Lessons from 17 Years of Podcasting - Jordan Harbinger
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Oh, by the way, before we get into this episode, I would love to tell you a little bit about Life Notes. Now, Life Notes is a weekly-ish email that I send completely for free to my subscribers, and it contains my notes from life. So notes from books that I've read, podcasts I'm listening to, conversations I'm having, and experiences I'm having in work and in life. And around once a week, I write these up and share them in an email with my subscribers. So if you would like to get an email from me that contains the stuff that I'm learning, almost in real time as I'm learning it, you might like to subscribe. There is a link down in the show notes or in the video description.

A lot of high performers, they're grinding really hard. They feel the people breathing on their heels right behind them at all times. They've always been that way. That's why they have excelled. So when they all get into one room, they're like, "Oh crap, everybody is intelligent and hardworking. I'm not special anymore. That's hot."

That is really hot. What you're about to hear is a conversation between me and the wonderful Jordan Harbinger. Now, Jordan has been a podcast host for the last 17 years. He had a podcast since way before it was cool, and he's interviewed all sorts of high performers from all different areas of life. If you want to trade something about your life with someone else, you really kind of have to trade your whole life with that person.

You can't just be like, I want to be as successful as Tom Brady in this area and as successful as Barack Obama in that area. That's ridiculous because nobody is all those people put together. Why are you doing this to yourself? We talk about the age old battle with imposter syndrome that all high performers have. We talk about another age old dilemma, which is passion versus money. I think if somebody is asking a lot of you and they're not entertaining any requests from your end,

there's a good chance that they're taking advantage of you. The only way to know that is... And we talk a little bit about this relationship between money, fulfillment, career success, and all of the stuff that we like to talk about on the pod. If you want to be financially successful and at the top of your game in your 40s and 50s, you should not...

Jordan, welcome to the podcast. Yeah, thanks for having me on, man. Thanks for coming on. Who was Dave and how did Dave have an impact on your life? Oh, Dave, yeah. So Dave was a partner at my old law firm. So I used to be an attorney, just like he used to be a doctor. Good thing we did all that schooling, huh? That was nice. Those student loans are fun.

And I was at one point just like fumbling through figuring that they were going to fire me at any point working at this law firm because I had imposter syndrome. But back then I didn't know what that was, right? I didn't think that everybody thought they were going to get found out as a fraud and fired from every first job that they had or every school they went to. And it turns out that's something that high performers deal with all the time. And I'm not saying I was a high performer. In fact, I really thought I was at the bottom of the barrel.

barely got into law school, was not in the, you know, those bars on websites that show like, this is what our average scores are. I was like the bottom of that or below that. So that's not a great way to start law school or medical school. You just go, oh, I'm like below the average person that gets in here. Not a good feeling.

So when I got to the law firm after graduating law school, Dave was never in the office. And I thought, okay, if I also figure out how to never be in the office, they won't find out that I'm secretly a moron and fire me. I can work from home and it'll take them longer to find out that I'm a total fraud and shouldn't have ever been hired in the first place. By which time I may have figured out how to do this job and be useful enough that they won't fire me. Right. It's,

it still sort of makes sense when I, when I, when I put it like that, I hope so. Dave was also supposed to be my mentor, which is basically at that point, a checkbox on a forum that human resources makes them sign. So other people's mentors were like, let's go out for drinks once a week and talk about your career. And again, Dave is never in the office. So I did HR is like,

How is your mentorship going? And I'm like, I don't even I've never seen the guy. I saw him one time. And so I think they made him come into the office, which he loved, by the way, and take me to coffee at Starbucks in the basement of our building. Meanwhile, other like I said, other people are going out for drinks. They're going to the steakhouse. They're going to see Blue Man Group like they have a real relationship with their so-called mentor. And I don't.

and Dave's like, ask me anything you want. And he's typing away on his BlackBerry, like, sure, ask me anything, kid. And I'm like, how come you're never in the office, but people say that you're one of the highest paid partners? And he's like, wait, people are saying I'm never in the office? So now I'm like, cool, I'm definitely getting fired now because I stepped in it at a Starbucks in the basement of this office building. Well, he wasn't thrilled with that, but he didn't shoot the messenger. And he told me, well, I'm usually out

generating business for this law firm. I'm not being in the office is it's a waste of my time. Billing hours is kind of a waste of my time. Yes, I need to do it, but I just oversee projects. So it's like, are you working from home? He's like, no, my yes and no. My job is to go play racquetball or squash with clients that are people that might become clients cycle with those people do jujitsu with those people play golf with those people go on fancy dinners with those people. And he's like,

Then I bring in business and he goes, candidly, if I build 2000 hours a year, which is a ton, that's not every hour you work. That's just like billable hours to clients. You're working 4000 hours to get that done, which is a ton. You get a bonus of, I can't remember. It was like X percent. If you bring in a new client, you get a percentage of the total billing and it might only be 5%, but what if you bring in a $2 million client?

So you bring in a couple of those or $10 million client or $20 million. So you bring in a couple of those, your compensation is massive.

So he was just focused on that. And a lot of the guys that were like workhorse lawyers who would keep their heads down all the time, they made bonus and they were in the office on Sundays and Dave was never in the office and he made more money than those guys. So I was like, whoa, I've accidentally stumbled onto the cheat code. And I thought, why doesn't every lawyer do this? And I started asking the other partners and they were like,

Man, you know, some people are relationship people and other people aren't. And I thought that's definitely not really true. They just didn't want to do it because it was kind of scary or they weren't that great socially or they found that keeping their head down and being a workhorse was easier.

But I think that's because overachievers who go to law school are naturally disciplined, heads down kind of people. So if you get out of that situation and you can be a salesman also, you just have disproportionate rewards. But if you just stay in your habit of grinding all the time, you end up a workforce lawyer. Nothing wrong with that. However, in 2008 when the economic downturn hits, everybody gets forced out of this firm. The firm closes, 140-year-old law firm.

closes. Dave goes to another law firm because he's got all the clients. He's got a whole book of business. They hire him right away. Maybe the dude even got a raise. The other workhorse lawyers, nobody really wants those guys. There's no work anymore in real estate finance at that point in time. They worked for a firm that's no longer around. Every other partner views them as competition because they essentially are, except for Dave who brings in more business. So

I thought, okay, not only is this true inside the legal realm, this relationship thing is like an insurance policy. So I tripled down on that right away. Nice.

Yeah, this reminds me of something I've been hearing a lot recently around entrepreneurship in that like having a job is where you're being trained to do the work. But being an entrepreneur, really the value add is in winning the work. And this sort of distinction between winning the work and doing the work, I think up until a few weeks ago, I hadn't quite

quite had it clear in my head that those are two very different things that require two very different skill sets and really school and the education system and everything trains us to do the work. Whereas really the value is added in these like law partners and consulting partners in actually winning the work. How do you bring in new business?

I agree with that 100%. I mean, you and I are in a slightly different kind of field, right? Because we're creating things. So you can probably stretch it to that if you think about it. But yeah, we also – a lot of CEO-type people are great at making decisions and they're managing people and they have great ideas. We have to kind of do some of that but also –

I can never, at least me, I can never run my business without, I can't automate myself or do it because I'm having conversations. It's a podcast, right? You can't automate like this part of your business. It's not possible yet. And so I do agree though. I think school clearly has failed most of us in that way, especially in the United States. I don't know if you know this, but school in the United States is generally,

designed to it was designed for like an agricultural revolution back in the day and now it's industrial revolution where it's like the bell rings it's sort of factory assembly line everybody do the same thing lowest common denominator is where the work line is so if you're intelligent and you're in a public school or a regular school in the united states it's very hard for teachers to serve you because they have to catch everyone

And that is a terrible way to create innovative thinkers, for example. Yeah. No, it was broadly the same in medical school as well. Like I went to a fancy medical school. And even then, most of my friends and me, we taught ourselves using the internet because-

the, even in the, in the, in the university system, the, the people who lecture, they're not lecturers because they're good at lecturing. They're lecturers because they have good research output and lecturing is their side hustle that they happen to have to do to tick a box and keep their paycheck for research coming in. Cause really they care about the research. Whereas the dude on YouTube, if you just fricking loves making YouTube videos about physiology, wow, how incredibly useful is that? Whether or not they've got like a research background. Yeah.

That is definitely the same in the United States. You'll get somebody who – I remember taking a math class. I'm not good at math and I – it's – I'm never going to be good at math and I don't care. But thank God now. But in college, I took calculus and the person who taught calculus was a German guy with a really strong accent.

Nobody knew what was going on. There were kids that were so good at it, they could just do these crazy math problems in their head. And they were like, this is so stupid and easy. Then there were people like me who are like, I don't get it. And you'd go talk to that teacher and he would just be like, it's so hard for me to explain this. And I'm like, it's literally your job to explain this, man. I'm like, try it in German.

Because I spent an exchange year in Germany. So I'm having this guy tell me in German and he's like, oh, I'm so glad I can tell you this in German. And I'm thinking, holy crap, the requirement to understand the teacher is knowledge of a foreign language.

This is the University of Michigan, man. I should be able to take this class and understand it. And he's like – he was very candid because he was German. He's like, look, I'm here because I'm doing research with this well-known professor. They're making me do this. It sucks. And I thought, really glad I'm paying $40,000 a year to learn from somebody who resents the fact that they even have to teach. Okay. So final tangent before we go back to the law story. Sure. You mentioned –

every high performer goes, like suffers from imposter syndrome. Yeah. Can you elaborate on that? Yeah, I can. So if you ever talk about imposter syndrome, well, let me back up. Imposter syndrome is essentially thinking I'm a fraud. Everybody else is better than me who's around me at this particular time. So low performers or average people, like if you talk about this concept at a high school, they won't know what you are talking about because teenagers are young and they haven't really hit this yet. And also it's just a high school. So they're like,

whatever, I don't have this problem. When you go to a place like Harvard or Apple or an Ivy League school or an advanced law school or a medical school, if you do, when they do sort of hand-raised polls, how many of you think, I don't belong here, maybe, it's only a matter of time until somebody finds me out? You'll see like 95% of the hands go up. How can that be true? How can 95% of these people think that they see, there was a mistake made in the admission of this person?

And it's because a lot of high performers, they're grinding really hard. They feel the people breathing on their heels right behind them at all times. They've always been that way. That's why they have excelled.

That's why they were the valedictorian of their high school, right? They just felt someone's right behind me. The truth is maybe there was one person right behind them and everybody else was not paying attention or was way behind them and couldn't even see them at that point. But these people always feel a fire lit under their butt. So when they all get into one room, they're like, oh crap, everybody is intelligent and hardworking. I'm not special anymore. And that heat is hot. That's hot. That's hot.

That is really hot. So then you're looking around and you're like, oh, I thought I was kind of hot, hot ish because I was valedictorian and president of this and the chess club and on the football team. Then you get there and someone's like, I was all that. And I speak five languages. And my dad was a diplomat. And I spent years in various countries. And I also founded this organization. And you're just like, oh, crap, I'm a big fat nobody. Yeah.

Yeah. So you have that imposter syndrome. And of course, that guy who grew up all around the world speaking five languages and yada yada, somebody else next to him, they're a child star from a television show. So they're like, oh, look at them. They were on Full House, you know, or whatever. So everyone feels that weird sense of lacking.

and it's unhealthy because what it does is it can cause some people to check out and and put so much pressure on themselves that they become depressed the problem is you don't really outgrow it let's say you go you let's say you feel that in medical school well when you get to the hospital then what oh that doctor has a decade of experience this person's been here longer wow this person has uh so many other advantages over me i don't know much about the medical industry but in law it's just like that too you you feel like oh finally i got through law school

You get hired at a firm that takes the top 10% of law schools. Great. Now I'm at the bottom again. Right. So it's just never ending. And you end up feeling that imposter syndrome for years and years and years and years. It's just, you're basically your own worst critic. Yeah. What do you do about it? Yeah. What do you do about it? You first, the first step is always awareness, right? Okay. Everybody feels this way. And if they say they don't, there, there's a really statistically good chance that they're lying about that.

