and having those periods of silence and quiet time is when you figure out and identify what those nonlinear opportunities are. What are some of the things that you learned from Tim Cook? explain that so yeah um so tim and i met at the gym um it's kind of a funny story i mean i was like

working in my first job coming out of school is at that at that private equity fund i was working really hard um i wanted to make sure i was in the office by 630 every morning and so i still wanted to work out because it was still important to me and one of my big hobbies and so that meant i had to get to the gym by five every day um in order to get to the office by 630 so i'd show up at the gym, Equinox in Palo Alto, at five every single morning. There was like eight people that would show up at that same time every day. So, like, you've got to be kind of crazy to show up at opening time. You know, like people were waiting outside at 455 to let the doors, you know,

they'd be like banging on the doors to get let in. And, you know, you kind of get close to those people, talking to them every single morning. It's the same group of eight people because no one's that crazy. A lot of people would trickle in at 530, not that many at 4.55. And so I'd talk to the people after about six months. I'd been talking to this group of people, and I was talking to one of the gentlemen, and someone came up to me and was like, do you know who that is?

He said, no. He said, that's Tim Cook, the CEO of Apple. And I was like, damn, shit. Like, I didn't know that. And I'd be talking to this guy for six months. I was probably sounding like an idiot. What were you talking about? It was just random gym stuff.

I don't know. Like, what are you doing? Like, what, you know, what's going on? Like, how are you doing today? It's just like basic stuff. You're like shaving in the mirror and you're like, talk, whatever the news is of the day. Like, random things. It's just people.

But I wasn't in tech. And so like I wasn't investing in tech. I didn't know tech. I hadn't really come through the tech world. And so, and he didn't wear glasses in the gym. And so like I didn't recognize him. He just didn't look familiar to me. And he wasn't nearly as famous then as he is now.

Like he was the new CEO at the time. His, you know, prominence hadn't quite grown as much as it has today, obviously. And then I figured it out, obviously, from that interaction. And so I cold emailed him. I had talked to him that morning about an article that I had seen. And I cold emailed him and sent him. and sent the article and just said, hey, I'm guessing your email address here. Why wouldn't you just bring it up the next day?

I just, like, I went back. I just talked to him about the article, like 10 minutes before. I got into the office, and I was like, I'm just going to try to send him the article. Okay. Because I just talked about it. Let me just kind of shoot the shot. And so I guessed an email address, sent it. And within five minutes he replied.

And it was like, oh, thanks for sending this. You guessed the right email address. you know, whatever, quick your response. And so then I basically then just was like, okay, now that he's replied once, I might as well just like, be bold here. And so I asked if he'd be willing to get a coffee

and, you know, chat. Like, I'm not looking for a job. I'm not looking for anything, but I'd love, you know, your advice perspective. Yeah, I was like, I'm in. And he knew I was in a role that I liked because we'd been talking about different work stuff at the gym.

And he was willing to do that. So we ended up having a breakfast. and basically it led to what, you know, what has now been 10 plus a year, like nine year, I guess, wonderful relationship, mentorship. And, you know, I've gotten to do a lot of amazing things. As a result of him, went to the Berkshire Hathaway annual meeting with him one year, which was amazing, got to meet Warren Buffett.

Really? Yeah, I mean, it was like incredible. And he's just been like an amazing, amazing influence and, you know, involvement in my life. He was a big part of my decision to, you know, make my life. make my life change and pursue these things that I'm really interested in. He's been very supportive. And, you know, I'm not like texting him every day, asking for advice. It's not like the mentor, the formal version of mentor that people talk about like, hey, will you be my mentor? But he's had

an amazing influence in my life in a very, very positive way. And I think for me, the biggest thing that I've gleaned from, at least our relationship building was that it was never driven by any, like, transaction. I wasn't looking for him to invest in a company. I wasn't trying to get a job at Apple. You know, like I wasn't looking for anything from him other than to just learn. And people in those situations and in those roles, all they get all day, 24-7 is people wanting something from them. It's just someone coming with their handout, with their handout asking for something.

And so I think in those situations, when you can actually just come from a place of being genuine and not looking for something, not transactional, not quid pro quo, it stands out. And so I think, I mean, the fact, frankly, that I didn't know who he was for the first six months. Like, I've joked about this with him later, stood out because I wasn't just like, you know, there were tons of people then over the like months until he wasn't able to go to the gym anymore at a public gym where like, you know, some guy would walk in and be like, hey, Tim, I want to pitch you on my startup idea. And like, okay, dude, it's probably not going to work, right? Like, you're just very transactional. It's just kind of a weird thing.

