Sam and Shaan look back on 2023 after hitting nearly 100 million views across platforms. They share their biggest personal and professional lessons from 131 episodes, covering everything from the power of consistency over virality, negotiation tactics, tax planning through real estate, the decision to go up-market with content, the importance of choosing your own game, and why achieving goals never eliminates the desire for more.
Speakers: Shaan Puri (co-host), Sam Parr (co-host)
Introduction and 2023 Numbers [00:00:00]
Shaan: So Sam texted me this morning and he goes, “We did over a hundred million views this year for the podcast.” A hundred million. I thought he was wrong. I was like, “No way, you got to go double-check that.” He was right. We did. And that is way more than I thought we did. That is a bonkers number. I remember when we started this podcast, that sounded completely crazy.
What we wanted to do today — it’s the end of the year — we wanted to look back and find what were the key takeaways and lessons that we learned from the hundred million views that we had this year on the podcast. So what were the biggest things that stood out when we look at the whole year? What were the biggest takeaways that we had? Sam, where do you want to start?
Sam: Yeah, let me just get the lede out the way. Let’s start with the numbers. So I’m going to be transparent about a bunch of numbers, but not all — just a few.
All right, so we have ten days left in the new year. We’re not actually at a hundred million. I think technically we’re at 95 million. But the past few months it’s been like five million a week. So on YouTube we got 80 million views so far — that includes YouTube Shorts, which pop off sometimes and we’ll get millions of views, so I don’t put too much emphasis on that. YouTube was around 80 million. Then downloads for the actual podcast — so we call everything “the podcast,” but there’s basically the RSS feed, that’s Spotify, iTunes, whatever you listen to your podcast on — that was around 15 million. So collectively we’re at about 95 million.
We did 131 episodes, which is a ton. By the way, this job is fun, but that’s a lot of work. Do you agree? Or do you still think every episode is fun?
Shaan: Every episode’s fun to me. And I feel like I’m able to improvise well. So it is a lot of work, but some of our best episodes are ideas we have 90 minutes before we record, and someone sends a text saying, “Actually, what if we tried this?” And those turn out really well sometimes.
I think it’s because what we tried to do is make this podcast the byproduct of the other work we do. So the basic business model is: do interesting business stuff — invest in businesses, create businesses, talk to interesting people — and then the pod is just distilling the most interesting ten percent that you’re allowed to talk about. And if we do that right, the pod’s pretty easy. When we don’t do that right, the pod gets pretty hard.
But it’s kind of like exercising. Some days I don’t want to do it, and then almost every single time — even if it’s a bad episode or something I didn’t love — I feel happy and I’m proud that I did it. So for me it’s like exercise.
Most Popular Episodes of 2023 [00:03:30]
Sam: All right, I’ll give you a few more stats. Do you want me to go through the top three most popular episodes?
Shaan: Yeah, what are they?
Sam: So we actually have two categories, which is weird, because the most popular episodes on YouTube are not the most popular on podcast.
The three most popular episodes on Megaphone — that’s what we use to track this — the first one is “The Greatest Businesses of All Time: Scoops as a Service, Work Harder Not Smarter Hack.” The second one was “Brainstorming ChatGPT Business Ideas with Billionaire D.E. Shaw.” And the third one, shockingly — I didn’t think this was going to be one of the top ones — was Nick Huber, “How to Make Millions from Content Without Selling Ads.”
The top three most popular on YouTube: it was the same one actually — “Brainstorming ChatGPT Business Ideas with the Billionaire.” That has 450,000 views. I don’t know this for sure, but I think D.E. Shaw did something to manipulate this. I think he for sure emailed this out to his audience. I wouldn’t be surprised if he bought ads or did something, because D.E. Shaw loves to win and be number one. So he’s number one on YouTube.
The second most popular one on YouTube: “10 Years of Money Wisdom in Under 20 Minutes” — 425,000 views. That is you by yourself. And I think you made that episode with YouTube in mind, is that right?
Shaan: Yeah, I made that as a YouTube-first video and it worked.
Sam: And then the third one was very recent, November 2nd: “How I Bought a Multi-Million Dollar Carton Business for $0” — 391,000 views on YouTube with Sarah Moallef and Shaan. And then the fourth one was Martin Shkreli, when we interviewed him — that had 257,000 views. So those were a bit surprising. What do you think about that?
Shaan: Those make sense to me. I mean, each of those — when I read the title I’m like, “Yeah, I’d click that.” And that’s basically what works on YouTube: “I’d click that.” Then you got to deliver on the promise.
Maybe this whole content thing is a lot simpler than people think. You just got to get the titles right and then you work backwards from there — the content off the title.
Sam: And this point is for any content creator out there. You and I, this show — we are kind of bastard children of content creators. We started without YouTube. We only went for podcast downloads on podcast apps. I think we had a YouTube channel, but it was really like — you and I went to Best Buy and bought a camera and just set it there and just uploaded it. We didn’t really care about it.
I think we only started caring about a year ago. And what’s crazy is, if you really want to do it the right way, you start with one platform in mind and you go all in on that. We didn’t go all in on YouTube. I don’t think we should have, but I understand the argument that we should have, because what works on YouTube doesn’t always work on RSS feed and vice versa.
The Gentleman’s Agreement and YouTube Growth [00:07:00]
Sam: Speaking of YouTube, here’s a few more stats. We did 131 episodes, we added about 210,000 subscribers. We started the year at 150,000 and we ended with 360,000. And you want to know the biggest needle mover besides actually caring about YouTube? Do you want to know what it was that got us subscribers?
Shaan: I’m gonna guess it’s the Gentleman’s Agreement. Is that not it?
