Jack Raines - Why We Should Play Infinite Games

You have to be willing to be vulnerable, get laughed at. People are scared to be real, especially on the internet, because you put something out there that people don't like. But if you aren't willing to be as real as possible about stuff, you can't attract those genuine connections.

Jack Raines, it's great to have you here on the Learning Leader Show. Welcome, man.

Thanks, Ryan. Appreciate you inviting me.

I was reading about an influential person in your life, a guy named Dr. Jim Jackson, and I believe it was a few years ago that your mom introduced you to him. And I specifically love learning about stories of impactful people and impactful people's lives like you are. What was it about him that he helped you with and how it maybe changed your perspective on your career and your life?

Yeah, it was about January or February of 2021. And for context, I've been working for about a year now. I graduated December 2019. COVID obviously hits 2 months later. So I was in the office like a normal corporate finance job at UPS in Atlanta. I was in the office for 4 days. We go remote and then it's basically like a Groundhog Day of wake up, go on a Zoom call, updated a spreadsheet, didn't really know anybody I worked with. It was a, a pretty terrible way to start your work. And it was fine for a while. And it was like, everybody's working remote. You can hang out with your friends a little bit more, whatever. But it, I just woke up one day and realized I had been in this Groundhog Day of doing the same thing over and over again. Didn't feel like I was making any progress. I just felt like I was treading water. And then at the same time, I knew I was going to business school at Columbia. In a year and a half. So it was like I was just sitting there thinking, do I really want to just keep doing this same kind of monotonous thing for the next 500 days until then? And like a little deeper than that, it was also the first kind of oh shit moment I had where I was thinking, is this what my like post-college adult life is like? It's just going to be doing a bunch of kind of tedious tasks over and over again, get a promotion, do more of these tasks, manage people who are doing these. And I just hated the idea of this kind of like setting the foundation for what the next 40 years looked like. And then you retire and then you die. And I just honestly felt like pretty lost as a 23, 24-year-old. And lucky for me, my mom— I never said all that directly, but she could tell that I was like freaking out in my head a little bit. And this guy, Dr. Jim Jackson, he a long time ago was a pastor. I think the Methodist Church in Ashburn, Georgia, really small town. Anyway, his like career took him to the point that he was a pastor at a really large mega church in Houston. But I was like a little bit skeptical at first just because like I grew up Christian, but he actually does like consulting and stuff for leaders of Fortune 500 companies, multi-millionaires, like 9-figure net worth. He's a guy who gets it. I went through and read some of his stuff he's published online. He's a very sharp dude who just gets life. He was tight with my grandparents. My grandparents both were out in MD Anderson Hospital in Houston like 10 years ago. They both had cancer diagnoses. They're both like completely clear now, but they were friends with Dr. Jackson. So when they were in Houston, he was still working and living out there, and they got to be really tight. So anyway, long story short, my mom, through my grandma, put me in touch with them. And so we hop on the phone and I just basically blurted out every single thing that I felt like I was going through, from work stuff to school stuff, girlfriend stuff. I was in a position where we might go into this later, but I made a lot of money trading stocks, so I didn't necessarily need money for the next year or two. And I just didn't really know how I was doing everything, how it was going to fit into what I wanted to do. And he just sat there and listened to all of it for like 20 minutes. And then at the end of it, he just chuckled, and he was like, all right, the first thing is you're 23, you're gonna be all right, this is normal, let's talk about it. And he just gave me a lot of clarity and how to think about everything from relationships. No matter what you choose to do with this one, it's not the end of the world. You're still very young. This isn't like a life or death type of thing. But it was a good time where if I didn't see that going anywhere and it ended me and my girlfriend at the time would both have the opportunity to figure out our own stuff still in our early 20s, and it wouldn't mess up either of our lives with work stuff. How, like, I had a unique opportunity to go to business school, a good— at a good business school in a year and a half that I already knew I was going to. So spending the time before that doing as much. So from all those conversations, it got me to this point that I was like, okay, that thing that I wanted to do was go see as much of the world as possible as soon as it reopened. This is coming out of COVID I'd done a study abroad before, but I'd never really traveled for any long length of time. And I figured that I don't know when else I would have a chance to go and see as many countries as possible without any responsibilities, without having to worry about anyone else, that I haven't to worry about how it would affect my career. I ended up thinking, all right, it gave me— that conversation gave me a very clear kind of how should I segment the seasons of my life based off of where I am. And the free business school was go do as much fun stuff, like, with no regard for anything else, because you're not going to be able to do this later. And your career is going to be fine because you're going to a good business school and you're probably going to meet a lot of interesting people along the way. Then go to business school and then evaluate where your career is, where your relationships are, and all of that from there. And that was the first time I really mapped out and been very intentional about what I was going to do, like, in this season of my life, this season of my life, this season of my life. And I still talk to Dr. Jackson every few months now. He reads my stuff. We email a lot. I talked to him on the phone like 6 months ago. But yeah, I mean, that conversation was huge for me in steering where I was going and what I wanted to do.

The post that you talk about him is called The Case for Living Life Backwards. One of the quotes is, you should write your obituary and then try to figure out how to live up to it. Is this an exercise that you've done in your life and now you're trying to live up to it?

So I've never gone as far as directly writing my own obituary. Yeah, but I have taken— I have thought about what are the things that I'm going to wish I had done when I'm on my deathbed or the end of my life. And I feel like this is because I also mentioned Jeff Bezos talked about when he was launching Amazon in that same article, how when he was 80, he would look back and wish he had taken that shot, even if it failed, versus he was a very successful hedge fund manager. He would have had a lucrative career either way. But that was the thing that he knew that he was going to wish he had done. So it's— I look at it like trying to have— trying to be able to use hindsight before you get there, in that I'm 26 now, there's stuff I can do now that I'm not married, I don't have kids, I don't have a full-time job right now in a traditional sense. So I just have a lot more freedom to try and experiment different things. Where the risk is really low. Like, anything that I mess up right now, there's— it's easy for me to start over. It's gonna be harder 10 years from now, 20 years from now. So yeah, in general, no, I haven't written an obituary per se, but I do have— I'm pretty aware of the things that I'm going to wish I would have done. And also that there's kind of opportunity cost associated with different parts of your life where you don't want to— you're gonna have stuff, you're gonna have stuff that you can only do in your mid-20s that you can't do later. And if you try to, it's not going to work. And vice versa, there's stuff that I probably can't do now that I'll be able to do in my 50s. So just doing all those things when you should do them is kind of like my takeaway from that. And if you do it all right, then you'll have a pretty exciting obituary.

It reminds me of Bill Perkins. I think you've quoted Bill, and I had him on the show. Die with Zero is the name of his book. But that mentality in that conversation is to— that I had with Bill reminds me of this kind of outlook of especially too with age and aging, where Bill would say, dude, you want to go hiking in Scotland or wherever, you probably won't be able to when you're 80, so go right now. You might— you probably— hopefully you're healthy enough, but there's a chance you won't be, so do that right now. And I think trips, especially as you get a little bit older, because I'm older than you, it, it's harder and harder. So you just have to book them, you have to get on the calendar, you have to go, you just have to do it. And if you don't have that intentionality behind it, it just won't happen. Life goes too fast, and it feels like you figured this out much earlier than most.

