5 Questions that Will Change Your Life

So I haven't seen any of these questions. So it started out from a tweet where someone said like, here's 10 questions to get to know people. Is that— is that right?

Yeah. Listener of the pod. And I think your friend Blake— Blake Burge, I think is his name. He had tweeted out a thing like, you know, whatever. There are many questions, but few will change your life. Here's 10 questions that will change your life. And, you know, thread goes viral. So, you know, normally it's kind of like IRL.

No, it's good. There's this thing, Ben, you'll have to look it up again. No research here. There's this thing I remember years ago. It was called like the New York Times like 21 Questions, and it was like, here, ask these 21 questions on a first date, right? Well, on a first date, I thought. And it was like, here's how you get intimate with people. And like, as a single 21-year-old, I read that. I was like, oh, like, here's how I can hook up with girls. And I remember those questions, and they're very similar to what these guys' questions are. But it was like, when did your father make you cry? Or like, like, it was like pretty deep questions like that. Right. Um, and so I'm down with these questions.

So, so I actually read these questions and I was like, these are actually good questions. But, um, the way he presented it, I think, uh, you know, no offense, this is how most people do Twitter. It's like, here's some general advice or some general questions. What's interesting to me is not the, like, the question, but it's kind of seeing somebody struggle with their, their answer to that question. So for example, Um, he would ask a question like— and I'll give you, give you the first question, which is going to come out here in a second. So Ben, read, read question number 1. I'll explain how he tweeted it and how I think we should answer it instead.

Read question 1. In what areas of my life am I settling?

Okay, so what areas of my life am I settling? That's a powerful question. It's a good thought-provoking question. Now, his— the rest of his tweet was like, you know, just enough or just okay is not good enough. Identify the areas of your life you're just settling. So to me, that's the part where it was like, no, no, no, Blake, I want to hear your answer. Like, you tell me, like, if you're going to put out one of these bullshit-ass threads that's like, you know, generic, generic, generic thread, um, to try to get likes, I think that the next level of this like bullshit thread thing is people are going to get a little more vulnerable. They're going to put their actual answers in the thread rather than general advice.

Who's invented this, this theme I'm seeing? So like Upworthy was like, here's 10 things you're not going to believe, number 7. This new one that I'm seeing on Twitter is There's 8,000 of this thing. Here's the 4 best.

8 billion humans on this earth. Not all of them are worth following. Here's my 11 friends that are worth following.

Who created that? Did one of our buddies make that, or is it—

I have no idea who started that, but that's whatever.

That is the formula. Well, Ben, all right, what's the first one? I just tried it.

It's, uh, in what area of my life?

You go first.

You made a lot of progress so in a relatively short amount of time, you just got to keep going.

Yeah. So I would say I'm settling there. And the other one I'm settling, I think, is me and my wife. Like, we have two little kids and there's like, you know, this feeling of like, you know what? Like, we put a lot into work. Okay, then you put— you're putting a lot into your fitness, you're putting a lot into your kids. And it's like, oh, whatever's left over at the end of the day for each other, like, you know, we take what we can get as scraps of like, you know, the energy, the kind of like just the effort we put into kind of your relationship. As I think we've both kind of settled on that, which is like, it's fine. They're not, they're not leaving. They're not going anywhere. It's fine. We can always, we can always see later when the kids grow up.

Is she going to listen to this?

No, that's the beauty of it.

You should have her listen to this. I think that that's good that you said that. Maybe, maybe that will make her like you more.

Yeah. Especially because I didn't say that she is doing all this. I said we are doing it, which is, you know, the key.

All right.

What about you? What areas of your life do you think you're settling?

My consistent diet needs to— I think I could— I'd like to improve that. I looked at my goals over the last 10 years, so I created a goal tracking thing 10 years ago when I was about 21, and I hit all of them except for wanting to weigh 190 pounds. I've always struggled to lose 10 pounds, and I just— I've always wanted to do it and I've never done it. And so I'm sucking at that. The second thing, career-wise, I've settled a bit. So I purposely set out a period where I was like, one year, the sale and plus one year, I'm going to chill. I'm just going to read. I'm going to learn. And I still am not ready to, like, go all in on something. I'm not there yet. And so I'm kind of being a little bit lazy and I feel a little guilt around that. And then I'll do a relationship one. Dude, I'm super dependent on Sarah. Like, if someone, like, wants me to come speak somewhere, I'll be like, Sarah, can you just, like, handle this? Or like, do you want me to go speak here? Like, let me know. Like, I'm only going to— and oftentimes because I don't like to fly, I'll be like, By the way, I'm only going if you're available. Like, if you don't go, I don't want to go because I enjoy being around her. And I think I should learn to do a few things by myself a little bit more than I have been lately. I just tend to rely on her so freaking much that I need to— I need to go do stuff by myself.

Give me one that's— give me one that's a settle that you— I feel like all those settles, maybe that both of us said, are like settles that we're kind of cool with. What's a settle you're not cool with?

The weight thing. Yeah, the weight thing. I'm not cool with that. Like, I get up, like, I'm pissed off. I'm like, why can't I just be consistent? If I was just consistent for like 5 months with an— ate a certain amount of calories, I'd be good. I would be good. I would hit it. But it is so freaking tempting and I just give in to that shit and that pisses me off. What else? I don't know. What am I— I do think that So tell me if this is a settling thing. I create— I've created a couple of little small products in my free time, and I get so excited about making like $500, $100, $1,000 a day. I get so much joy from that. And I'm like, dude, I could crush this if I want to. I can build— I can build things that are huge. Why am I not— why don't I have the motivation to do this? And so I feel like— I feel soft and like I'm settling in that aspect.