And if you drink enough whiskey with enough lawyers, you'll find out that everybody kind of thought, holy crap, I didn't even think I was going to pass the bar exam. How did I get hired here? Right. It's only a matter of time. And everyone has that. So when you realize that that's a universal feeling, it makes it a hell of a lot easier.

And as you gain experience and you realize that everybody is winging it and you start to specialize in your area, it starts to go away gradually as you build professional competency in whatever you are doing. I wouldn't say it goes away entirely for a lot of people. I know – I mean I'm 44. That ship sailed a long time ago for me. However –

I've been in podcasting for 17 years. A lot of people, it's new, right? And they'll go, oh, I'm never going to be able to do this. And I'm like, I remember thinking that exact same thing. So as you build real skills and you get real, actual real life feedback on something, you realize you're not faking it, right? If you're a doctor for a decade and people are like, you saved my son's life. Eventually you start to think, maybe I do know what I'm doing. I did take out that kidney and that person survived. You know, there's a lot of objective feedback that says you're doing it right. Right.

But it takes a long time. It does. Yeah. Like I've been doing YouTube now for seven years and teaching for way longer than that. And still, I, you know, as you were saying that, I was thinking, I still often have that feeling, even in the world of YouTube where, you know, my channel is fairly big in the personal development world. Yeah, it's massive, yeah. But it's like, oh, damn, these new kids, that 21-year-old living in New York, oh, the vlog style is just so good. Oh, man. Yeah.

right on my heels. It's like, I don't, I didn't consciously think that, but it, it's still that same feeling of like, oh shit, like there's some sort of race here and I've got to keep on grinding to stay even vaguely in the, in the running because who knows, like whenever, you know, the algorithm or whatever, or like people might just realize that I don't, I actually don't know what I'm talking about. And they might realize that,

shit after seven years and 800 videos that's when he's run out of things to talk about right he's done he's cut that's that comparison is also that sort of pure fuel on the fire for imposter syndrome the comparison thing off almost never ends however once you start gaining professional competency in something you start comparing yourself a little bit more fairly unless of course this has just gone wild in your head in which case it's helpful to like literally talk to a therapist but

the comparison is so much easier now especially when there are metrics like you can look at someone's engagement or youtube subscribers and you can go objectively that person's doing better than me in that particular area but you don't really know what's going on in their life i do this with podcasts i still do with podcasting i'll go man how does that person have so many reviews

Oh, maybe, maybe I'm not getting it. Oh, does that mean my engagement is lower? How is that person's engagement so high? Let me figure out what they're doing. And sometimes they're doing something really cool and innovative, like asking for reviews in a certain way, or their social media is really taking off. But other times, and I always have to remember this lesson, I was working, you know, you know, those guys that DM you and they're like, do you want new subscribers for your whatever? And I'm like,

what I've started doing, and this is gonna ruin it, but whatever, I've done it enough. What I started doing is I started saying,

Can you show me proof of results? And what some of these brilliant individuals will do is send you screenshots of them talking with another popular podcaster. And they're like, look, I've worked with this guy for years. And I'm like, so what you're telling me is this popular show is buying downloads from you, a dude in Bangladesh who runs a click farm. And I'm like, oh, I spent a lot of time feeling pretty bad about how I was doing in comparison to that person, and they are cheating.

Not everybody who's doing better than you is cheating, but some people are. And it's important to sort of remember, even when I've seen plenty of people who aren't cheating and they're doing really well with something. And again, you meet that person in real life, you put a couple of whiskeys in them and they have a chat and you realize, oh, they're a complete workaholic. I would not want their life. This is not just cope. There's something I've learned

from I think Ryan Holiday and I should really pinpoint where I picked this up. If you want to trade something about your life with someone else, you really kind of have to trade your whole life with that person. You can't just be like, I want to be as successful as Tom Brady in this area and as successful as Barack Obama in that area and as successful as LeBron James in this area. Like it's totally that's ridiculous because nobody is all those people put together, even the people that you just mentioned who are world class.

Why are you doing this to yourself? So if you are willing to trade one area of your life, look at this guy, he's got 15 million subscribers and I only have 5.6 or whatever it was this morning when I checked your channel.

You have to be willing to trade your life. Say goodbye to your beautiful fiance. Can't have that. You got to be this guy over here who all they do is live, eat, and breathe YouTube. Is that what you want for yourself? Probably not. This person still grinds hardcore like it's day one. Why? They're miserable, secretly or not secretly. Do you want that person's life? Because if you do –

You'll get those 15 million subscribers, but at the cost of your sanity and the fact that you have work-life balance. There's a reason people achieve certain things, and it's because their whole life is geared towards those things.

Yeah. So you've interviewed a lot of high performer type people on your podcast. Have you found many examples of, because I guess when someone's being interviewed on a podcast, usually it's once they're already successful and then they'll say work-life balance is the most important thing and blah, blah, blah, blah, blah, blah. Yeah. But usually like when I interview them, I find that like, okay, well, there was a huge period of grind at the start and maybe they were very imbalanced in their twenties or whatever the thing might be. Is that broadly the pattern you found as well? It is. So you find varying levels of

delusion and or self-awareness among these people. And what I'm, I don't mean all successful people are delusional. Hear me out here. The person who says you need work-life balance, to your point, often had absolutely no work-life balance whatsoever through their 20s and likely their 30s. And the cold truth is, if you look at statistics, I think Scott Galloway, who you may or may not know, he goes through this. And he, I think he's the one who told me this.

You should not seek work-life balance in your 20s and probably your 30s if you want to be financially successful and at the top of your game in your 40s and 50s. It's just not realistic. There's nothing wrong with seeking work-life balance.

But in those early years, that's great. Live a good lifestyle. You will not have the same career results as the person who worked 60, 80 hour work weeks at the law firm. That person will become a partner. You will either be transitioned out or you'll hate it enough to where you transition yourself out.

There's nothing wrong with that, but it is a choice. It's delusional to think for most industries. Again, if you're an entrepreneur, maybe it's literally impossible. If you're a Wall Streeter or a surgeon, maybe it's impossible. For most careers, there may be a varying degree of what you can get away with and do.

But for a lot of high performing careers, no, you're not going to have work life balance in your 20s and 30s. You're just going to grind really hard, sacrifice a lot, maybe go out on the weekend sometimes, but maybe not. And then you are going to be...

wildly successful in your 40s and 50s because of what you put in early in the game um another another sort of trope that I hear a lot that I think is nonsense is people will say follow your passion none of those successful people barring maybe a few artists and creators have followed their passion uh again Scott Galloway I think is is one who said the person who told you told you to follow your passion made billions of dollars in iron smelting yeah

And that could not be more accurate. I hear these guys say, follow your passion. And I don't think they are lying. I think they think that's what happened. I've heard, I don't want to throw anyone under the bus. I've heard billionaires say, follow your passion. That's a great commencement speech. They didn't do that. Or their passion was sleeping on a floor while they started a clothing company. Was that all passion? No.

I think it's debatable. It's debatable whether that's all passion. They made billions of dollars in clothing or they made billions of dollars in a tech thing and then in investing. Maybe they were passionate about that. You have to ask yourself if you are passionate about that. The answer is usually no.

yeah i've been uh i uh over the weekend uh i went on a binge of podcasts that scott galloway's been on and it was like you know because i i'd heard his name but i hadn't really heard any of his stuff until like two days ago and then it turns out he lives in london so i want to get him on the pod at some point yeah yeah um but so i'm curious about this this follow passion point um

One thing that, for example, the philosopher Alan Watts would say is when kids ask him, what should I do with my career and stuff? He asks the question, well, what would you like to do if money were no object? And then he waits for their answer and then says, okay, well, so go and do that thing. The thing that you would do if you weren't being paid for it or if you had 100 million in the bank may be the thing that you want to do with your career as well.

Which sort of overlaps with the advice of follow your passion to an extent. I wonder what's your take on that? Yeah, so I'm completely okay with that. Here's the kind of cold truth, according to me. So take it or leave it. You can follow your passion and you will probably be happier than somebody who just gets a lucrative career. You probably will.

But you can't expect to follow your passion and also have a lucrative career. Not impossible. I certainly followed mine into podcasting and creating audio, and it's a very lucrative career. I am really freaking lucky that that worked out. I was early to market in podcasting. It's been 17 years, like I said. So I was early in the game. No, this is how early I was.

When I was interviewing authors and deconstructing high performers and talking about that stuff with Tim Ferriss, he hadn't written his book yet.

And no one was interviewing successful people and talking about what they did. That was a novel concept. Now, if you say I'm starting a podcast and I'm going to talk to successful people and break down what they do, people are like, oh, really? Cool. We need another one of those. Right. It's just like ridiculous at this point. So my show's evolved over time, obviously, but it was novel back then. That's how early in the game this was. And I

I expected to take a massive pay cut from being a lawyer. I was a Wall Street finance attorney. That was one of the best sort of banky jobs that you could get. I remember the conversation with myself saying, "Am I comfortable making like 30% maybe, if I'm lucky, of what I was making on Wall Street and just loving what I do?"

And then I had to budget and see if I could afford it and talk to my parents and see what that was like. And they were like, you can still live a decent-ish lifestyle if your wife has a good job as well and blah, blah, blah. Now, of course, I make in two weeks what I thought I was going to make in a year. But that's largely due to luck and timing. And that's not a strategy that anybody should seek to replicate.

Oh, by the way, quick thing. In case you are interested in starting and or growing and or monetizing a YouTube channel, then you might like to check out my part-time YouTuber Academy. It is a course that has dozens and dozens of hours of content in it, along with templates and worksheets and resources that basically open source absolutely everything that me and my team have learned about growing my YouTube channel and also this podcast YouTube channel over the last seven plus years.

So you can check that out at academy.alibdahl.com. That'll be linked down below in the video description and the show notes as well. Feel free to check out the Part-Time YouTuber Academy. Yeah, I like that way of thinking about it. I often also arrive at this crossroads between essentially money and passion, where...

For example, this podcast is no longer a podcast that we're taking that seriously from a monetization perspective because I decided, well, I started off being one of those podcasts that was trying to deconstruct successful people, et cetera, et cetera. I then sort of, as the podcast grew, we sort of over-optimized it. So we'd have batch filming days and we'd get people in and authors would be promoting. Turned your hobby into a job. Yeah, exactly. And then it's like the sponsor revenue is going up and stuff. And I'm like...

why am I doing this again? And then a few months ago, I came to the realization that when it came, when it comes to certain areas of my life, including the podcast,

I'm actually totally comfortable with leaving money on the table in return for following my curiosity, i.e. you're in town. And so let's just do a pod in the middle of the day. I've got another friend who's in town from Miami this evening. So we're going to do a pod and just have some dinner. And maybe the conversation is too niche for it to go viral or whatever, but I don't really care because it's just a cool conversation that I would have wanted to have anyway. I appreciate that. And two, I agree with that. Turning, it's funny because in my notes to talk with you about, I had turning your hobby into a job. I almost always think that is a mistake.

Because, and again, with podcasting, I happen to be really, really interested in it and love the conversational element. You can tell there are a lot of podcasters that really, they're not that curious. They just want a lucrative business and they are really good at social media or something like that. And that's fine. That works for them. But it's definitely work and you can tell.

For me, it doesn't feel like work, which is so fortunate and lucky, but I don't, again, I do not think that's a strategy most people can replicate. I think a lot of people rush to turn their hobby into a job and they ruin it. They ruin it. If you love painting, the last thing you should do is try to make a living being a painter. Sell your paintings all you want. Once you quit your day job and you have to paint and they have to sell and you have to market them,

you're going to enjoy 10% of that job. So we turning your job right into, into a passion. It's just, it's sorry, turning your job into a business. It's often a terrible idea. There's a lot of bad advice out there. Again, I won't throw anyone under the bus, but you see these influencer guys being like, go all in, quit your day job. And then you have, you know, burn the ships and then you have to have your business succeed. That is a terrible piece of advice.

Because what happens is you then have to do whatever it takes to quote unquote succeed. But what that usually means is pay your rent. Now you have to either cut corners, maybe do some sheisty sales stuff, sell a product that's not ready. There's absolutely no reason to burn the ships and go all in. If you're starting a business, and I'm wondering if you kicked off this way when you were a doctor.