Yeah, I— and I listened to your episode with Bill. I listened to— he was just on Chris Williamson's podcast. I've listened to— listen to 3 or 4 podcasts he's been on the last month or so, and he's— yeah, I know his thing about the seasonality of life. He explains it more clearly than anyone else, and he had an example in his book talking about how when he was like 24, his roommate in New York took out like a payday loan from a loan shark and went to Europe for 3 months. And then he came back and there was like no tangible difference in where the two of them were in their careers. He— they obviously both ended up being successful and that like $10,000 loan or whatever, he ended up paying that back, no problem. But Bill's roommate like had a lot more memories from his early to mid-20s that were just fun while Bill didn't. Bill goes to Europe, when he's 30, but you're not in that early 20s reckless hostel hopping. Like, the stuff that would have been fun at 23 or 24 becomes a little bit weird once you hit that, like, 7, 8 years later. But yeah, he's— he was talking about the last time he went, might have been wakeboarding or some water sport. He just knew that that could be the last time he did it, just because it's like he was late 40s, early 50s. I think it's hard for people to think about that though, because you have to realize, like, your own mortality to go through that thought process of, oh shit, I need to do thing now.

Yeah.

And that's not a comfortable thing to think about for people. So I consider myself pretty lucky that my quarter-life crisis hit like a month before I turned 24. So it was early enough that I hadn't really missed any of those, any of those chances to do any of those things. But yeah, that's real. Like you have to be pretty intentional about doing things at the time. It's the best time to do them.

The obituary or eulogy exercise. I actually do this with some leaders. Who almost are in a way afraid of that. Michael Easter is another great guy to talk to about this, who wrote The Comfort Crisis, who I had on, and we talked a lot about death. And I don't think in a morbid way, but in an inspiring way. But when you write it, I suggest people writing it in the voice of someone you love very much. So in my case, I wrote it in the voice of my 8-year-old daughter, hopefully giving it many years from now. Yeah. But I wrote it as more of an aspirational thing that she said I did. So my dad did this for me, or we did this. Now, some of them are things we've already done in her 8 years of life, but there are other things that are like, you got to live up to this. And I think doing that exercise really makes you think and really makes you create something to live up to. It can be pretty powerful because it's not necessarily all true yet. You have to make it true. And I think that's a good exercise for, for people to do.

I've never gone that far to actually do it, but when you write it down, it makes it real. It's like, this thing's gonna happen, make these things happen on the way there. Yeah, that's cool.

I, so I view you as a mentor, and this is out of the inspiration from George Raveling. I, I went to LA to interview George Raveling in person, an amazing guy, right? You saw his character played in the movie Air, helping get Michael Jordan signed to Nike. But George when I went there, I think was his early to mid-80s. He just had a birthday. He's older than that now. And when I went into his office, it was interesting to me. He had a number of people who were probably a third of his age or younger than that. And I asked him about them, like, hey, you're surrounded by like very young people. Ryan Holiday is one of his big mentors, and Ryan Holiday is like less than half his age. And he said, you've never ever stop surrounding yourself with people who are certainly mentors who are older than you, but some of these people who, as they get older, they feel like younger people like can't teach them anything or they don't have enough life experience. That is such a giant mistake. And so I think about him often as I started reading Young Money and started reading all the stuff you published. I'm like, Jack could be one of those guys that is at a different stage of life that can be a mentor. How does that make you feel? Is that a weird sensation? Because it's got to be coming more normal each day that you publish.

Yeah, I— the first time it hit me that was a thing was probably like 5 months ago. There's a guy that runs like a really big like RIA out of the Atlanta, Georgia area, and he hit me up. We set up a call and he was just saying how he loved my stuff. He sent it to a bunch of their clients, a bunch of the people who works at They're firm. And he was like, he— I never really thought about that aspect, what I do. My writing for me was almost like I have a lot of stuff in my head that I'm trying to get out in the clearest way possible. But he was talking about— his name was Jay. Jay was talking about how there's so many people who get the money side of finance right. And he was saying how he has all these clients who got pretty wealthy at a pretty young age, either through like tech company stock options. And they're sitting there at like 36, they have enough money, they like don't really have to work again, and they never figured out what to do with it or how to prioritize the non-saving and investing money side of their finances. And you can tell from your stuff that you get the numbers side of it— valuations, markets go up, this and that— but you also seem to have grasped prioritizing how to actually use your money over the course of your life so much better than I had up until about a year ago. And it was just a pretty enlightening conversation for me that somebody who was like twice my age had that strong of feelings about my stuff. But yeah, it, it was weird at first cuz I'd never saw myself as a mentor. It was different when it was people my age or a year or two younger than me that were like, dude, this makes so much sense. Or I'm prioritizing like taking a shot with a startup, taking bigger gap between jobs to do stuff I wanna do this or that. I'm like, yeah, that makes sense. I'm 25, 26, you're 25, 26 between that first and second job. When it's somebody twice my age who's like, this guy gets it, and I'm sending stuff to other people my age. It was, it was weird at first. It was a little overwhelming, but after that I was like, it's cool. I think it is. I don't— I wouldn't say I have really any mentors younger than me right now, just because at that point it's like you're getting into the, the college student age. But I do have a lot of mentors that I would also call friends that are around my age that are also finding their own paths and their own specific things. And yeah, I hope that as I get older, I try to stay aware of people who are like my age now, like when I'm like 35, 40, 45, people 10, 20 years younger than me. David Perel wrote a piece one time talking about how important it is to have mentors 10, 10 or more years older than you and 10 or more years younger than you, because those groups are also just so much more in touch with like kind of the zeitgeist of their age too. They're gonna have insights on pretty much anything that you want. Like for me, my, I guess, generation is very much a, we started working when COVID was a thing. Like it marks a pretty defining thing that nobody else really gets with early career stuff. And I think that changes how a lot of people in their, in their 20s are viewing work-life balance, flexibility. And also there's a lot more optionality now, I think, in doing your own thing, being an entrepreneur than there would've been 20 or 30 years ago. So we have a fundamentally different view than somebody your age would have, or somebody like George's age would have.

Speaking of that, getting back into the office is a big deal. And there are some companies that hire exclusively college grads and they're just trying to promote from within throughout. And that, that's, I think it can be a really useful model, but there are, there are those who've never worked in the office because they got hired in 2020 and now it's been a while since then and, and The people who are the senior-level leaders, they're the ones who grew up in an office. So come on, let's go, let's get back, let's go. And I'm in that same boat. I grew up in an office, I learned a lot, and I was a sales rep for 12 years and then moved up the corporate ladder before leaving to do this stuff. And so I'm, yeah, of course, get back in the office. That's how I grew up, that's what it was like for me, so everybody should do it that way. In your case though, and I'm asking you, I'm asking you to speak for people your age, but How do you— when you hear those messages, get back in the office 3, 4, 5 days a week, not that you have to do that given what you do. What's your overall feelings on the messaging from senior leaders saying, yeah, that's how we build our culture, being in the office, everybody get back in the office, even though some of the people they're talking to have never gone to the office?

