243: We Spent $50K to Fly Private (Was It Worth It?) with Tom Patterson and Chandler Bolt

I’m sitting on a private jet with Tom Patterson and Chandler Bolt, and the obvious question comes up: when does this kind of spending actually make sense?

 

Once your business starts producing real money, the decisions don’t necessarily get easier. Do you keep pouring everything back into the company? Spend more to save time? Pay for experiences and access to better rooms? Or are you just copying the lifestyle of someone who’s ten years ahead of you?

 

We get into the tension between frugality and leverage, why entrepreneurs can spend years being able to afford something before feeling comfortable buying it, and how trying to look successful can actually hurt your credibility with the people you’re trying to impress.

 

We also talk about the role relationships and proximity play as you scale—and why being around people operating at a completely different level can change what you believe is possible.

Mic Drop Moments

• “We want to invest in experiences rather than stuff.” – Tom Patterson

• “When you realize that your bucket list items are actually cheaper and more attainable than you think.” – Chandler Bolt

• “If it doesn’t make you money, you shouldn’t buy it.” – Chandler Bolt

• “It’s interesting that you don’t get the hate or the critique from people who are above you. It’s almost always from people who are below you.” – Chandler Bolt

• “You only experience things you think you’re worthy of.” – Tom Patterson

• “Comfort is the hardest thing to get out of.” – Tom Patterson

• When Flying Private Actually Makes Sense
• Buying Back Time And Better Experiences
• The Cost Of Looking Successful
• When Can You Afford To Fly Private?
• How Tom Patterson Thinks About Spending
• Don’t Copy Someone Else’s Lifestyle
• Where New Entrepreneurs Should Invest
• Why Fake Success Fools The Wrong People
• Why Relationships Compound Over Time
• Normalize Bigger Goals Without Overspending
• Balancing Ambition With Financial Discipline
• Why Success Attracts Criticism
• Why People Tear Successful People Down
• Proximity Changes What Feels Possible
• The $2B Data Center Opportunity

Brad Weimert: I think a good starting point is how do you rationalize… So, everybody is at… We were talking about this on the heli over maybe, or somewhere in the last 12 hours, how people tend to assess someone’s success based on what you see or what assets they have. And the irony of that, of course, is like you have the fu*king pseudo, you have the real influencers that are fake rich because they’re renting everything and just fronting like they’ve got money, or they have a little money and they spend it all on something stupid, or you have somebody who has real money, but you don’t know what ratio they have to assess a purchase.

 

So, somebody could be worth 100 million and not spend a million dollars on bullsh*t, or they could be worth 10 and spend a million dollars on bullsh*t, and you don’t know. So, we elected to take a plane to Dan Martell’s thing in Baldface, which we’ve been going to for years. How do you think about rationalizing a private flight to something like this?

 

Tom Patterson: Oh man, that’s a good question. So, how do you rationalize flying private?

 

Brad Weimert: Yeah. How do you rationalize… So, I think you have a bunch of different scenarios flying private, right? You’ve got like, “I’m flying alone to some place.” You’ve got, “I’m flying with my family to some place.” And you’ve got, “I’m going to an event with homies.” And there was probably 100 other scenarios you could carve up there, but yeah.

 

Tom Patterson: Yeah. Well, I’m not proud of this, but I’m almost at 2 million miles on Delta. So, I’ve flown a lot of miles in commercial. Spent a lot…

 

Brad Weimert: B*tch, I’m just under you.

 

Tom Patterson: Yeah. Yeah.

 

Brad Weimert: I’m like 1,7.

 

Tom Patterson: Isn’t that the worst when they go like, “Congratulations on being a million-miler,” and everybody’s like this? But we’ve spent a lot of times in terminals, taxis, Ubers to and from airports. So, I feel like you go through this process where you really appreciate the flying private experience by not having to do that. So, there’s a huge convenience factor, but also just the time, right? Getting to the airport, parking, carrying your luggage, checking in. Even if you have TSA or CLEAR, it still takes a while. And there’s delays, getting in, and I think for this, for us living in Austin, you got to go to Salt Lake to Spokane, already a long day of travel, and then you’re going to go three and a half hours in a car on top of that.

 

So, if you can cut out time and go straight there, which I think was the goal, I mean, you save just a ton of time. And you show up refreshed, great energy. We’re doing extreme sports, and I think we want to optimize these experiences. You don’t want to be jet-lagged. And it’s dangerous, right? It’s not for everybody. So, you’re out there in really dangerous avalanche-y type conditions where stuff can go wrong really quickly. So, I think when you do that, it kind of shows how you think. And you kind of want to be your best in these experiences, whether they’re risk-taking, life-ending experiences or life-optimizing excitement, dopamine experiences.

 

And then having kids and a family, like I want to get home to them. I don’t want to get stuck in an airport. I’m coaching basketball this week. I’m taking the kids to school in the morning. Like, I know how I operate when I’m tired, you know? So, to me, that’s the way I rationalize it, and I think everybody spends their money on different things, but I think we’re all in that state right now. Like, we want to invest in experiences rather than stuff. And I think that’s what’s so cool about the Maple Summit is everybody’s there wanting to do the same thing.

 

Brad Weimert: Part of the reason I think that the question is interesting is because you gave me like 17 ways you rationalize, right? And none of them were directly focused on a number ROI. And I think for people that are like looking at the front end of it, that’s sort of this ethereal answer that’s similar to, “Hey, focus on your mindset,” when there’s somebody trying to get to their first million, and you’re like, “Yeah, yeah, just get your fu*king mindset right.” And that feels like, “Hey, fu*k you. Tell me how to make money.” You know what I mean? You’re like, “Hey, just give me the tactics.” And you’re like, “Yeah, the tactics aren’t the point. The point is the strategy,” right? So, I’m with you on all the above.

 

Did you run any calculation monetarily where you were like, “My time is worth X, and it’s worth doing this,” or was it just like, in general with private, is it just like, “Yeah, fu*k it. All the things you just said are true, and the money doesn’t matter because, in general, this makes sense for me”?