If you're starting a business, you should outsource everything possible that you cannot do yourself. And then and only then, once your time is the bottleneck on the business, should you even think about resigning your actual day job? What I see is a lot of folks that they quit their day job and then they're like, okay, I guess I got to do social media now. And they spend all their time tweeting and doing, and it's like, whoa, whoa, whoa.

someone else could have made all you're editing these little videos what are you doing you're spending three hours editing tick tock videos you can outsource that crap and you could have kept your job designing semiconductors that paid you four hundred thousand dollars a year no now you're struggling to make forty thousand dollars a year selling sheets on the internet what did you do that for yeah yeah i generally find that um you know the the thing that held true for me was when you've got a day job and then you're having to side hustle the business in the evenings

it sort of forces you to only do the high value things. And it forces you to cut corners on things that it's okay to cut corners on. Like for example, making YouTube videos, it's like, well, you could always put more hours of editing into a YouTube video, but if you literally have a day job, where it takes an hour to commute to work and back, and you've got the evening, maybe like an hour in the evening to edit, and you want to do a video a week, that means you've only got a few hours to edit that video. Assuming you can't outsource it, which is something that took me way too long to do. Two years into it, when I outsourced it, it was like, oh my God, this is incredible.

And I find that when people ask for advice around the quit job thing, I'm always like, no, you should be able to build... If you are going to succeed in business, then...

you should find a way to succeed in a business, in business as a part-time gig. And then, yeah, I agree with you. When your time becomes the actual bottleneck and now the value of your time working on the business is actually worth more than the value of your time working at your semiconductor job or your doctor job. At that point, okay, let's think about cutting down the hours. Most employers are okay with you going part-time because they'd rather keep you if you're actually good. And then once we've got a very, very, very comfortable business going along, at that point, cool, let's think about quitting the job. I also don't like this advice of like, quit the job, go all in.

Well, I don't know. In some cases, if you're like 22, fresh out of uni, you know, taking a bit of a gap year to have a go. Sure. Assuming you've got, you know,

You can live with your parents for over a year or something like that. Sure, why not? But I think especially if you have rent and you have bills and stuff, it's very, very stressful to rely on a fledgling business to make that money. It doesn't make any sense. It doesn't make any sense. Look, startups or something like that, totally different case. Then you're getting investors. They're essentially paying you to live or you're living in the couch in the office. That's a very San Francisco type thing.

But you're not quitting your day job. You're just going all in on a really piss poor slash unpaid startup. That's a different scenario. You see these influencer guys being like, quit your day job and go all in. So you get a guy who's a waiter and is making enough to survive and then is doing, I don't know, let's say flipping something on the side, e-commerce business.

Then they quit the server job. Okay, so now you're just going to have to imagine what to do with those extra hours. You're working a ton, but you're still getting basically the same results out of your e-commerce thing. So you're not getting enough to survive. You're stressed as hell. Your back is against the wall.

Some people need that motivation. That's unsustainable though. So if you need that level of motivation to just work on your business, is that the right business for you? I don't know about that. I think if you're going to run away from your day job, you should be running to something like, I can't wait to edit my YouTube video after work. Oh, I have so many great ideas for my next video.

I love this podcasting thing. I can't wait to do that. I love this. I wish I could do this all day, every day, but I've got to go to this job. That's what you should be running to. What most people do is they are running from something. I hate my boss. He's terrible. He makes my life miserable. I hate my job. It makes me feel insignificant. So then they start a business. That's their escape hatch. So they can't wait to flip that shit open and dive through there, right? They're running away from something. That is not a good idea.

Okay, so let's get back to Dave. So you realize that Dave's making all this money. He's never in the office and he's bringing in the work rather than doing the work. How does that realization change the way you approach your career? So I start realizing that bringing in business is a relationship game and it's not like a hard course. I literally at that time thought,

Huh, I guess people don't find lawyers by just looking in the phone book and looking up law firms and hiring them. Of course they don't. These are super high trust deals, right? An investment banker gives the deal to his roommate from law school because that's how it works. They can't afford to have this screwed up. They know the guy's really smart. They can trust the guy. They can call him at home if they need to. They're not going to trust this to some random schmo. This is a multi-million dollar deal or more that's going to go on for years at a time.

So you have to build those relationships. And I remember asking Dave, so how do you build those relationships? And he was like, just be cool, man. It'll all be fine. And I was like, let me tell you something. If just be cool was actionable advice, do you think I would have become a lawyer in the first place? Lawyers are known for a lot of things. Being cool, not one of those things. Okay. So this guy was not giving me something that I could really use.

He was really just giving me platitudes. And the more people I asked for their networking or relationship advice, the more platitudes I got. I even took Dale Carnegie courses and stuff like that because I was like, these guys have it figured out. And a lot of that was...

principles that were useful, like be interested in other people. But if you're not getting a job or a deal or whatever it is, it's not because you didn't look them in the eye and have a firm handshake. It's because they liked and trusted someone else more than you.

Like that, like and trust stuff that's not built off of like, oh, he looked me in the eye and he gave me a firm handshake. That's getting a minimum wage job at a supermarket. And the owner takes a chance on you because he looked me in the eye and he had a firm handshake. Nice kid that Ali. Right. That's that. No one's giving you a million dollar deal because of your handshake. Yeah. So you have to do more than that. And so even these Dale Carnegie courses where they're teaching you like the memory palace to remember that some kid, some guy's kid played tennis.

Those people come across really fake and you just can't actually fake being interested in somebody. It doesn't work very well. At least I'm terrible at it. It's hard to do. I have to actually be interested in somebody. So the quickest way I found to develop relationships is to help other people without the attachment to getting anything in return. And it's scalable and it's very tough to do that over time because most people want something

And you have to help other people thinking this person may never be able to help me with anything ever. And I just have to be okay with that. And I'm not talking about like designing websites for free for everybody who asks. I'm talking about making introductions to other people who can help them. That's the only way this is scalable. So let's say that you're like, hey, I want some interesting podcast guests when I come to California.

I don't have to book those guests for you, but what I would do is introduce you to people that live near me and in the cities where you're going that I think are interesting, that I think would also say yes to doing your podcast. And I can just do that kind of thing, right? And I can do that for somebody who's looking for a job in a field. I might know somebody who runs a business in that area and I can ask them for advice. Or I could say, would you hire this person as an intern? They're actually pretty cool. If I know, if I can vouch for them, right? I do that kind of stuff every single day. It's usually done by email, right?

The difference is what I hear from, and I thought this is not rocket science, but what I hear from other folks when I give this advice is they'll go, yeah, I know people have asked me for this.

but I just kind of never responded. I'm thinking what a missed opportunity this is. Well, yeah, but I'm really busy and I get a lot of email. I believe you. However, I'm pretty sure that you don't get more email than I do. It's not a contest, but you and I get a lot of email, I'm sure. I try to, I will help any random person that reaches out to me if I can with advice or with an introduction. And that has earned a crap load of social capital and goodwill.

Those people I normally assume will never actually be able to do anything for me in return. However, I'm wrong at least 1% of the time. And that 1% of the time turns out to be kind of a big deal because I helped somebody the other day with something completely insignificant, in my opinion. And he goes, let me know if you ever need a guest for your podcast. I thought he was talking about himself. I was like, thanks. I appreciate that. And he's like, yeah, because I'm working with a list celebrity on a project. And I was like, really? Uh,

That person would be amazing. And he goes, oh, yeah, I'm literally seeing him tomorrow. I bet you he would do your podcast. I'm going to ask him. And that blew my mind because this person was asking me to introduce them to my web designer, which so I earned my web designer a referral. He was very stoked. And this guy was like, thank you. I've gone through five web guys and the first three ripped me off and the other two did a crap job. I'm like, oh, you're going to be taken care of.

And now I might get this really, really interesting guy for my podcast because he has a good relationship with him. I had no idea that he had that relationship. That is not why I helped him. So when you help 100 people, if 99% of them never do anything for you, but you're helping them in a scalable way, you are kicking ass. You get the short end of the stick 99 out of 100 times. Collect all those short sticks. Yeah.

How did you apply this in your day job back when you were a lawyer? I tried. It was quite difficult. But what I did was I realized going to those meetups where you drive across town and you're like, lawyer's happy hour. That was a nonsense way to do this.

It's just it's a lot of takers at networking events because they go to network. Most people, again, only build relationships. The phrase I've stolen is dig the well before you're thirsty. They usually people don't do that. They are dying of thirst before they decide to network. And what that means is they go up to you and ask you for a job. And if you can't help them, they move on to the next person or whatever. They ask you for something.

You don't meet good connections or network or build relationships at networking events most of the time. So what I started doing was applying the help other people without the attachment of anything in return and how I applied that during my very short-lived legal career was I

When people were asking me how my law firm job was, I was brutally honest with them, the positives and the negatives. I asked other lawyers in the firm for their advice or opinions on things people were asking me who are still in law school or other lawyers who were thinking about joining our firm. I arranged groups of people to meet up and go out that were maybe thinking about switching jobs. And I just facilitated those nights of drinks where we would all go hang out and just turned out to be just like a clique of dudes that liked each other and a few women.

And I also, what else did I do? I help people who are moving to New York, regardless of what industry they were in. Because when I first, this is sort of probably a problem that doesn't exist anymore with the internet and all the websites that are out there. But back then, you...

you could look on craigslist and maybe find an apartment that wasn't a scam but most people didn't know where any of the neighborhoods were how quick it how they needed to move around the city none of that so i sort of translated a lot of those things and said you're working on wall street don't live above all right sorry don't live yeah above you know whatever 14th street because it's going to be a pain in the ass during rush hour and i would say these are the neighborhoods you should be looking and here's the abbreviation for those neighborhoods that you'll find on craigslist and you

I just continue. In fact, I still do that. When I moved to LA, I still did that. I got a call from a friend who grew up with my next door neighbor as when I was in law school. And he's like, yes, so-and-so said I could call you. I helped him move to LA and years later,

I ran into him. He goes, Jordan. I was like, do I know you? He's he goes, yeah, you helped me move out here. I said, oh, right. I remember that call. He's like, I'll never forget how much you helped me when I moved out here. And I said, so what do you do here? And he's like, I'm in charge of booking all these studios. I said, really? And he's like, yeah, anytime you need a studio, I will make sure you get one. And you're never you're not going to pay for it. I'm always going to comp it. And that wasn't something I could have planned.

Right? And it's really easy to do this stuff. This is not a massive time investment per person. Somebody sends me a text. What is UWS again? Upper West Side. Oh, thank you.

Don't go there. It's too far from where your office is. Oh, okay. Good to know. Hey, this person says this. That sounds like a scam. Don't bring them any cash. You're going to get mugged. Okay, thanks. I mean, that's what I was doing. You can do that 100 times a week and it's no skin off your nose. That's very cool. Have you come across a book called The Go-Giver?

Yeah, is that Bob Berg? Yeah. Yeah. It's so good. Yeah. Amazing audio. If anyone's not listened to it or read it, would 100% recommend. I've been on like three road trips with friends where we were like, what audiobook should we listen to? And three times I've suggested this and everyone was just absolutely blown away. Yeah. Because its whole thesis is that like, if you give...

stuff and help people without the expectation of something in return. Crucially, all of the good things will happen. So it's funny. The reason I said give without the attachment to getting something in return is because I used to say give without the expectation of getting something in return. And I was having dinner with Bob Berg and he goes, well, the attachment is better because expectation, he had this whole reason. So I just switched, I switched to saying attachment because you can expect something in return and

but if you're not attached and you don't get anything, it's fine. But if you are attached to getting something in return, now you're keeping score. And I don't know how philosophical you want to get on this, but if I drive you to the airport,

and then I drive you to the airport again. I'm a good friend. But if I drive you to the airport a bunch of times, and then I ask you to drive me, and you go, hey, dude, I can't. I've got a podcast, and I can't help you with this one. If I'm attached to getting something in return, I'm like, Ali's such a selfish prick, man. I've driven that guy to the airport three times. I ask him once, and he's got a podcast. Suddenly, he can't do it. He doesn't feel good, and he doesn't even try to help. So now...

