Every Business I Tried Before Making My First Million

Summary

Podcast Summary: “Every Business I Tried Before Making My First Million”

Podcast: My First Million (HubSpot Media)
Date: November 17, 2025
Hosts: Sam Parr & Shaan Puri

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Overview

In this episode, Sam Parr opens up about the many businesses he started—and often failed at—before ultimately making his first million at age 31. Alongside Shaan Puri, he takes listeners through each of his hustles, sharing lessons learned, hilarious anecdotes, and the winding (and sometimes humiliating) path most entrepreneurs face on the way to success. The episode is candid, motivational, and funny, emphasizing the virtues of scrappiness, relentless learning, and the importance of choosing the right projects.

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Key Discussion Points & Lessons

1. Early Flips and Learning the Basics

[00:59] – [02:07]

• High School Flipping:
  • Sam’s first “business” was in high school: collecting old sports equipment (often free) from graduating seniors and selling it on eBay for $2,500 over a summer.
  • Continued a version of this in college, storing and reselling textbooks and items left behind by students.
• Lesson:
  • The power of finding value where others don’t (“flipping assets that other people...might even not value”)

    “Most of the time, I didn’t buy it. They would just give it to me...I made $2,500. That was my first business where I actually started making online money.” – Sam Parr [00:59]

2. The Hot Dog Stand: Grit, Salesmanship, and the Limits of Manual Labor

[02:07] – [04:08]

• Southern Sam’s Hot Dogs
  • With $500, Sam started “Southern Sam’s: Wieners as big as a baby’s arm” in college.
  • He worked long hours, sometimes making as little as $50/day, other times $1,000 at big events.
• Lessons:
  • Sales and copywriting are essential, and selling in person teaches foundational skills.
  • Manual labor business isn’t scalable: “It was so hard...I realized, what if I could do this on the Internet, where I could write something one time and have an infinite amount of people come and read it and I didn’t have to sell constantly.” – Sam Parr [03:50]

3. The Gray Hat Phase: Moonshine and Risky Ventures

[05:44] – [07:14]

• Online “White Whiskey” Shop:
  • Entered the “moonshine” business, selling what he believed was a legal novelty online.
  • Made $10,000 in a month, but legal advice quickly ended the operation.
• Lesson:
  • Quick-money, “gray area” schemes teach about legal risk and aligning with personal values.

    “...if you’re gonna do something like this, you better really do it right, and you better pick something that aligns with your values.” – Sam Parr [05:44]

4. Networking in San Francisco: The Anti-MBA Book Club

[08:41] – [10:41]

• Building a Network:
  • Created a book club for non-MBA types, attracting 2,100 sign-ups and forming meaningful friendships (including his future best man).
• Lesson:
  • Community building can be more valuable than initial monetization, and sometimes “forcing functions” push personal growth.

5. App Experiments: Roommate Matching and Bunk

[10:42] – [12:13]

• Roommate Matching Platform (“Bunk”):
  • Partnered on a roommate finding/project matchmaking idea, hosting events.
  • Briefly pivoted to “Tinder for Roommates”—which mainly attracted people looking to date.
  • Acquired (“acquihired”) after 9 months.
• Lesson:
  • Roommate apps are classic rookie mistakes; monetization is tough. Choose product & target market carefully.

6. Developing the Right Skills

[12:13] – [13:57]

• Top three must-have entrepreneur traits:
  1. Money-making skill (sales, copywriting, creating value)
  2. Tenacity and scrappiness (“animal inside” to hustle through hard times)
  3. Project selection (choosing scalable, non-risky, meaningful projects)
• Sam credits copywriting as his critical skill, and countless hours of “getting after it.”
• Notable Quote:

  “Copywriting. And also just like tenacity, but like getting after it. But copywriting was the one. And marketing.” – Sam Parr [12:38]

7. Contrasts: Scrappy vs. Fancy

[13:57] – [16:32]

• Shaan recounts working in a flashy, 30,000 sq. ft. office, while Sam and friends hustled in a barely functional, shared apartment/office.
• Ultimately, scrappiness led to real results—big teams aren’t always better.
• Notable Moment:

  “You had a chef there every single day. We had a masseuse. On Fridays we had open bar... And you actually were the one who was building something successful.” – Shaun [14:47 – 15:35]

8. Project Selection and Risk Minimization

[16:32] – [24:16]

• The Process:
  • Eliminating “bad businesses” through hard-won experience.
  • Sam’s current criteria: “Can I bootstrap it to $100 million in ten years?”
  • Looks for “forgotten businesses” in less-competitive spaces, markets where “serious operators don’t take it serious.”
• Risk vs. Uncertainty:
  • Entrepreneurs aren’t reckless—they minimize and control risk, aiming for high certainty in “non-obvious” but proven models.
• Notable Quote:

  “The name of the game of entrepreneurship is just, can you handle the fear? And can you handle—what’s worse is the uncertainty—over potentially 5 or 10 years.” – Sam Parr [19:45] “You are a good example of what most entrepreneurs really do, which is they’re actual risk minimizers. It’s like, how do I win while taking the least amount of risk necessary?” – Shaun [22:18]

9. Failures and Odd Hustles

[25:22] – [30:00]

• Itch Juice:
  • Attempted a short-lived “poison ivy treatment” business, learning again that quick profits can't replace passion.
• Frisco Disco Taxi:
  • Novelty “disco taxi” on NYE (before Lyft/Uber); $800 in one night.
• Events and Real Estate:
  • Ran successful conferences/newsletter (The Hustle) and tried real estate (not for him—needs “diligence on the buy”).
• Lesson:
  • Many hustles fail; only through trying many things (“process of elimination”) do you hone in on what actually works and fits your talents.