I think most, like, most young people would actually prefer being in an office. There's this idea that everybody that's younger hates the office, everybody that's older wants it. I think people hate being stuck in an office doing bullshit work. For example, if you're doing a job where you can probably get everything done in 15 to 20 hours a week and you have to be in an office 40 hours a week, obviously you're going to prefer remote work where you can do your thing. You can play the game of appearing available if needed, but you have a lot more flexibility to actually use your time more effectively. If you're doing a job where you're actually doing 40 to 60 hours of work a week, then people prefer an office if you're actually using that office time, because it's just better being around other people. Both— I think it's more efficient because you can actually collaborate, pop over to someone else's cubicle or desk, ask them about something. You just pick up on all those little sparks of people being around each other that you miss when everybody's isolated. But there's nothing worse than being forced into an office and all that time is filled with meetings that could have just been emails. Like, you're trying to pretend like you're busy because everybody else is pretending like they're busy. And most of my friends, so like I'm between my first and second year of business school, probably 80% of them are in office either full-time or 4 days a week. And, but pretty much all of their internships, they're busy, right? Because it's like they're doing an 8 to 10 week program. These companies are trying to evaluate if they want to give these kids full-time offers. The students are trying to figure out if they want to work for this company full-time. So there's not a lot of wasted time in there. And there's people doing, there's people working for startups. Banks, consulting firms, venture capital, search funds. But everybody seems to enjoy being in office and being around the other interns, like the full-time employees, being in that culture to get a feel for it. I think back to office is good, but also if the companies are doing it right, you don't have to force people to go back to the office. It's not that young people are lazy, it's that a lot of times companies do a bad job of actually like creating a job that needs an office environment in the first place. And the bigger that a company gets, especially in the very traditional, like, finance or accounting or whatever roles, a lot of times there's just so many people hired that it's like these companies have so much money, they just keep hiring people to do more and more simple tasks where you don't really need as many new hires as you have, and people get stuck not doing much. So that's when people hate offices. Obviously there's exceptions. Like I just do internet stuff, right? So I don't necessarily need an office, but I still like working in coffee shops or doing stuff, right? I don't want to just sit in my apartment all day. People like being around people when they're doing stuff.

To me, it was everything. Working in sales, I never sold a thing in my life. And I, as same to you, a former college athlete, and a lot of those guys go into sales jobs. And I was, because I didn't know what I wanted to do. But I, I had absolutely no clue. And so being able to sit in cubicles and listen to calls and have them sit with me and then go to the Thursday or Friday happy hours to build kind of the culture. And two of those people that I met my first job ended up being in my wedding. I just had dinner with one two days ago. In fact, these are guys I wouldn't have known if I wasn't in an office. So I like how you put it, because if you're doing good work and your company does a good job of making it a great place to do good work, then yeah, let's go all 5 days. Let's do it. It seems like a place that you want to be. But if it's not that and you're like, just get in here, I could see why not only a young person but any person would say, why? Like, why are we doing this?

You know? Yeah. And it's— yeah, 100%. And like, with me right now, even though I don't have an office, I have other friends that are doing like similar stuff, or they're doing their own thing on the internet. They've rented out office space like in SoHo in New York. I'm about to live around the corner from them and I'll go like work out of their office because it's 4 other entrepreneurs doing their thing. But you still get that. We're still bouncing ideas off of each other because we're doing related enough work. There's some— there's like a Venn diagram of overlap where we can benefit each other just from being in the same space. That dynamic is 10 times more effective when you're actually on the same team or in the same company. But yeah, it's, it's the work has to be something where like people actually have to be working. Like nobody wants to go to an adult daycare. And that's what a lot of the— that's what a lot of company leaders miss.

I know about you because of your guts and willingness to consistently— big word— consistently publish online for years. And when I work with leaders, I push them to one, hone their writing voice, and the only way to do that is to do it a lot, and then hopefully get to the point where they have the guts to publish it online because it works as a magnetic force to bring people to you. I know David Perrelli, who you already mentioned, talks a lot about this, but this is— I can imagine, I want to ask you about it— created a lot of opportunities. But let's start at the, the first part, which is just the writing element. To me, writing, like getting book deals, you write the proposal and you sell the proposal, and then you actually have to do the work of finishing and writing the whole book, which is much bigger than just the proposal. That is the ultimate tool for clarity of, wait, what? I'm writing a book on management? I thought I knew a lot until I got a book deal to write the book. And then you work 2 years to get that done. And I learned so much through the process of actually writing all of that stuff out. So let's start with that for you, Jack Raines. Writing as a tool for clarity of thought, how has that helped you? And just talk about overall the benefits of writing for you?

I think when you have like a thought or an opinion or an idea on something, you can't really— it's impossible to have a fully formed, well-defined idea on anything just in your head. Yeah, because I look at it like your thoughts are almost like— they're almost like an ocean, right? There's a lot of waves going by, and as soon as you start to have it, the wave crashes, there's a new one, and you can't fully picture every aspect of this idea. It could be an opinion on financial markets, politics, religion, life, just prioritizing anything, career stuff, whatever. You can't get to that second and third and fourth derivative of that idea without writing it down. Like, our brains just will get distracted by a new idea. It's like a cat seeing a laser pointer. All of a sudden it changes. So you start writing down, like, your thoughts on something. I'm just, like, looking at my page right now. Like, one of my pinned articles is The Case for Traveling More. Okay, I think travel is important. I think it's important for people to travel at an early age, but that's a pretty broad opinion that a lot of people share. But as soon as somebody hits you with why, I don't know, it's good to meet other people, it's good to see other countries. Okay, but why? And you can't answer those questions without writing them down. So you sit down to start writing down that idea. Okay, then what was my inspiration for that idea? So then I have to start thinking, where did that come from? And it's a pretty grueling, tedious process of basically figuring out, one, where the origin of all these ideas came from. And along the way, your opinion might change completely on stuff. I've written stuff where I thought one thing, and then I used to be very strong on this. Everybody should buck the system, do their own thing, whatever, because I'd done that and I thought about it. And there's a lot of benefits to traditional jobs, to traditional career paths. It's a lot more subjective than what I would have said a year and a half ago. But you have to sit down and start writing out what you think that idea is. And then you— that's the only way to see when you all of a sudden reach a point where you realize, wait, like, I can't back this up, I don't want to back this up, or now that I've written more and more about this thing, I'm starting to realize I don't actually feel as strongly as I do. You don't find those, like, judgment lapses, those almost like, like those, I'm trying to think, you don't find those like controversies in your thinking, right? You just don't reach those points without writing it down. Because as soon as you put the stuff in writing, it solidifies that thought. It can't get lost again because it's now in concrete. And then you can build off of that versus it always being a jumbled mess in your head. And writing's just, it's, you would know as well as anybody, it's really hard to write something that's coherent, flows well, reads well. And gets a point across because the hardest part of writing isn't just getting it all down. It's then removing all the fluff. Like nobody wants to, like anything that takes 20 minutes to read off its first draft should probably be cut down to take between 7 and 10 minutes to read. And then once you get rid of all the fluff, all you're left with is that raw idea with everything that supports it. Yeah. I obviously like publish blogs and stuff once or twice a week, but I journal pretty frequently too, on much more personal stuff, relationship stuff, friends, relationships, like me trying to navigate the specifics of my own career, because it's the, it's the most effective way to actually figure out what I actually think, like to remove all the noise and see, all right, this is what I actually should do.

Why is it still so rare for people to have a regular writing practice?

