Sam and Shaan open with Sam’s tattoo gun experiment and a riff on the hidden costs of living in Brooklyn. The episode centers on two builders who found ways to make $10M+ fast: an anonymous indie app developer who built multiple App Store hits to $100M+ net worth, and a deep dive on serial entrepreneur Scott Painter, who has continuously reinvented car ownership online. They close with TechTarget’s surprising $400-500M B2B media empire and a viral LinkedIn crying-CEO post.
Speakers: Sam Parr (host), Shaan Puri (host)
Intro and the Tattoo Gun Story [00:00:00]
Shaan: They told us to do intros now, so: this is My First Million, the podcast where we tell you a hundred ideas — half are good, half are bad — and it’s on you to figure out which ones.
Sam: This is My First Million, where I make fun of Shaan about how he talks, he makes fun of me about how I look, and in between we squeeze in a few business ideas.
Shaan: Supposedly we’re successful people. The reviews say it’s like sitting at a bar with a bunch of successful friends — dare I say — multi-million-dollar friends — just hearing what they talk about. Yeah, just a couple of deca-millionaires hanging out.
Sam: How are you supposed to brag about that? Regardless of the deca-millionaire nonsense — I did something a few weeks ago that I think was amazing. I bought a $60 tattoo gun on Amazon and let my wife give me a hand tattoo instead of wearing a wedding ring.
Shaan: Wow. Totally worth it. Let me be the judge. What is it?
Sam: It’s an X. Like an axe — where something was there, then it’s dead, and you put an X there. Or like triple X on a moonshine whiskey jug. Something like that.
Shaan: And she wanted to do this or you wanted to do this? She seems more sensible than you.
Sam: I set it up and within two minutes it was done. I handed her an orange: “Go right on that orange. Great, I’ll do that on my fist.”
Shaan: People always ask what’s the secret to being a deca-millionaire. We tell them: it’s threats. You’ve got to threaten your business partners, your marital partners, all your partners. Sam, you do use this — what they say in It’s Always Sunny — the implication of danger. You use the implication of things going wrong, don’t you?
Sam: What’s an example in my management style? I like the second path — the implication of consequences if we don’t do X. Like, if I can make a million dollars or not lose a million dollars, I’m more motivated not to lose it. I set my life up so that if I don’t do it, there are consequences.
Shaan: They tell their therapist about it years later.
Sam: I used to do it with my employees all the time. They’d say they hated it. Then whenever they left, eventually they’d say, “Yeah, but I did so much cool stuff and we got a lot of things done.” People actually like it.
The Real Cost of Living in Brooklyn [00:04:00]
Sam: Can we start on something that’s been blowing my mind? Yesterday I went on a long walk — a ten-mile walk around fancy neighborhoods in Brooklyn — and I started pulling up Zillow as I walked. The houses I liked were $8 million, and I started thinking about how much money I’d actually need to live the life I want to live there. It is astronomical.
Shaan: Walk me through it.
Sam: I’m going to talk about the life I’ll live when I move to Brooklyn. There will be listeners who say, “Sam, no one needs an $8 million house.” I get it — all I need is a bucket of water and some Crocs and I’m happy — but this is the life I choose. So anyway.
I found a brownstone in Cobble Hill. Only 3,000 square feet. $5 million. My down payment: $1.1 million. Mortgage and interest: around $20,000 a month, not including maintenance — probably another $2 to $3K.
Furnishing it: $50K on the low end, $150K for Restoration Hardware-type stuff. With two kids, I’m spending $40 to $50K a year on a nanny. Food: around $30K a year. It adds up to roughly $600 to $700K a year to live the life I want in Brooklyn. But here’s the kicker — if you’re making over a million in New York, half goes to taxes. So I need to make $1.2 million just to break even.
I talked to two friends. One spends around $500K a year in Brooklyn. Another spends $800K, but that includes a second home in Rhode Island. Strip that out: $650K. This is crazy.
Shaan: A lot of these homeowners bought before the houses were worth $5 million. In 2010 that brownstone was maybe a million and a half. So your monthly payment is way lower, your property taxes are lower. That’s how they can live above their weight.
Sam: I had four takeaways. First: there’s a story behind everything. Not everyone just earned their way in. Our reporter Zach Crockett looked up the property records on a bunch of $5 million brownstones. He found the owners were teachers, artists, professors — people who couldn’t possibly earn enough to buy those homes. Conclusion: they got help. A lot of financial help from family.