10. The Podcast Journey

[31:42] – [34:17]

• “My First Million” itself started awkwardly—shared AirPods, few mics, borrowing chairs—with almost no initial revenue.
• Over time, random, scrappy efforts lead to surprising results.
• Notable Moment:

  “Honestly, it got to be pretty cool. When we were in person together, it was pretty amazing. I wish we could be doing that.” – Shaun [33:44]

11. Reflections, Nostalgia, and Advice

[34:21] – [39:44]

• The “Come Up” is Fun in Hindsight:
  • Despite wanting anything to “work” at the time, the struggle provided the best memories and learning.
• Advice to Listeners in Their 20s:
  • Enjoy the ride; if you keep hustling and learning, it works.
  • Success is more about your “rate of learning” than a single idea or moment.
• Notable Quote:

  “We have a lot of like young guys listening to this who are in their 20s. Enjoy it, man. It was, it was such a blast. It doesn’t feel that way, but I would say with a high degree of certainty if you do the same thing or you try really hard for 10 years and keep taking risks... It works, you just gotta do it.” – Sam Parr [35:27]

12. Final Lessons on Growth and “Rockets vs. Cars”

[37:37] – [39:44]

• Looking back, even when business was growing well, it never felt like enough—founders always compare to “rockets.”
• Most startups are “cool cars”—not all need rocket fuel (VC money).
  • Focus on sustainable, personal businesses rather than chasing unicorn-style growth.

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Notable Quotes & Moments

• “I was broke. I had my PhD: poor, hard working and driven. I was.” – Sam Parr [03:38]
• “To win in business, you gotta have... a money-making skill, tenacity, and good project selection.” – Shaun [12:13]
• “Entrepreneurship is sort of like, how much uncertainty and fear can you take and still continue moving forward?” – Sam Parr [19:45]
• “The secret to success is weak competition.” – (Charlie Munger, referenced by Shaun) [19:00]
• “We’re just going to go in that direction and I pray and I hope that we’re going to find something... that’s what the uncertainty feels like.” – Sam Parr [28:00]
• “Rate of learning. How quickly are you figuring things out?...If you do that, success is pretty much inevitable.” – Shaun [36:03]
• “You never made the mistake of building something nobody wanted to, which is maybe the main mistake.” – Shaun [36:54]
• “VC is like rocket fuel. And you know who deserves rocket fuel? Rockets. Not fast cars. Not cool cars. Not cars that you love. Rockets.” – Sam Parr [39:00]

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Timestamps for Key Segments

• Sam’s First Business (Flipping Sports Equipment): [00:59]
• Hot Dog Stand Stories and Sales Lessons: [02:07]
• Moonshine Business and Legal Scare: [05:44]
• Building the Anti-MBA Book Club: [08:41]
• Roommate Matching App “Bunk” and Startup Fads: [10:42]
• Three Entrepreneur Must-Haves: [12:13]
• Scrappy vs. Fancy Office Life: [13:57]
• Project Selection and Risk Minimization: [16:32]
• Process of Elimination in Business, and Ikigai: [17:15]
• Risk vs. Uncertainty (Mohnish Pabrai, Branson Story): [20:56]
• Oddball Hustles—Poison Ivy, Disco Taxi, Real Estate: [25:22]
• Newsletter, Podcast Beginnings, Janky Setups: [31:42]
• Nostalgia and Advice for 20-Something Hustlers: [34:21]
• Car vs. Rocket Company Metaphor: [39:00]
• Closing Thoughts & Announcements: [39:44]

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Tone & Style

• Conversational, irreverent, and self-deprecating.
• Practical and tactical: heavy on “lessons learned” through mistake and hustle.
• Motivational, speaking directly to listeners who are early-stage entrepreneurs.

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Final Takeaway

Sam and Shaan turn the “overnight success” myth on its head, sharing that the path to your first million (and beyond) is paved with failures, experiments, wild pivots, and more than a little self-delusion. The secret? Stay scrappy, learn fast, and don’t worry about taking a decade to “figure it out”—that’s how almost everyone gets there.

(Next episode: Shaan’s own list of failed and forgotten startups.)

Transcript

[Sam Parr]

All right, everyone. On this podcast, we talk a lot about the successes, but I want to talk about the failures. So here's about 10 different companies that I started before I made my first million. Almost all of them, they sucked. It didn't work. But I'm gonna explain how much I made for each idea and the lesson that I learned.

[Motivational Speaker]

I feel like I can rule the world. I know I could be what I want to. I put my all in it. Like, no days off on the road. Let's travel.

[Shaun]

What's up, Sam?

[Sam Parr]

What's going on?

[Shaun]

Let's set this up. Name of this podcast, My First Million. When did you make your first million?

[Sam Parr]

So cash, like, cash million? I made it when my wife worked at Airbnb and it went public. And that. That's when we made our first. And then about three months later, I think it went later in December. My company sold in February, and then we made a lot leading up to that. We were doing pretty good too, but I don't think we had crossed 1 million.

[Shaun]

Okay, so you made your first million. Let's call it 31 years old. Here's all the businesses you tried before that before making your first million, which I think is pretty fascinating. I want to go down this list. Does it start in high school?

[Sam Parr]

Yeah. All right, go.

[Shaun]

Go for it. Give me number one.

[Sam Parr]

In high school, I made $2,500 one summer by buying graduating seniors old sports equipment and selling it on ebay. And so what I used to do is I would just buy, like, people's, like, track spikes or, you know, whatever, and I would sell it on ebay. And most of the time, I didn't buy it. They would just give it to me. They would hand it to me, and I. On ebay, I made $2,500. That was my first business where I actually started making online money.

[Shaun]

And this is flipping, basically. This is flipping assets that other people not only undervalue, they might even to not value to the point where they're just happy you took it off their hands.

[Sam Parr]

Yeah. And frankly, I did this in college, too, which I didn't list here is when at the end of the college year, I would. I would stay a few weeks after the end of the school year. And when people were moving out, I said, I have a storage unit. You can come and put it here and just give it to me. You're going to throw it away? Just give it to me. And then I would resell it.

[Shaun]

Exactly. I saw people doing this in college with textbooks. They would just say, oh, at the end of the year, you don't want to take all these heavy textbooks home. You're done with that class. Class. Well, guess what? The next semester, there's a bunch of people that are going to need that exact textbook that were happy to buy it used. And so they would just go buy up people's tech. They would just take people's textbooks, and each book was like, you know, a 40 or 50, you know, future sale that they were able to pick up for free.