Sam: The Gentleman’s Agreement. And so for all the listeners out there, here’s another takeaway. When you hear a YouTuber say “click the subscribe button” and all that, and you hear everyone say that and it gets you — you think it doesn’t matter. We saw a distinct point in the chart where we asked people to subscribe and it went up. So it absolutely works.
It’s sort of like when people say, “Why are you buying ads on Facebook? Nobody uses Facebook, no one clicks ads.” Nonsense. That is absolutely not true.
Shaan: And actually that was one of my takeaways for the year. When we were like, “All right, we should start growing on YouTube,” we asked ourselves what’s stopping us from wanting to do that. And one of the things is — dude, I don’t want to be that guy who’s like, “All right guys, if you like this video, click the like button and smash the subscribe button and turn on notifications as well.” It’s like, oh God, I got to turn into inflatable arm YouTube guy — you know, like in front of the car dealerships, that waving inflatable arm balloon thing.
But you had a really great idea — the Gentleman’s Agreement. Basically: how do you do the cringe thing in the non-cringe way? How do you turn lemons into lemonade?
I think we also did it recently with the “Thrill of the Shill.” It’s like, yeah, all right, look — we want to have ads to promote our businesses, cool, that’s fine. And I think the audience gets that. But how do we not make this an experience that’s annoying for us to do — like sit down and record these ad reads — and on the audience side they just want to hit the skip button? What would be fun for us and actually fun for them to listen to? When we switched to the Thrill of the Shill, I feel like that was a good idea.
People should do more of this if they can pull it off. You should set a standard of like, “No, I’m going to have my cake and eat it too.” I feel like we did that in two areas this year, and that’s something worth remembering. Instead of something that’s kind of lame or a drag or just extra work, how do you make it awesome for us and the audience? It didn’t take much more effort, it just took a little bit of charm.
Sam: And it wasn’t hard at all. The problem was the Gentleman’s Agreement — we would always tell people about it, but it faded out. We forgot, it got not novel, and we were like, “Oh, we have to come up with another one.” And I watch all these YouTube videos and I just see one and I write down, “Copying that, copying that.” And I just have forgotten to say it. So we screwed up by not being consistent.
Lesson: Consistency Beats Virality [00:10:30]
Sam: Do you want to go tip for tat a little bit and just go through interesting things that you’ve learned throughout the year?
Shaan: Yeah, all right. I’ll go first with one.
So this podcast is “Steady Yeti.” This podcast is the tortoise, not the hare. It grows very steadily. You could pull up this chart from Social Blade — our YouTube growth — and it’s great, in that we started the year under 150,000 and we’re ending the year almost 400,000. But there’s no spikes. This thing is just a line that’s creeping up. Like, if my uncle goes for a hike, this is what it would look like. It’s his Strava right there.
And I’m like, what is this? This is so different than everything else I do, because I am much more of a “go for the home run, try to do something incredible” type. And then if it doesn’t work — or even if it’s good — I just don’t really follow through. That’s a leak in my game. But I kind of took some pride in this.
Let me give you some examples. On Twitter, we all joined this group chat called the 100K Club. We all had 10 to 20,000 Twitter followers and five or six friends all wanted to hit 100K. We all did it, we all surpassed it, but we all did it very differently.
Nick Huber did it and he’s kind of polarizing. He’ll say controversial stuff that he believes, but he’ll spice it up a little bit. He knows what he’s doing — he uses controversy to grow.
Sahil is like, every day I wake up and I open a fortune cookie and I type it out. Whatever it was, I’ll put that on Twitter. And I’ll do a thread every Tuesday and Thursday. Why would I not? It works. And we’re like, “Why would it not?” Because it’s so boring to do that. But he did it and he grew the most out of all of us. I think he’s got a million. And he did it with what I’ll call more cookie-cutter stuff — feel-good, kept it safe, no controversy, no real original storytelling or wisdom, but more like general best practices packaged well. He’s posted so many videos of children and titled it “Humans Are Amazing.”
Sam: I love my son. I’m like, I’m never gonna write that stuff. I looked at my son and I was like, “Hey, listen — you’re never getting that. All right, you’re never getting that from me. I’m not using you for that and you’re not using me for that.” But jokes aside, Sahil was more about consistency. He just hit base hits. He base-hit his way to a million.
Shaan: And I did the opposite. I didn’t have a schedule, I didn’t draft things, I didn’t have a ghostwriter. I just had probably six tweets that went viral — one was this Clubhouse thread, one was about the metaverse, one was about Elon Musk. I just had a couple of these things go really viral and I would go weeks without even tweeting.
I got to maybe 350,000. And so here’s the lesson learned — the joke’s on me in the end. I was like, “Your boy’s a home run hitter. I just go for the big swings, I don’t have to do all that consistency BS. I just come in, mic drop with a viral thread, and I peace out.” I was so happy with myself.
I kind of looked up at the end of the year and was like, “Huh.” The people who did the consistency thing got way further and they didn’t have to pull a rabbit out of a hat to do it. And I felt like I was having to pull a rabbit out of a hat in order to get growth to happen. And because that’s so hard, I could only do it so often.
The podcast — because I do this with you, and you are a more structured, disciplined guy — you’re like, “Let’s set recording dates and let’s never miss them.” And I’m like, “Dude, what if we did ten episodes in the next two days, but then if I’m busy let’s not do an episode?” I would have had a totally different schedule, and such worse results.
When I look at this, it’s like — damn, consistency wins again.
Sam: This brings me — I think we’re 550 or 520, so we’re 500-plus episodes. That’s a lot. And we record like clockwork — same time, same days, every week, no excuses.
Shaan: I would have never done that on my own. Some excuses, but — sickness, children, and that’s about it.