It just takes a long time, especially now with— it's, it's a cliché, like, oh, social media is a distraction, but it is, right? There's so much stuff going on that you can always fill your entire calendar with things that you probably need to get done, whether it's stuff around your house, job stuff, whatever. And then you can fill all your free time with tedious social media scrolling or just seeing what friends are up to, this or that, where it's tough to make writing a priority. Because you don't have to do it. Like, it would— I think it would improve anybody's life, but it's not something that anybody actually has to do, life or death. So it's very easy to push to the back burner. It— like, it's the— like, writing is the ultimate victim of procrastination, where you can just never do it because you don't have to do it, even though in the back of your head you probably should do it. Like, for me, whenever I'm— like, this afternoon, I'll— like, my kind of like writing habit is I have this app called Freedom that blocks— you can block specific websites, apps, whatever. I have it on my phone and laptop. I'll block every social media site. I'll block any app that's like social media adjacent and then put my phone on do not disturb where like I can get texts and phone calls, but that's it. And then I can search the internet, but I can't accidentally get on like a Twitter or Reddit rabbit hole or anything like that because I have to block off every single one of those things where it could be a, I'm thinking about something. Oh, let me check Twitter because I thought I saw something there related to that. And then you're on Twitter for 35 minutes. Like, I literally have to block off every possible distraction to sit down and write anything. Otherwise I won't get anything productive done.

How about using it as a magnetic force to bring people to you? This podcast has a similar effect. Yeah. If you ship consistently, you got a chance to bring people into your orbit that were— that are literal heroes. And build genuine, real relationships with them. That part is so powerful. Now you gotta be really good, right? It's gotta be really good or it's not gonna happen. And, and I know I've read about some of your heroes that have become friends of yours because of your willingness to ship consistently, thus them reading it saying, ooh, that's good, or that's funny. I'm— and they want to talk to you. Share more about how it's built relationships for you.

Yeah. So when I started writing, my whole end goal at the very beginning of this was I wanted to get like a remote writing role as a staff writer for Morning Brew to write for a year with them while I was traveling. It was a remote gig and I had basically no writing experience. I did a few freelance articles on Seeking Alpha just to make an extra $150 a week a few years ago, but I hadn't really written anything. I start this blog with the idea of I'll just do this for 4 months to get a portfolio of work to show that like I'm a decent writer. And then reapply and see if I get anything. So I'm just like publishing a couple of finance blog posts a week. And this guy Nick Majuli, who I'd never met, but he had 100,000 Twitter followers. I saw he worked for Ritholtz, which is a big wealth management company here in New York. Like in this, there's like a Twitter ecosystem of people who I thought were doing very interesting stuff that were also good writers, good podcasters, whatever, that had like their own little community. And it was people Austin Reith, CEO of Morning Brew, I consider was in that. Morgan Housel, partner at Collaborative Fund, New York Times bestseller author. There are a lot of guys that were friends with him through Twitter. And Nick had posted this— most of his content is really about more specific investment advice, commentary on financial markets and personal finance. And he wrote a piece about the dangers of investing in individual stocks and had a really good analogy of It's tough to evaluate your skill because you can't really weigh the luck versus skill. And I replied and I was like, yeah, so I actually wrote a piece. I was like, this is a great piece. I have a personal anecdote where I lost $150K in a day trading SPACs after I'd made $400K, and it was very much that I thought I was good, but there was a big luck aspect that I overlooked. Here's the piece. So he DMs me on Twitter, he's like, dude, this was really good. This is actually an insane story. Do you care if I share it? And I was like, no, please share it. Like, you've got like 100,000 followers. This is insane. I've been reading his stuff for like probably 6 months at this point. So I like really liked his newsletter. So he shares it. And then some people in that kind of community follow me, subscribe to my newsletter. And that was the first event that marked a very specific shift from this is like a hobby that I'm just doing for myself to, oh shit, there's people who I think are like way up here. That liked my writing. And it was one, it was the first moment that showed me I might be good at this. And two, that like I basically just speed ran like 3 years of networking through putting a blog post out there because someone likes it. And 3 months later I'd read Morgan Housel's book, The Psychology of Money, right after it came out. I had no idea who Morgan Housel was. I don't even know how I found the book. I think I just saw it like on Amazon recommended. It blew my mind. And then I saw that he followed me on Twitter.. And I'd send him a couple of my pieces or something. Like I would send stuff I'd written all the time, never in a, hey, I want you to retweet this type of way, but in a, hey, I saw you wrote something, I wrote something similar about it, thought you'd find this interesting. And he ended up following me and I met him in person last fall. But again, this is a guy who's like a New York Times bestselling author, partner at a pretty big VC firm. And we were just kicking it in his office because He liked my blog. He's like way up here. Doesn't have to meet with some first-year business school student, but we're like Twitter friends. So yeah, by putting content out there, whether it's written content, whether it's podcasts, art, whether you have your own startup and you're connecting with other people, like people that are doing interesting stuff are just genuinely attracted to other people doing interesting stuff. And because the internet gives you distribution to anybody with an internet connection, it makes it so much easier to— if somebody reads your stuff and it like aligns with them, like it like they feel like they get it. They automatically trust you through the content you've put out there, and they're more likely to be interested in what you're up to. And then you combine that with now living in New York— everybody either lives here or visits here at some point. So now it's like those two things, between having a pretty big internet presence and living in New York, made it where I reach out to people, we start chatting. I'm like, hey, let me know next time you're in New York, let's grab coffee, let's grab a beer. All right, I'll be there in two months. Like, let's put it on the calendar. Yeah, it's been insane. It's probably been like a 20-year career advancement move for me in ways that I don't even know yet, just because I have so many connections and genuine friendships with people that are doing interesting stuff. But it's all because either I like some content they put out, they like some content I put out. It's insane. And people just don't— they don't get how valuable that is.

But it's got to be good though. That's the thing. So the natural question is how to get good. I've read you wrote about this. How did you build your newsletter? I think these numbers are old, so you can update them, but somebody asks you, or it might be an FAQ on your website, how do you do that? I published 450,000 words in an 18-month period. You got to get reps, right? And so I think that part of it is it can be daunting to get started, but it's important to— James Clear says you got to get going to get good. And I think that's so true with whatever the daunting task you're thinking about is get going to get good, and then consistently again a common theme of this entire conversation, consistently do it in order to get good, where then somebody reads it and says, oh, that alters my perspective. That maybe makes me rethink something. Oh, that's funny, which is very hard to do. And I'm going to talk about in a second. That part of it, I think, is so important to how you've got to where you are right now.

I think you also have to be willing to be vulnerable, get laughed at, whatever. People are scared to be real, especially on the internet, because you put something out there that people don't like. And people are pretty ruthless on the internet. Like, they'll— like, I've had people tell me to fuck myself, like, stuff like that. You put stuff out there that people don't like, they'll take your opinion as a personal affront to what they think. Because the internet— like, people say stuff on the internet they would never say to you in real life just because they have a shield of a screen. But if you aren't willing to be as real as possible about stuff you can't attract those genuine connections because if you just start posting big platitudes that everybody agrees with and you get that a lot on Twitter and on LinkedIn, like people just posting stuff because they know everybody will agree with it, it can get a lot of likes, but you're not going to get— nobody's going to look at that and be like, this guy's like a deep thinker. This is a really interesting idea. You're not going to get any sort of genuine interest.