[Sam Parr]

Okay. And then at 20, I started a hot dog stand, which everyone makes fun of me for talking about. I have a hot dog stand. You have a sushi restaurant. They're sick of us talking about it, but I had one called Southern Sam's. A wieners as big as a baby's arm. Basically. I knew a guy named Doc who had a hot dog stand. He let me rent it from him with very little money up front. I had. I was able to pay him on the 30th, as opposed to the 1st of the month. So he hooked me up, and with $500, I went to Restaurant Depot and I bought a bunch of Vienna sausages to get my supply. And I was in business, baby, within a week of having this idea. And I used to live in a bad neighborhood. Rydell was my next door neighbor, and he became my best friend. He had served 20 years in prison for attempted murder, and somehow we became best friends. He had. He had the spare key to my house. This was my guy. And Rydell ended up working with me at Southern Sam's. And we spent all day outside, and it was a pain in the butt. Some days I would make 50 bucks. Other days I would go to a concert or like an outdoor place that was popping, and I would make a thousand dollars. And I did that when I was about 20 or 21.

[Shaun]

This is summer in college or what were you doing?

[Sam Parr]

I was in college. I was in class, and so I would work until 3pm I would go to classes from 3pm and to 8pm and then I had a night session where I was out by all the bars. And that would be like 9pm to like 1am that's amazing.

[Shaun]

How did you have the idea to do the hot dog stand? You just saw somebody else doing it.

[Sam Parr]

I met a guy who had a cart and I wanted to do something. Yeah.

[Shaun]

Did he tell you, like, I'm making 300 bucks a night or something? What did.

[Sam Parr]

I saw a video online of a guy saying how much money the Home Depot hot dog guys make. They make $100,000 a year, the ad said.

[Shaun]

And you were like in. I was a man.

[Sam Parr]

I was. I was broke. I had my PhD. Poor, hard working and driven. I was.

[Shaun]

Would you do this again? This one?

[Sam Parr]

No, man. It was so hard. It was so hard.

[Shaun]

Not now, but like if you were 19, 20, and you needed to.

[Sam Parr]

I learned how to sell so well, man. This is what inspired me to get into copywriting. I realized that you had to, like, wheel and deal a little bit. You had a schmooze, you had a flirt, you had to do this. And then I realized, what if I could do this on the Internet, where I could write something one time and have an infinite amount of people come and read it and I didn't have to sell constantly.

[Shaun]

Didn't have to stand there in the heat.

[Sam Parr]

And didn't have to stand in the heat. I will post a photo here. I had these horrible. I mean, look at me. I'm like the whitest guy ever. I had these horrible sunburns that when I took my tank top off, it still looked like I was wearing a shirt. Just a white, like, beater.

[Shaun]

There's this, there's this tweet, tweet that's been going viral. That's. They said flirt with everyone. Flirt with, flirt with women, flirt with men, flirt with old people, flirt with kids. Just flirt with everybody. It's non sexual, but literally just be the most playful, charming person you could be at all times. Like, practice this muscle. And I actually think this is 100% true. I know a couple people in my life that are like this. I'm not really like that, but I've been starting to do it just for fun, just as a little mini game. You know when you're just living a pretty routine life, you're just going to the grocery store, it's either going to be a forgettable experience or you try something to make it a little more fun. I've been doing this and it's kind of amazing.

[Sam Parr]

You know what I call it? You know how people say nonchalant? Be shalant. Be shalott. Don't be nonchalant. Be shalant.

[Shaun]

Shalon as hell.

[Sam Parr]

Yeah, be shalott. Try hard.

[Shaun]

I. I emailed my wealth manager at Morgan Stanley and I was like, hey, I made this trade and it like, it was like a commission of like 100 something bucks. @ the end of like the trade, I was like, is there like a magic button you got over there, man? Like, you got this magic button you could push that makes all Those fees go away. And that was what I sent. You know, the private wealth manager. And he goes, he just replied, magic button pushed. Trades commissions reversed. Enjoy your trading. And I was like, just flirt with everybody. Like, I could have been an annoying Karen. I could have just. I could have just took it, done nothing. I could have been a Karen, complaining. Just flirt a little bit. Everybody likes to be flirted with.

[Sam Parr]

So my next business after that, I started this thing basically in Tennessee at the time, White whiskey, which it's called Moonshine. Moonshine technically means illegal whiskey. But there was these companies making whiskey that was in a mason jar and it. They called it moonshine. And I started selling that online. And I thought I was doing it the right way because I kind of like googled it. And I talked to like a lawyer where I was like, selling it as a novelty because it was kind of like a gift item. I did that for about two or three months. And then I went to my university's, like, entrepreneurship program where they had free legal advice. And I was like, hey, I've made 10 grand in like the last, like, you know, 30 days or something selling this whiskey online. I think I'm following the right rules, but is there anything else I need to be doing? And they're like, yeah, brother, you gotta. You better shut that down tonight. And so that was like my second Internet business, which inspired me to get into the game of the Internet. And my lesson learned on that one was, if you're gonna do something like this, you better really do it right, and you better pick something that aligns with your values. Around this time, I was still drinking and I didn't even like alcohol. But I mean, you know, I had a love hate relationship. And I was like, why am I gonna start selling this alcohol? I don't want to do. This is stupid anyway. But you're going to see there's a pattern. It was definitely like a quick money, which I think everyone who becomes a good entrepreneur, they. They do the gray hat. Gray hat area phase. And this was my gray hat phase.

[Shaun]

Okay, I like it. You started it online. Did you learn about online marketing through this? Like, were you. I mean, how'd you. How'd you get the 10k? Where'd you. Where'd you get your customers from?

[Sam Parr]

I posted on forums, like motorcycle forums. Like, so basically, like, this whiskey that I was selling, people were already searching for it because the guy drink and drive of. Yeah, that should have been the name. People were already searching for this whiskey. But it was very early. And so I was able to rank super easily on Google. And I posted on message boards, forms of people who wanting. People who wanted it. And that's how I made money. Nice. All right, so a lot of people watch and listen to the show because they want to hear us just tell them exactly what to do when it comes to starting or growing a business. And really a lot of people who are listening, they have a full time job and they want to start something on the side, a side hustle. Now, a lot of people message Sean and I and they say, all right, I want to start something on the side. Is this a good idea? Is that a good idea? And again, what they're really just saying is just give me the ideas. Well, my friends, you're in luck. So my old company, the Hustle, they put together a hundred different side Hustle ideas and they have appropriately called it the side Hustle Idea Database. It's a list of a hundred pretty good ideas. Frankly, I went through them, they're awesome. And it gives you how to start them, how to grow them, Things like that gives you a little bit of inspiration. So check it out. It's called the side Hustle Idea Database. It's in the description below. You'll see the link, click it, check it out, let me know in the comments what you think.