I've poisoned the well. I'm mad at you. You have no idea why because it's unreasonable. But it's because there's a covert contract, right? In my mind, I decided you owed me that. That's not really a good way to go through life. But you can expect that at some point you'll drive me to the airport or maybe you pick up dinner once or something like that and, hey, we're good. So you don't want to start keeping score. That's one of the big no-nos of any sort of relationship in your life. Yeah.

um someone might be thinking that thinking that or listening to this thinking well people are just going to take advantage of me then yes i don't want to be a doormat right i agree with that i think if somebody is asking a lot of you and they are never doing what you uh any and they're not entertaining any requests from your end there's a good chance that they're taking advantage of you the only way to know that is over time you

You should definitely not drive somebody to the airport and then they don't pick up your calls and never hang out with you or do anything for you unless they need something and they call you. These people out themselves eventually because you never hear from them unless they need something from you. There's a lot of people like that in the world. Some of them are very selfish. Others are just unaware. You get to decide what your boundary is. But it's not always that person's taking advantage of me. Sometimes people are just self-centered.

You get to decide what you will tolerate. Of course, there are reasonable limits. But again, you get to decide what those are. I hate to prescribe something. Like if you drive somebody to the airport three times and they never drive you, they're not your real friend. I wouldn't go that far. One thing that I have often gotten a lot of value out of is A, kind of being the organizer of things.

In the sense that, you know, how you're organizing these kind of meetups and things. I found that like everyone kind of wants to hang out, but everyone is really bad at organizing things. And so if I can be the one to organize the things, then great. You know, that's like a value add to the people, bring people together and stuff. And the other one is sort of having a low threshold for having random coffees with people, which has become a lot harder over time. Yeah, it's hard. But even then, sometimes I'll see a coffee on my calendar and think...

ugh, the ROI of this, it's like, oh, the time value, blah, blah, blah, blah. I could be working on X, Y, Z. But then I think, no, like, it's actually useful to have some amount of time carved out for

Things that don't actually have a clear, immediately obvious outline. I wholeheartedly agree. That's what I'm doing here in London, by the way. There's something called the podcast show that's going on right now. And I'm giving a talk or two there. However, I've carved out the whole week. I've got interviews and stuff like this one. However, if someone's like breakfast tomorrow, I'm not like, what company is this person at? Do I want to spend that time? What else could I be? I'm like, yes, right? Yeah.

Because I'm saying no to the random coffee that's next week when I'm off, when I'm hanging out with my family. Mm-hmm.

So I carve out time to do that. It's almost always at events because there's people from Spotify and Apple and other companies that down. But there's also people that I are working for companies I've never heard of that might be doing something. And I will spend time with all of those people all week long. It will be exhausting and fun. And then I don't feel bad about saying no when they ask me in a month. I say, no, I'll catch you at Podcast Movement in Washington, D.C. in August.

What's your take on hopping on random Zoom calls with people? I don't do that. Well, actually, that's an overstatement. I usually don't do that. There has to be a certain bar that gets met. If you introduced me to somebody and they were like, let's chat, I would say yes. If somebody emails me cold and is like, I would like to get to know you, let's hop on a Zoom, I will probably say no. And the reason is...

Because they haven't told me what this thing is about. Even if they were like, I really need to learn about this and you're the only person who can teach me, then I would probably say yes. But if they just seem to have passing curiosity, that is not enough for me to justify that kind of thing. But if they wrote to me and they said, I know you can't do Zooms, but I don't understand how this works and you're one of the only people who can explain it, I'll probably send them a message back and explain it.

So I try to accomplish that without just saying yes to every sort of random request. Yeah. So I guess, yeah, this is something that I'm trying to figure out the balance of because I guess over time,

My willingness to help someone who has not done the work. Yes. It really starts like plummets. Yes. Like if someone messages me and they're like, Hey, I'm on a hundred thousand subscribers. I'm really struggling with like scaling my team. You know, I know you talk about this. Can we hang out sometime? I'm like, dude, no,

Or gal. Like, hit me up anytime you're in London. Let's grab a coffee. Let's go for a walk around the park. I'll give you hours and hours of my time because... But if someone's like, hey, I'm a brand new YouTuber and I've made three videos, I wouldn't even respond to the email. I wouldn't even see the email because it's just...

There was almost a bar of like a proof of work kind of idea. I agree with you. I agree with you. People will say, what are some, and these are well-meaning people, so I'm not trying to be a dick. They'll say, what are some of your tips on starting a podcast? And I tell them the truth, which is I am the worst person to ask about a launch.

Because I launched my show 17 years ago, and then I started a new one seven years ago on the back of that one when I was already well-known in the space. I am the last person you should ask for advice on how to launch when you don't have that done. Mm-hmm.

But you're right. If somebody goes, hey, I'm getting this many downloads and I'm wondering how you do X, Y, Z, then I, yeah, I understand that there's not many people that can do that. Here's a hack and feel free to take it. What I do now is I offer consulting to anyone who asks and that money goes to charity. So what happens is you have to put down your $1,000 an hour. Yeah. You have to pay me $1,000 an hour. However,

That money's not going to me. So I'm not a selfish jerk for asking you for $1,000 an hour. That money is going to go build a school in freaking Africa or whatever I choose to do with the cash. You cannot write it off, though. It's going to me. I'm using it for what I want later on, which is, you know, it's charitable, but I'm using it for the charity that I want. So then when my friend says, hey, can you buy a table at the charity gala for children with leukemia? I go, here's $8,000 and I don't have to think about it because I earned that money consulting.

What this does is everybody who is like, your value is zero, but I'm going to ask you anyway, and I'm probably never going to take your advice. That person is never going to pay you $1,000 an hour.

And if they do, you've wasted your time, but at least you made $1,000 an hour. They're never going to do it. And I likewise will do any podcast that anybody asks me to do. I won't evaluate if it's big or small. I just say, here is the charity honorarium that I require. If you pay me this, I will go on your show. I don't care if it's the first episode and you never air it because you have paid for my time.

And I donate that money to charity. Nice. That's really good. It's a bar that you can cross with money. That's a really easy thing. I don't have to spend any time evaluating this. Yeah. My thing for podcast requests is I would love to be your 51st episode.

Yeah, which cuts out 99% of people. Right, because they never make it. Yeah, because they never make it to 51 episodes. And so sometimes I get emails three years later being like, hey, three years ago, I DMed you on Instagram back when you were a student. And you said you'd be worth 50. And I'm like, okay, fine. Yeah, fine. Yeah, sure. I mean, you've done the work. Good thing you saved the email. Yeah, so that's a great bar as well. And I totally agree with that. I used to do that same thing. Now I'm like, there'll be people who pay for consulting time and...

I'm shocked when they use the advice that I give them. I'm impressed, I should say, but I'm very surprised. There's other people who pay for consulting time and never use it. But again, I don't have to worry about that. Now I can ask anybody for that. I can help anybody that I want because if it's that important, well, they know how to make it happen. But again, you don't feel like a jerk because you're not just using the money to like buy a new iPad or whatever.

How do you... Okay, so personal question. Selfish question, rather. How do you keep track of your...

I look at my WhatsApp and it's like freaking hundreds of unreads and I feel really bad. No wonder I stood outside for a day. Or my iMessage, even worse, because it's not like synced with text.com. So my assistant can't see the iMessages or like emails and it's just like... Wait, synced with text.com, what's this? Oh, texts.com? Yeah, what is this? Oh, it's an app that like, it's like superhuman, but for your messages. No, I need that. So it brings together WhatsApp, iMessage, Twitter, Instagram. You can disable, you can enable whichever ones. I, oh my God. You can delegate access to that to an assistant. So my assistant looks through my WhatsApps and...

flags up anything that's like time sensitive it's game changing i need this so good

Yeah, I'll send you an invite. Yeah, please, because I've never heard of this. That's amazing. I have 18 inboxes. How do you keep track of things? Do you have a work number and a personal number? How do you do it? So basically nobody has my number. Well, you have my number. But basically nobody has my number. They have my wife's number, which is a little bit weird now that I say it out loud. But she works with me, and she screens a lot of his stuff and helps keep it private. Honestly, I dedicate...

about 40 minutes per day to communicating just with the fan show fans. So that's email, Instagram, DMS, LinkedIn messaging. And I just do that myself. And then when that timer is up, I am done. Or I, uh, and it depends if I'm slow, I'll often just use this counter app on my phone. That's like a ticker and I'll go, all right, I'm going to do 20 LinkedIn messages each day. And if once I hit 20, I don't care if there's a hundred more in there,

I'm doing 20 a day. Nice. And I do 30 fan mail messages and I tick those down and there's 200...

In there that are for later, I'm a month and a half behind on fan mail. Oh, well, most people ignore their fan mail anyway. So people can wait a month. That's just how it works. But I'm getting back to them in a systemized way. Sometimes if I'm just like bored to tears in an airplane lounge and the book I'm reading is not doing it for me, I'll be like, you know, I got to burn off some nervous energy and I'll just plow through like 80 pages.

fan mail messages and it's, it feels good and it gets done. Nice. But otherwise I, I realize I'm never going to chip this Mount Everest down to zero because it's always refilling. Like you're just bailing buckets of water out and, but it's not hopeless either because it's enjoyable. Yeah. So if you give yourself a finite goal,

Then it's fine because you're getting back to people in a systematic way. It's not just building up and building anxiety. I don't know about you. You get anxiety. You're like, I've got 75 unreads now. This is making me feel awful. I just go, it doesn't matter how many are in there, 1,000 or 100 or 10.

They get chipped away this much every single day. And what about keeping in touch with like friends and family and people who do have your real number who are messaging you? Like, do you carve out admin time to look through messages each day or are you always on your phone? Yeah. How does that work? I'm not always on my phone. No, but I do. I like most people in our line of work probably do. I silence my phone. And then at the end of the day, when my kids are coming, my wife goes, I'm going to pick up the kids from school. And that's like 530 or something like that. Yeah.

I go, okay, I wrap up whatever I'm doing on the computer and I go to my phone and unleash the beast, unleash the torrent of incoming texts and stuff that was silenced all day. And I just reply to everyone. It doesn't take that long. Yeah. Yeah. I'm not, I don't have that many people that like me, Ali. It's really, yeah. Fair play. Yeah. Okay, nice. So what was the transition from law to technology?

not having a real job. Yeah. Abrupt, man. What happened was I, in law school, started the podcast and

When I got to New York, I kept doing the podcast and a friend of mine was supposed to go and do a guest spot on Sirius XM Satellite Radio, but he was driving in from Virginia and he's like, I can't make it. It's the traffic. Something happened. It's going to be like five hours and I need to be there in three. So he called the show that he was supposed to be on and said, I can't make it. You should interview these guys. They're really good. And they were like, well, we're screwed. We don't have a guest. So they invited us to go to Times Square.

I did a guest appearance on that show. The station manager happened to be air checking the show, which means listening at the time. This is why I say a lot of stuff comes down to luck. Yeah.

He was really blown away by the novel things that we – like of what we're talking about now, which 15 years ago were quite – or more than that. Almost 20 years ago were novel concepts. And he's like, that was so interesting. And I said, I have this crappy podcast. Do you know what a podcast is? He's like, actually, I've heard of those. So I gave him a cheapo business card that I probably printed up on an inkjet. And I said, here's our show. Check it out. And I followed up –

like four billion times because he was terrible with email. He was actually vision impaired, which is why he wasn't created email, but I didn't have his phone number. So finally he got back to me and he's like, I checked out your show. We're building new talent for the network. Do you want to have your own radio show on satellite? And I was like, yeah, that sounds amazing.

He's like, the pay is garbage and time slot is going to be not prime time. So I ended up doing a satellite radio show. So I was moonlighting with law and radio. And that was when it was like, one of these things is really lighting me up. And the other thing is sort of drudgery and scary and not interesting. And so when the economy tanked into that, well, it was before the economy tanked. When the banks started to close, those were major clients of the law firm that I worked at. And they said-

So there's not going to be any work for a while. It's February by May. Well, all this will be fine and we'll be back to business as usual. That obviously didn't happen. Banks, more banks started to close. And then they said, hey, everyone, we hired 63 of you.