Second: you’ve got to earn a lot. If you make $1.5 million a year and spend around $25K a month, it takes about 15 years to save $10 million. That’s extremely challenging.
Third: you probably have to sell a business. To pull in a million-plus as an employee, you’re basically in finance, law, medicine, or consulting. Or you own your own business — which is lumpy. Nothing, nothing, nothing, then a lot, then back to nothing.
Fourth: there is so much money out there. You walk down any block in Brooklyn and you’re like — three people each paying $12K a month to rent a floor of that brownstone, just home, home, home. There’s so much opportunity.
Shaan: That’s why those TikToks are popular — someone stops a person in a fancy car and goes, “What do you do?” The guy says, “I paint houses.” Wealth is a complete mystery unless you grow up with it. If you do grow up with it, you know there are a thousand paths and it’s up to you to pick one.
Sam: If you don’t, wealth is this mysterious unattainable thing. And when people hear about it they either react with bitterness or inspiration. Ninety percent go bitter. But the ones who take inspiration start collecting data points — that person did it with a mushroom farm, that person made $15 million manufacturing treadmill belts. Once you have enough examples, possibility expands. Things become a lot easier because you can see paths.
The Person Making $10 Million in a Year [00:16:00]
Sam: We have a friend in our group chat who created an app or service, and every day they’re posting a chart of the growth: $100 a day, $500 a day, $1,000 a day, $3,000 a day… Fast forward two weeks and this person is going to have a chart showing $200,000 in revenue in a single day. And nothing has changed — they just let the growth carry on.
Shaan: That’s the HOV lane. That’s the fast lane.
Sam: I remember when this person told us they were thinking about ideas that can make $10 million or even $50 million in a year. And I was like, “Sure…” But he was like, “No, I’ve been studying. There are apps in the App Store that do this.” And he was showing us examples. I’d never heard somebody state a goal like that before. I’d heard “I want to build a billion-dollar company” — that’s normal. But “I’m looking for a way to make $10 million in three months” — that was new. And once he gave me ten examples, number eleven didn’t seem so farfetched. And now it’s actually happening.
Shaan: I think it’s still too early. Anything that comes fast can go away fast. But he called his shot and we are watching it come into reality, which is awesome. Peter Thiel has a line: what’s your five-year goal? Then how can you do that in six months? This guy took it further — how do you do it in three months?
Allan Wong and the App Store Fortune [00:21:00]
Sam: There’s another guy who’s done this publicly. His name is Allan Wong. You know the 5-0 Radio app — the police scanner app?
Shaan: Yeah.
Sam: He posted on Reddit in 2013. He goes: “I’m a person in his 20s who went from rags to riches during the recession. How I did it: I develop apps. My most popular app is called 5-0 Radio. It lets you listen to police chatter around the world. As of 2012, my apps have been downloaded by 20 million people.”
He’s also posted in the fatfire subreddit, which has this thing where the mods verify your financial status. His verification: $100 million liquid plus. He says he has three apps — 5-0 Radio, Police Scanner Plus, and one more — and at the time he wrote this, he was “the only person in app store history to have three apps in the top 10 overall in both paid and free categories simultaneously.”
If you Google his username “Rego Apps” and “fatfire,” you’ll see his posts. He talks about what it’s like at different tiers of wealth. Someone asked about the difference in money levels. He goes: at $100K to $1M, you can tip generously and be okay with it. At $1-5M, you can fund some medical expenses and maybe a college tuition for a family member or friend. At $5-20M, you can pay off a handful of college tuitions. At $50M+, you can create several nonprofits. He talks about all of this constantly through that subreddit.
Shaan: Pretty cool. I’d like to do an AMA on fatfire. Let’s get verified.
Sam: Yeah, let’s do it. I post there under a name no one knows, but let’s make real accounts and get verified.
Scott Painter: Serial Entrepreneur of the Auto Industry [00:27:00]
Sam: Okay, let me tell you about this guy Scott Painter. Do you know who Scott Painter is?
Shaan: No.