[Shaun]

Okay, so now you moved to San Francisco. I think you, you don't. You just do like a cross country motorcycle ride to get to San Francisco as well.

[Sam Parr]

I do it at a later date, but this time I flew out there because I had a job offer at Airbnb which got rescinded when I got there because I'd lied on my resume about getting a dui. And so I was out there, I'm like, what the hell am I going to do? I got to meet people. And so I started a thing called the Anti MBA Book Club. And I tried monetizing it, but I couldn't really at first. And so what I did was I posted ads on Craigslist and on Reddit and I think I posted on Facebook and I got 2,000 people to sign up. And here was the premise. It was called the Anti mba because I was very envious of Stanford students and Berkeley students. I was very envious that they had this network and said, I'm going to read it. One book per month. We're going to break it up into a quarter. So a week, A week, a week, a week. And I'm going to find an expert on that book's topic and we're going to come and discuss it with that expert. I'll organize and get the expert. You come, it's free. And I got 2100 people to sign up to my emailing list. And I had about 20 people show up every single week. Some of those people include C. Eva, who's now one of my best friends is one of your close buddies, Neville Medora, who's now who is the best man. My wedding came from that. And so my best friends came to the anti MBA book club. And if. And I posted a photo. If you zoom in on the top left of the photo, you're gonna see a skeeball machine. I found an arcade that let me host the book clubs for free in that place as long as we play skeeball.

[Shaun]

And you were reading books. Now what kind of books were you reading in this? Is this like, were the books actually useful for you in business or was selling white whiskey the right way to learn business?

[Sam Parr]

I don't remember everything we read, but it was like, it was like Tim Ferriss book the four hour workweek. So you know how like you want to like if I was a techie, I would have built like clubhouse or something actually cool. But I didn't have like anyone discuss these books that I wanted to read. But it was kind of a forcing function because I was like, like, I need to get good at business. I better like get educated. What I could do is I can get these people to come to this book club and I'll just read one week in advance and take really good notes and I'll sort of teach it. Because when you do a book club, by the way, no one reads a book. Just the one guy who is organizing it. And so I was just going to organize it. Organize and talk about it.

[Shaun]

Okay. What came next?

[Sam Parr]

Okay. And then around that same time, when I moved to San Francisco, I met a guy who had an idea for a roommate matching app. And I was like, hey, I don't have anything to do. May I please join you? And so I previously had a pickup truck in Nashville where I live. I sold it. I had roughly $5,000. He had a little bit of money. We put it together and we started with this idea called Bunk. And the idea with Bunk was it was a roommate matching party website. And so we went to landlords who had two, three, four, five bedrooms. And we would say, we're going to post an ad on Craigslist and we're going to advertise this three bedroom as a one bedroom apartment. Meaning instead of a $3,000 three bedroom. We're going to advertise it as a $1,000 one bedroom and we're going to get 100 people who are interested and we're going to host parties to help them team up and move into this apartment and potentially other apartments. Sounded interesting and it was somewhat interesting. Couldn't figure out how to monetize it. Roommate matching apps are one of like four businesses that every just graduated college kid tries to start. That's one of them. It doesn't really work. So we got Acqua hired roughly nine months later, which basically meant we got a job and got some bonus money if we, like accomplished a couple things. But what we did do that was interesting and I was not able to do this. I was definitely like the marketing guy. But we turned that idea into Tinder for roommates. And that was really dumb because most people, when we launch, when we got. We actually got tens of thousands of people to sign up for it via these infographics that I linked to that we made. But most people or many people who were using it were just meeting it to date. We should have just done Tinder for Tinder. It would have been way smarter. And so that didn't really work out.

[Shaun]

Okay. So I think that to win in business, you got to have essentially three components. The first component is you need to have a money making skill, meaning you have to have something that drives value. This is either going to be learning to sell, learning to make things, learning to hunt down interesting deals. Right. You know, you need a money making skill. What was your money making skill you were developing during all these. Across all these different little projects?

[Sam Parr]

Copywriting. And also just like tenacity, but like getting after it. But copywriting was the one. And marketing.

[Shaun]

Marketing, right. Learning to sell, in your case, learning through sell, learning to sell through getting.

[Sam Parr]

Website traffic and getting the web visitor to do what I wanted them to do.

[Shaun]

Cool. The second thing is you gotta learn to be sort of tenacious and scrappy, which comes not as a thing you want to do, but as a thing you are forced to do, because you really have no other choice. But once you find that gear, you now know you have it. That's how I would describe it. Is that accurate? It sounds like it's what happened in your case too. Nobody wants to be scrappy, to be clear. Right. Like, if you had the option to not have to tough it out, you would probably have taken that. But when you're forced to do it, you learn, okay, I have this sort of animal inside. I can do this. And Now I'm going to use this in every single thing I do. Whereas somebody who doesn't know if they could do that, they're hesitant to go for it.

[Sam Parr]

Yeah. And what's funny about that tenacity, or, sorry, being scrappy is there's this chart where basically like you, you start that way and you don't like it and then you like, kind of get some, a little bit of fancy. But then once you already are fancy or successful, you realize you should always be scrappy. You know what I mean? There's like a reason that like Amazon has like the pizza rule where it's like you'd only have a team of people that are like four people, because small scrappy teams do significantly better in many cases than bigger teams. And so, yeah, so when we, when.

[Shaun]

We met, it's actually hilarious if you had just taken a picture of both of our offices and you had said, which of these two guys is a successful entrepreneur?

[Sam Parr]

My office was like a museum. You had a dude. If you walked up to Sean's office, I'm not exaggerating you. In San Francisco, we lived by Yosemite and the redwood trees, they're huge. You could drive it, you could cut a hole in it and drive a car through it. Sean's office as. It's as if they made a, like a coffee coaster for your cup out of a redwood tree. And it was the size of like 18ft long. It was like a 18 foot in diameter circle that was like a probably a half a million dollar table.

[Shaun]

Yeah, it was. We had four stories. We had an entire apartment built in with heated bathroom floors, so if you needed to stay the night, you could sleep there. Every, every wall was made of one way, one way mirrors, so you could like see out, but they couldn't see in.

[Sam Parr]

You had a chef.