What's an example of that? Like where, like of the platitude? Because I've definitely done that, that part of it. The— I try to do the other part of it too. What are the examples of the kind of, hey, whatever, work hard, hustle, the platitudes that everybody puts versus maybe something you've done that is vulnerable, is real, that, that creates connection?

I see it. I see it more on— you do see it on Twitter and LinkedIn. I guess it's on both. There's content strategies that work to build an audience. Like for example, on LinkedIn, you could go on there and put something about how you can just write, yeah. It's, I don't know, like you could write like, yeah, it's stupid that companies are trying to force everybody back in the office for 40 hours a week, 5 days a week. And it's going to get a lot of likes from a lot of pissed off employees who are mad they're going back in the office. Yeah. Versus going on and writing a pretty detailed— I haven't written like a detailed piece about that specifically, but writing like a blog post that's say like 3,000 words. That's a lot more nuanced about, yeah, back to office sucks. Or it's okay, like what we talked about earlier, like back to office seems to suck. But the real issue isn't that. The real issue, it's not just about the office, it's that people want to do real work. People don't hate the office, it's just people want to feel like they're doing real work that contributes to something and matters. And here's some thoughts from like some of my friends and family that are going through that right now. A lot of people aren't going to read a whole blog post. It's not going to get the clickbait. You're not going to get the pissed off employees who are mad they're back in the office basically rage liking it. But there could be somebody who is, say, like a high-up executive of the company who reads that through somebody liking, somebody sharing it, who's like, oh shit, like light bulb moment, this makes sense. Like, we can't be— it's not that we should be forcing everybody back in the office, it just needs to be a compelling enough work offer that people are excited to come back in. It's going to get a lot less engagement, but you're going to have a higher chance of making a genuine connection where that type of person will email you or message you on LinkedIn and say, Hey, I thought this was very valuable. Can we chat sometime? And that's the difference. Or it's like my case for traveling more piece. It was a very detailed pulling from my own life, why I think people should travel more, more so than, oh, traveling's valuable or wanderlust or whatever. Austin Reith, he's a pretty good friend of mine now, Morning Brew CEO. He tweeted that out and tweeted, I think Jack Raines is the best new up-and-coming writer on the internet. He texted me, he's like, I sent this to my fiancée. This is a great piece. We're actively trying to take a big trip at some point in the near future. And it got a lot of views on Twitter, but it's not like it didn't do a million impressions or whatever. But somebody who I think is an important person and a pretty valuable friend of mine, that piece marked a huge, okay, I like this guy's writing a lot moment from him. Yeah, that's, yeah, that's what I think on that.

When I sit down and try to be funny when I write, it's a real struggle. And yet I'll go on LinkedIn and I'll see these satirical posts from you that are hilarious and obviously made even more funny by the comments of people who don't get it. But where do these come from? And maybe if you want to share an example or two of the, of your favorite ones, but where does that come from of the satire, of the humor, of the style that sometimes, not all the time, that sometimes you use, especially when posting on LinkedIn?

So, The LinkedIn one, there was actually a means to an end with this. And like, for context with what Ryan's talking about, I regularly go on LinkedIn and just post like just blatant satire, which really just is a huge stark contrast to LinkedIn. It's the most buttoned up social media site. But one of my friends who has a newsletter was saying he's seen a ton of newsletter growth from LinkedIn as an organic source. I was like, that makes a lot of sense. LinkedIn has, I think, 3 times as many daily or monthly, like active users as Twitter. There's not a lot of good content on LinkedIn because it's a weird spot where LinkedIn is like, it's a professional network, so you can't post controversial opinionated stuff on there because you don't want to risk hurting your employment prospects. So nobody's actually posting real edgy stuff versus Twitter where Twitter is just, it's like a free-for-all, like anarchy wasteland of like controversial opinions, people screaming at each other. LinkedIn is not that at all. It's just everybody congratulating everybody for getting new jobs and promotions, except there's the kind of fake entrepreneur types who are going on there posting the kind of vague life advice platitudes, or the, you have to grind and do this and that to be successful, sign up for my course or my class or whatever. And it's just a little bit obnoxious. Like, it works, but they're getting a lot of traction because there's so little noise on LinkedIn. Those are the only posts that stick out. And if somebody likes a post on LinkedIn, unlike Twitter, it sticks around for a week or two. Like it can resurface on people's newsfeeds for a while. So it just hit me one day, I was like, all right, I want to post more content on LinkedIn, but I want it to be in my voice. I don't want to go with that guru, ooh, get you hyped up type of voice. And then I realized I could just make fun of that stuff by being so over the top that, that it's obviously satire. Let's see how it works. Because I have this guy, Alex Cohen, where I guess like internet friends, works for a startup and does some angel investing. I've seen him do it like his company's completely cool with him to shitposting. I call it shitposting, shitposting on LinkedIn. He posted one thing about saving his company money during a work trip by cooking chicken in the coffee pot in the hotel room instead of buying food. And it blew up. I think it got mentioned on Yahoo Finance at some point, like this crazy employee or whatever., and his LinkedIn was just blowing up. And I was like, okay, I can do that. I started posting all sorts of stuff. I posted one about how I made $100,000 as a side hustle by getting vaccinated 1,000 times. It was back when Mayor Adams was like paying people $100 in New York to get vaccinated, and people were commenting like, this is insane. But then some people get the joke, right? One guy commented and said, wow, after reading this, I got the vaccine 20 times today. Now I get cell phone service in the subway. This is incredible. Like you get those, but there's about 5% of people who just don't— because LinkedIn isn't a site for satire and you can't necessarily convey a complete voice online because you're missing the non-verbal cues and all that. Some people just assume everything they read is real. So I have people comment on that post saying I was like stealing vaccines from my marginalized people and was probably making the COVID pandemic worse. But I'm like Could you not think for a second that I— if I got vaccinated 100,000 times, my body would probably explode? That just doesn't even make sense. The best one was I put a post out claiming that I hadn't paid for food in Manhattan in 4 months because I was going to different hotels, eating the continental breakfast, signing off on different rooms, going back for dinner. And it got to the point that somebody like emailed Columbia Business School about it saying, this is bullshit that you guys have student who's bragging about petty theft on LinkedIn. I actually met with our dean of students about it. She was so cool with it. She realized it was just like a satire thing. It's a marketing strategy. It's very easy to come up with content where you're making fun of a current thing. Like, it's, it's my original thoughts, but it's just like—

I don't think it's easy, man. I think it's hard. I'm so impressed, more, almost more so by the humor and satire than— I like the other stuff too, obviously, but I think it's really hard, man.