We're probably gonna have to let go of most of you. Does anybody wanna go? We'll give you the rest of the year. So like nine months at that point, full salary and benefits, but you're gonna have to find another job. And before they even finished that sentence, my hand was up. And meanwhile, my friends were like crying, right? They were like, oh my God, my life is over. And I was like, nine months salary and benefits.

Holy smokes, where do I sign? Can I get it today? And they were like, yeah, you don't even have to come back. And I was like, this is absolutely amazing. They're like, you can use the office for anything you want for your job hunt. You can use your computer, you can use the printers, the copy machines. So I was like, so let me get this straight. I've got an office in world financial number two that I can do anything I want with. And you're going to give me like $100,000 for doing jack shit, right?

And I have health insurance, which is like, you know, in America, you kind of need that. And I thought, no way is it going to take me nine whole months to get my show and business off the ground. By the way, that was delusional. But it took me like years plus that nine months. But whatever. I lived like a college student. So I used that money. I paid off my student loans, which –

Having no debt is equals freedom, especially in the United States. And I just lived frugally and I took that savings and I just drip drip that for years and years and years. And so it was abrupt, but it was was it traumatizing?

No, other people for other people. It was and it was all because I had something that I was running to. Yeah, even though I had gotten my butt kicked right on the way. I like don't let the door hit you in the ass. Here's all but also here's on the grand can't really beat that.

Yeah. So it was an abrupt transition and it could have been traumatizing, but since I had this iron in the fire of something that I really loved, I was excited about it. Nice. And you still enjoy podcasting 17 years later? Yeah, I do. And how do you keep it fun for yourself? You know, this is going to sound remarkably simplistic, but I follow my own interests. Let me, let me qualify that.

When I see YouTubers, and you know way more about this than I do, when I see YouTubers, I've got a few friends who are big YouTubers like yourself, they'll tell me things like, I have to talk about this because this is what gets views. Yeah. And

At first, they didn't mind that. I've got a friend who's a great journalist and he started a channel and he's really good at what he does. And then he did a video about, I think, Scientology and it got a lot of views. And then he did another video about Scientology and it got a lot of views. And then he did a video about Tom Cruise and Scientology and it got a lot of views. Then he did a video about something else and it was dead.

And he went, oh, I need to do videos about Scientology. But I really am getting sick of this topic. Maybe I'll do a video about other celebrity related stuff. So he was like, well, I'm British. Let me talk about Harry and Meghan. And it got a lot of views. So he did another one about Harry and Meghan and he got a lot of views. And I remember the text where he goes, I –

want to ram my head through the wall knowing I have to do another video about Harry and Meghan. And he goes, but I'm also making like 10 times more money than I was doing this other thing that I really enjoyed. Mm-hmm.

So with podcasting, there is no algorithm that you have to please. So I'll do a show with a guy who steals tanker ships back from dictators that commandeer the ship in a port. And then the next episode is an episode with Ray Dalio about investing. And then the next episode is a dissident from China. And then the next episode is a celebrity that I'm interested in or a creator that I'm interested in.

And since it's a podcast, an audio podcast, primarily people just see it in their feed and they download it and they listen YouTube. They don't even see that crap if they haven't clicked on the last one. Right. So like my most popular video is a guy named Musab Hassan Youssef, who

Actually, Cesar Millan the dog whisperer is the most popular. Mossad is anti-Hamas. His father was one of the founders of Hamas, and he speaks out against Hamas. That video got like 1.5 million views. The next podcast I did was with an Israeli who was anti-Zionist. That did really well on my podcast feed. Guess how it did on YouTube?

Not so good because I had this massively like Zionist audience listening to the anti Hamas guy and the guy who was like pro Palestine. Well, that didn't jive well with the last viewers of the last video. So it was my most disliked video. My YouTube team goes, wow.

I've actually never seen this ratio of dislikes this quick. And they were like, I guess because you can't do this and then run it into this next thing. With podcasting, I was getting emails like, so interesting how you had the anti-Hamas guy and then you had the pro guy right one after the other. What a cool variety of viewpoints. Really interesting dichotomy. On YouTube, it was just like,

the algorithm just went, I don't know what to do with you. You're not going to create something that I understand, go into the closet and never be seen or heard from again. It's very frustrating. You have to create for this invisible God, the algorithm. And if you do it wrong, you're screwed. So then you also would have had this choice between follow my curiosity versus follow the dollars. Yes. How do you navigate that? So I only follow my curiosity. And I don't

worry about the dollars at all. But this is a privileged position to be in because if you have a small podcast and you follow your curiosity, you better hope other people are curious about the same things. If you have a big podcast, then you can be rest assured that a

decent sized percentage of your audience is also curious enough about that same thing, or you've built enough trust with them that they will indulge you on something that looks like they might not be interested in it. And I get emails to that effect all the time. Jordan,

I did not think that ship guy was going to be interesting. I did not think that that such and such guy was going to be interesting, but you've surprised me over and over throughout the years I've been listening to your show. And oh my God, that guy was so interesting. YouTube, you don't get that luxury at all. Most of the time, anyway, at least in my experience. Again, you know,

Way more about this. So I know in my sponsors don't get to choose what kind of episode they go in either. So I don't have to worry. Podcasting discoverability is hot garbage, right? If you have a new show, like no one's going to surface it unless you sign up with Spotify and they like you and they put you in everybody's device.

You're screwed otherwise. That's also a blessing because what it means is there's no algorithm to favor you or disfavor you. So you can create whatever you want. And if your listeners listen to it, you make a living. And if they don't, they don't. On YouTube, I found, I thought naively, oh, they subscribe. So they'll see all my stuff. That's maybe how it worked like 10 years ago. But now it just-

if they don't engage it's over so you end up making harry and megan videos and hating your job yeah so you live in california where the taxes are really high yeah two kids yeah do you not like well one thing i often worry about is like well i'm popular on youtube right now who knows how long this fame will last surely i should be trying to make hay while the sun shines and you know

A few years from now, yeah, maybe I should just make videos about passive income ideas or some shit like that, that will get the views and will have high CPMs and blah, blah, blah, blah, blah. Because what if when I have kids and maybe, I don't know, they need to go to private school because the state schools in the area are a bit shit or whatever, then will I regret my past self for not having chased the money?

Any advice? Yeah, sure. You seem to be doing okay, right? So the way that you do, the only way, in my opinion, is to do the math. And it's funny because every year I kind of do the math and I go, okay, how long do I need to do this and earn at this level? And what happens if I lose 50% of my income through some, yeah, tragic turn of events like podcasting CPMs, the amount people pay for ads goes way down, right?

What can I survive with? How do I make more money doing different things, put other irons in the fire, like, you know, product or something like that. That's, that's something I actually believe in. Or like, maybe one thing I do now is voice acting for video games. It's not a massive run. It's not a, yeah, it's not a massive income stream, but it's like, oh, if I quit podcasting and I only did that, I could earn a living doing that. Yeah.

It wouldn't be the same living, but I could do it. So you, then you do the math and you go, all right, if I have this much now, and it's generally going to appreciate a 5% per year, and I only need to do this for X number of years until I have this, in which case, if I have this amount of money and I needed to withdraw from that every year, cause I was retired forcibly or otherwise, how much money would I have each year to survive on before that hits zero? And it better not hit zero before I'm dead.

Right. So as you earn more, you realize, oh, OK, I have more years of runway. So right now, the way that this in fact, I have the app on my phone. It's called compounding calculator or something I should show you. But I've calculated that if I stopped working right now, I could live on a pretty damn good monthly draw in perpetuity and still leave money to my kids. Hmm.

It's actually the same amount of money that I happen to live on right now. If I do it minus like the cost of doing business and stuff like that. So that's a really good place to be in. You are quite possibly also there. You just haven't run the numbers. Never run the numbers. Yeah. So it's scary. It's like scary thing in the back of my mind. What if I run out of money? What if I run out of money? But I've seen videos where you talk about financial stuff. And unless you are just recklessly spending, you are probably fine. Yeah.

And you should run those numbers. Like, okay, if I do this for three years, I'll have this. And then if I need to withdraw, oh, I can withdraw $40,000 a month until I'm at 94. You don't need, you know, you won't need that. Kids are expensive, but they are not that expensive. Yeah. Okay, nice. That's a good action point. I'm going to do this, figure out how to set up this charity consulting situation and also the whole running the numbers thing. Okay.

Okay, but running the numbers is one part of the equation. Like, you're also living in California where you probably, the sorts of people you hang out with may well be the sorts of like tech, multi-decker millionaire type people and blah, blah, blah, blah, blah.

To what extent do you – how do you prevent like lifestyle creep and mimetic desire from thinking that you need a Lamborghini, whatever the fuck it's called, or this sort of stuff? So you have to have your values clarified really well. This is going to sound probably, again, simplistic, but if you get a lot of money – I've seen friends of mine who sell their company for like $100 million, and I'm like, what are you going to do with it? Like that's real FU money. Yeah.

And then one guy will say, there's huge differences, right? One guy was like, I'm going to get a yacht. I'm going to buy a place in Marbella, Spain. These are different people. I'm going to buy this. I'm going to get that. Other people are like, oh, I don't know. I don't really need anything. You don't need anything? Well, I'm probably going on a trip with my wife. Okay, you should definitely do that. Imagine one of those people is probably a little bit more satisfied with their life than the other, right? And

I've got another friend who is also selling his company for like over 100 million bucks and he lives part time in Spain and he's very healthy about what he's going to do with this. He's like his primary concern right now is raising his daughters in a way that they don't end up being totally ruined by that amount of money.

And I'm like, that's a really good thought. Most people are just fantasizing about how many cars they're going to get with this or something. So if you have your values set up straight, lifestyle creep doesn't really have to be a thing. I know a lot of super wealthy people and they have like car collections and stuff. And Jen and I are like, wow, look at all that stuff that guy has. And she goes, yeah, but would you want that? And I go, no.

No, actually, I would not want that. That is not, I don't even have, I share a car with my wife, for God's sake. Why would I want a car collection? I don't even drive. I let her drive all the time. What am I going to do with a car collection? And so my value, it would be more like freedom, right? Oh, what would I do with 100 million bucks? I'd probably...

not change my lifestyle much at all. And how do I know that? Because I went from one area to another in terms of income and I didn't really, I order more DoorDash, but that's because I have kids. I worry less about retirement because I've got that money in the bank earning interest. I did not buy another house for the summer. I do not have a car collection. I did not buy a boat.

I bought nicer lighting that I don't know how to set up. I got to get one of these. But like that is because I had my values set up straight. The problem is once you add money and you don't have those walls built to bounce off of, you just go all over the place trying to make yourself happy. If you figure that out when you're not dealing with a hundred million bucks, it's not going to change that much when you do. Yeah.

You know what I'm saying? So you see these guys that get really, really rich and they don't know how to, they're not happy. So they keep trying to buy it and it doesn't work.

That's how you end up with a car collection and a yacht collection and a house collection. And you know what's interesting also is you see these guys, they're just prisoners of the crap that they own. I know this guy is probably close to or actually a billionaire. I haven't asked because that's a rude question. And he was telling me

about some stressful thing he was dealing with about his house and i was like wait how can you say you said your house is being redone but where do you live now and he goes oh no this is one of my other houses and i go oh okay well how you know how many houses do you have and he's like 15 how do you live in 15 houses i was like do you rent them out he's like no

So you're stressing out over a house that you will never live in, that no one lives in. And he's like, yeah, it's kind of silly when you put it like that. Yeah, silly is an understatement. This guy's worth almost a billion dollars or actually a billion dollars. He spent like 20 hours a week talking about this stupid property, either on the phone, dealing with it, thinking about it. What a freaking waste of life. Yeah.

Like sell that shit, man. Are you crazy? Get rid of that right now. Sell it now. At a loss and be done with it. It's the dumbest thing I've ever heard. This guy, 15 houses. Very crazy. Because I was like, oh, is it for investments? No, they're not even investments, man. He just owns properties because he liked the way that they looked. Never even goes to these things. It's the stupidest thing I can think of to spend your time and money on.

Yeah. One of the nice things about having this podcast and interviewing people and now increasingly hanging out with people who are very rich is that I can start to kind of notice the desires within myself and try and like actively counteract them in the sense that a question I often ask myself is if I woke up with a hundred million in the bank, what would change about my calendar? Yeah.