[Shaun]

We had a chef there every single day. We had a masseuse. On Fridays we had open bar. So every Friday we had so all these things. It's a 30,000 square foot office decorated by Ken Folk, one of the fanciest designers in the world. And that was my office. I remember Sam came over one time and he picked up the ashtray, which nobody smokes inside. I don't even know why we have an ashtray. It's like illegal to do that. And he picked up the ashtray, flipped it over and he goes, this is a $700 ashtray. Because the sticker was still on it. And I was like, I don't know what to tell you. I. I don't know What? I don't know what I'm doing here.

[Sam Parr]

And I stole it.

[Shaun]

It's like the, the Titanic got built and then they just plucked like a 23 year old idiot. And they're like, you drive. And I was just driving that, that company into the ground. And you had this like half an office. It was like literally like somebody's apartment.

[Sam Parr]

It was an apartment that was $700. Me and C shared it.

[Shaun]

Yeah, like, like the bathroom didn't have a door. Like you just had to be like, hey, I'm taking a. You know, like it's like it was like the craziest scenario. C was just sit. Even a part of your company. Just like another guy was just there and like the, the, the wall. Like there was. Everything was so strange. Like nothing made any sense. You like didn't have wi fi and you were building this Internet company and yet you actually were the one who was building something successful. And at that period of our lives, like you were actually onto something. And I was sitting here just like, you know, making things that nobody wanted. And so, you know, your scrappiness was well deserved at that time and, and, and earned you some good things. I had to go through my scrappy period at a different time. So the third thing I would say, so one was the tenacious side, developing that scrappy mentality of being willing to be at the bottom and like survive at the bottom. Two is the money making skill and three is project selection. So starting to figure out like almost through process of elimination, what are all the bad businesses that you should not be in.

[Sam Parr]

I was in the elimination phase for sure.

[Shaun]

Yeah, you eliminated like, hey, I probably don't want one where I'm standing outside in the heat selling hot dogs because I'm going to be capped at like how long I can stand outside in the heat. That's probably not a good. Right. So manual labor, it's not scalable. You know. Another one that you did was like illegal business. Like, oh great, a lot of people want this moonshine. But like it's only going to go. The bigger it gets, the more likely I am to go to prison, fail and go to prison. So that's probably not a good project to select. So you were going through process of elimination on project selection. And so you go through this roommate matching app. You're making apps now. That's already better. If I say like, what's the sampar criteria now after the, after doing all 10 of these things, what is a good project to be in for you?

[Sam Parr]

I believe in Ikigai, which is like, what's the world want? What's the world want to pay for? What am I good at and what I'm passionate at? And I try to find that in the middle, but I. My goal. And then, okay, so that's like the woo woo stuff that I totally believe in. But then the other side is, can I get something? Can I bootstrap it to 100 million in revenue in 10 years?

[Shaun]

Okay, but can I bootstrap it? So there has to be some. Something you're answering underneath that. That's like saying, you know what my strategy in chess is? Checkmate. Right. Like, okay, yeah, I get it, but how do you get there? Exactly. So what do you look for? That's going to be a thing you can bootstrap. So are you looking for. I can see that somebody has done a similar thing in another space that I can recreate or apply over here. Seemed like the Hustle was very much that way.

[Sam Parr]

Yeah.

[Shaun]

The newsletter, right. You looked at the scam, you looked at a couple others, you were like, oh, I get what they're doing. And I could do that just in my way.

[Sam Parr]

Yeah. So I like to. I call it like a forgotten business. So there's a lot of these businesses that I haven't even talked about on mfm, but basically, like, there's a bunch of businesses like Hampton that are doing hundreds and hundreds of millions of dollars a year in profit. And what I tend to do when I look for, I mean, Hampton's my only company. That's what I'm going to be doing for a very long time. But before I started it, I research and I go and talk to the owners and I do diligence. And I thought of it this way, but then when AI started coming in play, it really solidify it, which is like something that can't be disrupted easily. I also like looking at things that serious operators don't take serious because I think that there's less competition. So, like, with the Hustle, people laughed at me when we started it, but I was like, well, if you do the math, it definitely can get to 100 million in revenue. And I sold before it got there. But Austin Reif, who founded Morning Brew, he only sold part of the business and still kept running it. And they're in the 80 or 90 million revenue, I think, range now. So, like, the math was right. And so I look for things that can be real opportunities, but the ballers aren't taking it serious.

[Shaun]

Yeah. What Charlie Munger says, the secret to success is weak competition. And so if I was to say from afar, I've known you for, I don't know how long have I known you?

[Sam Parr]

12 hours, maybe.

[Shaun]

Yeah, long time. Three Obamas. And what I would say is, I've noticed that one thing you do really well is you're very good at sniffing out interesting things in spaces where other people are not. Not even looking, which is you mostly just following your curiosity and taste. But you go and you do a lot of research, you come across nonchalant, but you're pretty fucking shalom about the research. Very like, you go, you go really detailed. You go meet them. You, like, talk to the bankers, you talk to a lot of people in a space to get a real, like, a real idea of, like, what those companies look like.

[Sam Parr]

And because I want to eliminate the uncertain. Like, okay, so entrepreneurship, I've been thinking about this. The reason I think entrepreneurship is almost philosophical to me and a lot of people is because entrepreneurship is sort of like, how much uncertainty and fear can you take and still continue moving forward? Because entrepreneurship is basically like, you work on the same thing for 6, 12, 18, sometimes 24 months, and you're like, I still see barely any progress. Is this going to work? And the price that you're paying for potentially a big outcome or potentially for building a business or potentially being free, it could take five or 10 years. And the ones who win are the ones who can handle that uncertainty for a long period of time. That is what entrepreneurship is ultimately, in my opinion. It's dealing with uncertainty and dealing with fear. You have fear over hiring someone when you only have $30,000 in your bank account. You have. I remember when my first employee had a kid and I was like, it feels like I had a kid. I felt so much fear. Now this really has to sustain itself. You have fear over finding your first customer and thinking, I am promised them one thing. Now I really have to work my butt off to, like, make it work out for them. You have fear over getting hate and people making fun of them. And so the name of the game of entrepreneurship is just, can you handle the fear? And can you handle. What's worse is the uncertainty over potentially 5 or 10 years.