Yeah, shoot me an email. Like, I'm sure I'll get back to you. So, I mean, that's, it's been an amazing, amazing relationship in my life. I'd say the most interesting thing I learned from him was probably like in his own career journey, the role of kind of like this, this idea that Steve Jobs had around not being able to connect the dots looking forward.

Have you heard Steve Jobs' speech on this? Steve Jobs obviously was a huge mentor in Tim's life. Steve gave this speech at Stanford in 2005, the commencement speech. And he talks about the fact that there are these dots in your life, like these events that happen. And you never know how they're going to connect looking forward. Like when you do something, you never know how it's going to lead to the next good outcome.

You can't predict those things in kind of looking at it forward, but you can looking back. So his example of that, Steve Jobs, was that he took a calligraphy class after he dropped out of college. He walked into a calligraphy class and like beautiful handwriting and stuff. And he says there was no possible way that was going to benefit my life. That's like a ridiculous skill set. no one's going to need to be a calligrapher. But then 10 years later, when they were making the first Macintosh computer, it was the first computer that had beautiful custom typefaces and fonts.

And that was driven by his love of calligraphy. And so he couldn't have connected those two dots, from taking a calligraphy class to building the first computer that had that looking forwards. But looking back, you can say, oh, my God, the fact that I did that class has led to this incredible innovation that we've created. And Tim's was, he was at IBM, like rising through the ranks as an executive there, just like kind of plugging away. And he ended up leaving to go join this startup at the time, Compaq, which was like a small computer startup.

And he happened to go do that. That was like the crazy decision that he made because IBM was like this great big company. He was doing really well at it, et cetera. Went to Compaq. When Steve Jobs was looking through resumes for someone to bring on for operations at Apple, he looked through the resumption. he looked through the resume and he saw Tim Cook and he saw IBM and he was like, oh, big company guy. I don't want a big company guy.

He's not going to be a fit. But then he saw that he had left IBM to go to Compact and he'd only been there like a little bit of time. And that in his mind triggered something like, oh, there's something different about this guy that he left IBM to go join this weird computer startup. Maybe he's interesting. We should have a conversation with him. They had the conversation and obviously now the rest is history. And so it's another amazing example of just that of like, He never would have known that by making the decision to leave and go to this computer startup,

which has now obviously failed, would lead to this incredible career trajectory and path that he's had. But in reverse, you can look at that and say, like, oh, okay, I made this decision and it led to something good. So it's just these examples of following your intuition around things, like where you think your interests lie and where your passions lie, that I think create these amazing, amazing outcomes. So what are some of the questions that you would ask, Tim? how do you make decisions around, you know, challenging things that happen? Like, I would never ask him around Apple questions. I don't know that I've ever talked about Apple.

I mean, I don't think I've ever asked him a single question about Apple, my entire relationship with him. A, because I just don't care. I'm not investing in Apple stock. It doesn't matter to me. And B, I'm much more interested in general in how people make decisions. Like, you know, for him, he's like a head of state, right? Like, you're the CEO of one of the biggest companies in the world.

You're effectively ahead of state. Like, you have to make decisions with so many complex variables, constituents involved, all of these different things. Like, how do you actually do that? And so learning from him, you know, how he thinks about, like, having one or two guiding principles or values, like a razor that allows you to cut through the noise and make decisions in those contexts was really, really fascinating to me. So there's more things like that.

And, you know, like, look, he's very connected in political circles and he knows a lot of interesting people. So just like talking to him about like what different people are like and, you know, what they are thinking about, what does the future look like for them? What are they interested in? Like that kind of stuff I find really, really interesting. What's the most surprising thing that you've learned? In general. No, from that, from that relationship with him. I would just say how deeply principle driven he is as an individual has been surprising. I mean, my perception of CEOs prior to knowing him was that they're very Machiavellian. And everything is just about, you know, profit and, you know, who cares at the end of the day.

And people say that about Tim. And, you know, people look at him and say that from the outset looking in that he's like entirely about profit and makes all these decisions. I have experienced him to be extraordinarily value-driven. and really guided by like, you know, a higher good in what he thinks he's doing, you know, on a day-to-day basis and the impact that Apple can have on humanity and as, you know, as a society. Do you think that if you are so fixated on profit, like that is what you put above all else, that that will yield better returns than if you focus on something else, maybe? Short term, probably.