 

Tom Patterson: Yeah. I mean, I feel like this is one of those things where every time I try to rationalize it, and I say, “You know what? That’s too expensive. I’ll go do the two flights and drive.” Like the type of people that we meet in this environment and the connections and the network, the ROI you can’t even measure, right? So, to me, it’s easily justifiable for the cost and the experience being here and getting to know people on a different level. It’s just hard to do in the day-to-day life. So, for me, like people pay for these experiences, or you go and pay and go on them together with people that have the same mentality and mindset. So, for me, I’m willing to invest in experiences where everybody’s going there. They rationalize it maybe different, but as a whole, I think we all kind of rationalize it the same.

 

But we only do it now because we’ve not done it and regretted it in the past. And I feel like any time I felt like I’ve overspent, nine times out of 10 I then realized it was totally worth it, and I probably would’ve spent more if I had to.

 

Chandler Bolt: Yeah. I think, to answer your first question, like for me, it’s time and experiences, right? And then the accidental byproduct is proximity to people who you respect and who challenge you to grow. So, I mean, from just us texting about this from the get-go, it was like, “Will it save me a Monday? Will it save me a Monday? Will it save me the Monday?” Okay, like that is the singular, like…

 

Brad Weimert: I would like to say that I fought for your Monday aggressively.

 

Chandler Bolt: Yeah, which I appreciate. And to be honest, I probably wouldn’t have done it if it didn’t save me the Monday. But then there’s the experience, which is I feel like I have an unlimited budget to save time and do experiences, which is weird. My wife and I sometimes be just like, “Hold up. You’re spending money on that, and we’re not spending money on this?” It’s like I’m driving the car that I’ve been driving since high school. It is a piece of crap. And she’s like, “You’re going to go fly private but not replace the Altima, that’s arguably a hazard to drive?”

 

Brad Weimert: Hold on. I got to spot check that. So, last I checked, there was a Model 3 in your world somewhere. That’s pink for Gateway.

 

Chandler Bolt: There is a Model Y.

 

Brad Weimert: Is it pink?

 

Chandler Bolt: It’s not actually pink. No, no, no. It’s just in the app. What you saw was the app, which shows it as pink.

 

Brad Weimert: Okay. It’s a likely story.

 

Tom Patterson: So, salmon.

 

Chandler Bolt: Yeah, salmon. But I think it’s the time and the experiences, right? And then the accidental byproduct is proximity to people that you respect. And so, for me, it’s an unlimited budget for experiences and to save time. But then I think the interesting thing you mention is, and I didn’t even think about it for this, but we get up to the lodge, and people are like, “Oh my gosh, I want to meet Tom.” It’s like, yeah. And I just said, I’m like, “Oh, wow, I didn’t think about that. I just had seven hours with the guy that I would’ve just been in a flight.”

 

Brad Weimert: Well, let me… So, I’ll give you another part of that, which is that, yes, the people that you’re with, right? But the other part of it is, so we go to, I mean, we’re in an elite of elite group at this event, right? I don’t know that you know this, but there’s more than one person in that group that had a billion-dollar-plus exit. That’s some sh*t. And then there are a bunch in there that are in the multi-9-figure exit range. And you don’t know that unless you know that. But having been there for quite a number of years as you have, one of the things that is also interesting about this is that when you come in, and you have come in in style, you can say what you want about it. All things aside, there are multiple people there this year that were kind of not so warm in past years, and this year were super fu*king warm.

 

Chandler Bolt: Totally.

 

Brad Weimert: And that has to be a product.

 

Chandler Bolt: I hate that, by the way.

 

Brad Weimert: I hate that, too. But it has to be a product of the perception of your success relative to it.

 

Chandler Bolt: Status.

 

Brad Weimert: So, that brings me to this thing that I don’t like either. Well, actually, let me give you the tactical relevant thing for other people, which is, when does it make sense to do it purely because you know people are going to perceive it that way, and when do you stretch the limit for it? Meaning some people will hear that and be like, “Oh, so it’s a networking tool, so I’m going to flex by being like, ‘I flew private,’” and then blow out their fu*king budget, which they don’t have anyway, right? Somebody that makes $500,000 a year, a million a year, put a number on it. And they’re like, “Okay, great, so I’m going to go blow $50,000 on a private flight to fly solo somewhere because people will see me doing it.” So, how do you think about the line between that and it being a networking tool there and don’t bother?

 

Chandler Bolt: Yeah. I personally hate that.

 

Brad Weimert: I do too.

 

Chandler Bolt: And I think it’s actually, in a lot of ways, been to my detriment. And I think there’s two sides to this coin. Like, I hate the influencer flexing, beating their chest, all the stuff, and I think honestly it’s me not even doing it a little bit has robbed me of a lot of opportunity. Because you look around and you’re like, “I know that my business is way more successful than all of these cats, and yet they’re getting asked to speak at this event, or they’re…” So, I think in some ways I’ve just never done it, because I hate it and I think it’s super douchey. But I don’t know. But then simultaneously, much like you guys, it’s like I could very easily afford to do it before I decided to do it.

 

And I feel like that’s a whole other thing is like when you realize that your bucket list items are actually cheaper and more attainable than you think. Like, three or four years ago, this was a big eye-opener. I’ve always wanted to go to a Grand Slam tennis tournament, and every year I would rationalize, “No, not going to do it, not going to do it.” Finally, my wife and I were like, “All right, we’re going.” The whole trip, probably $10,000. And this was like very nice seats, went to the US Open, and just after that I realized I could’ve done this so much earlier. And it’s this mystical thing that feels far off in the future. So, I feel like sometimes it’s just the mental hurdle of growing up super blue collar, frugal, and not wanting to spend money on stuff even though you got the money. That’s not the question you asked, but that’s the other side.

 

Brad Weimert: No, but I think that’s the question really like the intent of the question is when you are pushing the envelope on something, how do you rationalize the expense? That’s sort of the genesis of all of it, right? And so, I think one of the interesting things to look at and assess is how that question intersects with different stages of entrepreneurship, right? So, when you’re new, what are the things that make sense to blow the budget on because there’s an ROI? And that ROI, by the way, could be investment in relationship, and you could rationalize it that way. Or it could be actual return on investment in capital right away. Or it could be return on experience that’s going to come back later. And how do you think about it?