It's— I've just been doing it for a while now, so it's gotten to the point that like I'm just used to it. Like I can think about what's going on right now, how can I make this like a hustle thing? Like I put one yesterday about most people were spending the Fourth of July drinking beers, aka destroying their bodies for the sake of fleeting dopamine hits. But I've been like cold emailing people who graduated from my class of '98 knowing they're hitting a midlife crisis to try to sell them term life insurance because I work for Northwestern Mutual.. And I hadn't put like a shit post on LinkedIn in a while. I have people like somebody commented how to say you're a loser without saying you're a loser. But then when those people comment stuff like that, their whole network sees the post and a lot of them will think it's funny. But there is outside of my initial plan with this was like, I'll do this to get a bigger LinkedIn following because my content will stand out. What I didn't realize was that these type of posts have an extra benefit in that people who get the satire. Like almost subconsciously think, okay, this guy gets it. It being just thinking stuff through to the point that he's making fun of a current thing. I find it funny. He's probably smart. I probably agree with his opinion on stuff. So like I posted a whole fake thread about how people get obsessed about BlackRock owning the world because they don't understand that BlackRock has a lot of ETFs that have stakes in every major company. So I post this whole thing about BlackRock owning everything, but then me actually owning BlackRock through my retirement account. So technically I own everything and it blew up. And then Josh Wolfe, CEO of Lux Capital up here, I saw that he followed me on Twitter. Gary Tan, CEO of Y Combinator, he followed me on Twitter. And these are guys with fu money that are like controlling some of the biggest in the— especially in the venture world, some of the biggest organizations in the venture world. They just see this and think it's funny and they're like, all right, this kid's like pretty entertaining, but also I like how he does this. I'm going to follow him. So it's been the same benefit of the blog post in that like it, that stuff goes viral and that a lot of people think it's funny, but some really important people almost trust me because of my ability to make fun of something that they find annoying. And I didn't know that was even like a possible outcome from all of this until it started happening, but it's been super valuable.

It's just like stand-up comedy. What they do is they take something that you've probably agree with or you thought of, but you don't know how to put it into words. And so they're able— they're such good thinkers. That's why I love studying stand-up comedy for any profession. It will make you a better communicator because they're masters, one, at economy of words, but also at taking something that you vaguely thought of but weren't able to crystallize it And then they do, oh God, that's so good. And it's funny. And right. I think that's why after seeing a number of your LinkedIn posts, I emailed you and said, I want you to write the copy for my website. Remember that? I was like, I want you to re—

it doesn't have to be funny. I'm still down to do that, by the way. Okay, good. I know we talked about that a while ago, but yeah, we can circle back on that because I'm—

just because it's—

yeah.

But you, you still wanna make it your own personality and stuff, but it's like, hey, let me work with somebody to help me with this who gets it. I think that's what people say. Oh, this guy obviously gets it and he's do— has a unique spin. I think that is a tough thing to develop. And I am curious that this may be a hard one for you because it just comes natural and it's a lot of reps, but how have you developed such a unique voice when it comes to what you're able to put out? Because all leaders would be better served for developing their unique voice. So it doesn't have to sound like Jack Raines, but they need it to sound like themselves. So I'm curious how you've developed that.

I think it's almost a fear slash just disdain putting stuff out there where, like, I would never want anybody to read anything that I wrote and then meet me in person and not see the correlation between the two. And it's partly because I've seen people get big audiences on social media by chasing a hot trend, whether talking about like different ways to use AI technology to improve your productivity. And then they try to build a big audience doing one thing and then switch to another, and it doesn't work. If you build an audience off of one thing and then go to another, it doesn't work. So I never wanted to commoditize my online profiles to the point that I build up this certain thing and then it doesn't align with how I actually am, because my end goal is getting more people to read my blog, to— that's primarily how I make a living from selling ads on the blog. And then also for, like, I've talked to some book publishers about very early stages, potentially planning a book proposal. I want anybody who finds me on any possible site to look at my LinkedIn or Twitter or book or blog post and hear that same voice in all of it. Like the LinkedIn one might be more sarcastic, but you still know that's part of my satire thing. And the same thing with Twitter, I might be a little bit louder. Or sometimes like a little bit more— I don't know if controversial is the right word, but just like louder with my opinions because there's more noise on Twitter. But you still know that's me. It's just me yelling in a crowd versus me talking to somebody in a cafe. And then the LinkedIn one might be me attempting to do stand-up comedy versus me just hanging out with friends. But it's all still me. It's just different slight facets of me. And I think it's because my end goal is having everything tied back to something like, like I need the most 1-to-1 conversion from— if you find me on any site, you're going to find me entertaining on any other site— has been a good North Star for me. But it just matters what the end goal is. Like, there's some people who want to build up a massive newsletter following on AI or crypto so they can sell that newsletter. I used to think that stuff was really cringe, and this is something I've changed my opinion on. I might not like the content, but I completely understand the means justify the ends if their goal is build a massive newsletter or like to productize something to sell, flip this newsletter. Yeah, that works for me. It's— I don't really have an endgame of trying to sell my newsletter, this or that. It's just more and more opportunities that come from my ability to write stuff. So I need everybody to see— they— everybody needs that finds me from anywhere needs to just know that's my voice across all fronts.

Have you changed your thoughts on ever wanting to get a job? Because it's part of your bio too, is like, I don't want to get a job. You're in Columbia Business School right now, so obviously you're going to have job offers. You're going to have a lot of things when you finish up there. Have you changed your mind, or what do you think about that?

Yeah, I, I've pushed— I, I have changed my mind. I'm not as strongly, I never want to get a job, as much as I am. I have enough leverage now with what I'm doing that I can be very picky at a job that I would get. And I would be open to a few different things, like across kind of the media and finance/investing sphere. But it would have to be something where I would still have full freedom to keep writing my blog, building my own email list, because that's the most valuable asset I have. Say I could— say like a VC firm's hiring investment associates to do actual investing work. I think it would be pretty valuable for me to actually have to study startups, meet with founders, this and that. I think it'd be valuable for a VC firm hiring me because I've got pretty big distribution and a lot of connections where it's like a win. I wouldn't take that job if I didn't have full freedom to write whatever I write and me still own the IP on that, own my email list. I had someone reach out about potentially working with them on a media company they're building out, either as an editor for a newsletter or as like potentially writing an opinion column. And I would be potentially down to do that as long as I could keep writing my own blog separate from that. And probably promote it a little bit through this, linking back to my site. Because there is something nice about the stability of having a salary job, an employer, all that. It just takes a lot of pressure off of me from having to keep figuring all that out. And I think it'd be pretty valuable— like, I'm writing about a lot of career stuff and market stuff. If I was working in one of those fields, like, maybe my content would be better because I would have more experiences to pull from that are more related to my audience versus being this guy who only is just like a freelance writer who's trying to give life advice, but his life isn't even like applicable to everybody else's. I do think now there's a ton of benefits in having a regular job, but it can't be something that would distract from the other stuff. I also don't need one. So if I see an opportunity for one that checks all those boxes, especially if it's with a company or with a person or people that I already know and respect and trust, Yeah, I'd be interested in it, but it would have to be pretty specific.

I mentioned earlier, you played football. I played football. You played in college and you've written about this. I love reading about it because you've put some of the things into words that I've been thinking but haven't documented that well. What are some of your greatest takeaways from being a college football player that has helped you now post, post your playing days?

I think college football is probably the toughest thing I've ever done, and I think for a lot of young men, short of actually serving in the armed forces, playing like a college sport at a high level is one of the most high-pressure situations you can be in between the ages of 18 and 22, where it just— how is it—

sucks.