And usually my answer is not very much. And if major things would change about my calendar, I'm like, okay, well, let's change those things before I have a hundred million. Because a hundred percent, why not? You kind of mentioned this in a way in your book, a friend of mine, he said, I said something like, oh man, you know, you've got this all figured out, blah, blah, blah. This is so great. It must be so great to have all this money. And he goes, well, you've got it all figured out too. You're doing fine. And I was like, what do you mean? He's like, you have two kids, your wife, you're, you've told me earlier, you were happy. You have your own house.

You like what you do. That's you basically are winning on like every level. And I was like, oh, that's really cool to hear from a guy who's like a shitload of money. And he's like, yeah, it and he goes, what would you do with $100 million if I gave it to you right now? And I was like, oh, I just put it in the bank and earn interest on that. And he said, why? And I said, oh, because then I would be able to safely retire at any time. And he goes, I bet you could safely retire right now. That was what got me running the numbers. And I was like, oh, and then I realized I don't need to win the frickin Powerball lottery to

To get to feel safe. Yeah.

And then that was a massive awakening for me, right? And he's like, no, really, what would you do? And I was like, I would hire a healthy food chef. And he goes, is it impossible for you to get healthy food? And I was like, no, there's a freaking Whole Foods like three blocks. I could literally walk there. He's like, so you don't really need a healthy food chef to live or be in your house. You could just, you could even buy, take DoorDash healthy meals from like a vegan restaurant or whatever flavor you want. And I'm like, that's true.

All these things you think you would get with that money, you pretty much don't need that at all. And you can get it in a different way. Yeah. It's so ridiculous. If you just keep asking why, the answer is always like safety. Yeah. It comes down to that. Yeah. I had a great convo with a guy at a birthday party that I was at a few weeks ago where he was like, he'd followed my channel for a while and he was asking me, how do I become financially free? Yeah.

And I started off with like, with this why question, like, what does financial freedom get you? Sort of, firstly, what's the number? For him, it was like, oh man, if I could have an extra million in the bank in the next 10 years, I mean, I'd feel really financially free. I was like, okay, but like, what would that get you that you don't already have? Because he's married, he's got kids, has a job that he more or less enjoys. He's a teacher. So he has like summer or summers off and like loads of holidays and stuff. Yeah.

What does financial freedom get you? And in his case, it was like ability to quit the job because he doesn't enjoy it all the time. Ability to like get a housekeeper or a cleaner or something, which he could probably afford anyway. For sure. And it was like, I think a lot of people have this thing of when I get rich, then dot, dot, dot. Yes. But if you speak to people who are already there, it's like, I don't know. I just think with any goal that we have,

implicit or explicit, it's worth speaking to the people who are already there and seeing like, you know, I was, you know, when I, when I would speak to doctors who were 15 years ahead in their career than me, I would ask them about their life and almost run a mini podcast interview with them over coffee or something. And I find out so much stuff. I would just be like, okay, I can avoid all these traps and,

They all recommend, they all wish they'd spent more time going through training because they didn't, they wish they hadn't rushed to be a consultant. They wish they'd taken more time off. They wish they'd done part-time training. Huh, okay. That's useful to know. Yeah. Rather than just sort of going fully on this path with any goals, whether it's a money goal or a career goal or anything. I could not agree more. And I really think

It's so humans do this thing, right? Where we say, once I get this, I'll be happy. And then, you know, that that's wrong because you listen to podcasts like this one, but then you do it subconsciously anyways. And you have to constantly, at least I have to constantly catch myself doing that. Like, why are you doing this? Oh, because if I had this, then, oh, then I think I'd be happy. But then what I would really do is compare myself to the other person who has more. So you realize that you're on this path.

hedonic treadmill, this hamster wheel, and you realize you can get off at any time. And

For me, I have to constantly remind myself that I can get off at any time. My wife is like, why are you working late? Well, because I want to finish this thing. What if you just finished it tomorrow? That's a valid, can't argue that logic, right? Cannot argue that logic. And I find myself watching cartoons with my kids and I'm like, this is so much better than reviewing that document that I will finish tomorrow, maybe. I've been noticing this in my life in two specific instances. Number one is,

I bought a PS5 a few months ago because I was like, you know what? I could have bought a PlayStation 5 at this point. Let me buy a games console. And it'll be like two days ago. It was like a Sunday and I had nothing to do all day. And then I should probably write my email newsletter which I write on a Sunday. Cool, whatever.

And initially my thought was like, okay, there's all this work I can do. I can, you know, I'm giving this talk at ad corner that can prepare that. And this, you know, I was like, well, why? I mean, I could just do that during the week. I've got enough time during the week. What if I just played PlayStation? I'm like, yeah, but there's all this work to do. I'm like, yeah, but what's the point of the work? Is the point of the work not that I can feel sufficiently safe so that I can in fact play PlayStation on the fucking weekend. I was like,

I could just play PlayStation right now. So I spent the whole day kind of like, I went to a cafe for breakfast, went for a walk around the park, sat down, played PlayStation, went to another cafe for lunch, sat down, played PlayStation. It was so glorious. Yeah, that's what Sundays are for. Meanwhile, you and me are like fighting the urge to zero inbox. And it's like, what are you doing, man? Yeah. Come on. The other one is like often I should send my email newsletter on a Sunday night because, or on a Sunday, because I called it Sunday snippets like six years ago.

and it gets to a sunday night at like 10 p.m and i'm like well i haven't finished the newsletter i could just send it tomorrow that's right and no one will care that's right it's sunday somewhere that's not how time works but whatever yeah yeah it's like well it's good it gets to 10 p.m will i be more grateful that i've had a better night's sleep or will i be more grateful that i sent my new fucking newsletter at 24 hours only like yeah no one cares how

Coming soon. Tuesday snippets. Yeah, Sunday snippets is what the team calls it because sometimes they get sent on a Thursday. I'm like, well, you know, at this point in my life, I'm going to prioritize. They call it Sunday snippets? That's hilarious. At this point in my life, I'm going to choose to deprioritize consistency.

for the sake of like more important things. I, yeah, I think that's totally fine. And how many people have emailed you furiously complaining that they, their Sunday snippets came up? The only complaint I get is like, for the last six years, I've been signing up, signing it off with my name and then two kisses, like XX, just like casually. Yeah. And like twice, I forgot to do that. And people replied being like, oh, you know, it was kind of weird, but like, I really missed those kisses that you put on the end of your email. Oh, that's cute. That is cute. That's cute. So you've got kids now. I do. Any, any tips?

And man, it's tough because parenting is a really sensitive subject for a lot of people. There's a lot of experts on it. But the problem is you don't know what kind of kids you're going to get. And people think, and maybe they're right. Maybe I'm wrong. People think they're going to read that they create their kids and by giving birth to them. Yeah, sure. But that's kind of the rest of it is a dice roll. And there's a lot of, oh, if you take your kids traveling early, they'll get used to it.

That didn't happen for a lot of people. Oh, if you tell your kids this, they'll get used to this. This kid. So you and you'll get and this will be your favorite. You'll get advice from people who aren't parents. And that was like with my son. He just he eats when he wants to and he doesn't when he doesn't.

And we tried everything, forcing him and all that stuff and shaming him and all this horrible crap. And he would gag at the sight of food. And we realized like, oh, that's not good. But then you let him screw around for 45 minutes and finish playing. And he goes, I'm hungry. And then he just houses whatever you put in front of him. He's obviously not faking a gag reflex. He's four. Meanwhile, we've got, I don't want to out anyone. People used to, people who come over to our house often will say,

i wasn't allowed to do that when i was younger so what you're saying is just don't allow my four-year-old to eat when he wants to or not eat when he doesn't want to good luck with that when you have your own kids person who knows nothing about children so you don't you can't come into having children with certain types of expectations you know you really get what you get in a lot of ways and i think your ability to craft your kids in your own image

is not as great as people think. And I also think that those who try really hard to do that end up with resentful kids.

And I would, I don't think that's a good plan at all. I'm not saying don't enforce discipline on your kids. I'm not saying don't have structure, don't have rules, let your kids eat junk food all day. I'm not saying any of that, but I think coming in with a, the idea that your kids are going to be a certain way is a recipe for disaster for both you and for them. And that is probably one of the worst environments, an environment in which a kid is not meeting expectations is probably one of the worst environments to grow up in, you know, like

Your mom probably really wanted you to be a doctor. Did she? Once I got into med school, she really wanted me to be a doctor. There you go. That's fine. We all know people who are like, their mom wanted them to be a doctor when they were nine. Yeah, that kind of thing. And now they're a doctor. Are they the happiest doctor? Maybe not. Not always. Was childhood nice for them? Maybe it was too much pressure involved. I don't know. So...

having a healthy detachment from outcomes, I guess. I think so, yeah. I guess similar to a lot of other areas of life as well. It doesn't mean you shouldn't have, I shouldn't say it, maybe expectation is the wrong word. It doesn't mean you shouldn't have an idea of what your kids could achieve and you should support them in getting there. But I think a lot of people, you hear these stories about bad parents, right? And it's almost always something like that. There's horrendous cases, but it's the sort of

stuff that seems sort of everyday pedestrian is, oh, my dad always really wanted a boy and he ended up with a girl. And you're like, oh, and then you just hear how that has messed with this person's self-confidence and self-worth every single day of their life. And you're like, wow, what a weird...

bad what a crappy environment to grow up in or you hear my dad always thought that i would be an engineer like him but it said i'm an artist and it's like you can just sense the you can feel the disappointment from the parents coming through the kid yeah and they're for they're 40 and it's still there their parents are gone and still there what a that's that's ugly it's really bad

How do you guys approach balancing the kids thing with the career stuff? Yeah. So this, I liked this a lot, this subject, because having kids changes you in a lot of ways. And it certainly limits your career much of the time. I don't think it has to, but I think if you're going to be like a really involved father, then it probably should limit your career in some ways.

But you almost don't even care. And that's a weird feeling because I was like, nothing's going to stop me from achieving this. And now it's like, and I used to work till like 8 p.m. and really just bust my, and then when my kid, now when my kid comes home, I'm like, okay, I'm done working.

And he wants to play Legos or throw water balloons outside. And I'm like, all right, this is what I'm doing. And I don't go, oh, God, I have to do this thing instead of doing this or creating that. It's just the change is maximize time spent with kids, especially while they're young, because there's a day that comes –

And you don't have any warning where they don't want to hang out with you. They want to go hang out with their friends and your heart will explode at that point or implode, I guess is maybe a better term. And that could be any time or they could be taken away from you by something horrible or you could be taken away from them by something horrible. So what are you going to do? You're going to spend an extra hour?

that going through the spreadsheet again, you know, it's there. Are there days where I work a little bit later, even though my kids are playing? Yeah, of course. But it's not something that I try to avoid it, first of all. And it's not something that I've set up to, I've set up systems to avoid that for the most part. And it's great. It really reminds you that the most important thing in your life is raising those kids. Even if you don't end up with

the same amount of YouTube subscribers you would have or whatever had you not. For friends that you have who have well-adjusted teenagers, what are the patterns you see in those families? I know. God, you trust me. Now we're like, oh my God, what did you do? Yeah.

And unfortunately, a lot of what I'll ask my my cousins, they're so well adjusted and they're adults now. But they're as teenagers. They were also just so nice and really awesome and didn't fight. It's a brother and a sister. And I asked my aunt, what did you do? And she's like, I wish I could take credit, but they've just sort of always been this way. And it's like, damn it, because you look at your own kids and you're like, oh, I don't have the same experience. Yeah. So what does that mean?

I will say that there are some, it's not that there's no patterns, right? Parents are involved, but not too involved.

Right. The parents are interested in their lives, but they're not controlling their lives. They're not trying to steer them all the time. They are encouraging of good behavior, but they are not domineering. They encourage their kids to explore curiosity. They set up a safety net so that when they fall, they're caught, but they don't set up a safety net. So there are no consequences to doing something stupid or bad or against advice, you know, all good advice.

They don't plow the way for them. They let the kids fail, but they're there to support them when that happens. It's a delicate balance, but I don't think it's impossible. I think what's hard is watching your kids fail, wanting to do something, realizing that you shouldn't, and then letting them deal with the consequences. That seems to be hard.