 

And I think I feel the same way, which is like there’s a huge wave of let’s call them influencer entrepreneurs that are so caught up in the aesthetic that they’re willing to overspend for the click or for the view or for the like, right? And there’s not ROI. And even if there might be, it’s like a bet the farm on it kind of sh*t, right? And it’s not in the name of the business. So, I don’t know, I guess if you look at it a bunch of ways, but I think that the question’s interesting for that reason.

 

Chandler Bolt: Yeah. So, I mean, it’s kind of like we were talking about on the mountain, is that it gets people to pay attention that might not otherwise pay attention.

 

Brad Weimert: So, let me back all the way out then. Give me a business size or annual revenue or give me any metric that you can associate with a point in time where you’re like, “Oh, then I felt like it was okay to spend money to fly private.” And by the way, let me frame this a little bit by saying there’s a big difference between me taking a private plane solo for $50,000 or $100,000, or me being like, “Hey, I’ll get some buddies,” and then the flight is $10,000 for me.

 

Chandler Bolt: So, you flew solo last year?

 

Brad Weimert: Fu*k no. I’m not taking a fu*king solo flight for fu*king $50,000 like an asshole. So, my current frame is not only that it’s an egregious waste of money. Could I spend $50,000 on a flight? Do I have $50,000 to fly? Yeah. Is there any possible world in which I rationalize that being socially acceptable or monetarily responsible? No. Not none. There is a world in which that makes sense, but no, I think it’s really a fu*king dumb use of capital.

 

Chandler Bolt: It’s a mental hurdle. I don’t know. I mean, this is the first time I’ve done it. You guys, this is like… I don’t know, man.

 

Brad Weimert: So, at what point… So, you’re like right now, right? So, 8-figure business for multiple years now, and this is the moment when, which is also high-margin, which is the moment where you’re like, “Okay, I will allow this to be part of the construct.”

 

Chandler Bolt: Which is so crazy, because if I was just putting my rational brain on telling this to someone else, I would say, “Your business spits off six figures a month in cash. This is a $10,000 flight.” That is single digits percentage of your monthly profit on a flight.

 

Brad Weimert: I think where we’re going is fine.

 

Chandler Bolt: 100%. Like, to a place where you’re going to be with the top of the top, like, it would be like that’s so stupidly obvious.

 

Brad Weimert: Yeah.

 

Chandler Bolt: And yet, I don’t know, frugal upbringing, man. Like, my parents met working night shift at a factory. My mom was clipping coupons. It’s just like that stuff is just hardwired into my brain.

 

Tom Patterson: Yeah. And you never had this. Probably none of us ever had this exposure.

 

Brad Weimert: Oh my God.

 

Tom Patterson: Right? We were like, “Wow, how…” And I think we’re all like, “How do you get there? How do you do that? How do you even create a life where you have the opportunity to do that?” And I think that’s the cool thing about this trip, and I think how we all justified it, is the group at Baldface, in a lot of ways, I would guess 75% or 80% of us are all cut from very similar cloth, right? So, there’s like a respect and appreciation for like the filter down of going there, but also the other filter of like, we can all ski and snowboard at a very high level, right? So, that’s like really rare. I can’t remember who, I was talking to Dave about this like, would you rather sit in a Marriott or a Four Seasons and presentations for two days, or sit in Sno-Cats for two days and probably have deeper, more meaningful connections with so many people? Like, to me, it’s like night and day different. And your advantage is you’re doing it way younger than I did. I don’t know when you started doing this stuff.

 

Brad Weimert: Chandler is, without question, a bizarre anomaly. He’s a subset of 1% that like is driven enough when they’re in their 20s to get the reps and figure out the game that early. And my perception is a big part of that is being endlessly inquisitive. And very few people have that.

 

Tom Patterson: And skipping college.

 

Brad Weimert: It’s very, very, very unusual. And you should be able to see that by looking at the age group around you and be like, “I’m unique in this.” And I think really the unique thing is being inquisitive. The unique thing in humble enough to know I don’t have the fu*king answer. Like, the most irritating thing ever is… Was I in the hot tub with you at Prestige? Yes. So, we’re talking to this guy at Prestige. So, we’re talking to this guy before we go to Baldface, and he’s like, I don’t know, he’s probably 45, 50.

 

And he’s talking about he just started his business three years ago, and he’s looking at buying a commercial piece of real estate for like a million or so. And he’s convicted in his approach to do this, but he’s also told us point blank that he’s never done it before. And we’re trying to give him advice, and he’s not hearing it. He’s not listening. He’s not absorbing it. And we get out of the hot tub, and Chandler’s like, “Yeah, so there are three guys in the hot tub. Two of us have done it before a bunch of times, and one of us has never done it before, ever. Who do you listen to?”

 

Chandler Bolt: Yeah.

 

Brad Weimert: So, you should see that in the group. Yeah. No, it’s real. So, yes, I think that rationalizing going to the group for sure. You have sold a billion dollars of underwear, mostly because you want to make sure that all the men you know have comfortable balls.

 

Tom Patterson: That’s right. Yeah.

 

Brad Weimert: At what point in that journey from a revenue perspective or net or whatever metric you want to give did you start looking at, “Hey, a private flight might make sense”?

 

Tom Patterson: Gosh, not until we sold part of the company and we had a pretty meaningful financial event. And we probably could have before, but we were making $100,000 a month, right? Like, we were just putting it back into the business, back into the business, which I probably… I mean, look, it worked out, but it’s also a level of risk and uncertainty, too. Are you ever going to get it back? Like, where I think you’ve built yours very differently. We just chose a different path. But even after we had our event, like that’s the one thing my wife and I had always wanted to choose: like what is it like to fly private? And it was everything we thought it would be and more.

 

I mean, but you can never rationalize the price. The price is always kind of stupid comparing it to flying commercial, but I think you don’t get time back either. And I think the older you get, the faster time goes, and I hate waiting around in airports and terminals, and I’ve done it so long. So, I really calculate the door-to-door time in my mind because I’ve been stuck so many times. And when you fly private, you just cut all of that out.