[Shaun]

Beautifully said. Mohnish Parai had a good addition to this, which he said, understand the difference between risk and uncertainty. So he was talking about it with the stock market. He goes, basically, the stock market investors hate uncertainty. Like, if they don't know whether your earnings are going to be good or bad, they will just sort of assume bad, right? Like you basically get a huge discount for uncertainty, but it's not the same thing as actual risk. And risk is, what do you have to lose? Uncertainty is just not knowing what's going to happen. And so people think that entrepreneurs take a lot of risk. But I actually think that you are a good example of what most entrepreneurs really do, which is they're actual risk minimizers. It's like, how do I win while taking the least amount of risk necessary to win? I'm not trying to take risks. I'm not trying to take unnecessary. I'm trying to vaporize risk everywhere I can. And whatever's left over, fine. I'm willing to live with what's left over. And he tells the story of Richard Branson. So he says Branson is seen as this, like, freewheeling gunslinger, Mr. Risk type of guy, partly because of his look, his brand, et cetera. He goes, when Branson started his airline, which is a very, what people would think is a very risky business to be in. Most airlines fail. Even today, most airlines don't even make any money. Even the airlines that exist are very razor thin margins. And when he started Virgin, he called up, I think it was British Airways, and he was trying to get one plane. So he was like, hey, do you have like, whatever, a 747? And they were. They were telling him, no, we don't just give out. We're not going to sell you. Random guy on the phone, like, he called the customer support. We. We don't sell you a 747. He said, can you just connect me to the person who does sell 747? We don't sell 747. He's like, all right, do you guys have extra capacity of 747 so you're not currently in use in your fleet? They're like, yeah, we do. He goes, okay, well, would you lease one to me? And basically, he started Virgin by leasing the plane, not buying the plane, which reduced risk. He released it, and he was only on the hook for the payments, like 60 or 90 days later. But he was already going to pre sell the tickets for the flights. Like, the airline business works where you sell the tickets before you end up paying for the plane and the fuel and all the. The actual cost of operating it. And so he realized, like, actually, well, what's the worst case that happens? I just give them the plane back. That's all I'm on the hook to do is give them the plane back if I can't follow through on my commitment. But if I can get it to work. I'll know ahead of time because I sell the tickets up front. So it's actually a very like risk reduction approach to doing what other people see as taking massive risk. And I would say you're the same way where when I've seen you go into a business, you're looking to reduce risk everywhere possible. So you're like, does another business like this already exist and work? So I know that there's demand and I know the business model works. Can I apply it into this space where there's not a lot of competition or there's weak competition, there's not a lot of other really smart super geniuses running around San Francisco trying to do what I'm doing. Cool. That's a way of reducing risk. A third way of reducing risk is you try to bootstrap it. You don't take on external investment. You try to do it where I can start this with pretty much no money. So what do I have to lose? Just my time. I'm not actually going to be in the hole if I, if this goes wrong. That's another way that you reduce risk. And the fourth one is, can I use basically my copywriting skills to attract demand before I have to fulfill the service?

[Sam Parr]

I would sell sponsorships before, yeah, I sold sponsorships. I went. But yes, I would, I would pre sell as much as possible.

[Shaun]

Right. And so you know, and you would do a bunch of research to reduce risk. You would talk to the bankers to figure out, you know, what works in these businesses. You talk to the X CEOs, the EX employees to understand what works, what doesn't work in this business. And so I think you're a master risk reducer. And so when somebody sees the businesses that you do, they all sound kind of random, but I would say like where you've come to, I think at the end is you've figured out your money making skill, you figured out how to be tenacious and scrappy. And then lastly, you've gotten better at project selection. And ultimately we'll use sort of a risk reduction method to pick a project that you think is like kind of a, I wouldn't say slam dunk, but like you're not hoping for this sort of one and one in a hundred outcome. It's kind of like I have to fumble execution for this to fail. Today's episode is brought to you by HubSpot because using only 20% of your business data is like dating somebody who only texts you in emojis. First of all, that's annoying. And second, you're missing a lot of the content. But that's how most businesses are operating today. They're only using 20% of their data. Unless you use HubSpot. That's when all your emails, your call logs, your chat messages, they turn into insights to help you grow your business. Because all that data makes all the difference.

[Sam Parr]

Learn [e-mail] you should hold your breath still on saying I had good project selection because in 2015 I started a business called Itch Juice, a poison ivy treatment.

[Shaun]

Scratch your own itch, as they say.

[Sam Parr]

So stupid. So there was this like type of lotion that mechanics used. It was like a, called a green scrub. I forget exactly what it's called but it turns out it was also had the same ingredients as poison ivy treatment. And I bought in bulk like a, like a, like a barrel that you, you would have at a mechanic shop. And it was like 20 cents an ounce. But that as poison ivy treatment it sold for like $20 an ounce. And I realized I could rank high on Google. And so I was, I got in the poison ivy treatment business and I learned the same thing there or that I learned in the alcohol business which was, and this, this did this was starting to make money which is like do these short little get rich quick schemes that you jump into without like doing the ikigai preparation of like what am I actually passionate about? They're stupid. So I learned that one.

[Shaun]

I feel like I was a lawyer who just stood up and told the jury my client is innocent. And then at the very end you were like, I did it by the way. Yeah, it's like, oh, I told you, just don't say anything.

[Sam Parr]

Now. I think I did good at selecting new things. So I got rid of that and then I started working 10 years ago.

[Shaun]

I think that I have the same story where it took 10 years for me to even figure out what a good business is.

[Sam Parr]

Dude, I don't know how like I read about these prodigies who do who like are so mature when they're like 26, 27. And I just, I'm like am I was I just like slow to develop? Like when I see some of these smart 26, 27 year olds, I think to myself, I still don't behave that way and I'm 10 years older than that. So I don't like when I was 26 and 27, like I didn't know anything, I knew nothing. And I actually felt this way about you. And I was like, he writes stuff On a whiteboard. And he's got these like frameworks way of thinking. I don't think it frameworks. I just like, do.

[Shaun]

Yeah. While I was sitting there being like, why am I just on a whiteboard? This guy's out there just doing it. I gotta do what this guy's doing. It took me 10 years to even figure out at all what the hell was going on. 10 years and. 10 years. You could say that. Look, I said that in 10 seconds. It took me 10 years. Watch. That was so quick. When you're in it, 10 years is like an eternity. Especially because you don't even know that. If I knew, by the way, It'll take me 10 years, but I'll figure it out. It would have felt so much better at the time. It's like the tunnel is still dark and I don't even know where, if and when the tunnel ends. And I don't know how much time I've got left to get there. So it feels much worse in the moment. So for anybody who's out there, who's in their kind of tenure doing dumb stuff. Arc, I feel you. It's normal. It still works. Just keep going.