With toddlers like I have, there's not a ton of that. It's small, low stakes. Oh, he can't build the Lego thing and he's getting really frustrated. I'll just build it for him. No, I should really just patiently help him do this and realize that he can do it himself. But with teenagers, it's

They call you from jail or something like that, and you're like, I'm going to go bail them out right now. And you go, actually, that might not be the best course of action if this is their third time getting arrested. Maybe they need to sit there for a few days in scary jail and realize they can't just call dad and get them bailed out of jail because you see that patterns with bad parents.

And kids who are super spoiled and those patterns are remarkably similar. So unfortunately, a lot of it seems to be the dice roll of having kids that just are like get along and are intelligent enough and don't throw things at each other. How are you thinking about not spoiling your kids?

Yeah, it's tough because I grew up with significantly – we weren't poor by any stretch. I don't want to indicate that. My parents were both hardworking. But my mom was a teacher and my dad was an auto worker. So now we live in California and we're in the higher income bracket than I was when I grew up. My kids have way too much crap.

I told my parents this. They agreed. My kids had way too much crap. And then they said, but you had way too much crap. And I go, yeah, that's true. So every generation thinks the next generation has too much crap. What I've found, though, is my kids don't really care about material things. They like new stuff like anybody else, but they're not –

super attached to that stuff and i don't know what it is we did right or if we have done this right but they don't seem to care as much because they don't have any sort of sense of scarcity right they might not want to share their legos they might not want to donate their old toys that's just a toddler thing but they're not really attached to that stuff and and it's interesting to see that

So, when you show somebody the value of experiences, and this is hard to do with toddlers, but me and my wife are big on experiences over things, right? Like I said, we share a car. There's no need for us to really do that. We just do. That, I think, is a good – all the science shows that happy people prioritize experiences over material things. Material things, you just end up on the hedonic treadmill. Experiences build character and stories and shared experiences and things like that.

So we're planning to show them that early on. Like money can buy you things like freedom and being debt free and getting good experiences and enjoying those experiences and lower levels of stress.

What we're trying not to show them is money can buy you every single freaking Lego set. Money can buy you every toy that you want on a whim. Money can buy you every little material thing that you want, even if it's just temporary because you're bored. You want to go buy something. That stuff is – that's a dangerous slope. And I grew up with kids like that. I grew up with like wealthy kids in my school. And a lot of them turned out to do absolutely nothing. Their parents indulged those materialist whims and they've never accomplished anything. What do you wish you'd known?

before you had kids if anything i i would my my wife and i agree we had no idea how much work it was going to be which sounds remarkably naive now everybody with parent or with kids is like you didn't understand that kids are a lot of work we understood that kids were a lot of work understanding and really understanding it's very different yeah you know it's like

Running a marathon is probably hard. I've never done it. I'm pretty sure that's an understatement. And if I went and ran a marathon, I would be like, why did I decide to do this? This is terrible. Right. The pain, you know, you hear about people running a marathon and they have like raw nipples. They're bleeding. That's what having kids, that's the level of pain that you get from having kids like, oh, it's going to be a lot of work. You're going to have to, your life's going to change a lot. And you're like, yeah, no, totally. I get it. And then you have kids and you're like, I don't know.

Nobody said we weren't going to... I mean, you said we'd get less sleep. You didn't say we weren't going to sleep for three years. You said it was a lot of work. You didn't fully convey...

how much we were talking about like i was like i'll change a dirty diaper yes you will multiple times at four o'clock in the morning after they peed on the bed which includes you and now you're soaking wet too are you gonna take a shower by the way you have to get up in two hours to go on a flight or something with those kids it's like you know it's just it's like oh yeah that that wasn't really like you said it but you didn't i didn't get it i didn't really sink in

There's a lot of stuff like that, man. There's a lot of stuff like that with kids. So if someone had been able to help it sink in, would that have changed anything? No. But I'm also really glad. There's a reason that evolution has made it impossible for someone to understand just how much of a pain in the ass it is to have kids. Because this is, I swear, like science. You know how women don't remember how much childbirth hurt? Have you heard about this? Yeah.

That's for sure evolved because the women who were like, damn, that was terrible. They only had one kid. The women who were like, you know, the miracle of birth. Yeah, I remember it being uncomfortable. They had like eight kids, right? And a bunch of them survived. So we have evolved to not really know just how much this, how brutal this is. So I am glad that it's impossible for me to tell you how much having kids is going to change your life.

It's impossible for me to convey it in a way that you would fully understand it. And that's good because if I did, you might make a different decision. What I do say to people who are on the fence about having kids is I say, if you're on the fence, you probably should not do it. Hmm.

And the reason is because it does, it changes everything about your life, your career, the amount of free time you have, the amount of sleep you get. It ages you prematurely for sure. It stresses out your relationship in a lot of ways. It limits a lot of the things you can do, a lot of the things you can accomplish. I think the trade is fair. But I was like, I definitely want kids. And my wife was like, I definitely want kids. And then we had two kids and we're like, we definitely would have more, but it's a little bit late in the game. I'm 44, she's 38. And it's like, oh, let's quit while we're ahead.

That was a conversation I was having with your friend downstairs earlier. If you're on the fence, though, or you're like, I don't really want to have kids, but I feel like I'll regret it if I don't. I'm like, don't do it. Do not. Do not do it because of FOMO. That's the worst reason to have kids, fear of missing out and thinking, oh, what if I regret it later?

I don't know if that's setting you up for success. Yeah, interesting. Yeah, because I've met a lot of people who are in their 40s and don't have kids who regret the fact that they didn't take dating seriously when they were like in their late 20s or early 30s. Sure. Really wish that they had found someone and they were quite career-y when they were in their 30s and now look at that and think, ah,

I'm now still a career when I'm in my forties and it's now sort of lost some of the charm that it once had that sort of thing. Yeah. Which to me feels like FOMO for like the sort of regret for not having had kids earlier. And I would ask those people, do you, when you were younger, were you sure you wanted kids or

or not. Because I think for a lot of those people who regret not having kids, they probably thought, I will, I definitely want kids, but now's not the right time. Oh yeah. But there's a lot of those people who probably don't necessarily regret not having kids. And they were like, I don't know, maybe I'll have kids if I meet the right person. Maybe I won't. I don't know. Those people probably are like, oh, well I'm 45 and I don't have kids. Yes. It's not happening for me. Not sure how much I care. Anyway, I'm going to fly to Italy for two weeks.

you know let me know how the wiggles concert was and i'm like flipping double birds as they fly off into the sunset right while i'm holding a poopy diaper in my pocket so there's that's what i would ask those people because i think if you're young and you think or young if you're thinking i have all the time in the world to have kids you're wrong about that for sure biology says otherwise

But if you don't really care, I would say don't have them. That's my personal opinion. Now, leave room for your opinion on that to change. If you're like my cousins, like, I don't know if I have kids. I'm leaning towards now. I'm like, bro, you're 26. Calm down. You know, in 10 years, you might have a different opinion.

they're open to that yeah but if you're 37 and you're like yeah i don't know i'm leaning towards no yeah it's a it's an adult decision you're you're a grown-ass man a woman and you made that decision that's probably qualified you are qualified nice um how long you've been married for now oh god i should know this right off the bat i have been married for six years yeah and how long were you together pre-marriage

four years okay so 10 years relationship yeah any tips for healthy happy long-lasting relationship anything you wish you'd known yeah let me think i i think for me i was unaware of how my programming as an only child came into play how comes into play in my relationship so my wife has a older brother but me as an only child i was used to kind of like only thinking about myself it's really hard to break that habit i'm not

In my opinion, I'm not like super selfish or anything like that, but it's really hard to think, what does this other person want in this relationship? And that sounds dumb to say. It sounds silly out loud. Of course, you have to think about the other person in a relationship. It's not like I never think about the things my wife wants, but it's not a habit to be like, what are we going to do as a pair? And we really take time and we're like, what do we want to do this year? Our mutual friend Noah Kagan was like, plan out your year in January. We did that and it was awesome.

It was like, okay, we're going to probably be able to take one or two international trips. One with the kids, one without. Where are we going to go? When do we think we want to do that? Okay. Taiwan with the kids, Spain without. Great. What do we want to do in the business? Five things is a lot. How about picking two? Okay, cool. We pick those two things. Those two things get done. And then you review it at the end of the year and you're like, we did all of this. This is pretty cool. And we decided on it in January because what I've found is if you just float through the year, at the end of the year,

one of you is going, well, we didn't do this thing with the business and that's disappointing. And the other person's going, well, I didn't get to do this thing and that's disappointing. And you're, and you realize you totally could have done that. You just didn't plan it for it. And if you let that stack up over years, uh,

What you end up with is, wham, my relationship and kids have stagnated my business. And the other person's going, we never do anything fun. That's not good. That's not, that's, that, that resentment builds over time. Yeah. And that's, that's not good. So I would say,

But shockingly, planning out your business in the beginning of the year and adding the personal stuff in there with your partner is a really good idea. Because then you're at least aware, you have a little bit of a roadmap and you've both bought into it. So that's been helpful. Nice. Yeah, with my partner, we found that she wanted to go on vacations and stuff. And I was like,

Sure. And then none of us sat down with a calendar to block the time out. And then six months later, it's like my calendar is blocked out because work will always fill stuff and there's always things going on. Yes. And she's like, so when are we going on that vacation? And I was like, oh, we didn't block it out in the calendar. So now we have calendar blocking sessions where we like look at the spreadsheet and we're like, okay.

What's the plan? Yeah. You're like, how's November? It's like April. That kind of thing. That's not what I had in mind. I was kind of thinking like next week or the week after. And you're like, best I can do is three months from now. Exactly. To what extent do you bring the wife along on business trips? Or like, how do you guys think about business travel and travel as like a thing? So we used to do everything together before kids. It was like, oh, I'm going to London. Great. All right, let's do this. Here's all this stuff we want to do. Here's all the people. And she would have been in here like,

doing what your friend does with the cameras and stuff like that. And they would pay him record. She's like doing producer. And it was, it was stuff like that. Now she's at home. Cause we have two kids and she's like, they're not getting like, this is, you get these text messages when you wake up, like they're not eating, they're not sleeping FML. And then it's like,

How's it going? And they're all fine. They fell asleep. And you're like, thank God. Right. You just don't know what you're waking up to. So we have to we really do have to block this stuff off. You know, before it was like, yeah, we just go everywhere together. Now it's like, all right, I'm arranging child care. Luckily, my parents live across the street. Her parents live 15 minutes away. There's an aunt that lives really close. We have a nanny that helps her in the day. So we have a lot of help. Yeah. And we could ask those people like, all right, we're going to be gone for five days and we can go to Spain or something like that.

That stuff now though has to be planned in advance what you guys have now Your calendar fills up I think though if it really if it meant a lot to her to do I really want to go to the running of the Bulls and it's next week you could figure that out That's not the case with kids necessarily. It's like well, they're in school. What are you gonna do? Mm-hmm Like grandma and grandpa screw up their diet and sleep and take them to school like how's that gonna work? Can't take them with you. They got school so

You really do have to plan more and you have to be open to not always getting your way, which is weird because you're like not getting my way. I'm the boss. I'm the one who earned all the money and blah, blah, blah. And then you're like ceding to a two year old kind of BS is this. Who made you in charge? The answer is you, you know, like that. You're really kicking yourself. Like I gave birth to you and now you're dictating my whole life because they want cocoa melon and they want it now. Yeah. Yeah.

What are the ways you've found, you mentioned the nanny, what other ways are there where having money gives you happiness when it comes to kids? It's funny you mentioned that because I was thinking that's one of the major advantages is I look at childcare and my wife and I go, how do people who can't afford this do it? And the answer is they run themselves ragged. Yeah.

Having money allows you to find quality childcare. Like one of the nannies we have is a nurse. Like she's a nurse from Mexico. So we pay her really well. And another person that works with us is Jen's aunt, my wife's aunt. She is family and she's in a position to help us, right? So we pay her too. But then I see like our line item for that and I go, holy cow, that is...