Do you journal? Do you have a history of journaling or goal setting? I've never journaled. Just like writing down like thoughts or targets that you want to achieve for different ages.

Not ages, uh, but like, do you like kind of have ideas in mind? But it's not, it's not based on how old I am. Like, I, I've done this.

No, I don't mean like in the future. What I mean is like when you're 21, were you like, all right, this year I want to accomplish this?

When I was 21, I did. I said, okay, by 30— I, I used to say by 30 I want to have a million dollars in the bank. And, uh, I had a couple of goofy ones. It's like, I have a million dollars in the bank, I want to have gone on Survivor, and I want to like, you know, I had like 2 other, like, I don't even remember what they were at this point. And then like, as I got older, I was like, oh, well, that number needs to be bigger. And then the second one, time isn't really a factor. And like, oh, I don't care about Forbes 30 Under 30. That's actually all bullshit. And like, you know, I kind of adjusted my like goals once I like wasn't 21 anymore.

Well, I think it's good to look at those things because I'll look at all my old journaling and writings and I'm like, well, what energy was I putting into there? What was I bummed about? What was I excited about? And then oftentimes I do one of 2 things. I either try to impress my past self or try to make my future self pumped where I'm like, what, what, what will I be really excited that I did now in 10 years?

So there's this thing, I don't know if you've heard of it. So Chris Sacca, who is, you know, one of the kind of best investors of all time, he was one of the biggest investors in Twitter and Instagram and a couple other badass companies. He, he had this thing which was like he, he read out somewhere, I think it was like on the Tim Ferriss podcast or something. He like, he read out a note that he had written to himself a note that he had written to himself when he was 20 years old. And he goes, I actually, I just found it while we were talking here. So this is perfect. I found the transcript. Do you know what I'm talking about? Do you know what I'm about to say?

Yeah, yeah, yeah. I remember it. I remember it. What did he say? I don't remember exactly what he said, but I remember this episode.

He goes, he goes something about, you know, what do you want to be when you grow up? He goes, so here I am. I'm 20 years old. I'm living in Cork, Ireland. And we'd start the day drinking at 11:30, blah, blah, blah. And I'd never heard of an investment banker.

at that point, I had never heard of a venture capitalist. And so I just wrote in there, I don't know what the job is called, but I know it's gonna involve a lot of talking on the phone, a lot of negotiating, a lot of yelling at people, high risk, high reward, unbelievably high stakes. And I'm gonna do it part-time from the mountains, part-time from the beach, whatever it does, whatever it is, I'm gonna be done with it before I'm 40. And then he's like, you know, fast forward, he— this was, you know, just, I think he was 40, 41, and he basically— billionaire accomplished almost exactly that. Yeah. So he's like, he's now a billionaire who does exactly that, makes deals. He didn't know what a VC was, but he became a VC, which is that deal. He has a house in Truckee and, you know, another one on the beach. So he had the mountains and the beach thing, and it was like, literally it all played out, and he retired from the game, and he was like done with it, and he moved on with his life, and he started doing other things. And so, um, So I always thought that was really cool, and I thought it was cool because it wasn't like these fucking lame goals. It was a description of his life. It was like a painting of his life. It was like a movie scene of his life. And I've noticed that the people who kind of do this, like they kind of call their shot and they manifest it, they don't really call their shot with like some— like, it doesn't feel like Excel. It feels like iMovie. It's not like a bullet point analytical thing. It's like a vision for how their life is going to be and what life is going to feel like. And then They don't even know the words to describe it or the route to get there. They're like, but that's it. That thing at the end, that's how it's going to feel. That's what it's going to look like.

That's what I'm going to do. I'm doing this tonight. I'm doing— this is good. iMovie, not Excel. That's a good one.

If you were going to do like, let's do a kind of off-the-cuff shitty version, right? Again, we do it for the entertainment. We do it for the people. What do you think would go into that? What do you— what's your— what comes to mind as your version of that?

I like physical places as opposed to internet places. So I like— it would really— I want to have a— I really want to own— I want to have some type of physical land or buildings throughout the country that I can entertain all of my friends all at one time. By the way, for all of it, I propose something here.

Yeah, I propose we do a 2-minute thing where we just jot down on our note here what we think it is. And we'll just cut that out.

No, because I'm not prepared. I'm not prepared. You— what's yours?

You got to do it. What's yours? That's what I'm saying. We got to write it down. We got to figure it out. Okay, so I think—

I'm not ready.

All right, look at that reaction. This tells you— that's what we call resistance when the boys go to therapy. That's— we've identified some resistance.

I have to figure this out. This is like such a hard thing to do. Next question, Ben. Fuck.

Are you guys ready for the next question?

Okay, let me, let me give you my, let me give you my scene right now. Okay. My scene that I have in my head is you're already living where I'm living. No, dude, my house is like this. I already know the house. It's this big ass house. Everything's fucking white inside. My, I'm at this, I have the same, I have a chef like I have today, but it's like on this like giant area. There's people just coming in and out of my house because we're like the fucking lobby. Like my whole life and work is so integrated that like My trainer's showing up, they're having brunch with us, and then the, you know, I'm having this meeting with this other person, but they're also going to work out with us, and the whole thing is just integrated into one big-ass thing. My mom's over, my sister's over because we all live nearby because we all made it. The second thing is I take a nap midday because with no guilt, so zero guilt midday nap. I already know that that is like, that is the, that implies that the rest of the shit worked itself all out. And then the last piece is um, all I get to do is just meet interesting people and, uh, be super curious about them. And then I just either, I don't know, record or type or something like kind of like what we're doing right now. I just take the interesting bits, I put it out there, and it's in millions— it's in a million people's ears or eyes, you know, the next day because they are following it. Um, they love the content, like they love the content package that I put out. And I never meet those people. I don't have to talk to them. I'm not their consultant. I'm not their motivational speaker. I just kind of— I'm taking little bits of what I'm curious about and I'm putting it into a million people's ears every morning.