 

Chandler Bolt: It’s an interesting parallel to entrepreneurship, is you said you can’t rationalize the price. It’s kind of like entrepreneurship, you know? Like, you can’t rationalize the price, but it is worth it. You know what I’m saying? Like, trying to explain to someone why you’re an entrepreneur or why you made the sacrifices you did to build your business, it’s like you can’t rationalize this. It’s trading a 9:00 to 5:00 so you can work 24/7. You know, it’s like…

 

Tom Patterson: I mean, I’ve heard stories where kids of very wealthy people, like our age, will send the pilots from like California back to Tennessee to get their bourbon collection. Just the pilots there and back so they have their bourbon for their vacation that they forgot. You talk about wasting 50,000, like to me like…

 

Brad Weimert: Well, you know what’s so fu*king dumb about that is just rebuy the sh*t for $13,000 or whatever. I think there is a point of…

 

Tom Patterson: Clearly, they didn’t do the math, or they don’t have the respect for the money because they didn’t earn it. That’s a whole different topic, but about the flying by yourself on a flight, how about nobody flying on the flight and just the pilots are going there to go get it for you? That’s wild.

 

Brad Weimert: All right. So, I think one of the reasons that I think it’s an interesting topic is because you’ve got two categories of people, right? You’ve got brand-new people that want to flex and are in a race to do it. Then you’ve got people that have sort of made enough money to rationally do it but are uncomfortable doing it and trying to cross that chasm. Then you’ve got people that are like way the fu*k on the other side and have a mental block, and they’re like, “I would never spend money on that.” And you’re like, “Bro, what is your time worth, and are you kidding right now?” Right? So, the obvious large one that need to hear it the most, albeit not the one that I actually like talking to, is the first group, is the group that’s trying to flex, trying to figure it out, and they’re like, “Hey, I want to do it.”

 

The group that’s most interesting to me is the middle group, which is where I feel like I am, right? Which is like, “Hey, I totally can afford it, but I have this constant internal struggle of should I spend money on something like that or should I be looking for ROI all the time?” and that’s what I always talk to, right? Like, that’s who I’m always talking to. That’s what I’m always curious and pulling the thread on. But I think it’s like we’re all remiss to not speak directly to the group that feels like they’re supposed to be here and they’re trying to replicate the behavior of somebody that is so far ahead of them, not realizing that that’s not what you’re supposed to replicate.

 

What you should be replicating is the activity of the person that’s far ahead of you when they were in your stage, right? So, like, “Oh, dude, I have a very good friend who is 10 years my senior and is pushing a billion dollars annually, and I can’t model him. His phase of life is so far beyond mine.” And it’s hard because as a peer, as a friend, and as a peer in that way, he’s like, “Oh, yeah, just come do this.” And I’m like, “Bro, it’s a Tuesday. I’m not going to fu*king London with you,” right? And he’s like, “You totally can. Like, why are you your own boss if you can’t?” And I’m like, “You shut the fu*k up right now. Don’t give me that sh*t. Like, you know why I can’t.” And to his credit, he’s like, “You’re right.” He’s like, “I appreciate the grind. Go get it.”

 

But we don’t all have mentors that say sh*t like that, right? So, I think it’s really important to recognize that. So, if you’re younger, and let’s say this is your inside of five years in business. I don’t even care what you’re making, right? You’re inside of three or five years in business, where do you deploy capital? Do you spend it on experiences? Do you spend it on education? Or you plow it all back into business like you did?

 

Chandler Bolt: Man, you don’t buy things. I think that’s the clear no. The no bucket is you don’t buy things.

 

Brad Weimert: Can we delineate a difference between depreciating or appreciating assets with that?

 

Chandler Bolt: What?

 

Brad Weimert: Because a house is a thing.

 

Tom Patterson: How about the Ultima?

 

Chandler Bolt: Yeah. I mean, yeah, if it doesn’t make you money, you shouldn’t buy it. I mean, it’s an oversimplification, but I think that is just the stupidest thing, and we have a society that is not willing to have delayed gratification, and there’s this book called Set for Life that talks about this. You get into this keeping up with the Joneses like, “I got to have a dog. I got to get married. We got to have a kid. We got to buy a house. We got to do this, this, this, this, this,” and then you blink, and you’re 40, and you have no money in retirement. And you’ve got nobody to blame but yourself. And so, I think you don’t buy things. You invest as much as possible into yourself and into the main thing that’s making you money. And then experience is along the way.

 

Like, life’s short, so that’s where this is like, you know, early on I was bringing my dad, surprising my dad with tickets, one of the national championships so we could see Clemson football. Just like that type of thing that brings people together, I’ll write checks for that all day long. But I don’t know. That’s my take. Be curious, yours.

 

Tom Patterson: Well, I think spot on with the delayed gratification, right? We didn’t have cable TV. We didn’t have Netflix. Like, we cut off all the things. Like, we didn’t know about the series Game of Thrones or Breaking Bad like everybody’s talking about because we weren’t sitting on the couch watching these series for three hours a night. Like, we were working around the clock. So, I think that delayed gratification, being consistent with it, it compounds, and all of a sudden you’re surpassed really quickly. But it didn’t happen overnight, right? Like, it takes a long time of that, I would say discipline and focus, where I think the influencers you’re talking about that are just spending it all, I think they get distracted about the perception of what people are doing, but they don’t really understand what they’ve done to get to what they’re doing to have that experience. So, whenever I see that stuff, I’m like, I kind of take it with a grain of salt unless I know them and really understand the true story of how that happened.

 

Brad Weimert: Yeah, I think for me, and I think for the lesson that I think is relevant for most people coming up and trying to figure out life is like the people you’re tricking aren’t the people that you think you’re tricking, right? The people that you think you’re impressing are only the people under you, and the people that are ahead of you see what you’re doing and aren’t impressed by it. Because we’re all looking at it and thinking about it from a rational perspective. And so, if you’re way ahead of the game and you’re like, “Hey, I’m buying a Ferrari, and I’m buying this, and I’m flying on a private jet,” most businesspeople that are ahead of the game look at that, and the first thing they do is think, “Where’s your business right now? Is this a rational expense? Does this make any sense for you?”