Lesson: Did You Even Learn the Right Lesson? [00:15:30]
Sam: But this takes me to one of the biggest lessons I learned, through the podcast. We met Andrew Wilkinson — people know about him — but I also met his business partner Chris. And Chris said something at a dinner that I’ve shared on the podcast, but it was the question of the year.
Somebody was talking about something they did, they failed, and then somebody else kind of patted them on the back: “But you know, you learned so much.” And they’re like, “Oh my God, I learned so much. So many lessons learned.”
And Chris goes, “Like what?” And you would think for somebody who went through this traumatic experience and had so many lessons learned, they would be like, “Number one: this. Number two: this.” But those lessons weren’t at the tip of their tongue. In fact, the lessons weren’t even in their head. They learned actually nothing.
And Chris correctly called it out. I had never heard anybody question this assumption that when somebody says “I failed but I learned.” He was like, “I don’t think people really learn.” And in fact, some people, when I ask them what they learned, they say something that tells me they learned the wrong lesson.
Shaan: And I think that’s what happened to me this year on the consistency versus big home run virality thing. I think I learned the wrong lesson. I was cursed by the fact that I did go viral a few times and I did pass my 100K goal. And actually the lesson was: dude, if I just had consistently tweeted every Monday, Wednesday, and Friday — probably would have took me 30 minutes — I’d probably be at a million followers instead.
Chris’s question of “did you even learn the right lesson from this experience?” showed up everywhere for me this year. Everybody I talked to, I realized more people fell into that camp. The outlier was somebody who went through something and had the right takeaway from it. The outlier was that.
Is Being Popular on Social Media Even Worth It? [00:18:00]
Sam: Well, I would say to you — and this isn’t a leading question but it is for me when I ask myself this — is that even worth it? Is being popular on social media even worth it?
I talk to a lot of people who are significantly more successful than I am in terms of traditional success — they’ve built bigger companies, whatever — and they’ll ask about getting popular on social media. And my immediate response is, “But why? You’re doing awesome and you could be private. That sounds way better.”
So I would wonder, is it even worth it to have a million for you? In your case, actually the answer is probably yes. But that’s something I always ask people when they talk to me about social media. I think for a lot of people the answer is no. It’s almost the cliche example of “play stupid games, win stupid prizes.” If you play the “I want to be popular on social media” game, you win the wonderful prize of having a bunch of followers who don’t really know or care about you, and you basically turn your life into a performance for them.
Shaan: So you sort of win the stupid prize in the end. For me, after a bunch of soul searching, it became very obvious that the thing I actually wanted to do — the thing that would bring me the most joy in my life — is if I get to be kind of like one of these thinker guys. I don’t actually want to be Elon Musk. I want to be Tim Ferriss.
And once I realized that and that sounded very true for me, I was like, okay, I got to do that. I got to go learn cool stuff, synthesize information from a bunch of places, and then try to teach it. I like teaching it. I’ll try to share it. I’m so excited about the stuff that I’m figuring out, I’d like to create content. And I’m good at creating content, so it’s a good fit for me.
For me, it is probably the right game. I wouldn’t say “being popular on social media” is the right way to phrase it. I think it is like getting to be a thinker — making that your actual job.
Sam: Me calling it “popular on social media” — it’s like calling it a “creator.” It just sounds cute. That’s not how I meant it, but that’s how it sounds.
Lesson: Negotiation and Getting Comfortable Being Uncomfortable [00:21:00]
Sam: All right, the biggest thing I learned this year — and I have a bunch of them, but number one, the biggest thing. I’ll set the stage here.
I think last spring — do you remember what month? — so basically when I sold the company to HubSpot, I had a two-year deal where stock had to vest, whatever. That ended in February. And then we had to renegotiate some contracts. I think we started that end of April, and it didn’t end until September — August, September.
So we go to negotiate this contract, and I’m a pretty soft guy. I have known all along that I’m bad at negotiating. Hard on the outside, soft on the inside. I’m just not good with uncomfortable conversations. I don’t love confrontation. I want people to think I’m easy to deal with. But I leave a lot on the table. I leave a ton on the table.
And we go to negotiate this contract and, Shaan, you were like, “Let me take the lead on this.” And you did so many things that I thought were the stupidest thing ever. I was like, “You’re being rude. This is stupid. You’re asking for too much. You’re being difficult. You’re in the weeds too much. Why do you care about this one?” It’d be a five-page or eight-page contract and you’re like, “This one sentence, guys — we need to talk about it. We need to change this word from mandatory to optional.” I think we probably had ten revisions. We had to hire a lawyer to go through all this stuff, and we sweated the details so much.
In my heart, I was like, everything about this is wrong. And you want to know something? I was wrong. You were right. You negotiated this wonderfully. And I learned so many things.
I could summarize this in something you said — I think someone told you: “The person who can be most uncomfortable in a negotiation will oftentimes win.”
Shaan: I think that’s it. So the way you said it isn’t actually the way I would say it. You said whoever’s more uncomfortable will win. And actually, the first thing negotiators realize is it’s not about winning. Both sides want things, usually different things. You have to make sure both sides get what they want so that both sides feel like they win.
But it is true that you have to be willing to be uncomfortable — almost like the definition of the word uncomfortable — for longer than you’re comfortable being uncomfortable. That’s what I was trying to say. Because it’s very easy in the moment to say, “If I push this button, the pain stops and the uncertainty goes away and the item goes off my to-do list.” It’s very tempting to want to push that button.
Sam: Well, at The Hustle we did enterprise sales — $100,000-plus advertising deals. I wasn’t particularly good at that, but one thing I learned early on — and it’s true for any salesperson — it’s best to not be like a hard-hitting “I’m gonna sell you this” guy. Instead you say, “All right, so what are you guys looking for? What are you trying to get out of this? Do you need more customers?” You basically ask them what they want and then you tailor a solution to fit their needs.