I think, uh, you're almost— I think you're practically there. I don't know, you got to get the house and the fancier chef. Dude, you could take a nap now, I'm sure.

Dude, the midday nap right now with kids, that's indulgent.

If you take—

well, if you take it like 2 years, that's like— that's like giving the middle finger to your spouse. I'm gonna go take a nap right now.

What, uh, what's the next question?

By the way, that million people's ear things, that was old. I said that before we started this podcast. I had told Sully, he was like, what do you want to do next? When I was selling the company and we were on like a fucking 10-mile walk, we just kept walking in the middle of the night and he was like, tell me more. What do you, what are you thinking? I said, dude, I think what I want to do is I just want to have some way that I could just get my thoughts out there and it gets in a million people's— I remember calling it earballs. I said, it's in a million people's earballs in the morning. I said, I just think that that would be so cool if I could just be in people's ears while they're on their commute to work or whatever else. And that was before the podcast. Now the podcast is getting close to that.

Yeah, you have that.

All right.

Next question.

And you can go out of order, Ben. Pick, pick the questions that are interesting to you.

Um, let's go with question 10. You should choose your battles wisely. What battles do I choose?

Oof, dude.

I choose so many petty battles. Like if I, when I'm driving and I see someone behind me and they're driving like an asshole and cutting other people off, I like go out of my way to slow down and purposely like block it. So I'm going just as fast as the fast lane so they can't get by me. Also, I reply—

you're like, I go to their destination.

Yeah, dude, I'm really— I'm just— it pisses me off that someone's rude. I also reply to just so many comments that I shouldn't reply to where I think someone has said something and it's just kind of ridiculous and I reply to it and there's no reason why I should be doing that. So I pick a lot of really, really, really dumb battles. Your HOH battle that you had, I would die on that one. That would— that would— that this would not stand. That's what I would say. I mean, I would go hard on that one. What was the question, though? What battles do you pick that you shouldn't?

It's basically— it says choose battles wisely. What battle do I choose? So which really— which is saying, what battle do you want to be choosing? Another way of looking at it is what you said, which is what are the shitty— what battles am I stupidly choosing right now that I need to not be choosing?

Dude, I choose so much small stuff. Like, I just, for some reason, I stay like hardcore in the dirt. Like, for example, I'm out at my ranch and I've got people here like setting up my Airbnb and stuff and like people are like doing the stuff, but like I just have to be here and I'm like putting shit together or like, fuck it, I guess I'm going to rent a car and go to Costco. It's like, no, we're already doing that. I choose the smallest stuff as opposed to leveraging my, my skill set. And so that is an unwise battle that I should not be picking. Instead, I need to be thinking about much bigger things. And I just, I simply don't. I think having kids might change that. I think there's a world where that— where I'm praying that having a child is going to like somehow like show me the way. You guys could tell me if I'm wrong, but dude, I picked the smallest. I focus on tiny, tiny, tiny issues.

That's like I have a friend who the like, they're a couple. They're like kind of going through problems right now as a relationship. And then she said something. She was like, I just feel like I need to have a kid and then that's going to like help us. And I was like, oh my God, no, that is not the answer. Like, I understand why you think that that will make this relationship better, but it is going to do the exact opposite.

I think it could be the answer, to be honest. Having a dog is like 2% of having a child, not in the sense of I'm taking care of it, but it's like I've got something that I need to protect and take care of, and it makes me a little bit happier. I imagine properly having a human being where you're like, oh, I have to dedicate my, my life to this person. It's beyond me at this point. I have a feeling that is— that can be very inspiring. And that's why I think a lot of like 35 and 40-year-olds who are childless and are like getting messed up on psychedelics all the time and feel depressed, I'm like, dude, just fucking pop out some babies. I bet like you won't be asking yourself, how do I find myself? You're going to say, how do I just like make this kid happy? And like when you dedicate yourself to others, I think you're happier.

Uh, can I read you something cool, by the way, uh, that I just— Do you disagree with that? Um, no, I think you're right in that, in two ways. So I think you're right that having a kid definitely takes the focus off yourself. So that, that eliminates like a huge number of worries that you have, but it replaces them with new worries. If your habit is to worry, guess what? Whatever situation I put you in, you're going to find something to worry about.

It's just better to worry about other people though. It's, it's more rewarding.

It is an improvement. It is an improvement. The other thing is that, yeah, some bullshit just gets thrown out the window because you don't have that bandwidth. You don't have that extra time. To think about stuff and do stuff and make that trip to Costco, because it's just off the table. You don't have the time. And so, so that's one thing, but it doesn't fundamentally change the nature of the problem, the root cause of the problem, um, which would be, you know, like a focus on minor things. Because guess what? Then you're going to start to focus on, you know, why your kid's, you know, pinky toe is a little bit crooked and why they have this little rash on their knee and like why they're not eat— why they didn't eat all, you know, a balanced lunch. And like there's a million— there's a zillion things you could worry about with a kid And you can even justify them further because it— you're— I'm a martyr, I'm a great parent for doing so. So you got to be careful with that. I don't think it goes away, but I do think it like changes the problem a little bit.

So what's yours?

Um, okay, I'll answer the question. I'm going to read you this thing. So the battles, um, the battles I should pick— I should pick— the battles I want to choose are, um, health. So being in the best health that I can be and having a healthy lifestyle for me and the people around me.

Is your wife healthy? Because does she eat healthy?