 

And that’s actually the criteria by which they’re judging you, ironically. And it’s the people under you that look at that, that give you the likes and the follows and the subs, and they’re like, “You’re important, and that’s not who you should listen to anyway.

 

Tom Patterson: Well, I think that about the delayed gratification too, like are you investing in things or investing in yourself? Like a Tony Robbins event, masterminds, like there’s so much ROI in those things versus a lot of these others like physical cars, boats, whatever, right, stuff. And it’s weird, there’s a common thread: investing in yourself instead of investing in things. Those are the people where I want to go or where I wanted to be, right? So, you start to see these patterns of like the real successes versus like faux successes or at least the level of success I think I wanted to have. And that was like a commonality. I’m like, “I’m going to go into the commonalities that these people have and what they’ve done to do that.” Does that make sense?

 

Brad Weimert: Totally. Yeah. My answer to that question is that I had a hard time spending money on anything at all. And the only thing I could rationalize spending any capital on were things that I saw a return on relationship. And it wasn’t even… I couldn’t even rationalize an experience. I could rationalize it through the lens of a return on relationship. And part of the reason for that is that very early in life, I realized that, as you go through different phases of life, you don’t have certainty on the outcome of the business venture that you have. You don’t know where your business is going to be, how much you’re going to be worth, what you will have made. But what you know for sure 10 years from now is that the relationships that you build along the way can serve you 10 years later.

 

You don’t know that you’ll have 10%, 50%, 100% growth, 1,000% growth. But what you can know for sure is that your relationships can compound. So, if you want to donate money into a fund, the one that will yield a return on relationship 10 years from now is your surest bet. And so, I look at stuff like this as part of that equation.

 

Chandler Bolt: Are you getting emotional about that?

 

Tom Patterson: I’m not gay.

 

Chandler Bolt: I thought you were getting choked up for real. I was like, “Is there a deeper story here?”

 

Tom Patterson: What was your first five years? Like when did you realize you could rationalize it?

 

Brad Weimert: No, dude. I mean, I’m still rationalizing it, you know? But I think that the private flight thing’s an interesting unique one. And I think a big part of that is your contacts growing up. So, like I was talking to our friend, Erik Huberman, and he has a family member who was a child that grew up. The kid’s eight. And they took a flight together on American or something. And they get on the plane, and the kid looks up to Eric, and he goes, “Why are all these people on my plane?” Because he had never been on a commercial flight before. He’d only been on private flights. So, I think if you grew up in that context, you have a… I think there are very bad things about that, but I also think that the irony is that while a lot of people probably find that funny and ridiculous and whatever, and gross, the irony in that situation is that if you have normalized private flight, you will find a way to get there faster.

 

Tom Patterson: Right.

 

Brad Weimert: And I think there are a lot of interesting things about that with your relationship with money, that if you normalize it at some point in your journey, you get there faster.

 

Chandler Bolt: Well, that’s where I think an interesting question or thought experiment is: how do you get around people who normalize things that aren’t normal at all, and that are multiple jumps ahead of you? Which, in a way, comes back to spending frivolously on stuff like this, which is that’s where I really wrestle with that question, because I’m like, I hate it, and I didn’t want to do it, but if I’m honest, it probably would’ve been an awesome investment. So, it’s like, almost like the…

 

Tom Patterson: It would’ve been an awesome investment.

 

Chandler Bolt: Like, getting on private flight, like doing stuff like this, because I would’ve automatically gotten in the room with people who would’ve expanded my thinking. It’s just like even to the first time coming to Baldface, of just like, at that point, it was thousands of dollars. And heli-skiing, or heli and cat and all that, and just texting Dan and being like, “Yo, that trip looks epic. I want to be on there next year.” And how that single getting outside of my comfort zone, spending money in a way or whatever, has totally changed things for me. It’s like how many of those have I missed out on by either caring about what other people think or being too frugal?

 

Tom Patterson: Yeah. But there’s probably things you’ve already normalized now that you’re not aware of, right? As you level up, every level gets normalized to a certain point.

 

Chandler Bolt: Like having assistant or stuff like that. But that’s where it’s like I really wrestle with some of the stuff, and that’s something I really respect about Dan, is just he just does not care what people think at all with this kind of stuff. And so, that’s where sometimes I think to…

 

Tom Patterson: He cares what I think. He said he does.

 

Chandler Bolt: Oh, he did?

 

Tom Patterson: No, I’m kidding.

 

Chandler Bolt: But it’s just like, because there are so many of those things that, I don’t know, it’s the reason you don’t do it is because you don’t want to come across as a douche, or you don’t want to whatever, but you got to break that. Hiring an assistant was the big one for me. Hiring somebody to clean the house, do groceries. I mean, I don’t know. It’s just big, big unlocks that people around me are like, “Yo, what? What are you doing?”

 

Brad Weimert: Yeah. I think that there’s a, I mean, I think that there’s this odd delineation that has to happen between the mental side of it and the pragmatic side of it. So, you’ve got this mental struggle of reprogramming yourself to execute in a certain way, and then the balance or the dance of, yeah, but does that pragmatically make any sense, right? And where do you draw the line? And I think that that’s a constant struggle in lots of areas of entrepreneurship. You know, we’re talking about an elitist edge of things for most people, and almost all, right? But I think the thing to remember for anybody that’s coming up and looking at that is there’s this whole other side of this equation of the people who are like, “You’re flying a fu*king Lear 60? Why aren’t you on a global?”

 

Which, by the way, you even say that to almost everybody, and they’re like, “I don’t know what that means.” You know what I mean? And then once you enter that level, you understand that there are so many other levels past you, right? And so, part of the game is how do you accelerate through all of it? But how do you do it without blowing money in a stupid fu*king way? So, there’s access to the circle, right? And then there’s the pragmatic approach and how you balance it.

 

Tom Patterson: It’s like when they say like, “Oh, you’re flying a Lear 60,” you think they’re like, wait, are they giving you a hard time because you’re not realizing what they’ve realized? Or are they so far out of touch with reality that they can’t even rationalize a Lear 60 compared to what they’re flying now? Like, just by that comment, I’m curious, how do you think about that?