Short term, I think you probably like, if you focus on profits and you like are optimistic, minimizing all the different things. Yeah, I think you can probably have a really good outcome in the short term around that. My guess is long term, the companies that endure, you know, need to have like an X factor, something that kind of is driving them on a deeper level in the long, long term. Yeah, I feel like it's hard to stay competitive after a certain point, because innovation, I think, will eventually take over. Yeah, and it's hard to like profit innovation, right? I mean, that's the big knock on Apple now, right? Just as a company. The knock on Apple is like it hasn't really innovated around new products since the iPhone. And, you know, can they continue to innovate and create the next iPhone without Steve Jobs at the helm or without Johnny Ive or whoever the big people were that kind of really drove that stuff? And they've done an amazing job of really profiting from their core and like the iPhone and the services business is like growing and all these things they've done really well. Can they continue to do that? I mean, the reality is like most companies don't last that long. Right? There's like, you know,

how many companies have lasted 200 years? Most of them are in Japan, which is just like an interesting. There's this new article that just came out of study of companies that have lasted 200 years. Like 60% of them are in Japan. It's like this crazy.

But isn't that because they passed down their businesses from generation to generation? Very few sell. Yeah. It's my understanding. Yeah, maybe. Maybe. And a bunch of them had like under 200 employees.

I found that really interesting. They're mostly small. I kind of stay under the radar. There's probably, I'm sure there's like, you know, reasons that are kind of driving these different things. but will a company that exists today in 50 years exist in the exact same format? I don't know.

It's like really, really hard to bet on that. I find that it is on history. When you look at the S&P 500 from 1980 through today, all the top companies, I think besides like Exxon, just not there. Yeah, it's completely gone.

Don't exist. Yeah. And I love watching the thing, the visualization. Yeah, where it shows the company's growing and like Google spikes up, but then IBM takes over threefold and just tanks. What company?

that is enormous today, do you think, will not exist in 25 years? Will not exist at all? Oh, geez. If you were to guess, one. Netflix would have to... I wouldn't even count,

like, of the really big companies, like of the Facebook, Google, Amazon, Apple. Google's here to stay 100,000%. Well, we don't know. Do you think so? So I might put my money on Google because I would say, like, what if, you know, Open AI

completely kills them or something. That's what I would be worried about. But then again, Google's very nimble to like adjust. They have 8,000 layers of middle managers sitting there, though. Yeah. I don't know. Google has YouTube.

I mean, it's hard to compete with YouTube. That's true. Except if you're a TikTok, in which case YouTube can kind of like compete a little bit. Yeah. Netflix is pretty big. I feel like it's going to be hard for Netflix to innovate in such a way to be around 25 years. That's possible.

Google, I have a good feeling about it. Yeah. Microsoft, though, is just a beast. I don't know how. it's such a beast. It's amazing. You're still doing so well. So well. Satya and Adela is that, yeah, that's possible. Apple, I think

I bet money on Apple. Yeah, I think so too. I mean, it's just, they'll have to navigate succession. Tesla. Yeah, Tesla would be the interesting one. I don't think Tesla will. You don't think Tesla will be around? I don't think so. There's too much competition and I mean, I'm going to get like attacked by all the people that are like, it's not a car company.

It's not a car company, but it kind of is a car company. I don't know electric vehicles is like every single company is going to make electric vehicles and you can't tell me that Toyota is not going to be able to manufacture electric vehicles better than Tesla like they're the gurus of manufacturing like Kaizen it was created there and so I just I think it's going to be really challenging to compete on just being the electric vehicle in the market the cool electric vehicle there will be so many full self-driving yeah which case how quickly could other companies and this is coming from someone I have two Teslas I think they're cars. I love them. I think they're great. But does the full self-driving really full self-drive? Or does it like randomly break on the highway and like freak me out? I don't trust the full self-driving. It's terrifying sometimes. The highway speeds are great. Yeah. Yeah. Adaptive cruise control essentially. Yeah. But yeah, I don't know. I wouldn't be shocked. I wouldn't be shocked at that one.

I mean, like Elon Musk is an interesting character. But will he like have an Icarus moment where he flies a a little too close to the sun and, you know, gets melted and crashes. I don't know. I would love to see, I'd love to see Apple come out with a car. Apple would make a really, really cool car. Google car, I think would be really cool. Waymo. Yeah, yeah.