Yeah, she, she, uh, she's in and out. She, she can be— when she's on it, she's super clean. She doesn't have the problem I have of discipline. Like, once she flips the switch, she'll just never eat bad again until she flips the switch off, uh, and then she'll eat Oreos all day. And so it's like, you know, one or the other, um, And so, but, and same thing with working out. She's like hardcore intense about that and hardcore intense about her diet. Um, and like she doesn't waver at all. So, uh, but it's just a matter of what mood she's in. Um, like, and the mood is like a year-long mood, not like a daily, daily fluctuation. So I think health is the first one because I've seen that once your health goes a little sideways, nothing else actually matters. None of the other battles have like any relevance anymore. Uh, I think the second one is like probably the, probably the second battle to choose is like, uh, I don't know, probably something around parenting, but I don't even know how to phrase it. Like, I don't know, being like not constantly, um, trying to like rush through parenting, parenting and like getting the job done. Uh, that's probably the second one is like the battle of enjoying being patient with my kids. And then the last one is probably like, I do too many projects. I have so many fucking projects at once and they're all good projects, but they're probably collectively together a bad number of projects. And so that's probably the worst one.

I know I always say it, but how many people criticize you about that?

I don't know if my friends and people who actually care about me, like, I don't know, the people who know me and care about me, they do. They do. And the people who don't are like, oh, that's cool. You do so many things. And my friends are like, that's not cool. All these things could be cool, but you got to do them. You got to do them right. And if you're not going to do them, you got to figure out how to like hire somebody who's going to do that thing for you.

I would— if I was you, I would only do 3 things. I would do the podcast because that's not that hard and it kind of drives the other thing. I would do Milk Road and I would do investing.

Yeah. The problem is I'm too deep in on e-commerce, and so I got to like either hire my way out or sell this thing or I don't know what. I don't know what the other—

you got to sell it. I think you sell it or something. I think that everyone talks about hiring someone to run shit. They're still like involved somehow. Like you're not actually— I think that that's actually really hard to do.

When you did it for The Hustle, you were pretty good about it, right?

Yeah, but I thought about it all. I mean, I still felt like I was working there, but yeah, I didn't do other projects.

Dude, that's the hard part.

That's the hard part. Exactly. And like, you know, you read this and you nod. And then it's like, have I been smart enough to figure this out in the first place? What do I even want? And then do I, do I like both you and I, we have developed the skills of hacking reality, but we get a little loose on remembering what, what we actually want and what doesn't matter, what we don't care about. And like remembering which game to actually play.

Yeah. Bending reality is in my opinion, the easy part. Knowing what you want is the way, way harder. I don't know.

Where'd he write that?

I know he, he said this on like a Twitter Spaces or something like that. This guy's Zach. Zach Pogrob tweeted it out.

I liked it. That's good. Ben, let's do another question. What's another one?

All right. I think this is an interesting one. What are you letting in? So in other words, like he says, turn off the news, don't read the comments, quit interacting with negativity. Think of it as mental fitness.

Like what?

What things are you letting in? What noise are you letting in that you shouldn't let in?

Oh, that you shouldn't.

I have a— Yeah. What, what are you letting through the, through the window or the door that actually, you know, you shouldn't be, shouldn't be getting through the—

what are yours?

Well, I had, you had written something on the doc that I think is interesting. It was about feedback. So let's just zoom it into feedback. What was your question around feedback?

So I have a few ways that I go about doing this, but you could do this when building a product or when, um, just asking people about your personality, which I think you should do. Like, what do I, what do I suck? Where do I rock? And what you'll notice, and it's very clear, I tweeted out, what do you like about the podcast? What do you want more of? What do you want less of? And for every person who says they want a longer podcast, there's an equal amount of people who say they want a shorter one. There are some people who say more guests. There are some people who say no guests. And that makes things really hard to, to figure out feedback. And so I was going to ask you, how do you decide which feedback to listen to and which to ignore?

So I started off like, I used to, the way I used to think about this was, dude, feedback is the key. You need a feedback loop. You need to talk to your customers. You need to know your audience. And there was all these like, you know, books written about how important that stuff is. And so I became fucking Mr. Feedback. I would, you know, if I had a project idea, I'm taking the designs out to a mall and I'm stopping people and say, hey, will you give me feedback on this idea? And you know, every coworker, I was like, hey, I would love some feedback. What do you like about me? What do you hate about me? What's good about me to work with, et cetera. I was fucking Mr. Feedback. And then I started to get what you, what you just described, which is information whiplash, which is, it's like information overload, but it's not just an overload, it's contradictory information. Yeah. And so then I'm like, oh shit, what to do? So I got paralyzed. So then I went to Steve Jobs mode. Fuck feedback. People don't know what they want. Why would I ask them what they want? They don't, they don't even know what they want for breakfast. How could they tell me what they want out of this, out of this app they've never heard of? How could they tell me how to be a better boss?