The other thing we're able to do is buy healthy food that it may be prepared by us or prepared by someone else. A lot of families that I know, they can't do that. Healthy food in America is expensive. And-

Pink slime, fast food junk is cheap. So you can afford to feed your kids good stuff. Not that they freaking want it, but you can afford to feed them good stuff. If you want, you can afford to take care of yourself. I have a personal trainer that I work with to keep me in good physical shape, which helps me stay in good mental and emotional shape. My wife also works out. That stuff is one of those where you go, I'm privileged to have this and I'm lucky and you couldn't do it without money. Yeah. Yeah. Yeah.

But it's a luxury. It's not impossible to do it yourself. But I'm not going to sit here and be like, you can do it. I've got a personal trainer in Nanny, but you can totally do it. Just work out on your own and take care of it. Like, that's just ridiculous. You know, I would never tell two parents that don't have those things or a single mom or whatever that they should have the same thing.

stress level and diet or whatever is me. It's just kind of a, I fully realize how lucky and privileged that we are to be in the position to do that. Yeah. Um, but otherwise your, your money can only get you so far, you know, you sure. Super rich people probably outsource raising their kids. How well adjusted are those kids?

You hear these horror stories, man. I've got friends who work with very wealthy people. And one of the stories this guy told me was awful. So he worked at a really – works at a really bougie school. A kid – God knows how this – it's a boarding school. God knows how this happened. The kid fell out of a window and landed on a railing. And he had to go to the hospital. And he was in the ICU for two months because he like – I think he like smashed his rib or something happened with his liver. Yeah.

And he had his spleen removed and all this stuff. No one visited this kid in the hospital except for an au pair, which is basically a nanny that came after a month of him being in the hospital. His parents were traveling. They weren't even working. They were just on like a long extended trip to Italy or something. And they didn't fly home to see their kid. And it makes you think, who raised this kid? And the answer is probably the nanny that came to visit.

That is so sad. So you see these rich, spoiled kids that have everything that they want and like crazy money, and you would never trade your life with theirs. Like you would never do it. You'd have to be – you'd have to have had a hard lot in life to want to trade with one of those kids. So we kind of touched on this a little bit, but like what are the patterns you see amongst people you know who are rich and happy versus rich and unhappy? Yeah, yeah. So rich and happy people –

I think, again, to our earlier conversation, have this – they figured out their values early. Like, I want to be able to spend more time with my family. So they used their $100 million windfall –

To make sure that they can live close to their kid's school. Maybe when their kids go to a really badass school, so they move closer to that school, even though it's in a ritzy area. Or they use it to take months of time off because they hire extra help at work. Or they hire a COO that works with them. And then they can set up the ability to go away for the summer and do things remotely or whatever it is. Or they retire their spouse.

with the money. These don't even have to be super wealthy people. There was a time when my wife had a separate job. She was an accountant. And I remember, what was the situation? I wanted to go to New York City for four days over a weekend. And she goes, I can't, I've already taken all my PTO for the year and I can't take any time off right now. And I remember thinking,

I did not work this hard to ask your boss, who's like 10 years younger than me, if you can have time off so we can go do something. So I was like, I'm hiring you for my business. And that was like the beginning of the, I mean, her career ended like a week after that. And then she was like, this is amazing. And now the reality of actually having to work with me has set in, but too late now. But that kind of thing is a luxury, right? To work with your spouse and not have, because corporate America, it's like,

Oh, well, we do well and my husband wants to go. They don't care. Sorry, it's tax season. You're going to be working 60 hours a week. To what extent have you seen this as a pattern? Like a bunch of friends I've spoken to are in a position where only one of the two is working because they're like entrepreneurs or they're rich or something like that.

And I also have friends where both of the pairs are working and they seem way more stressed than the pairs where one of the parents is working. Does that hold true for the pattern you've seen as well? Definitely. And part of the reason is there's all this stuff to be done at home and you can't really hire it out. You can hire a housekeeper, but someone's got to manage all the stuff that happens with a house. You see really wealthy people and they're often like, oh my God, there's so much to do. There is so much to do.

Someone's got to figure out, even if it's just stuff that we would look at as trivial, who's managing the renovation on the gym that you're building in your backyard or something, right? Like there's some, but somebody has got to do that. You're not hiring somebody to do that. That's ridiculous. And if you're hiring somebody to do that, who's managing that person? So two people working with limited power over their schedules. Now they do less with each other. There's less family time. There's less time to bond with each other just as a couple. Yeah.

There's a massive to-do list of stuff from someone's fixing that squeaky door in the bedroom and the others. When are we going to take all that crap to the donation place? And how do we get rid of that rug? It's heavy. I need your help doing that. That stuff adds up and it's like cognitive bandwidth that just gets taken. And also, I think there's probably something to be said for it.

When you have dual income, it's because you need it most of the time. Not always, but most of the time. Or you're both career-oriented. So what happens if two busy doctors are in a relationship? Even if they work at the same hospital, how often are you seeing each other? Can you coordinate your time off? Yeah.

Are you able to relax when you do get time off? You know, there's all kinds of stuff like that. If one person is working, the other person can sort of say, my wife told me, she's like, let's take July off. Like, it's impossible. She's like, we can do it. It's possible.

So since she manages my schedule, she arranged me to interview a bunch of people before then. I still have to record ads and stuff like that, but it's a very light lift. So she just cleared my schedule and we're going to do a bunch of stuff. That's really hard to do when both of you have jobs where you are not the boss. And if both of you run companies, maybe that stress level is lower. I'd love to see –

data on like two people, one, each one runs their own company and then they're both sort of equally busy. Two people who are professionals, they don't run their own companies. They're really busy. Two people, one of them works, the other one works in the home, out of the home. Like I'd love to see the different varying bits of data on that. Yeah. I think that'd be interesting. Yeah. I think a lot of, a lot of the reason for going after entrepreneurship or financial freedom and stuff is like, I think,

when I read the four hour work week, it was sort of my, my motivation when I was in like med school and beyond was okay, cool. I'm optimizing for freedom so that I don't have to do things I don't want to do. But increasingly I'm realizing that like, you know, I know I want to have kids fairly soon, hopefully. And I know that actually the thing I'm optimizing for is the ability to like, that's what the freedom buys you. The freedom buys you the ability to hang out with the kids when they're young, for example. Or,

or take vacations with the kids or whatever, hire help so that like both parents are not completely stressed or things like that that are not sexy sounding and there are not like the, you know, work on your laptop on the beach kind of digital nomad dream. But the ability to buy that freedom to then invest it in a family. Yes. That to me feels like part of the point. It totally is. And I can't, I couldn't agree more. You reinvest that freedom. That's a great way to put it. You reinvest that freedom in your kids. There's...

I say no to so many things now that I've had kids and I don't feel bad. Like my, my, one of my agents is like, when are you going to write a book? You could have written two by now. Cause it's been like years and years. And I'm like, I don't want to because every hour that I spend writing a book is an hour spent away from the family. And of course agents are like, no, no, no, we're going to hire a ghostwriter. You won't have to do anything. Really? Yeah. I've heard that. I've heard that.

bald-faced lie before and wouldn't have to do anything except for the five years of promotion that comes after the book is published. And I'm like, no, I'll write one when my kids are older. They're like, you can write one when your kids are older and you can write one right now. And I'm like, look, I realize you want a house in Nantucket.

but I am not going to take on a project that I don't want to do right now. And they'll say something like, you're missing out on like a million dollars or whatever, for example, and you have to make this calculation. Would that million dollars change my life? Not really. Okay. What would the time investment do to my life? No, thank you. Right. Cause you might be able to get that extra million dollars and, but then what?

Now you have to work till 7 p.m. every day instead of 5. Well, those two hours belong to your kids. You're stealing them from your infant children for money that you don't need, that when you die, you will leave them. Do you think they really care about that? Yeah, when they're 68 or whatever. Right. Yeah. It's like once you start running the numbers, you start to go, if I don't write this book

I'm going to leave them with this when I'm old and, you know, old and gray. Oh, that's, that's okay. And if I do write this book, I'm going to leave them with this. And it's like this tiny little like weird shift. And you're like, okay, this minus this is this.

That looks like a lot, but if they get this, are they going to be happy? Yes. If they get this, are they going to be happier? Not really. Would they trade that amount of money for an extra year with their dad? Of course they would. Unless you have absolutely no relationship with them because you were writing books all the time. Whatever, right? The math starts to work out to the point where you go, I really don't want to do this. Now, I'm not trying to be judgy for the dad who's like, I

I have to work 60 hours a week. I want to put my kids through school. I'm not saying that that person is doing a bad job parenting. You are doing a bad job parenting if you make $3 million a year and you want to make 3.5 and so you spend no time with your kids. Then you're a bad parent. You're making a bad choice. I think this also, one of the things I've been thinking about is, you know, I'm thinking about like leaving the UK and where we want to live long term.

And I think one of the major considerations is actually in a low cost of living place, because having a low cost of living means you have to work fewer hours to get exactly the same lifestyle. And

Right now, I'm in a stage where like, I don't mind working. I enjoy work. Work is fun. Every single parent I've ever spoken to has said, as soon as they had kids, when the kids were little, suddenly they wanted to hang out more with the kids. So I'm like, okay, cool. If I take a reasonable bet that I'm probably going to end up like that. I can't imagine it right now, but something shifts when you have kids, apparently. So it's like, all right, cool. So low cost of living place. So rather than living in bang in the middle of freaking central London, actually living in a random place that was maybe three hours away from London or not living in the UK at all or whatever the thing might be.

seems to also be sort of in a weird Tim Ferriss sort of geo-arbitrage-y type way, another way of buying back your time. I agree. Yeah, I agree. I think you probably, look, I'm taking a guess only based on videos I've seen from you and stuff, but I think you could probably afford any lifestyle you want in any city you want.

But then you're digging into like the retirement runway that we talked about earlier. Yeah. Potentially. But once you run the numbers, you might be like, oh, actually I can do this, this, this, this, and this all in central London. And yeah,

I can still retire with X number of gajillion dollars that I leave my kids and it's all good. You've really got to run the numbers. But yeah, you might also want to live at the seaside of Spain and live in a warm climate and work less and have –

a healthy food chef or whatever it is because the cost of living is much lower in Portugal or whatever. So there is that. Yeah. I agree. Having kids changes you. You should, anyone should bet on that. Thinking you're going to maintain whatever sort of trajectory and lifestyle you're on once you have kids, it doesn't matter if you're a billionaire or not. Once you have kids, something changes inside you. It doesn't matter what you have on the outside. So you have to be ready for that. I think it's wise that you're planning for that. Nice. Cool. Final question. I've just turned 30.

Really? Jeez, man. Anything you wish you'd known when you turned 30 that you could share with me? Snippets of life and vice. Everything I have now revolves around kids, right? So I would say anything you think you're going to do after you have kids...

That doesn't involve kids. Do it now instead. Because we, my wife and I were thinking, we're going to live in different places and we're going to go travel and do this. And we did a lot of that before kids. We thought we would continue doing that. But it turns out,

You really can't do that when you have a little kid. It's hard. It's very hard. And when you have family infrastructure, that shit is priceless. Those people are not going to go with you to Spain for three months over the summer. You might think that that's a great opportunity. They don't feel like doing that. You need the help. You're not doing that. That plan is gone. So do all that stuff before kids, but also plan, be realistic about your ability to have kids. I would also, this is,

probably TMI or whatever, uh, two in the weeds, I would get everything tested. If you know what I'm saying, because what you don't want is to be like, Oh, well, I'm a man. I can have kids all the way up to X age. And my wife, future wife, whatever it is, she's this way. And we're going to be like, you want to know whether you can do it. And if you need to freeze things or, uh,

start doing hormone stuff or if it's not going to happen, maybe you find out early and you realize that you can plan totally different. Yeah. Nice. That's a good idea. Yeah.

That's a very good idea. Blood work. Yeah. And whatever else goes into a cup. Yeah, exactly. I think that's a great place to end this. Thank you very much, Jordan. All right. So that's it for this week's episode of Deep Dive. Thank you so much for watching or listening. All the links and resources that we mentioned in the podcast are going to be linked down in the video description or in the show notes, depending on where you're watching or listening to this. If you're listening to this on a podcast platform, then do please leave us a review on the iTunes store. It really helps other

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