Yeah, we get a lot of those just drive into those little test cars. Oh, yeah, do they have them here? Yeah, because they did a lot of them in Scottsville. Yeah, Phoenix. I used to try in the Bay Area. They used to run a lot of their tests, obviously right around Google's campus. And they had one that would do a loop on. my drive from the gym to work every morning I would see it and I used to always like it was on a

two lane road and I used to always like speed up run in front of it try to like break a little bit because I was like oh man what if it hits me like if I get into an accident I come out and I'm like oh my neck Google hit me like I could get a big settlement out of Google probably like hey like if you pay me $10 million I won't say anything never worked out unfortunately but never know but I think the Apple car would be insane insane and imagine they came out with an Apple house like a prefab type of? Do you think people would be scared of that kind of thing?

No, I don't. Amazon people would be scared, but Apple, no. Yeah, Amazon, I feel like people would be paranoid. It's constantly listening to them. But Amazon, like, it would restock everything in your house that you needed at all the times. It could be kind of sick.

Yeah, but a prefab Apple house would be sick. Exactly. I think it makes sense. And then for Apple to also get into banking. That's one thing. I really wish that Apple card was more successful and integral to like the banking side of things. What did they do?

They partnered with Goldman Sachs on it? Right. I don't think it was, it was many people embraced it. But I think it was because of their association with Goldman Sachs. I think obviously people think, oh, Goldman Sachs. They wanted like an Apple branded product, I think.

Yeah. People were hesitant, especially millennials to bank with Goldman Sachs. Yeah. Yeah, it's interesting. I mean, it's such a, we've seen like, you know, the challenges of banking and the issues that come with,

maybe they could have circumvented that just given their cash balance and the things they have going on. But do they want to like navigate the public company, you know, challenges of all of a sudden trading like a financial services company on part of your business? And then if you could upsell products through your phone would be a big one. Yeah. Can you get, can you own the data and then sell that data back to that appraisers from your phone? I mean, there's so many ways that they could monetize.

Yeah. You should go pitch it. I think I mentioned this in an old Apple video where I thought, their potential when they came up with the first credit card was really to go really just dive head first into banking. Yeah. And issue loans. And just do everything under the sun just for personal finance for the millennial.

Yeah. I think their companies these days are kind of scared of, you know, expanding their purview because of the FTC's mandate right now and like how. For data we're talking about. No, just like just how aggressive the FTC is about policing like antitrust stuff in the U.S. I mean, it's. kind of crazy, right? Like they're stopping Facebook, Google, Amazon, Apple from doing like $20 million acquisitions, but then TikTok is just operating with free reign in the U.S.

Right. Like that's wild to me that they're focusing on these tiny deals that these companies are doing rather than policing, you know, a big issue. So I think some of the companies are just wary of that. I mean, Amazon definitely is because I think Amazon believes they will get broken up at some point and split between their AWS business and the retail business. But I think that like, you know, Apple all of a sudden going into banking, like all these companies going into all these different areas where they're controlling more and more of your lives, you just, like, congressmen are going to have a field day

with that being their viral thing that they can talk about to try to get on their news cycle. It is interesting though with Amazon basics. They, like you go and buy batteries first two results. Amazon basics cheaper than anything else with more reviews. Yeah. And better delivery. and you can get it today.

Why would I get the one lower down? The same day delivery is always insane to me that I could order something in the morning and it's like it will ride between 3 and 6 p.m. Today. How? I know. It's amazing.

How does that happen? That's why when people hate on Amazon, I'm always like, come on. Like, I literally ordered this USB cable I needed and it came two hours. I'm curious, I think they should have food. That would be a fantastic. Don't they do it?

Amazon delivered for food, do they? No, no, not groceries. Not groceries. I'm talking like. Oh, like a Uber. Yeah, yeah. Exactly. Like, imagine Amazon for like, you know, you want, like a protein bowl down the street.