People don't know what they want. And I became Mr. Steve Jobs in the turtleneck. Then I sort of realized, well, that's not good either, right? Because now I've isolated myself from actually getting feedback. So I, I have no signal to go off of. And so now I've come up with a better balance, I think, between the two, which is I seek out feedback from people who I think are gonna give me relevant feedback. So I don't just ask everybody. And then the last piece is The feedback is not the answer, it's the question. So when I hear feedback, I'm not looking for the answer to what we should do more of, what we should do less of, how I can be better, how I can be worse. I'm just looking for the feedback to just surface a couple of questions. So for example, if they, uh, if the feedback said, you know, longer podcast, some people said, oh, I want longer podcast. Some people said, I want shorter podcast. It's just a question that comes up, which is, what do I think is the right length of the podcast? What podcasts are great when they're long? What podcasts are great when they're short? You know, what would be the ver— what would be a great short version of our podcast? So I use the feedback to ask myself a better question, and then it's my job to come to the answer. It's their job to just gimme their opinion, which, which gives me a question that, that can ask. And so same thing goes with products, which is when I ask for feedback, we both like this book called The Mom Test. And the, the central principle is I only get to ask them about their problems. They don't— I don't get to ask them what solution they want. Um, and so similarly, when I go ask for feedback now, I'm just looking for them to say things that's gonna get me to ask a better question that will get me to, to come up. Then it's my job to come up with the answer to that. Uh, that's the main principle. When, when in doubt, there's one final thing, which is at the end of the day, I gotta like trust myself and I gotta know that ultimately if I just do the thing I think is right over and over and over again, I will happen to, I might, some people might not like it, but I will ultimately attract the people who love what I do. So that comes back to that, that saying my, my trainer gave me, which is, who are my customers? The people that love what I do. And it became that simple for me. So that, that's when I, that's what I fall back to. So it's like, if it was like an if-else statement, it's like, if the, if their feedback gives me a clear question and an answer that I know what to do with, great, I'll make an adjustment. But if not. Then I'm just going to do what I do. And I know that that will attract the type of person who loves what I do.

Right.

Exactly.

And, and so the qu— because if something's, you know, really long, it doesn't matter as long as it's badass. Or if I did a, made a 3-hour movie about Sean, you're, Sean's gonna watch it. And so it's really not about listening to the actual feedback, but why do I think they're saying it? So that's what I listen to.

Yeah.

All right.

This one, you guys get to talk about some other people. Um, this one is, am I surrounding myself with the right people Who are the 5 I want to spend time with?

Ooh, powerful question.

That is a powerful question.

So let's just, we'll make it, I think it's a heavy question, so let's make it light. So tell me right now, who are the 5? If you just said, I spend my time the most with these 5 people, who are the 5 people you currently just spend the most time with? Wife.

Sarah, probably number 1. Wife Sarah.

Yeah.

Uh, Neville Medora, my best friend and lives next, next door to me. Uh, Ramon, who you— a lot of people know, Ramon Vanmier. And then, um, Jack Smith.

That's 4. You got one more?

I wouldn't put anyone else in those categories. No, that's it. Your dog? Well, you know, I, I like you guys, kind of like, that's pretty in-depth, but I would say that that's— I would end it there.

And all right, so then let's, let's, let's just add one more. Who's somebody you wish was in that 5 that is— that you're not spending as much time as, as you Like in an ideal world, you would be, uh, Steph Smith.

I would add Steph Smith. Yeah. Nice. I think Steph Smith is amazing. Just like what?

I was like, just like our podcast listeners. They also want more Steph Smith.

So every time I talk to her, I like, damn, she's brilliant. She's a very special person. Uh, so maybe her, uh, anyone else like I sometimes I do wish like I had like some baller, baller, baller friends. A lot of my friends are like pretty great, but like fucking hanging out with like a Russian oligarch just to see how like some of these crazy people think who are like extreme. I would like— I like extreme people. So even though I may think they're a bad person, I would like to hang out with some of these extreme people who are just on extreme ends of success. Or it could even be an athlete. Like, what's it like to hang out with like the person who holds the world record in the marathon. So it would be nice to, to be around more extreme people.

Do the five and then the other.

All right. So my five would be Sonia, my wife, and my kids. I'll just put it, put it all together. Um, Uh, my mom is the next one. Uh, so I spend, my mom comes over one week out of every month. She stays with us. Um, uh, Ben, who's kind of like my, my right-hand man, my, my business partner across Milk Road, across in the fund. He helps with the podcast. He does a bunch of things. So I talk to Ben hours a day. Um, Andre, who I, I don't think you've met Andre, right?

No, no, no.

Andre's like kind of like the new Ben. He's like the next Ben. Um, so he's a new guy in the fold on that level. And Andre is kind of amazing because Andre's got this story, um, that he had some illness, that he had something, he caught some bug or got some infection that like it gave him like kind of like chronic fatigue syndrome or something like that. Like he basically like couldn't get out of bed for like, I don't know, like 2 years or something like that. Like he was in a wheelchair or something and nobody Nobody knew what it was, and it was just like— and then he kind of like recovered from it, but it was like this multi-year thing. And so this motherfucker is the most like grateful person you'll ever meet because he's like, dude, I walked today. And I'm like, you know, like it doesn't take much for Andre to be like high on life. And because Andre's around me all the time, I'm— I get that secondary high, you know, the contact high, right, off of Andre. And like, you know, because he, he kind of like was just battling and got out of it. And so now he's like, every day he like, you could tell he's just savoring every day. Like as if you, you haven't eaten in like 2 weeks and you're having your first meal. That's how Andre's like. And so I love that about Andre.

And who are the other 2?

Uh, the other one is Suli, uh, who's our mutual buddy. Um, and I don't hang out with him that much cause he moved, but he's a partner in one of my businesses. And so I talked to him, you know, because that— but the one downside is now that he's like an official business partner, we don't really just like talk to shoot the shit anymore. It's like we kind of— anytime I'm talking to him, I'm sort of talking to him always as he's— as if he's my investor or business partner instead of just catching up, you know? So I guess that's probably the downside. And then, so those are the— those are the 5 that I'm currently hanging out with the most. I would put you next as we hang out, you know, 2, 3 hours a week doing this. So that's more than most people. And then the one I wish I hung out with more was Ramon because Ramon is like the best human on earth. So, you know, the more Ramon in my life, the better human I would be. Just, you know, by default.

I completely agree. He teaches me a lot. He, he's a very thoughtful person. I learn a lot from him.