You did a really good job of that. You were like, “All right, HubSpot, tell me everything you guys want and we’ll try to accommodate.” And you’d phrase your solution to fit their needs. You did a really good job at that.
Lesson: Tax Planning and Real Estate [00:25:00]
Sam: All right, let me do a simple one. This year, my cash flow — my monthly income — went up by like four and a half X. However, I was very focused on making money and I didn’t — I normally don’t care about expenses. You know that phrase, “It’s not how much you make, it’s how much you keep”? That’s true. I just don’t really follow it very well.
The biggest expense is always taxes. And I didn’t do a lot of tax planning. So this is a very simple one — one of my big takeaways for the year is, lesson learned again, that taxes are your biggest expense once you start making real money.
I looked into a bunch of different opportunities, and only at the end of the year did I do something smart. I know somebody very well who is phenomenal at real estate. They have a very niche application of real estate. They crush it — I’m talking about going from zero to owning a billion dollars in real estate with no outside capital in like eight years. I watched them do that brick by brick. I know this specific thing that they do where they have a bit of an unfair advantage.
I never really asked them to participate in a deal. They don’t take any external money. But I know we have a good relationship, so I was like, “Maybe they would take it.” Finally towards the end of the year I was like, “Hey, can I deploy some capital here? Because if I can invest with you, I think I’ll get a great return, but I also get that sweet, sweet depreciation.” So I get a double return — the returns for the property but also the tax savings today.
I just started doing it, and it is so good. It is so smart. And I am so regretful that I didn’t take this more seriously earlier.
Jess Ma came on the podcast and she said — it was her that triggered me to take action on this. She goes, “I want to talk about what rich people do with their taxes.” We didn’t even really get to that in the episode, but during the pre-call I was like, “What do you mean?” And she’s like, “I think the general thing is that most entrepreneurs really don’t spend enough time on their taxes. I get it, they want to build their business, but if you just look mathematically — between 30 to 50 percent of all your income every year gets taxed, and 20-plus percent of all your investment gains. It’s financially irresponsible to not at least spend 5 to 10 percent of your time on this.”
Then I did the math and I was like, “10 percent of my time would be five full weeks of a year.” There’s no way I’m going to do that. But I should at least spend like one or two weeks where I’m actually focused.
Shaan: Did you do like a tax strategist?
Sam: I talked to a few, but the reality was it’s not that hard. Real estate really is the best way to do this. What you do is you take income — you have taxable income coming from one place — you take that cash, you deploy that cash into real estate. And my wife is a real estate professional, so we can offset the active income. You put the cash there, now that cash is going to grow in the property, but you get all this tax loss to wipe out your taxable income. So you get cash on both sides, but the taxable income gets reduced by using real estate.
By the way, it is hard — it’s hard to find deals that are good. That’s the key. I knew this for a long time. I was like, “Great, what am I gonna do? Go look for fourplexes in Missouri?” I don’t have the time or energy or expertise to do this. Then you have a bunch of fund manager types and you’re like, “I got to vet them and figure out if they’re any good.”
In this case I was lucky that I had a very longitudinal relationship with somebody I had seen do this with their own money — they’re not a money manager. And they get far above average returns. So that became the thing I’m gonna do. We should talk more later. You should do this too. I’m so convinced this is a good idea for people in our position. Most of our friends in our circle — we’re all internet money people, and we kind of suck at the real-world money stuff.
Shaan: Yeah, I suck at it.
Lesson: Loose Cannon, Loose Results [00:30:00]
Sam: All right, I’ve got another one. I’ve titled this “Loose Cannon, Loose Results.”
For the majority of my career, I’ve been a loose cannon. I would say silly stuff and it would get a reaction and I would get results — sometimes a laugh. I was in the media business, we are still in the media business, so I can go the obnoxious or blunt or ridiculous route and get clicks.
The problem with that is, as you get more popular, you have to decide: are you going to go all in on that, or are you not going to go all in on it? The medium ground is bad.
Here’s an example of someone who goes all in: Dave Portnoy. The guy’s a missionary for it. He says ridiculous stuff. He had a sex scandal this year — regardless of what the facts are, I’m not even debating the facts of his issues. He was accused of some really bad stuff. And he went all in on it, he confronted it head-on. There’s other things he’s done where he’s like, “Look, I’m so rich I can do all this stuff.”
But there’s a downside. The upside is he got lots of traffic. Whenever he goes through any type of scandal, he gets lots of views and somehow he gets paid through those ads. The downside is obvious — you are now this guy where you’ve got to live this life. You’re this loose cannon guy, you say whatever you want, and you’re a huge target.
Then we’ve gotten really close with Andrew Wilkinson, who is not a loose cannon. He says some stuff bluntly, he’s a very honest guy, but he’s reserved, more measured.
Shaan: Yeah, he’s more measured.
Sam: We had Syed Balkhi — one of the best guests we’ve had. Very measured. The guy’s only 32 or something and he’s in the ballpark of being a billionaire. He owns all these companies. And off-air, when I’ve hung out with him, he’s a little bit less measured, but on-air he was very like, “Look, my reputation matters. I need to have a good reputation.” And he cared about that stuff.
We also had Kevin Ryan — probably the second or third most successful guy we’ve had on the podcast. Very measured, very honest, very straightforward, but also calculating. Sarah Moallef was another person — she explicitly said, “I don’t want to be famous. I’m only gonna be here.” She still said good stories, but her reputation was in mind.