It's there. And then you go Amazon Basics. I mean, the beauty of those businesses, it's like the standard oil, you know, model from the Rockefeller days. The beauty of those businesses, when you're that big, is that you can be loss making in one area in order to acquire market share because you know you're generating profit elsewhere. And, like, that's what standard oil did so well is they would just, like, completely drop. out competition in a new region by undercutting the market and operating a loss because they knew they were generating profits three counties over or whatever the thing was. And so they didn't care. Like they would, you know, bleed you dry in your competition area because they knew they could

make it up elsewhere. And like that's what antitrust regulators are terrified of with all of this stuff. It's like more standard oils building. Do you think that's a bad thing necessarily? Because part of me believes, if it's pro consumer, I don't. Part of me believes that one company can lower costs overall because they have such a big market share. Yeah. Or, I mean, they could take the opposite approach or just charge whatever they want because they have such big market share.

I mean, I'm a free market guy in general. Like, I don't believe in a ton of regulation. I don't believe in a ton of intervention. And I think the markets sort these things out in general. So, I mean, I'm personally a proponent of just like allowing these things, allowing the market forces to work and allow it to be governed that way. I also generally think, like, Amazon's intention from the day it was founded was pro customer.

And everything was about lowering prices and everything was about improving customer experience. And so like there's not a data point, I don't think really in the Amazon story that says like they're gonna all of a sudden just gouge customers on prices because they own the market. I just don't think we've seen that.

They've gouged brands. They've said like, hey, you produce a bunch of these, you know, USB wires. Well, we have all the data until we're going to produce the same wires and sell them cheaper than you and deliver them faster.

But like the customer actually benefits from that. I'm getting it cheaper and, and faster. So that's pretty good. Right. And, you know, if you're a congressman, that's a benefit. I think the distaste for that is that they could do those at a loss just to drive out the other person.

Yeah. Which, yeah, I kind of understand the other person's point of view. It's anti-small business, anti-small entrepreneurship. Right. I'm actually a little bit shocked that you said you were like a open market person, but you think that the government should step in and intervene with TikTok. Why do you not view government stepping in and? like, let's say telling Apple you have to take this off your app store and placing restrictions on

things like that. What's the difference? Are you okay with that? Yeah. National security. I just like, I mean, China is our number one adversary. And the idea that they have control over something that controls the minds of 100 million Americans, like one third of our population is, I think, a mass.

I think it's the biggest national security risk that we face today. So if you were president, would you just do away with? TikTok. Yeah, ban it. Immediately. Done. Gone. Do you worry about what other things they might use national security for to ban? Like the slippery slope? Yes. Yeah, I think there has to be a go. I mean, I think there has to be checks and balances on these things. Like, I actually don't, I don't think it would be easy for the president to just do that overnight. But I think the legislative branch would get behind it. India banned TikTok. And people, you know,

complained about it for a month. And people were really upset consumers of it that, loved it, et cetera, and then everyone kind of moved on and said, like, Instagram's kind of similar. You think people in the United States citizens specifically are so attached to their freedoms. But like the people that are very pro-freedom actually probably don't. Like probably are the ones that would get behind this. You know, like, you know, it would be like more of like a right-wing, left-wing thing. And I think more like right-wing people would probably get behind the idea that China, you know, like they would put a good PR campaign on it, I'm sure, and say like, look what China's been

doing in the North Korea videos. And like, there's evidence of these things happening. and it's not, you know, manufactured. I don't have all the details, right? Like, I don't know how separated it is. I have people that I know that work at TikTok that say that there's, like, communication between the Chinese entity and the U.S. entity. So I don't know, like, how much of a real split there is because technically there's a

TikTok U.S. that's a separate entity. Who knows how split it actually is. I'm not involved, so I have no idea. If there's investigation and there is actually proof that there's influence that comes from the Chinese entity, I think it's, like, espionage. I mean, it's like it's a way of infiltrating America. culture at a very, very deep and organic level that is scary to me. So your president, what else do you do?

I want to know. Lower tithe. We're going to do a flat tax. Zero tax. No. No, I mean, look, I think that one of the biggest issues facing the country is that smart, ambitious young people do not want to go into public service. I think that's probably the biggest issue facing us over the next 50, 100 years is that

most of the people that end up in Congress. or, you know, in these higher offices are people that want to be like career politicians. And they go in and they're constantly just like horse jockeying for power over a long period of time because of lack of term limits, because of no campaign finance reform. Everything's a ton of money. You serve in the Congress and you're like. And then you leave and you get your $15 million. Exactly.