And then the category that I was saying, the people I have no exposure to is like I basically have no exposure anymore to people that are in high school and college, which is like actually pretty important as an investor and like, you know, person of the world to know. Like what? It's like, oh, I forgot. I used to think about these stupid things and they were the most important things in my life or like Oh wow, you know, we didn't have phones so we couldn't do these things, you know, that they're doing now in high school or college. So I have like zero exposure to that. Um, you know, like people in third world countries, like, you know, when I went down to Mexico, I was like, oh wow, like I kind of forgot like just how simple and like different life is for most people on earth. And like, you know, I used to live in Indonesia and China and stuff like that. So like I definitely was in it every day, but now, you know, I'm just sitting in the burbs in California, so it's easy to forget that. So I, I think I have a lot, like my bubble is pretty tight right now and I think I should pop that intentionally once in a while.

Do you wanna do one more question, Ben?

Yeah, we're doing 5 questions. 5 questions seems like a nice, uh, round number.

And you, Ben, you can remix it cuz some of these are sort of the same, so you could just ask a different question. You're a good question asker in general, so you can ask a different question.

I've been thinking about, uh, one of these, so let's go with this one. In what ways am I in my own way?

Oh, I can say that one easy. I lose my temper and follow my— I get very emotional where I'm like, no, fuck this. This is wrong. We have to do it this way. And I have lost a lot of money for doing that. For like, let's just say like it's an employee who I think like has maybe underperformed, even though they talk like they're hot shit, I would just fire them as opposed to like, well, we could definitely salvage this. Like, there's lots of ways to salvage things and make things better. So it's a net positive. But more often than not, be like, well, no, I just— I'm out. I don't want to deal with the headache. I'm over it.

Or—

and that is a very emotional decision. I make so many emotional decisions. Oftentimes it's Sometimes it's ego. Oftentimes it's temper, but mostly if it's like, oh, I think this person is trying to get one over on me, like, fuck them, I want to crush them. No, I'm not doing— you know what I mean? I make a ton. Yes, I make a ton of emotional decisions as opposed to practical decisions.

That's interesting. All right. I got two. I have one that's real, but—

but is that true?

Have you seen that with me? Yeah, for sure. You've been mad at me sometimes and I'm like, because you think I'm trying to, like, get one over on you. And I'm like, dude, I've I'm really not. And then once you realize I'm not, like, your whole perspective changed right away. And I was like, oh, that's what you thought? Like, oh, I had no idea because I wouldn't— like, it's so different than the way I think. So I didn't— I just never— I couldn't understand it, basically.

It was not like— we can give a real example. I got mad at you for being late, and I'm like, in my head, I'm like, you don't care. You don't care about this. He thinks he's better. And it was— reality was like, no, dude, my baby was sick, or like You know, I like that she was in the bath and it took forever to get her out. And that's like a legitimately good excuse.

Like even a bad excuse, which was just like, dude, I just— I literally like I was sitting here. I just lost track of time. I'm not doing anything. I'm not more important. I'm not like a diva. I'm not trying to do that. Like, I feel horrible every time I do. Like, I sometimes I literally don't even have a good excuse. But, but even that was fine with you. It was just like As long as you don't know I was sort of like actively doing it, it didn't bother you, you know what I mean?

No, it doesn't bother me. Or another thing that I do all the time, and I think everyone should learn from me and I'm working hard at it and I made this mistake, is replying really quickly to text-based messages. So whether that's an email, anything where it's like, dude, it's okay if you sit on this for an hour or even a day or even 5 days. Sometimes I'll get shit like a text or an email and I'm like, oh no, fuck that. And I quickly reply and I'm like, oh, I should have just sat on that for like 3 hours. What was I thinking?

Yeah, I'm— that's actually a great one. That's a great answer for me too. I'm massively disorganized, which affects everything. So it's like replying, like there are so many emails and text messages that like people are either like offering me something, they're trying to help me and I'm just not replying and people take it very personally. As you know, maybe I would too if I felt like I was getting blown off by this person, or I'll just miss a deal that like it's just like a clear win for me because I just don't reply.

Yeah, I forget to reply.

I don't see it.

I would say fuck them. You know, I actually don't think you should. I've been struggling with that too. And lately I'm just like, I'm just not going to feel bad about replying to these people. Like, and it is the most douchey. But listen, here's the most douchiest thing I could say. But just subtract this by like a lot. And that's the reality. Imagine you're Justin Timberlake and people like are always presenting you with stuff. You're just like, dude, I don't care. I'm going to do what I want to do. Of course, we are not that big a deal, but like a much, much smaller version where there's like lots of opportunities. And I'm just like, I'm just going to ignore all of them. I don't expect JT to reply to a DM, do I?

Yeah, that's true. But I'm talking about like people who I'm doing business with or they're my friends or something like that. Like those are people I do intend to be replying to or I've asked them for something and they gave it to me. I forget to do something with it. With it.

But what do you think, Joe?

What do you think? Laziness there. Like, imagine you're Joe Rogan.

Check. How much is that?

I, I don't want to show the check on, on screen, but this is a $13,000 check that's just been sitting here for like 6 months, and then it expired. And so now I just had to go like get a new check, and then I got the— this is the new check after the other one expired, and I still haven't deposited this one. Another month has gone by. Like, that's how shitty I am, and it's just sitting here because I'm just disorganized for no reason. Or the same thing with like my company's book. So here's the bad way it plays out, which is I don't like— I've never hired a bookkeeper. And so I'm like, oh yeah, like, I don't know, like, aren't the transactions just like on the credit card?

No, they gotta ask you.

I'm not eating.

Nothing good happens after midnight.