 

Brad Weimert: So, what’s interesting about that to me is that I think that there’s a… My experience so far is that there are people that at different levels, certain things become rounding errors. And so, there is a point where when you’re coming up in entrepreneurship, you’re trying to pinch pennies on everything, and you’re like, “Fu*k $59 a month, $79 a month, like, let’s work out a deal.” Right? “Does it have to be 79? Can you give me a month for free?” And you do it with everything, right? And at some point you realize, I’m focused on the wrong fu*king thing. So, all of us now look at the entrepreneur that’s doing $300,000 a year, and you’re like, “You’re focused on the wrong thing. Why are you focused on saving three pennies over here?” That’s how we would probably articulate that.

 

So, I think that there’s this bucket of people when you get to a certain stage that’s like, I’m spending 50 on a Lear or 70 on a Challenger. Who cares, right? Why are you even talking about this? But in order to be in that place, you have to be in this place, right? So, I think that there are those people where it just isn’t even occurring to them. But then I also think the risk that you run as you escalate through your life is ignoring, is thinking that it’s a small detail, but really you’re being irresponsible with the money as you’ve gotten going because you have it. And the delineation is difficult. I don’t know, you know?

 

Chandler Bolt: I think it’s interesting that you don’t get the hate or the critique from people who are above you. It’s almost always from people who are below you.

 

Brad Weimert: I think that’s true.

 

Chandler Bolt: So, not often is it the guy it’s kind of a little tall poppy syndrome, which that’d be maybe a question for you guys. Why do you think so many things that are actually, I don’t know, maybe a bucket list item or a total unlock are hated on, questioned, or judged by so many people? Hiring an assistant, having a nanny, having someone come clean your house, flying private, having a nice car, like buying a super, I mean, if you just name out all the things, not drinking alcohol, waking up early, like, why do you think that is?

 

Brad Weimert: I’ll tell you a story about sort of like when this hit me harder. And I think I started to formulate an opinion around this. And it came up over the trip, but when Jesse Itzler formed this Everesting event, it was a 29029 event, there’s a long story to this that I’ve talked about quite a bit, but something hit me, and I was like, “Oh, you’re challenging people to climb this mountain 17 times in a row.” And I heard the math and looked at the numbers, and I was like, “I could do that twice.” I was drunk when I said it. But I was like, “I could do that twice.” And then I got my foot in my mouth, and I got challenged, and I was like, “All right. I’m going to do this thing 34 times in a row in the time period that people do it 17 times.”

 

For reference, of the 150 people that tried to do it 17 times, 50% of them didn’t finish it. And I was like, “I’m going to do it twice,” and I did it twice. I come down at the end of the thing, and I’d been going for 36 hours straight, and Jesse’s at the bottom, and everybody’s gone. The event’s over. Most of the people that had tried and failed or tried and succeeded have left. Nobody’s there. It’s like 10 people left and the staff, which is a whole interesting element in and of itself in terms of what gratification you actually get from being the outlier, from doing the unique thing that’s important.

 

Chandler Bolt: Because you’re so high up that nobody sees it.

 

Brad Weimert: Nobody sees it, right? And so, I go down to Jesse, and Jesse, I’m at the board, and everybody’s marking their 17 laps on the board, and I had started marking their… It’s a triangle that’s in the shape of a mountain. Everybody’s mountain, mountain, mountain for 17 laps. So, I started going through and flipping mine and going upside-down mountain on top of my mountain, which looked like a Star of David, which is a little weird. But marking them all, right? So, I’ve got these 17 Stars of David-ish. And I see Jesse at the bottom, and he goes, “Oh, man.” He’s like, “Holy sh*t. I can’t believe you did that.” And I was like, “Yeah.” You know? And I’m just in my own little bubble. I’m like, “Yeah.” And he’s like, “Dude, you have a lot of haters.” And I was like, “What?”

 

And he’s like, “Yeah, man. There’s a lot of people who are talking sh*t about you, but you did it anyway.” And I was like, “Were they?” You know, because I just had my blinders on. He was like, “Oh, yeah.” And we didn’t talk about it in the moment, but it sat with me. And what I realized through that proposition was everybody’s going through their own journey with things that they perceive to be really difficult, and when somebody does something seemingly effortlessly that is significantly more than what they’re struggling to do, it’s frustrating to them. And the human response is to talk sh*t. And that was my takeaway, is I was like I have no issue with anybody in that situation. But it’s an interesting realization to say, hey, when I’m trying really hard and still having a hard time executing and somebody just blows by me and does it, fu*k that guy, you know? You must be, insert the rational reason that you can do it and I can’t, right?

 

Chandler Bolt: Which is a disservice.

 

Brad Weimert: I agree. Yeah. To yourself.

 

Chandler Bolt: To yourself, most of all. So, interesting. I mean, it’s kind of the classic if I want to make myself feel better in comparison to you, there are two ways I can do it: bring you down or bring myself up. It’s way easier to just bring you down. Way easier. Maybe that’s why. I don’t know. What’s your take?

 

Tom Patterson: I don’t know. It’s a complicated one. I mean, I’ve always been like, “Man, how do they do that?” Like, it just provokes curiosity versus like, “Hey,” like, “that is awesome.” Like, I’d have a zillion questions for them, and I think we all would, right, from the curiosity part. But I read somewhere recently that you only experience things you think you’re worthy of. And that really resonated to me, and so, whoa. Right? And you think about that like you wrestle with it for a while. And then I was like, “Well, what are the things I’m not experiencing yet now because I don’t feel like I’m worthy of it now?” And then there’s like a whole other subset of things you think about, so.

 

But then the people are like, it’s cool when you hear like, “Man, you know what? You deserve it. You worked so hard for so long.” Like, it feels so good because most people don’t understand. And I think when they don’t understand what it takes to get somewhere, their default is like trying to bring you down. And they don’t know what they don’t know. So, I like when someone asks questions because it shows they want that, you know? So, I don’t know if that’s helpful, but they see the harvest and not the farming. And they want the harvest, but they don’t want to farm. And I’m not on social media like you guys are, so I don’t have as many haters that I know about.