And I think that I’m not willing to go the Dave Portnoy route, for sure. I don’t want that flak. I’ve said very mild things and I’ll get flak for it. I just don’t want to live this life where I go hardcore. So anyway, a takeaway is I’ve actually wanted to pull back some public persona stuff — not reveal certain numbers, I don’t want to be a target, I don’t want to have to fight these battles. I don’t get joy from that. I used to get joy from that. I would respond to haters constantly online just to prove like, “See, you can’t talk to me. I’m a real guy, I read all the comments.” That’s stupid. I don’t want to be that person.
Shaan: That’s a pretty big takeaway. You’ve done a good job — you’ve had a few fires this year where you said some stuff that you got called out on, and you didn’t back down from it, but you also didn’t engage in it.
Sam: I don’t even remember.
Shaan: There was a time where you criticized someone who worked for you and it caused a little bit of a spat on the internet. I don’t remember another time, but that’s what I’m referring to. And in my head when I’m hearing you say that or seeing that, I’m like, I want to stay out of this. I don’t want any of this drama. I don’t want the stress.
We’ve seen it with Chamath a bit, where he put himself out there and he’s done some contradictory things and he’s taken a lot of flak. And I respect that he’s owned up to it and he faces it head-on. I don’t want to live that life. I thought I did. I don’t. As we’ve gotten more popular, I for sure do not want to live that life. I prefer to be more private now than I was in the past.
Lesson: Go Up-Market, Not Down-Market [00:34:30]
Shaan: That’s a good one. I have kind of a related one.
One of the best meetings I had this year was with James Currier. For those who don’t know, he is the founder of something called NFX, which stands for Network Effects. They have about a billion dollars of assets under management. They invest in tech startups. He’s been a Silicon Valley OG — he’s been building successful tech companies for like 20 years. He’s had multiple hundred-million-dollar-plus exits. Super fun guy.
So I go to his office. I drive down to Palo Alto. I don’t usually leave the house, but for James, I’m there. And literally it’s just me and him in the office. I was like, “Where’s everybody else?” He’s like, “We don’t really even have that many people, but also nobody’s coming to work anymore. Everyone works from home.”
So it’s me and him in his office for a couple hours, and he shared with me a piece of advice that really stuck with me. He goes, “Can I give you some unsolicited advice?” I was like, “Please.”
He drew this line on the whiteboard and he goes, “I really like what you guys are doing with your show, but I don’t know where you go from here. You’re kind of in the middle.” Meaning, if I think about really up-market — he’s like, “When we make content, we’re not making content where we want a million views. If we did a million views on a piece of content, we probably made the wrong piece of content.”
Because what he’s doing — he’s trying to invest in the next Airbnb, the next Twitter, the next whatever. He needs the most ambitious founders in the world who are building venture-backed tech companies to read their stuff, really care about it, and think, “When I’m going to raise money, I’m gonna go to NFX.” So you have NFX and a16z and others trying to be really up-market because they’re trying to attract a certain quality of founder, of which there’s only a smaller pool.
But they also care about different things. They don’t want to hear about the vending machine side hustle. Like, we’ll be like, “Oh dude, this 18-year-old has vending machines making $22K a month, isn’t that sick?” And he doesn’t care about that. They’re trying to get only people who are going to disrupt the healthcare system or something — such a big idea who even knows what it means.
Sam: By the way, I would disagree with him. I think they care enough to listen but not enough to actually do anything about it.
Shaan: Yeah, the vending machine thing — actually you’re right. I meet a lot of these people and they’re pretty fascinated by the economics of stuff outside their world because they’re business nerds. I think they care enough to be entertained by it. But that’s about it.
Then you have on the other end of the spectrum — and I love Gary Vee, but Gary Vee is basically motivation grind. His content will literally be like, “I’m gonna pull up to this garage sale and I’m gonna flip this VHS on eBay. And imagine if I did that every day, that could be your hustle. You could make a hundred grand a year.” It’s kind of a job that can do that, but this is the entry level of entrepreneurship.
He has a huge audience, which I respect. But the best investments Gary’s made, I think, came from his peers — his friends he hung out with — not from his listeners. Not his fans.
And it’s very easy if you’re in that position to be like, “It’s great because I get huge numbers, but I’m not necessarily learning back from my audience.” I’m happy to sign autographs and take selfies, but I’m not excited to go have dinner with five people in this group because I don’t feel like iron’s sharpening iron there. I’m a black belt mostly hanging out with white belts. When I’m trying to spar, I want to spar with black belts.
Anyways, he’s like, “You have a decision to make. You’re in the middle right now with My First Million. You kind of have a foot in both camps.” He’s like, “It’s going to be very tempting for you to go down-market.” He’s like, “Don’t do it. If anything, go up-market.”
In the long run, you’re going to be more interested in the topics that those people are interested in. You’re not going to want to keep saying the same beginner-level stuff — “Here’s how you make your first million, here’s how you quit your job, here’s how you get a startup idea, here’s how you incorporate an LLC.” You’re not going to want to make that content as you grow. His only advice was: steer up-market.
I think that was so smart. I don’t even know why he said that to me, because who’s even thinking about that? I wasn’t even thinking about it.
The Alex Hormozi and Genius CEO Examples [00:40:00]
Shaan: But now — I’m just gonna give you an example. Alex Hormozi, I think, is in one hand absolutely killing the content game. I think Alex is awesome, super talented. But I think he’s making a mistake in that he goes very down-market.
I’m just going to read you some titles of his videos from the last two months: “How to Make So Much Money It Makes You Sick,” “How to Get Rich This Black Friday,” “Watch This If You’re Tired of Being Broke,” “The Real Reason Your Business Isn’t Growing.” A bunch of these. So these are more down-market video concepts and they’ll get views for sure. And the comments will kind of show you — “Oh my God, you changed my life, you’re my hero.” And it’s not that he’s not doing a service for those people.