[Sam Parr]

So Lewis and Clark, it's one of my favorite stories ever. But basically they were sent out starting in St. Louis. Thomas Jefferson was like, hey, Lewis, Hey Clark, do me a favor, just walk in that direction and tell me, does it end and what's it look like and what's on the end? And they just go. And back then, obviously phones didn't exist, mail didn't exist. They were just walking around and they didn't know where they were going exactly. And it took them two years. So imagine that. Imagine sending someone off on a trip for two years and having no idea, like, what's going on, if they're ever going to come back. And that's what entrepreneurship kind of feels like. It could have took two years, it could have took five years. Who knows? But we're just going to go in that direction and I pray and I hope that we're going to find something that's like what the uncertainty feels like.

[Shaun]

Exactly. And every year you're like, now, I know now. And then you say that again the next year. Like, oh, well, last year we were so, so dumb. But this year, now we have it figured out. And it takes a certain amount of self delusion to not be like, hey man, listen, you said that three times already. And now do I really believe you this time? And so you need, you need delusion. I think actually that's also why you gotta move to San Francisco, is because you'll be surrounded by success stories and you'll see them, you'll be like, okay, cool. That guy's not special. I could do it. If you could do it, I could do it. And also, everybody around you is similarly deluded, which really helps because you sort of brainwash yourselves into this mode where you're going to keep going, keep taking shots, and that that's a normal, rational thing to do, even though it's a completely abnormal, irrational thing to do. I think it's one of the biggest benefits of coming to Silicon Valley.

[Sam Parr]

Can I rattle off just a few tiny ones? So I did this thing called. Called a Frisco Disco Taxi, where we dressed up in disco outfits with afros and we gave rides home for people on New Year's Eve.

[Shaun]

Was this like, before Lyft?

[Sam Parr]

Yeah, before Lyft.

[Shaun]

Or maybe like, literally had lift figured out.

[Sam Parr]

Yeah. Yeah, I did, too. Yeah. We made $800 that night. I did a copywriting class with Neville. We actually hosted it at your office. I think we each made $10,000 or maybe made $10,000 total. And then another couple failures. I bought some real estate. And I learned that basically the way you make real estate is through doing the most due diligence upfront and looking at tons and tons and tons of property because you make your money when you buy. And that is not my skill set. And then, of course, I had the hustle. The hustle started as a conference, then to a blog, then to a newsletter, which worked. We launched this thing called Trends, which was a fairly successful thing. And then we expanded our events. Business events, businesses. Horrible the way that we did it. Horrible. We had hundreds or thousands of people coming to each event. Way better to go after smaller groups and charging a lot more. But back then, I couldn't even imagine the idea of someone being willing to spend 2 or 3 or 4 or $5,000 per ticket to a trade show. And I wish I would have figured that out.

[Shaun]

Yeah. So me and Tyler, the CEO of Beehive, came up with a little challenge for you. It's the newsletter challenge. Now, if you know me, you know that I'm a big fan of newsletters. I got my own newsletter. I also had a business that was a newsletter business that was amazing. I wrote this newsletter about crypto. We grew it to quarter million subscribers and we ended up selling it after a year for millions of dollars. And I want you to be able to do the same thing in your business. So we're doing a challenge. Ten grand is on the line. Plus, me and Tyler will actually be in your corner as growth advisors. You just need to go to beehive.com mfm and you either start a new newsletter or you move your current newsletter over there. And five finalists will get picked to pitch. Me and Tyler, sort of like Shark Tank. And the winner gets ten grand. So go to beehive.com mfm that's beehive.com mfm to enter the challenge today. And then this podcast turned out to be a business. We didn't really realize it. You know, I defin. I started alone. I didn't. I definitely didn't think of it as a business. Then you join. I still don't think we thought of it as a business for, what, the first two or three years?

[Sam Parr]

For the first nine months, I'm almost certain it made $0.

[Shaun]

Right. No, I had a sponsor somewhere there. I mean, round down to zero.

[Sam Parr]

Yes.

[Shaun]

Like, you know, like, 10, 20 grand.

[Sam Parr]

So I posted this photo. I want. I want people to, like, understand this. So Sean came up with the podcast, I think, in July, and then I think I joined him in September. So he did a bunch alone. And then I joined him later on, I think sometime in December. So we're talking six months in. Lance Armstrong, for some reason, read the Hustle, and I became friendly acquaintances with him. He wanted to use my office where Sean and I were recording the podcast. And so he came that day when John and I were recording because he messaged me saying, I need to use an office to. For a meeting. Can I use this? And I said, yeah. We pull him into the podcast as we're recording, and I posted this photo of me, Lance, and Sean standing there, and we only have two microphones and two chairs. Two chairs. And Sean's two chairs. Mike's shots, like, sitting on, like, the arm of my chair. And during the. And during the episode, when John wants to talk, he has to, like, lead in to reach my microphone. And then another episode, we had someone, like, we had a guest call it. It was like, a digital guest. It was me and Sean in real life, not a guest. For some reason, one of us didn't have AirPods. And so we just, like, shared an AirPod. Like, we each had one in our ear, and I think we were recording on an iPhone. Like, it was so janky even six months into it.

[Shaun]

Yeah. Which was funny too, because it's not even like these were the early days of podcasting. It's, like, pretty late in the game of podcasting.

[Sam Parr]

Someone should go and look at those old chairs that we use. We picked these chairs because there was a podcast at the time called Fighter and the Kid. And they use these bright red chairs, the brightest red chairs that we figured. They use it so it sticks out on a thumbnail, which I don't even know if we did YouTube at the time, but we wanted those chairs. And it is just a hilarious looking set.

[Shaun]

Honestly, it got to be pretty cool. When we were in person together, it was pretty amazing. I wish we could be doing that.

[Sam Parr]

Oh, my God.

[Shaun]

So good.

[Sam Parr]

It would be the best. It would be the best. It was so much fun. And we had like a. We ran to Best Buy and bought like a video camera and we had an intern record us. And the shot is just you and I. Like, it's dead on, you and I talking. And the guys that we were copying was Theo Von and Brennan Shop, who obviously Theo Von is Theo Von now, but back then he was like a cameo. He came in as a cameo for this other podcast.