Nothing good happens after midnight. It could be eating or it could be fighting.

Yeah, exactly. It's like my sleep was shitty. My work was shitty. I was editing the Milk Road at night. Now I just, I sleep at like 10:30 or 11. I wake up at 6:30 or 7 in the morning. I write the Milk Road and it's, or edit the Milk Road and it's done. But, and like by the time the kids wake up, like I've already like finished my workday almost. And so I just cleaned that up and it cleaned up like 5 other things. But again, so fucking cliché to say sleeping early that I bleep this whole thing out, make it mysterious instead.

Do you remember how regimented Rob Dyrdek was about tracking his time in and like waking up at 6 AM or 5 AM or whatever he did. I actually like, like I, if that's what makes him happy, do it. And I also respect how crazy he is about that. I think I like extreme people. Part of me was like, ugh, but that's like, you don't need to do that. But then the other part is like, that would be kind of cool to do for like 2 or 3 weeks just to see what would happen. Just what would happen if you do get up at 6 AM and you are like, you have a very strict schedule. I actually do think that that sounds kind of fun to try it once in a while.

What time do you, uh, sleep and wake up typically?

Last night I couldn't go to bed. I went to bed at 1 or 2, um, and I got out of bed at 7. I normally always get out of bed at 7.

But are you like super regimented with your schedule?

I'm not productive though. Usually I'm not productive until about 9 or 10.

My, uh, yeah, so my baby wakes up at 6 in the morning usually, so that's when I'm up. And, um, I try and go to bed around like 10, 10:30, and then once or twice a month I'll go to bed at like 3 AM because I need to get something done.

That's why you go to bed at 3 AM? I, I— you're not like going out and doing shit? Wait, do you drink? Do you drink or do drugs? No.

It's usually like I—

God, this is the lamest trio ever.

When I do How to Take Over the World episodes, I usually do a bunch of it in one sitting that I'll do from like 9 PM til like 3 or 4 AM. I'll do that twice a month.

Sean, do you—

so let me recap these 5 questions. Uh, I drink if like the occasion calls for it, but not with any regularity.

No. But do you get drunk?

I, I used to, but no, like last 5 years I have not been getting drunk.

And do you do any drugs? No. God, that's crazy. What a bunch of prudes, dude.

I just drink green smoothies, bro. I, I don't even drink coffee.

We are so lame. All right, go ahead.

All right, I'm gonna recap the 5 questions. So the 5 questions were, in what areas of my life am I settling right now? The next one was, um, am I surround— oh no, that's not it. Oh yeah. Choose your battles wisely. What battles am I choosing right now? And what, what do I want to choose? So what areas of my life am I settling? Choose your battles wisely. What battles do you want to choose? Number 3, what am I letting in that I need to shut out? That's noise and information and opinions from the outside world. And then am I surrounding myself with the right people? Who are the 5 people I wanna spend the most time with? And what was the 5th one? Did we do 5?

Yeah. Question 5 was, in what ways am I in my own way?

Oh yeah. In what ways am I in my own way? What are the things you're doing that gets in your own way? Um, those are the 5. Ben, which one of those questions, when we said 'em, did you go off on a tangent thinking for yourself what your answer is? Which one shook you?

One of these questions should shake you. The first question shook me. In what areas of my life am I settling? That—

okay.

So, okay. You guys are looking at me. I thought maybe I'd get away with not actually giving you the answer because like, that's like, that's one that penetrates to your soul. But you both were just like, you're going to answer right now. And like, for you, both of you talked about like health and fitness stuff. And one area in which I settle a lot in my life is Like, I get super concerned about environmental pollutants, especially like plastics and microplastics and like stuff like that. And I always feel like a psychopath when I talk about it because everyone else is like, what, what, like plastics? And I feel crazy because I'm like, no, actually, like, this isn't a conspiracy theory. Like, the research is out there that like all these microplastics are like crashing our testosterone levels and like disrupting our endocrine systems and stuff like I'm not crazy, but the fact that everyone else is like, whatever, makes me feel even crazier.

And so a lot of times— That's a weird obsession.

I just like settle, I compromise, and I'm like, look at my baby, like putting this plastic toy in her mouth and like a part of me dies and I'm just like, whatever, I settle. I'm not going to fight this fight right now. But it is something that—

Do you have plastic Tupperware?

We have plastic Tupperware that I wish we would just like throw away.

So just do it.

Dude, that is not at all where I thought you were going with that answer when you first said it, because you were like, so it was like weighing so heavy on your heart. And that's what it was.

It matters a lot to me, Sean.

Most fucking random answer.

Is, is, is rubber is like a, like a, what do they call, like a binky or the pacifier thing? The pacifier. What is that? Rubber? I don't even know what that is. That plastic?

Yeah. So most of the time, no, they won't do plastic in pacifiers. So they'll either do silicone. Which is better, or they'll do rubber.

Yeah.

Which is also better.

And rubber is better. Okay. Right.

Silicone, I like have my doubts about, but it does not have like the same proven track record of disrupting your endocrine systems the way plastics do.

Do you, do you reuse water bottles?

No. In fact, I try not to use disposable water bottles because a lot of times they leach.

What do I go watch or read that's gonna scare the shit out of me about?

There's a Joe Rogan episode that I'll link up in the show notes where he talks with— she's a Harvard researcher who, uh, does a bunch of this stuff and she's really good. Uh, and it will, it will scare you a lot.

Yeah, dude. Plastic's pretty bad. Then like, you don't know that, Sean. You might, you microwave plastic, don't you?