You know, a deal. And so what I think, which I think is an interesting proposal, is you have to pay way better for people in Congress. and there's a very strict term limit. Like when you go and you get elected, you can make $20 million in Congress over a four-year period. Really? And the smartest people in the world

will all of a sudden want to be in Congress. And it's not just going to be these like, you know, eco-driven guys that just want to go and accumulate power over 40 years because it's a short stint. Maybe say it's six years, say it's eight years, but you're going to get paid a whole lot if you do certain things.

So say you incentivized Congress. You know who brought this up to me, Anthony Scaramucci, the guy that worked for Trump for like 10 days as communications director. Say you said to all of Congress, if you guys balance the budget at the end of the year, everyone is going to make $15 million. Every single one of you will make $15 million if you balance the budget.

You produce a balanced budget. All of a sudden, and you put a strict term, you said six years is the max you can ever serve. You'd have a whole lot of really smart people wanting to work across the aisle to get something done at a broader level because they would all be incentivized. to do it. It's like incentives are everything. So why not create incentives that drive

the smartest people to want to actually work? Government spending is like if you don't spend it, then it goes to waste. That's this mindset where we have to spend it. We get more money than if we spend it because then we need more. It's just a broken system. Yeah, I think I totally agree. That's why I think you need something radical that completely changes. The whole idea of the career politician is just broken to me. Like he was never supposed to be that way. It was supposed to be you worked in industry

and you went and did your public service and then you went back to it. industry. You did your four years. You did whatever it was. I was serving the public. And we've now morphed into this weird dystopian world of these career politicians who go and like accumulate power and wield their influence over the course of 40 years. I mean, I had a friend who was working for a congressman and he went, you know, got elected and went to kind of his first vote. And they were, you know, the people on his party were like, what are you going to vote on this? And he said, well, I'm going to vote no. And they were like, no, you're going to vote yes. And he said, no, I kind of ran on, you know, a platform that would lead my constituents to believe I'm going to vote no.

And they basically told him, if you don't vote yes on this, you're never going to get a bill passed in your entire time in Congress. And so, like, what the hell, right? I mean, it's a guy that just ran, that got elected that's not allowed to vote on the principles of what he ran on because of the whole idea of career politicians. And because he knows that he actually now has to vote yes if he wants any chance of accelerating and getting to be more influential in the future. That's the exact same thing.

It's terrifying. feed into that because otherwise you're not going to get any of your points across or any of your bills passed. You're not going to get the donors and you're not going to get the money. So it's like you have to like take a few shortcuts here to get this one thing that you want potentially passed. And it's like, you know, everyone kind of does each other favors. Yeah. And it ends justify the means. It all becomes this like Machiavellian game.

So I just think the idea of creating a better set of incentives and systems and severely limiting terms is an interesting one. And it would prevent the revolving door thing, right? like politicians wouldn't be just waiting to get their cushy consulting gig where they like make connections after you think that should be legal what people to go get like their cushy consulting gig after serving that's kind of a market thing right like they're paid because they have influence and they have relationships still and so i like is it legal i don't think stock trading i think like stock trading should be completely obliterated i think that's crazy that politicians have been able to do that index funds would you stop yeah no that's what i mean yeah you should be able to invest in the voo

Like sure, go invest in Vanguard They were trying to pass that Just for... Recently, right? Yeah, yeah, I think after the whole Nancy Pelosi thing, they were trying to say, well, they shouldn't trade individual stocks. They should just invest in a fund

while they're serving. Yeah, I completely agree with that. I don't know. I don't think you can ban politicians from like leveraging their relationships and consulting gigs. It would just be hard to police. Like what level is it, I don't know.

And your market value is high because you do have relationships and the network really matters. but I think it would all get reduced if you had less of these like career politicians there because then my influence would kind of leave with me like the people that I had worked with would be gone after the four years

and so it would be like I don't know am I still worth $50 million if I don't know any of the people that are in Congress now? By the way really quick I want to let you know that's an hour behind. Oh shit. Yes. So guys,

so we have to end it so abruptly. Thank you so much for coming on the podcast. This has been incredible. You're clearly a very intelligent person. So yeah. Or I'm just too confident. I don't know. One of the two.

This was a blast though, guys. Thank you. I'm glad you gave me the coffee at the beginning because otherwise I wouldn't have made it. You're welcome. And you do seem smart enough to get a free stock with a sponsor. Check out on Instagram.

Link down below. And of course, all of yourself will be left down below as well. Thank you guys so much for watching. And until next. Guys, buy Lexar cards, please. Thank you.