You go through like— most of college football sucks. And I say that while also saying college football was one of the most fun experiences of my life. But you're just getting basically demeaned by men that are 3 times your age because their livelihood is determined by a bunch of 20-year-old kids executing on a field. That's such a bad connection across the board for everybody. It's, you've got the, there's such a tough struggle of, I'm sure you went through this like quarterback battle where you want to be supportive of the guys in front of you, but you're also a little bit pissed because you want to play over them. Think you probably should be playing.

How bad you secretly root for every play when they're in to be an interception or to go wrong. It's, I would never have admitted that when I was younger. I'm like, oh, I'm a good teammate, but I rooted for them to fail every single time. Like every time as a quarterback, because only one guy gets to play. You almost have to rid yourself of that when you get into the world, because the world isn't zero-sum. I know you know this, but in, in that world, if that guy is better than you, especially as a quarterback, he plays and you don't, which happened to me. So I— and then even when you're the starter, you're still in that boat because you're like, that guy's better, they're gonna play him. If he's younger, gives him more time. So that's a weird dynamic and world to, yes, be a good teammate, but also like actively root against him.

Yeah, no, it's 100%. I have the same thing. I, I went to Mercer initially as a preferred walk-on, got put on scholarship after 2 years. I thought that I was better than one of the guys a year ahead of me that was getting more playing time than me, and it was just frustrating because I felt on every metric I was, but I almost felt like our defensive coordinator at the time still viewed me in that— it's tough when you come in as a walk-on to break out of that first impression lens. But then finally, guy was a year older than me, he graduates. Then the other defensive end, he was like all-conference, he was like good friend of mine, he was way better than me. I'd be the first to say it. But they both graduate, so I thought I was going to walk into a starting spot, one of the two DN spots. And then, uh, we go into spring practice, we have a whole new defensive coaching staff, and I like start off spring practice as a backup going into my fifth year. And I was like, I was pissed. But I ended up having the best spring practice of my life. D-line coach called me in the room and he was like, yeah, you were a lot better than I thought you were going to be. And it was— I'm like 6'3", short arms, look a little bit gumpy, especially when I was 260. It wasn't like a great looking 260. I didn't pass the eye test at all. If you're an underwhelming athletic prospect, you get really good at every technical aspect of the game, mental aspect of the game, reading the play before it happens, being able to cheat stuff a little bit, and that, that matters. But ended up starting— had like a very productive senior year, but it was like a byproduct of— I'd had— I tore my hip, tore my shoulder labrum, tore a wrist, wasn't getting any scholarship money for 2 years. Thought about quitting probably 10 times. I had literally applied to transfer to the University of Georgia and basically just party for the last 3 years of college twice. I was so close to pulling the plug, but I could never make myself do it because I just had this part of me that was like, what if it works out and you end up actually having a solid season or 2 seasons? And then it was also the other aspect was I'd gotten so tight with a lot of guys on the team. It's, do I really want to throw away those relationships because I'm pissed this stuff isn't working out? It was an ego check. Even if I felt like I was being a little bit unfairly treated, if I got to the point that I was head and shoulders better than somebody else, because the coaches will get fired if they don't win games, it becomes an existential thing for their career not to play the better player. So I twisted that into motivation, like, all right, I just have to get like absolutely objectively without a doubt better than these other people. Yeah, so I think football was so tough that anytime I'm struggling with something now, I'm like, dude, you used to do 2 days in August where you were waking up at 6 AM and just having to bash heads with a 320-pound offensive tackle for 3 hours, and now you're mad because your open rate on your last email was a little bit low? Come on, just grow up. It makes me not take stuff as seriously. Like, I just don't really get stressed about stuff that much now because I think college football is tougher than anything that I'm doing at the current moment.

I feel such kinship with that, man, because it's— there's nothing is even close to that, as hard as that is.

Nothing. Yeah.

Even when I'm a little nervous before going up on a stage, it's— this is nothing. This is nothing compared to playing in front of a lot of people with 300-pound guys who are as fast or faster than me that are trying to kill me. That's scary. And when think— when compared to just standing on stage and talking. Yeah, this isn't that hard, man. And in a way, it just— I think it creates great perspective. And this is why I think now as a parent, I just so badly want my children to, to be involved with something that is extremely hard, that they think about quitting all the time. I'm the same way of football. Like, I didn't— I was a scholarship guy too, but I didn't— but I had certainly moments from, this sucks so bad, like, why am I doing this? You know what I mean? Where you really question it because is is it worth it? And then you're so glad later on that you pushed through and didn't give in or didn't give up. And that building— that grit muscle is not my favorite word, but building that is what's so beneficial years and years later. It like impacts me for the rest of my life. It's pretty wild how that works.

There's also an interesting paradox where the shittier the situation is at the time, one, the tighter bond you have with the guys you're going through with And two, the funnier the stories are afterwards, laughing about some of the— I can't even repeat them, but some of the things our defensive coordinator said to me where it was like, you're in that pissed off emotional high, literally making tears come down people's face, and they go blow somebody up the next play. Those stories become so funny, like, after the fact with those guys, and you can't really replicate that without being in the sort of traumatic experience. But anytime I'm back with my, like, college buddies, we're back at, like, a homecoming game, or I'm back in Atlanta hanging out with them, It's the conversation is just like laughing about stuff like that over and over again.

The cool thing is you see them for the rest of your life. Dude, I was at a Savannah Bananas baseball game last week.

Incredible.

They're incredible. Awesome. The wildest thing I'm actually walking with, I've had Jesse Cohen a few times, the guy that owns the team and he's become a good friend and he's just the greatest. But anyway, he had one of his like assistant guys helping us get these kind of nice seats. And as we're walking to our seats, I hear a guy like, Hawk, Ryan, Hey, wait. And I look over, it's one of my receivers from Miami University. I haven't seen him since we played together and we embraced and talked like we saw each other in the weight room the day before. I was with my 8-year-old daughter. We started bringing up stories like, oh my God, it was literally like we were in love.

You know what I mean?

It's just you have that bond because you went through two-a-days, you went through the funny stories in the meeting rooms. In our offense, the quarterbacks and receivers always met in the same room. We built such a bond with these guys that even though I haven't seen them in forever, you still have that. It just never goes away.

And it's—

that's the part that's also beautiful, just about playing a team sport with somebody.

Yeah. There's a whole rugby league in business school, which I didn't know was a thing until I got here. Yeah. But I'm like one of the younger guys in my class and I passed the eye test for especially in a business school environment. Like this kid can probably play rugby. And some of the second years got me. It's been so fun going to Chicago or going to Harvard or going down to Wharton and just playing like a full contact sport, like 15 on 15 with all these guys. And it's a little bit ridiculous because some of them are like 32, 33, like should not be playing a full contact sport, but it's just fun being back in that environment because it's that type of bond again. Yeah. The team sport aspect of just life is so underrated for how valuable it is.