Only on this podcast. Yeah. I, I microwave everything and I, everything's in plastic in my house. So I'm like, oh shit. Okay. Um, so I've heard this, but I've like never I never got shook yet where I'm like, oh, take action in this. Um, but that's, that's why I asked, what do I need to go watch that's gonna like trigger me where I'm gonna need to, I need to be like, I, I will go and, you know, make it like dramatic change in my head.

But how do they know plastics cause that, you know, versus just—

because they do studies of— with rats and they're able to demonstrate it. The, the correlation.

Good answer. That's a very good answer.

And, um, what do you— what's, what's an example of something you swap out that's like a big culprit for plastic? Like, most people are doing this, but if you swap this, that solves like, you know, 20%, right?

But how do you reconcile that fact with the fact that you smoke? You told me that you smoke a pack of cigarettes a day.

Yeah. Noted chain smoker, Ben Wilson. That's what people know me for.

How do you do both? Well, and how do you— how can you have— how do you have 24 Newports a day and you're telling me not to microwave plastic?

You know, it's just one of those mysteries, Sam. I don't know how to explain it.

And how do you, um, can you test to see how much plastic?

I don't know. That's a good question. I would love to do it if you can. I don't know that you can.

I got a new business that we're gonna talk about on Monday that's gonna address that, by the way. I was all prepared for it today.

Really?

Did you say that? What is it?

It's called Float. Did you see it in the doc? It's called Float. What is it? What's the URL? Is it called Float Ben? Where's my fucking read? It's called—

No, it's called Fount.

For $5,000 a month, you're going to be touching my body.

Well, we'll see. Maybe for $5,000, maybe it'll make women actually want to touch your body. Maybe that's— maybe we'll do one better.

We're getting tested over here. $5,000 a month. What? $5,000 a month? That's such an absurd number. You're doing this?

No, I'm not doing it, but I think it's close to beta. $5,000 a month. Would I do it? I would sign up for 3 months for sure. I think you could do it in 3-month increments. For $15,000. Yeah, I would try that, dude. I had a concierge doctor at one time for like a year when I was really sick, and it was $25 grand for a year, and it was mostly amazing. Also, I understand why rich people and how rich people can get access to so many drugs, because like, if I wanted to, I could just like text the doctor and be like, hey, uh, can you refill this, uh, this Xanax for me? Uh, or like, hey, I need some more oxy. Like, it's like and you're paying them so much money that it seems like they're willing to do that. It is kind of crazy. This took a turn. All right.

Tonight, do we have— we're way over time. Do I have time to ask you guys one more question?

As long as it's 5 minutes or less. Okay.

I think you can be 5 minutes or less. I'm just curious about this. I don't know why this— I thought of this as we were asking the 5 questions, but if you were to, like, simulate your life 1,000 times, what do you think the ceiling is and what do you think the floor is? In other words, like, Are there a few little things if they broke in the wrong way, like Sam Parr is working at a McDonald's in Missouri right now, or like a few breaks where if things had broken the wrong way, you would be like a worth $100 billion, one of the richest men in the world. Like, what do you think your floor is? What do you think your ceiling is? And do you think you ended up about what your average is?

I think in my case, I could tell you, I think my floor is—

set the ground rules. The ground rules are same genetics and same, like, fam— not like I'm born in a different country.

Like, yeah, it's just like a few little random variables get changed. You make a few different decisions as you go through life, but same family, same situation, same person.

I think I was not far from being like homeless alcoholic drug addict. Like, I think that was actually potentially in the cards, or just like in jail because I would con people and steal. I think a lot of people honestly could say that though. Like, if they like If they like got it, if you ever like do certain drugs, like, oh man, like the, it's actually, I could see myself living on the streets. The best of like the limit. I think like a really attainable thing is I could have not sold my company and I think it could have been worth hundreds of millions of dollars and I could have been worth many hundreds of millions of dollars by the time I was 50. I think that could have done that. I think I could have pulled that off if I was willing to put it in, put the work in.

Yeah, but you'll probably end up there now anyways. You're 30 now. That's 20 more years.

Yeah.

Given where you're at now, it's pretty likely that you end up over $100 million.

It's very likely that I'll be worth 20 more years. It's almost guaranteed I'll be worth $90 million.

I mean, it's almost certain.

Yeah. So then fuck it.

Is he a billionaire?

I don't think he's personally a billionaire now.

Probably, but like a few hundred million in that ballpark.

I think he said on the podcast that he, that he hasn't hit a billion. So I think close, but I don't think he's hit it.

Yeah. Isn't that funny how you can achieve just what most every single person on earth would consider like the top of the top of the top of the top and you're like, yeah, that's funny how that works.

I Googled my, uh, my mentor and kind of this, my investor's net worth. And I remember being like, and then I Googled a whole bunch of celebrities. Like, so I think, I think at that time, like his, his kind of like my ballpark approximate, like my triangulated net worth for them was like $700, $800 million. And then I Googled like Britney Spears and it was like $25 or $50. And then I was like, wait, Britney. I was like, he's like, more than 10 times richer than Britney Spears. I was like, okay, Alex Rodriguez. I remember when he signed the biggest MLB contract ever, was a 10-year, $225 million contract, or $250 million contract at that time. And I remember being like, oh my God, he's getting 3— he already has 3 times A-Rod's contract. And it's just like, I just Googled every celebrity I could think of, like, Michael, more than all of them.

Did you know that you're richer than Ryan Sheckler?

I think I literally said that. I was like, you're 15,000 Jermaine Dupris, dude.

He's probably even richer than Denzel Washington. This guy's amazing.

That's what I'm saying. Oh, easily. Watch, you know, Denzel net worth.

I bet you Denzel's got to be worth 100 at least. Been in the game for a while.

Piss poor. 280. He's a double Denzel. You know, like, come on, man.

That's awesome. All right, I'm out.