[Shaun]

Yeah. Good times.

[Sam Parr]

It feels nostalgic going through this stuff, doesn't it? Because you are with me for most of it or a lot of it. But doesn't this. Is this kind of fun to, like, look back and like. It's crazy this, the stuff that we've done. Yes.

[Shaun]

I mean, when you're in it, you just want to get out of it so bad, right? God, I just want something to work. Anything. Is this gonna work? I really hope this thing works. And I just wanted to get out of it so bad. And then now you're right, you know, you look back and I've really never had as much fun since, as I did on the come up. Like, the come up was really. It was a lot more, I don't know, high variance or just like unpredictable. And like, crazy stuff happened. And it was fun things that I would never make the time to do now. Like, you're never gonna go do Sam's Frisco disco now. You're never going to go do the hot dog stand now. But actually those are pretty fun. Like kind of random projects, great stories, great photos, great, like, memories of trying to pull it off that you were at the time, you know, too dumb to know it was dumb. And now, unfortunately, you know, you sort of have the curse of knowledge. The further you go where you're less likely to go try random dumb things that might actually have high, you know, high. High upside or high fun or high memories, you know, that come at the.

[Sam Parr]

End of it, we have a lot of like young guys listening to this who are in their 20s. Enjoy it, man. It was, it was such a blast. It doesn't feel that way, but I would say with a high degree of certainty if you do the same thing or you try really hard for 10 years and keep taking risks. You and I, Sean, have dozens of friends from that same era and we have seen dozens of them. Like many, many, many of them succeed. Not always like total home runs, but we have many of those. But a lot of base hits, a lot of doubles, A lot of life changing businesses have been built and it's so exciting to like look back and be like, it works, you just gotta do it.

[Shaun]

I mean, it sounds corny, but the truth is at the time you think your success is about how hard you're working and maybe your idea or your team or your execution of the individual thing. And that's true, like at the project level, but at a personal level, the only thing that's going to determine your success is basically your rate of learning. How quickly are you figuring things out? Are you adapting and learning and getting better at your next shot than you were at your last shot? It's that rule of 100, right? Like do a hundred, try it a hundred times, and each time try to make one thing better. If you do that, success is pretty much inevitable. But at the time, you don't think like that. At the time you don't really realize that. But looking back, that's very much the case. I'm sure there's some people who have a way to get there a lot faster. You know, for both you and I, it took 10 years because we sort of through process of elimination, got rid of most of the dumb things. You did do one thing differently than I think most people did. You never made the mistake of building something nobody wanted to, which is maybe the main mistake. I did. I had a bunch of things that the business sounds great on paper. If it works, it's going to be huge, but nobody even wants the thing to begin with. So you, you don't. You die on the launchpad. Whereas you made the opposite. Everything you made, people wanted. Whether it was hot dogs, whiskey, whether it was like, you know, a way to get rid of their itch, whatever it was, you know, you, you had a way. You always made something that people wanted. Sometimes the business model was broken or the scalability was broken, but I feel like you did the, you did one thing really well, which is you never made the cardinal sin, which I would say most Entrepreneurs make, which is you do something that sounds good on paper, but nobody actually wants the thing you're making, and you spend all your energy trying to convince them why they're wrong and why you're right. And actually, no, they just don't want it. They don't need it.

[Sam Parr]

You know what's funny? I. Looking back, I like, for example, the Hustle. I think we were at 100,000 subscribers in year one, and then I think it was 500 in year two, and then a million and three, something like that. And that sounds lovely. It didn't feel like it at the time. It still felt like I was pushing a rock up a hill. And so you're saying I made things that people wanted. Looking back, I agree. But when you're going through it, like, I remember Ryan Hoover launched Product Hunt, and people were talking about his product way more than, like, my product. And I was like, that. That's what product market looks like, not mine. I've never experienced that. What the hell? And I look back at it, and I did have it. And so some of these things, when you're in the thick of it, you have to really work hard to try to come up with these lessons in this, like, at the time. And you have to, like, sit by yourself to come up with these lessons in the time. Because there has been so many things looking back where I'm like, had I only done this, I would have had so much more. I would have worked so much better. But I didn't learn those lessons in the process. So, for example, I used to think that it. I was like, I want to become a big company, so I have to act corporate now. I know you want to act small as. As long as you can, or if you have something that is growing at like 50 a year, don't mess with it. That's a great growth rate. Whereas if you see other people or I saw other people at time growing significantly faster. But. But. But they ended up, like, dying and blew up. But I was like, I want to grow that fast. What the hell? And I'm looking back, I'm like, no, no, that was. That was a rocket. That was fantastic. That was great. It was bootstrapped. It was beautiful. I think that. That I heard this line that basically says, VC is like rocket fuel. And you know who deserves rocket fuel? Rockets. Not fast cars. Not cool cars. Not cars that you love. Rockets. And the thing about rockets is most of them blow up and don't go anywhere. A cool car, a great car, a car you love. That could be an amazing life, and it could actually get to the destination eventually, but it might go a little bit slower. And I thought that was an insult to me. I said, but I want to rock it and I want it to work. Nonsense. I wanted a car. And I wish I would have, like, had the. The confidence back then and learned that lesson, that that was the way.

[Shaun]

All right, so that's Sam's story. Made his first million at 31. But instead of focusing on how he did it, which we've talked about before, it's the, you know, I don't know, 10, 15 things he tried before that. The stumbles and fumbles on the way to success. I'm gonna do mine. We'll do one next episode. I'll do my. I'll do my version of that where I tell you all the terrible, terrible ideas that I had going up to finally making it.

[Motivational Speaker]

I feel like I can rule the world. I know I could be what I want to. I put my all in it. Like no days off on a road. Let's travel, never looking back.

[Shaun]

Hey, let's take a quick break. I want to tell you about a podcast that you could check out. It is called the Science of Scaling by Mark Roberge. He was the founding CRO of HubSpot, and he's a guest lecturer at Harvard Business School. The guy's smart, and he sits down every week with different sales leaders from cool companies like Klaviyo and Vanta and OpenAI. He's asking about their strategies, their tactics, and how they're growing their companies. As head of sales or chief revenue officer, if you're looking to scale a company up, if you're a CRO or head of sales that's looking to level up in your career, I think a podcast like this could be great for you. Listen to the Science of Scaling wherever you get your podcasts.