However, I look at that and I think — for me, the game I want to play is definitely not to go down-market, to resist the temptation to create that content, and to focus on creating up-market content, which is going to have a lower view count but higher value per viewer. It’s like I’m creating a magnet, not an audience. I want to attract the right people. Anyways, that was a big lesson for me — I wouldn’t have otherwise thought about it.
Sam: Yeah. Sometimes some of the contractors who work on this podcast will suggest ideas because they’re just looking at YouTube analytics, and I’m like, “No.” Eight out of ten things I don’t think would work. If Apple sold iPhones for five dollars, they’d sell more units too. But if you’re building an up-market brand, if you’re Louis Vuitton, you don’t want to go down-market.
And even though you and I will fight it, sometimes we will fall victim to it as well. I don’t want to act like we’re above it. The only reason this lesson resonates is because it’s something I’m wrestling with. If I had it solved, I wouldn’t care about it. This is a problem I have, so I’m trying to figure out where to go, and this advice was very helpful.
Shaan: There’s another guy — have you seen this guy on Instagram, “The Genius CEO”?
Sam: Yeah, he’s in Austin right now. I think he’s so funny.
Shaan: So funny. When I met him, I can’t tell if his Instagram is a joke. There’s a lot of nuggets in there, but he’ll be like, “Bad Bunny is only making 30 million dollars a year? What a move. We’re gonna teach this guy how to make a billion.” He’ll insult these people and it’s pretty funny. He’ll be like, “This product is going to bust faster than a bunch of you chumps out there. So let me tell you how I would do it.” I was like, “Who — what a hook.”
But we met this guy in real life — total sweetheart and very smart guy. Super nice dude, humble. And I’m like, “Why do you have this ridiculous mustache, your fingernails are painted, you got this crazy chain and a Gucci purse?” He looks like a celebrity — tall, good-looking guy, looks like an IG model. But in person you’re a totally respectable, humble, nice guy and dad.
And he was like, “Oh yeah, I created this character. I realized what hits on IG is going to be fancy cars, fancy stuff, six-pack abs, hot girls. So I just do that. It’s my character. And I built a following.” He’s got 200,000 followers. His content is hilarious.
But he’s selling FBA brands — basically “I made my millions doing drop shipping and FBA brands. If you want to stay being a broke idiot, don’t listen to this video.” And then he’ll be like, “Here’s the first lesson for you. Do this. And I know what you’re gonna say — blah blah blah. Well, here’s what I say about that.” And then he flashes fancy stuff. “This is a video of me buying this Van Cleef necklace. Any questions?”
I’m like, “Wow, what is happening with this guy?” But I think he’s also gonna be trapped in the down-market thing. He’s selling a mastermind — you got to pay to get in. He’s going to make millions of dollars doing this, but I don’t think he’s got any way out. He’s cornered himself in that way.
Sam: Sure, sure. He’s a good follow. Very funny.
Lesson: Choose Your Game and Play It Hard [00:44:30]
Sam: All right, let me give you another one. The biggest takeaway that I want people to have from this podcast — we’ve done it now for three or four years — and at first, I’d go get a haircut and they’d be like, “So what do you do for work?” And I’m like, “Oh, I do this, I do that, I work on this podcast.” And they’re like, “What’s the podcast about?” And I’m like, “Well, it’s called My First Million, but the title is inaccurate.”
I’ll explain what it’s about, and what I tell people is: look, we’ve had multi-billionaires on this show, we’ve had employees at companies on this show. I think what we care about is people who create a path. And they do it not necessarily — I don’t necessarily think just because you are a billionaire you are particularly better than anyone else. What I care about is someone who says, “I’m gonna be great at this weird type of art.” They intentionally choose a game, and then they play the hell out of their game.
Shaan: Right. That is the description, because that’s what it is for me. That’s exactly it.
Sam: And so for example, the guy I talk about all the time — Brett Adcock. He’s not like me. He’s like, “I’m gonna raise billions of dollars and try to create a $500 billion company.” I’m inspired by that, but I will never do that. I don’t want to do that.
Or even this example we just gave — the Genius CEO. He chose to play that game and he’s playing the hell out of it. I respect that. I don’t want to do that, but I admire people who intentionally choose their game and then play the hell out of it. I admire the hell out of it.
Or we’ve had John Coogan — he started Soylent, which scaled to be a fairly large business. He’s got another company and now he’s a full-time content creator. He has a YouTube channel and it’s beautifully done, he’s doing it wonderfully.
Then we’ve had Rob Dyrdek on, we’ve had Laird Hamilton on — guys who aren’t the Silicon Valley type of lifestyle, but they kill it at whatever they do. And I admire all of them equally.
So the takeaway that I’ve had is: there’s a million ways to get to where you want to go. For a lot of these people it’s money, but there’s still a million ways to get there.
For example, when I moved to San Francisco, I was like, “You have to raise VC, you have to do this, you have to do that.” But then we meet Syed, who I imagine is worth $500 million to a billion dollars. He started a WordPress blog — which sounds crazy stupid if you don’t know what you’re talking about — turns out that killed it. Then he bought tons of gas stations. Now he owns 50 different WordPress plugins that collectively do over $100 million in revenue. He’s a young guy in Florida, not even a cool part of Florida. He’s not Miami — I think he’s in Tallahassee or somewhere.
Shaan: Yeah, no disrespect, Tallahassee. I see Ari, but there’s just — people just listen to this podcast, “Oh man, their hometown where they grew up.” Dude, Fort Lauderdale, I don’t care. I’m from St. Louis. I could say these things. I’m not from a cool place. So all the Baltimores out there — shout out to the tier-C cities. It’s objectively not the place to be.