Sam: This is my Billy of the week. He has that big Billy energy. Scott Painter was the CEO of TrueCar. TrueCar published car price information so you could figure out the actual price before going to a dealership. Before TrueCar, depending on which dealer and salesperson you got, there was a 30% spread in price for the same car. After TrueCar entered a market, that spread dropped from 30% to about 3%.
But the guy’s career is incredible. He starts in the Army as a Spanish interrogator. Then VP of marketing at 1-800-Car-Search in 1999. Then Dental Advantage, Vision Incorporated — he was helping companies do e-commerce before e-commerce was even a thing. Then he’s the founder of Cars Direct, which goes from $0 to $650 million in sales in year one. Then advertising.com, then TrueCar, then PriceLock.
At TrueCar, he becomes the largest individual shareholder, buys a ton of stock on margin, believes in it completely. They have an earnings miss, the economy slows car buying, the stock tanks, he gets margin called, has to borrow money from friends to cover it. He resigns from the company he built. Then: he gets divorced. And his house literally burns down.
Shaan: What?
Sam: The following week, he incorporates Fair.com. Fair was a way to “subscribe” to a car — you put in your phone number, pick a car, it shows up as one monthly price, you can turn it in whenever you want. Like Netflix for cars. It raised hundreds of millions of dollars including $300 million from SoftBank. Then the tech market turned, SoftBank started losing money on WeWork and others, Scott couldn’t raise more, and Fair eventually had to lay off 40% of its people.
Now he’s back. There’s a startup called Autonomy that placed $400 million in purchase orders for 8,000 Teslas. The idea: a lot of people want a Tesla but can’t afford it all in, so you pay a monthly fee for a long-term rental. He’s placed a billion dollars in purchase orders across multiple electric vehicle makers.
Shaan: What’s he like when you hear him talk?
Sam: Very matter-of-fact. A good storyteller. Quick and to the point. Reminds me of Frank Slootman, the Snowflake CEO, who wrote “Amp It Up” — that ethos of we’re here to win, let’s run this company to win. This guy’s like that.
He calls himself a multi-time college dropout. He tried 25 things and three worked. He has this thing where he says a car tells you a story about where you are in life — graduating, moving, getting your first good job, going into family mode. He had the insight that cars represent about 15% of all people’s gross income — half in buying the car, half in fuel, taxes, repairs, insurance. About a third of your net worth when you buy new. The TAM is enormous. That’s why he keeps raising so much money.
Adam Neumann and the WeWork Comeback [00:41:00]
Sam: Another guy who takes big swings: Adam Neumann. He just raised $350 million in seed funding for a billion-dollar apartment business — basically WeLive, the fancy co-living thing. What do you think about Adam Neumann taking another swing?
Shaan: I think it’s great. People crap on him for two reasons: one, WeWork “failed” — except WeWork didn’t really fail. It’s still a $4-5 billion public company, which is more valuable than anything we’ve ever built. Two, he lied and cheated — he licensed the “We” trademark back to WeWork for himself, he ran a summer camp where everyone got drunk, whatever. Those things range from “a little whack” to “understandable given hypergrowth ego-driven companies.”
Is he crazy good or crazy bad? Mostly good. When I read about him — and I’ve hung out with Miguel his co-founder — I don’t think he was lying. I think he got some things wrong. I think he was incredibly enthusiastic. When you paint the picture of the future and end up being way wrong, you’re not a liar, you’re just wrong. Delusional is different from fraudulent.
Sam: He’s one of those guys with such irrational self-confidence that they actually might pull off the crazy dream. The problem is they get high on their own supply. I’ve seen this play out. I invested in Terra — the Luna cryptocurrency. The founder was the same way: super smart, charismatic, unbelievable confidence. Smart people were all saying he’s crazy but maybe just crazy enough to pull it off. Then his ego ballooned and ballooned, he kept taking larger risks, then the market called his bluff and it crashed to zero. I lost about a million dollars in two days.
I owned Tesla stock when it was at $2-3 billion valuation. I calculated I would have had $5 million if I’d held it to $1 trillion. What happened: I turned $25K into $125K and sold because I started noticing Elon overpromises constantly — on the Cybertruck, on autopilot, on timeline for everything. Then there was very convincing evidence on Twitter that it was a fraud: they went through 20 CFOs in four years, the new CFO had never been a CFO before. Someone smart told me: follow the CFOs. They know the company health better than anyone. So I bailed.