I recently talked to Sherri Cole. She's a Hall of Fame basketball coach, University of Oklahoma. And she came to my workshop this year. And, and somebody asked her like, what do you miss the most? She said, what I miss the most is standing shoulder to shoulder with other people doing something really hard together. Yeah, what a, what a cool— like, she instantly— I miss standing shoulder to shoulder with people doing something hard together. I'm like, that's the thing. And it's— I want to keep putting like finding ways to create teams or do things where I'm standing— it's not playing football, but it's like doing stuff that's hard with with others, shorter, shorter, where you're in it together. Jack, there's one more thing before we go. I question that. I've actually quoted you in stuff that I've used to other people. This is in your post called Infinite Games, and I'll read it. I just want you to riff on it real quick if you're cool with that. Yeah. There are at least two kinds of games, finite and infinite. A finite game is played for the purpose of winning. An infinite game for the purpose of continuing to play. And this is the part I love that I quote, quote, the focus on outcome over everything leads to us discounting 99% of our lives for the sake of a few small fleeting moments that might provide some sense of satisfaction before the cycle begins anew. Beautiful stuff, dude. It really makes me think about the journey is the reward, right? It's about the person you become while hiking the mountain, not getting to the top. Like all of that type of stuff. You could probably write satire on this too, but yeah, that, that is, is so good. Can you talk more about the, the problem with focusing on outcome over everything and how that leads us to discounting 99% of our lives for the sake of a few small fleeting moments?

Yeah. I remember this was like, I was probably like a teenager when I first read this, but somebody was interviewing Tom Brady after his like second or third Super Bowl, just like how good it felt. And he was instantly just, or it was his classic quote. What's your favorite Super Bowl ring? The next one. And obviously it was like an athlete. He's undeniably most successful NFL player ever, but it blew my mind that this dude spent, he played football. For probably from like child all the way up 30 or 40 years. He played in the NFL till he was 45 and he is investing his entire life, like 110% of it into this thing. And as soon as that ring's over, he's thinking about the next one. And on one hand, I almost admired his just complete dedication to it, but also it blew my mind how that's the pinnacle of a sport. You literally can't do better than winning the Super Bowl and being the Super Bowl MVP. And he couldn't even enjoy it. It was just immediately on to the next thing. And I'm sure he like enjoyed the process of football too, or he wouldn't have been as good as he was. But just that idea— I think you could say you make— you climb the whole ladder, like whatever company you're at, you become the CEO of Goldman Sachs or whatever, and then you're sitting there and it's— you might enjoy that like moment of reaching that level for a day, a week, maybe a month, but then that becomes your new normal and then it's over. So in my head, the way I started looking at it was like, I think that feeling of waning satisfaction applies to literally everything. Is it supplied in my life? Like winning football games. I think getting put on full scholarship in front of the team was, as far as like emotional high, biggest high in my life. Like never felt anything like that. 2 days later, I'm back. It's 2 days, we're hitting people, and it's shit. This still sucks. So you get over it. So it's finding that, knowing that whatever you do, that is gonna be like, whenever you hit those breakthroughs, you're gonna end up normalizing it. Finding the one where you like the day-to-day activities or the grind of the thing that gets you there. It, you have to do that. It has to be one of those things where you want all the successful outcomes and milestones to be a byproduct of the thing you enjoy doing, where it's like, awesome, I got this promotion. Awesome, I got this book deal. Awesome, I got the starting spot. But you're just excited to get back to work where it almost, it was almost like you expected to have these things happen or things like this happen. But the goal of doing what you're doing with your career isn't to reach this point. It's to just do the things you're doing in your career. It's almost cliché about the process is the way or focus on the journey, not the destination, but it's true. Like all these destinations should just be byproducts of something that you enjoy doing, something that you find valuable.. Because if you do it the other way around, you can— we can rationalize in our heads, like, I have to get to this level in my career. I'm willing to sacrifice 5 years of my life doing stuff I hate to get there. You're going to get there and wish you hadn't done that. And I've told a lot of my friends that, that are like people in business school. There's 700 of us doing all sorts of stuff. Some people are really just interested in what they're doing or just curious and trying different stuff. That's, that's great. Some people really want to do the banking or the consulting or whatever. Or it sets them on a trajectory where they want to go, that's perfect. But if it's just a, I want to do this to get this job title because this sounds prestigious, you're risking wasting your late 20s or early 30s to win a prize that you're not even going to enjoy in the first place.

I remember, Jack, when I was working in the corporate world, this job that didn't look that cool, but if you took that job, that could then lead to this one job, which then probably would lead to this other bigger job. You got to do that. You got to be more well-rounded. That type of career advice. And I was explaining this to him. He's like, yeah, but that's 3 years and then maybe another 3 years. He's like, are you going to be a good husband those 3 years, those 6 years? A good dad? Are you going to come home pissed off all the time? Or because it's not a fun job, it makes no sense just to do that in order to potentially get that, to potentially get that. He's like, no, man, do the cool thing like that you want to do. You certainly got to make money, but do the thing now. Don't take a job with the hopes that it could lead to some other job that you might not even like anyway. And I found that I've gotten that career advice from Harvard MBAs and people like that. Yeah, dude, be— you're not well-rounded enough. You're too salesy. You only have a sales background. Go over here, then there. That could lead to that. I'm like, God, that sounds like a lot of stuff. I don't know how fun that would be along the way.

Derek Thompson, he's one of my favorite writers for The Atlantic, and just— I sent a in the chat of this piece, but he, he wrote this piece called Your Job Is Only 1/8 of Your Life. And it has, I think it's 10 different just advice points on career stuff. But point number 3 is just so well written. Don't do the job you wanna tell other people you do. Do the job that you wanna do. And he was talking about how, like pretty early in his writing career, he was thinking about taking another job just because it just sounded right. And another writer at The Atlantic hit him with that. The don't do the job you wanna tell people you do, the one you wanna do. And 5 minutes later, he turned down the job offer because he realized that, like, that it was just the— he almost put the idea of this other job on a pedestal. I think that's the best way to think about it. Just, it's very easy to take the job that's going to sound good at the happy hour, the cocktail party, but if you're putting 80 hours, 60 hours a week into something you hate just to tell people about it, to brag for 30 minutes, it's a pretty bad trade-off.

100%. Dude, I could talk to you all day. I really appreciate this. I highly encourage people to go to youngmoney.co. Youngmoney.co. That's Jack posts all this stuff. I read every time you publish something new. I know how hard that is, so I admire and appreciate the consistency. And I think the cool thing is it's really— I think, and you've written about this, but I think it's really just about living a pretty interesting life. Yeah, more so than a finance blog. And there's some of that which is helpful for me because I don't have that in my background, but it's more about how to view life and view opportunities and make connections and build relationships and travel and all of that. I think that's useful for really certainly any leader, because as leaders we're trying to influence and move people and create more leaders and create people who want to follow in whatever movement you're trying to do. And I think becoming a more interesting person, becoming more well-read, becoming more knowledgeable on a wide variety of topics will make you better at doing that. And so I think your work certainly does that for me, Jack. I really appreciate— I encourage people to go to youngmoney.com and check it out. And, and I'd love, as we've talked before, to continue our dialogue as we both progress, man.

Yeah, no, same here, Ryan. I appreciate you having me on here. This has been awesome. And we actually should follow up on the, the copy on the, on your website.

So I'm definitely down, man. I would love it because I want to— as I've said, when I look at the blank page, like, making it funny, or I should say trying to make it funny it's not very good. And so I end up just like, all right, I'm just gonna leave it like probably boring, but leave it basically not— no jokes. So that's something I also want to try to get better at, of injecting humor into writing, because I just admire that style. And I admire stand-ups as well because I've seen some of them become great writers, and I like all your stuff. But I'm down, man. I would love to do that.

I appreciate it. Let's do it. Thanks, man.