Sam: But what I’m saying is, I appreciate the hell out of people like that. And learning about all of these different ways — my biggest takeaway from this year doing the podcast is: there’s a lot of different ways to do it. You just have to choose where you want to go and choose what rules you’re willing to play by. But there’s not one way to do it.
I wouldn’t even go as far as to say there’s one that’s most likely. In fact, if I had to say, the one that’s most likely to get there is starting a small services business and just growing it over 50 years and paying yourself a good salary after year 10, and doing that for decades. Which is not at all what I would have expected. A normal small business owner that does it for a long time is significantly more likely to have a higher income and die rich than any other way. But there’s a lot of different ways to do it, and that’s one of the things I appreciate about doing this podcast.
Shaan: That’s a great one. And I do think that, if you zoom out, that is kind of the point of the pod. The point of the pod isn’t saying “do X” or “do Y.” It’s “check this out — you can do X, here’s how that works. You could do Y, here’s how that works. You can do Z, here’s how that works.”
By the end of it, you’re either going to be in one of two positions. Some people hear all that and get overwhelmed — they don’t know where to go, too many paths, too many possibilities. It paralyzes them. But I hope that’s not most people.
I think for most people, the net reaction is kind of like: “Wow.” Winning and being successful is this thing that feels scarce if you’re not around it. Where I grew up, I didn’t know any business people. Nobody in my family was a business person — not my cousins, not my aunts, not my uncles. None of them did businesses.
Sam: You’re raised in Tallahassee, born in Oklahoma.
Shaan: And so I wasn’t around it. It seemed like this far-away thing that I didn’t really even understand. There was no map. And I thought maybe there’s one path but I don’t know it, and I’m not invited to that party.
My hope is that if you listen to this podcast, you’re going to hear over the course of a year a hundred different examples of ways to win and how they work. And at that point it’s just a matter of choosing. All of a sudden, winning and success becomes this thing that instead of being scarce and difficult is abundant — it’s everywhere, and it’s right at your fingertips if you just start doing whatever sounds most intriguing to you, and then you just keep playing the game. It will work out for you. That’s what the pod ultimately does for people, I think.
Sam: Good. I hope it does.
Lesson: You’ll Always Want More — and That’s Okay [00:51:00]
Shaan: I have one more. Do you have one more?
Sam: You go.
Shaan: All right, my last one. We had Scott Galloway on. Scott Galloway is a guy who sat on the pod and goes, “I’m worth over $100 million.” And he also said in that same sentence, “I’m deeply afraid of running out of money.”
We had Morgan Housel on most recently, and he said something like — he knows that you shouldn’t necessarily set goals for money, and he knows objectively he’s got enough that he likely won’t ever run out, and he knows he shouldn’t check his net worth. But then we pressed him on it, and he was like, “But of course, if I’m laying in bed at night, just because I know what I’m supposed to do, I still wonder what it would be like to have more.”
And I don’t think we’ve ever had anyone on the podcast — maybe Jack Smith, but Jack Smith’s a freak — I don’t think we’ve ever had anyone on the podcast who, regardless of what they have, doesn’t want more.
That sounds like a really negative thing — “What, you have enough, why do you need more? Why do you need to achieve this and that?” I think it should be the opposite. The takeaway is: no matter what you have, you’re always going to feel that there’s another level, that you should one-up. And I don’t think that’s a depressing takeaway.
I think the takeaway should be: you will always want more accomplishments, more achievements, and that is okay. That is totally okay and that is normal. Just expect that wherever your goal is, once you achieve it, you’re going to feel satisfied only for a short amount of time and then you’re going to want to achieve more. And 99 percent of the time, that’s true. And that’s okay. It’s okay to want more.
I think there’s a healthy way to go about it and there’s an unhealthy way. I would say Scott probably has unhealthy ways. I would say I have unhealthy ways. And I think you can change those unhealthy ways to healthy ways. But no matter what, you will accomplish whatever your goal is, you will get there, it’ll take six months, and you’ll say, “What’s next? How do I do it again? How do I do more?” Just expect that that’s going to happen.
Infinite Games and Practicing Happiness [00:54:00]
Shaan: Yeah, I think when people hear that, it sounds wrong or sad or bad or something like that. But another way of looking at the same thing is the concept of infinite and finite games.
My understanding of it — a very simple understanding — is: a finite game is one where you play for the result. You play in order to achieve an outcome and you’re hoping to get to that outcome. An infinite game is one where you play for the sake of playing.
In practice — for me, basketball is something I consider an infinite game. I play because it’s so fun to play. My goal is not to win and stop. I wouldn’t stop if I won, not because it’s greed — it’s that winning is baked in, the scoreboard makes the game more interesting. In a small burst, yes, by the end of the fourth quarter I want to have the higher score. But ultimately, “All right, let’s run it back, let’s play again, let’s play till our legs fall off” — that’s how it’s always felt for me. That’s the closest thing I felt to an infinite game until business came in.
And it’s actually very similar. I like having a scoreboard — it makes it more fun. But I’m not doing work to get to a result and then stop working. I like playing. I plan to keep playing. I’m playing for the sake of playing. And the scoreboard makes playing a lot more interesting and fun and intense.
Sam: And that should be the takeaway. Because I previously had this idea: “If I get to this, I will not feel stressed and I won’t work anymore.” The reality is, I still felt stress — less stress, no doubt, a lot less stress. And six months later I was like, “But I have to go and do something. I feel like a piece of crap just sitting here.” And I feel good contributing.
Shaan: Why do you think you still feel stressed even after the event?