I was right about the principle — Tesla was constantly on the brink of collapse. He threaded the needle. He pulled it off. And I was $5 million wrong for selling early.
Where I’ve landed: some people are con artists, but some of the best entrepreneurs have the same profile — irrational, delusional, willing to run into a fire. Nine out of ten don’t make it. But the one out of ten who does changes the game. I lean optimistic, because even if I’m right about the pessimism nine out of ten times, I’d miss the one that pays for all the losers.
TechTarget: The $400M Business No One’s Heard Of [00:54:00]
Sam: Let me tell you about a company I think is making way more money than I thought, and I’m absolutely going to clone it eventually. Go to BitPipe.com.
Shaan: Okay, I see a Craigslist-looking website. “BitPipe is the enterprise IT professional’s guide to IT resources.” There’s a library of technical white papers, webcasts, product information…
Sam: Click one. See how they ask for your corporate email, name, company, job title, seniority, job function, number of employees, industry, address, country, phone?
Shaan: Yeah, it’s like “How to Choose an HR Software System” and then fill out your entire life story to download it.
Sam: This website is owned by a company that owns about 20-30 of these sites. It has only about 3,000 customers. It makes around $400-500 million a year in revenue. It’s a publicly traded company — ticker is TechTarget — market cap of about $2.1 billion.
Shaan: What? There is no way.
Sam: Here’s how it works. Say you’re the Chief Information Officer at a 5,000-person company. You Google “how to pick an HR software system.” You land on this ugly 1979-looking website. But it’s the website you find. You enter your info, download the white paper.
TechTarget has 200 or so large software companies as clients. Those clients will pay $500 for Linda’s contact information — she’s in the market, she just told us she’s evaluating HR software. Then they also track Linda across all their sites. She goes to ComputerWeekly.com, looks at an HR thing. Goes to their networking site, looks at cloud software. TechTarget calls up their clients: “I got a Chief Information Officer at Gartner who’s about to buy cloud software and HR software. You want to reach her?”
Shaan: This is insane.
Sam: It’s awful content on an awful website. The threshold of quality is basically zero. But people in this industry only number in the tens or hundreds of thousands, and they all end up on these sites because this is how enterprise buyers research.
Why aren’t we starting a company that just beats these guys? We put our spin on it like Mugshots.com did to mug shot websites. We do it to B2B media. We make it actually interesting. We do a podcast, an AM radio station for CIOs.
Shaan: “B2B FM in the morning.” I like it. And you have vendors on as sponsors but you do the cheaters radio bit — you get the existing HR vendor on the line and then call the CIO being like, “Hey, are you interested in switching?” When they say yes, you’re like, “Actually, we’ve got Workday on the other line. Workday, say hi. He’s going to cheat on you.” And we call it Churn Busters.
Sam: Nobody has ever laughed at this style of content until right now. We’re the first people to make TechTarget a fun topic.
The LinkedIn Crying CEO Post [01:05:00]
Sam: Last thing: the lamest thing I’ve seen on the internet in the past few weeks. A guy posted on LinkedIn a picture of himself crying. The post starts: “This will be the most vulnerable thing I’ll ever share. I’ve gone back and forth on whether to post this.”
He had to lay off a few employees. Says it was his fault. Then writes this long thing in the marketer style — one line, enter, one line, enter — and posts a selfie of himself looking into the camera. Crying.
Shaan: How many likes?
Sam: Fifty thousand likes, ten thousand comments. Most of the comments are just making fun of him.
The top comment: “Hang on, did you turn your ring light on before you took this selfie? Because I can kind of see the reflection.”
Shaan: That’s perfect.
Sam: That calls out the inauthenticity of the fake authenticity perfectly. I saw this and I was literally cringing. My face was changing shapes reading it. I have this tooth that’s a little sensitive — it just started ringing, like I ate too cold of ice cream.
This is the definition of small boy stuff. What do you think happens to this guy’s career? If I’m a customer and I see this, I think: if your product is even 50% as weak as you are, it’s not going to work.
Shaan: Some of these comments are hilarious. “Rest easy, my sweet child.”
Sam: Starts off like a serious comment and just deteriorates into — that’s the best content on LinkedIn ever. The combination of the post and the comments made LinkedIn the most entertaining social media of the day.
Alright, that’s the episode. Go tell your friends, tell your mom. This is My First Million.