 

Chandler Bolt: I’ve probably got far more haters than I know about. Brad definitely does.

 

Brad Weimert: No, everybody loves me.

 

Chandler Bolt: Dude, you’re not polarizing at all. That’s what they love about you. They love you in Australia, which that’s a great example of that. I think Australia and the UK, it is total tall poppy syndrome. Anyone pops their head up too high, and I think that’s why you went viral in Australia.

 

Brad Weimert: I think you’re right.

 

Tom Patterson: Australia’s like that? I haven’t been.

 

Brad Weimert: Oh, yeah. Australia’s a socialist capitalism. It’s not socialist, but it leans in the direction of sort of an unwarranted equality, right? We’re all deserving and equal. And I fundamentally think that that’s a beautiful sentiment. Also, if you lean out of the world of meritocracy, the incentive structure that drives humanity fails. And let me articulate that in easier words. If people aren’t challenged to perform, and you don’t applaud people for their actual performance, then people cease to be motivated and find value or meaning in their own life. And that’s the reason that socialism doesn’t work.

 

Chandler Bolt: You remove the carrot.

 

Brad Weimert: You remove the carrot. Is that right? What are you, a fu*king rabbit? Get after it, buddy.

 

Chandler Bolt: Oh, my gosh. Yeah.

 

Tom Patterson: If you think you would’ve been born in a country like Australia or the UK, do you think you would’ve immigrated to the US or found a way?

 

Brad Weimert: Nah, dude, I would’ve been a fu*king gigolo, man. Have you seen the people over there? I’d be sexy as fu*k. All the women would’ve been all over me. Never leaving that place.

 

Tom Patterson: Yeah, he does give off Euro vibes, doesn’t he?

 

Chandler Bolt: Like, mostly, like European pedophile.

 

Brad Weimert: Hey, listen. We got to leave the pedo sh*t out of this. Not okay.

 

Chandler Bolt: Have you guys seen it? So, ChatGPT the Epstein files.

 

Brad Weimert: What’s that? ChatGPT Weimert Australia. That’s actually where we should go with that. Fu*k you and the Epstein files. Fortunately, they won’t find anything, so I feel great about that. Unless you quietly let your Claude bot go out and claim a bunch of bullsh*t about me.

 

Tom Patterson: Claude bot. That’s funny. Whoa.

 

Chandler Bolt: Hey, hold on. I’m paranoid that that… Is that salsa still behind that?

 

Tom Patterson: Probably.

 

Chandler Bolt: Because it got moved around, and I’m paranoid that there’s salsa all over that seat.

 

Brad Weimert: So, that’s a no?

 

Tom Patterson: Yeah, maybe.

 

Chandler Bolt: Oh, perfect.

 

Brad Weimert: Stellar.

 

Chandler Bolt: Great. Well done.

 

Tom Patterson: Is that for you? Were you hungry? You want some?

 

Chandler Bolt: No, no, I’m good, I’m good. It’s just all I could think about. I don’t know why.

 

Brad Weimert: It’s good.

 

Chandler Bolt: But to your point earlier, equal opportunities, not equal outcomes. And we live in a world that’s trying to equalize the outcomes. Screw that.

 

Brad Weimert: Back on all that equal opportunities, not equal humans or equal outcomes, right? So, we can all have an equal opportunity, but we don’t all start at the same place. We are not all equal. But it would be great if we all had equal opportunities, but we are not all equal to start, right?

 

Chandler Bolt: Which is, in itself, an opportunity.

 

Brad Weimert: I agree. But I think people conflate the idea that we are all equal with we all should have equal opportunity, right? And then also the reality that the outcome you drive is on you, right? And that’s what you actually get rewarded for. So, we’re not all equal people. We don’t have an equal starting point, and we can strive to have an equal opportunity, but that’s an illusion anyway. And anything you do to do that is going to fu*k up something downstream. Butterfly effect to some extent.

 

Tom Patterson: Yeah. Well, have you heard the saying that the biggest indicator of your success in life is the zip code you grow up in?

 

Brad Weimert: Yeah.

 

Tom Patterson: Do you think that still plays out today?

 

Brad Weimert: Yeah, I do. And I think that’s actually a super interesting point because I think that you’ve got the difference today is I very much believe the Tony Robbins sentiment of proximity is power. And the difference today is that proximity can mean a lot of things. And so, you can be in a digital environment that gives you proximity to people, but nothing replaces human interaction together at all. And I think that we will see that in a crazy, accelerating format in the next five years. And I think that you’re going to see a… We’re already seeing a resurgence of community, social, physical community.

 

Tom Patterson: Gatherings.

 

Brad Weimert: Oh my God. And so, to the point of the whole conversation, like we modified schedules, spent an egregious amount of money, relatively speaking, for the sake of community and connection. Really.

 

Chandler Bolt: I agree.

 

Brad Weimert: And so, I think that the people that you spend your time around physically are probably the most important choices you can make. And I think second to that would be digitally, would be who you’re talking to all the time.

 

Tom Patterson: So, they always say middle class is the hardest class to get out of because it’s comfortable.

 

Brad Weimert: Yeah.

 

Tom Patterson: So, if you’re upper class, you have the connections, the networks. You understand how it works. If you’re lower class, you have an extreme hunger to get out, right? So, I just thought of this. Is being middle class in the US almost like living in a socialist country? Because you’re average. It’s not too bad. It’s not too great. But you have a comfortable life. And comfort is the hardest thing to get out of.

 

Brad Weimert: Yeah.

 

Tom Patterson: Right? And I grew up lower, maybe sometimes middle class, but I remember those lower moments, right? And you perceive things differently. You’re like, “I don’t want to live with this fear or anxiety to get out.” But I feel like in a socialist country, you can always fall back on the government to take care of you.