Sam: I think — to get therapeutic — it’s all baked into some type of childhood trauma, and that just takes years to unwind. But part of the stress is comparing yourself to others — you want to achieve more. And also wanting more stuff, which is — what do they say? Desire is suffering. Wanting more stuff, which I try to combat. I’m like, “No, that won’t make me happy.” Comparing myself to others, wanting more stuff, and also wanting to get rid of a chip on my shoulder.
Shaan: I’ll offer you a different answer that might be true for you — I don’t know if it is or not. But I believe this is more true, because I hear a lot of people talk about childhood trauma. It’s like, “All right, well, nothing I can do about that. That’s literally the past. It’s written.” And it sounds like a long unpacking process. I don’t want to do that. I still got suitcases over here I haven’t unpacked from vacations I’ve been on. I’m not trying to unpack years of childhood trauma.
Similarly, “I have to stop the feeling of envy or desire?” Oh my God, I’m wired as an animal.
I actually think there’s a simpler answer. The emotions you feel are much like muscles. You’ve had a lot of practice at stressing. What happens is people practice feeling a certain way and they don’t think about it as practice. But what does it mean when you do something all the time or regularly? You are habituating yourself, practicing, getting reps at it.
Then suddenly one day they change the environment, and they think that all that practice — that muscle they’ve basically developed — will just go away, and this new muscle called “contentment and happiness” will appear because the bank balance in their Bank of America account has changed? No way.
I would actually say it’s the opposite. If you want to change that feeling, it’s not the money. You have to find a way, on a daily basis, to practice having the feeling you want. You want to feel happy? You got to practice happy. You want to feel content and peaceful? You got to practice content and peaceful. You got to practice that more than you’re practicing anxiety and fear and stress.
So for anybody out there who’s listening, Sam is absolutely right — your feeling is not going to change. But I don’t think it’s because of these deeply rooted psychological and historical reasons. A simpler explanation might be that I’ve really just gotten a lot of reps practicing one thing, so that’s easy and familiar and habitual for me. I got to start practicing the other.
The same thing happened when we sold the Milk Road. I talked to Ben and was like, “Ben, how does it feel? First kind of big exit for you.” And he’s like, “Honestly? I’m kind of disappointed. It doesn’t feel like very much.” He’s like, “Maybe it’s because, maybe if the number was bigger, maybe this…” He started going down that path.
And I was like, “No, dude. It’s because you’re trying to feel this kind of victorious joy. How many days out of the last 365 days did you let yourself feel that? Zero. So what do you think — all of a sudden today you’re going to turn on and be really good at feeling that? No, dude. It’s practice. If you want to feel that, we got to do that regularly so that muscle’s there.”
Sam: Do you come up with this theory on your own, or did you steal it?
Shaan: Tony Robbins — when I was at that event, he has a similar thing. He calls it your “emotional home.” He goes, “Everybody’s got an emotional home.” He’s like, “Watch this. Raise your hand if you’re somebody who sometimes gets a little pissed off.” Everybody raises their hand. “Raise your hand if sometimes you are just super silly, having fun, being playful.” Everybody raises their hand. “Okay, so we’re capable of both. You are not just an angry person or just a super nice easygoing guy. We all fluctuate.”
And he’s like, “But it is true that we have an emotional home. It’s the place — like your home — it’s the place you spend the most time.” He’s like, “If your emotional home is that you are stressed out, it doesn’t matter if you sell your company for a billion dollars. If you grinded for seven years and you were stressed all the time, you’re not just going to become a different guy all of a sudden. Because that’s your emotional home.”
But he’s like, “Good news is, you can move it.” He’s like, “You can move it if you basically practice it.” He’s like, “You don’t want to wait for things to happen to feel a certain way. You want to have it on call, that you can change the way you feel that fast.”
And a lot of the Tony Robbins events, the reason why people feel like he’s almost manipulative, is because he literally is manipulating the way you feel. He’s showing you that you can go from focused to jubilant to Zen and calm and reflective to motivated and inspired in a 30-minute span, just by the way he’s prompting you. And the trick obviously is to learn to do that yourself so that you are in control of your own mood. You’re the master of your own mood.
That became a big focus for me after that event. That was my big takeaway from the event, and I started practicing that for the last six or seven years.
Sam: I wish you had come up with that on your own, because you don’t realize it, but one of the big three — there’s Sigmund Freud and then there’s two other guys who are considered the godfathers of 19th-century psychoanalysis — one of the guys is Alfred Adler. There’s a book called The Courage to Be Disliked that’s quite good. And what you are saying is exactly in parallel with what he has said about happiness. It’s like, “You’re anxious because you’re choosing to be anxious and you’re not choosing to do this other thing.” He’s got this whole book on it.
But you didn’t realize it — you’ve just discovered, relatively, the theory of relativity, just like Albert Einstein. You didn’t even know about it. So you’re kind of like one of the big three.
Shaan: Adler, the guy sounds like a smart guy. I like the sound of this. I’m gonna go check this out.
Closing [00:60:00]
Sam: So that’s it. All right, where do we go from here?
Shaan: That’s it. I think we wrap it up. Thank you to everybody for listening. Those views ain’t going to view themselves — it’s because of you guys.
We just talked about wanting more. Sam, are you satisfied? Are we done? Do we have enough subscribers?
Sam: We only have 360,000. Mr. Beast has 100 million. We’re nothing. We’re losers. I’m anxious about this.
Shaan: So if you’ve enjoyed this episode, if you enjoyed any of our episodes, subscribe on YouTube. Also go to Spotify, go to Apple Podcasts, and subscribe.
Sam: Could go to therapy and stop wanting this. Or you could just click the button and make us feel happy. Which one? Save us years of therapy and just click subscribe. And just say “you’re welcome” in the comments. And we know — when you say “you’re welcome,” it’s because you saved us years of therapy. You just gave us what we wanted instead.
Shaan: All right, that’s the pod.