 

Brad Weimert: So, let me reframe that. I would say that, because what hit me immediately is I thought upper middle class is the most difficult thing to get out of because you feel like you’ve made it to some extent. But what that led me to mentally was that all of that’s bullsh*t anyway. And I think the reality is that if you don’t surround yourself with people that are ahead of you, that’s what’s difficult to get out of. It doesn’t matter the class you’re in. If you don’t constantly expose yourself to the people that are ahead of you, then that’s difficult to get out of, right, in whatever class. The number of people that I know that are like, “I refer to myself as baby rich,” because, yeah, because it’s like, great, I’ve done well relatively speaking. And it’s a joke to tons of people I know. And the more people I’m around like that, the more I’m pushed to grow into that.

 

Tom Patterson: Yeah. I agree with that.

 

Brad Weimert: So, I know.

 

Chandler Bolt: Speaking of socialist hell holes, we are now on the verge of leaving New Mexico.

 

Brad Weimert: Leaving what one?

 

Chandler Bolt: New Mexico.

 

Brad Weimert: Our plane looks so big right there.

 

Tom Patterson: What’s your thing on New Mexico?

 

Chandler Bolt: What’s that?

 

Tom Patterson: What’s your thing on New Mexico?

 

Chandler Bolt: I think New Mexico sucks. Only place worse is Minnesota.

 

Brad Weimert: Minnesota. We are, for those that can’t see our digital scrolling map in front of us, or behind Tom, we are right on the edge of the great nation of Texas.

 

Chandler Bolt: Where’s your phone at?

 

Brad Weimert: Huh? Right there.

 

Chandler Bolt: Hey, where did you get…

 

Tom Patterson: This is my phone right there, buddy.

 

Chandler Bolt: You got your phone? You got your phone?

 

Brad Weimert: Yeah. What do you want me to do with it?

 

Chandler Bolt: Hand it to me real quick. Let me get a little…

 

Brad Weimert: The great nation of Texas.

 

Chandler Bolt: Oh, not the flash.

 

Brad Weimert: This episode has been brought to you by Hideout in some Podunk town in British Columbia. It was delightful.

 

Tom Patterson: Cranbrook.

 

Brad Weimert: Not a Podunk town. Cranbrook, British Columbia.

 

Tom Patterson: That’s a beautiful town, actually.

 

Brad Weimert: It was a beautiful town.

 

Tom Patterson: With those views, I could justify living there for a while.

 

Chandler Bolt: Speaking of socialism, how about Canada?

 

Brad Weimert: Man, dude, I talked to our buddy, Jason, and Jason is you brought him up last night briefly. Jason is raising $2 billion to build data centers in Canada. And for a frame of reference, he sold his last company that built data centers. So, the timing of this right now, he was like, I mean, he sold it for a lot, and he was like, “Well, the upside of this is $10 billion, which just fu*ks with my head, honestly. I don’t even know how to really grab that mentally. But he’s like, “I just felt like it was enough money that it made sense to spend a few months on it.” Literally what he told me this morning. And I was like, “Okay.” And we have an affinity for coffee, so we were talking about nerdy coffee sh*t.

 

Tom Patterson: Oh, that was the dude grinding his coffee in the morning too. Okay.

 

Brad Weimert: Too, right. Him and I, right?

 

Tom Patterson: Every dude I know from Montreal, when they’re not at home, has one of these coffee grinders with these very exquisite coffee beans.

 

Brad Weimert: Yeah. So, he’s grinding his coffee in his lap, suspiciously. And we were talking about… I actually brought up, I was like, “Tell me about the political elements of creating a data center in the US versus Canada.” And he’s like, “Well, there are really kind of three phases of this.” He was like, “US would be by far the easiest.” And actually, what he told me… Let me back out of this. The reason I asked this question was because he said in order to put a data center in the place he wanted to, which is outside of…

 

Tom Patterson: Alberta.

 

Brad Weimert: Yeah, it was in Alberta. It’s in Alberta. And he said, “In order to put it in Alberta, I have to go around to everybody that’s within some perimeter, and I have to physically talk to them. And if I go to their place three times and can’t get a hold of them, then it’s acceptable for me to just send a notification. But I have to show evidence that I have tried to talk to them physically three times in order to be able to do this. And then anybody within 1,000 square feet or whatever the number is, I can just send a letter to.” And that was what sparked the question, “How do you feel about the politics in Canada versus the US?” And he was like, “Well, it’s fu*ked.” He was like, “I’m spending $480 million on regulatory things for the data center in Canada that I just wouldn’t have to at all if I went to…”

 

The way that he said it was a red state in the US, namely an energy-producing or an energy-friendly state. And I was like, “Holy sh*t.” He also told me, though, that Canada had this divide between Alberta in particular, because Alberta’s a huge producer of oil and gas, versus Toronto, versus the east side. And I was like, “Okay, that makes sense, too.”

 

Tom Patterson: So, what if they knock on your door and they say, “No, I don’t want that near me”?

 

Brad Weimert: I don’t know.

 

Tom Patterson: Is it like cellphone towers near your house?

 

Brad Weimert: I think the whole data center thing is interesting. He told me a little bit, and he said that there is a department that can basically override the social decisions. And it’s like, doesn’t really matter what they say. There’s some department that can just be like, “Stamp, good to go.” And it’s like, well, why the fu*k are we doing this exercise in the first place if that’s the case? But I don’t know.

 

Chandler Bolt: We were in the Cat trying to convince him to give us equity.

 

Brad Weimert: Yeah. Somebody walked up, and they were like, “Hey, so Jason, I’m happy to throw $50,000 at your venture.”

 

Chandler Bolt: Yeah. No titty.

 

Brad Weimert: Yeah.

 

Tom Patterson: Did he say yes?

 

Brad Weimert: He laughed at them.

 

Tom Patterson: So, he’s like, “No, I need like 5 million minimum.”

 

Brad Weimert: Or 50. He’s raising $2 billion, fu*k $50,000.

 

Tom Patterson: How about snowboard and ski friends and family?

 

Brad Weimert: Yeah, exactly.

 

Chandler Bolt: Or kin.

 

Brad Weimert: Exactly. Yeah.

 

Tom Patterson: That’s insane.

 

Brad Weimert: Well, I feel good about that.

 

Chandler Bolt: Cool.

 

Brad Weimert: And I’m tired of holding this phone up.