Nov 22, 2022 · 58m · founders-journal
How Codie Sanchez Built a $50 Million Portfolio of Boring Businesses, and the #1 Skill to Learn in a Recession
Codie Sanchez · 36m spoken Alex Lieberman · 16m spoken Jesse Pujji · 2s spoken Sophia Amoruso · 1s spoken
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Crazy Ones, host Alex Lieberman interviews Contrarian Thinking founder Codie Sanchez on how she built a $50 million portfolio of cash-flowing small businesses. Sanchez breaks down tactical deal structuring, seller financing, operator hiring, and media leverage as foundational pillars for building sustainable wealth.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 30.3% of the talking time here. How this is scored →
Alex as informed peer 5.0 Guest teaching 5.7 Guest disagreement 1.4 Alex pushing back 1.6
speaking balance: gold is Alex, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 28:15 Rejecting ATM business models outright
Codie forcefully dismisses ATM businesses promoted online, pointing out their brutal 1-3% margins and declining cash reliance.
Hardest push from Alex ▶ 26:55 Challenging the saturation of the boring business trendAlex pushes Codie on whether popular small business categories like laundromats and car washes have already been saturated by late-inning interest.
Biggest teaching moment ▶ 34:05 Masterclass on media rights arbitrage vs labor tradingCodie educates listeners on how Reese Witherspoon leveraged audience book testing into studio production leverage, generating far higher returns with zero capital at risk compared to top-tier actors.
Alex holds their own ▶ 35:32 Synthesizing multidimensional celebrity business modelsAlex builds directly upon Codie's framework, articulating the progression from 1D talent wages to 3D audience arbitrage and equity ownership.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Alex as informed peer | Guest teaching | Guest disagreement | Alex pushing back | Why |
|---|---|---|---|---|---|---|
| Skill Stacking: From Investigative Journalism to Private Equity | 4 | 5 | 1 | 2 | Alex opens by asking Codie about her trajectory and catches an omission about her investigative journalism background. Codie explains Scott Adams' concept of skill stacking and how journalism uniquely prepared her for private equity and content creation. | |
| The First Small Business: Buying a Phoenix Laundromat | 4 | 6 | 1 | 1 | Alex asks about Codie's first small business acquisition and where it sat on the passive-versus-active spectrum. Codie explains buying a Phoenix laundromat for $100k, explaining that acquiring sub-$100k profit businesses is essentially buying a job rather than a truly passive investment. | |
| Mastering the Language and Psychology of Dealmaking | 5 | 7 | 2 | 2 | Codie explains why dealmaking is the fundamental language of wealth creation, dismissing traditional budgeting as minor upside optimization. She walks through advanced contractual terms and tactical psychology, illustrating the power of silence in negotiations. | |
| Structuring Favorable Deal Terms: The Gym Case Study | 6 | 6 | 1 | 2 | Codie breaks down her gym investment deal structure, highlighting the rule that one must control terms over price to protect downside risk. Alex synthesizes this effectively by framing it as risk prioritization and mitigation. | |
| Seller Financing, Asymmetric Risk, and Learning from Losses | 5 | 6 | 1 | 1 | Codie details using zero-down seller financing to create monthly cash-flowing annuities while insulating personal capital from downside risk. Alex contextualizes the remaining exposure as reputational risk, and Codie acknowledges past deal losses. | |
| Hiring and Evaluating Elite Operators | 5 | 6 | 2 | 1 | Codie shares tactics for vetting operators, including calendar audits and scaring away bad hires with brutal transparency. Alex contributes common ground regarding clear cultural standards and spiky hiring opinions. | |
| Macroeconomic Outlook and Sectors to Avoid | 6 | 5 | 2 | 3 | Alex asks if the boring business market is already in the late innings and probes Codie on margin profiles across asset classes. Codie warns of a lagging private market recession and forcefully rejects low-margin businesses like ATMs. | |
| The Power of Content Leverage: The Reese Witherspoon Model | 6 | 7 | 2 | 2 | Codie breaks down Reese Witherspoon's Hello Sunshine model, demonstrating how licensing and media leverage outperform traditional time-for-money acting or standard celebrity brands. Alex extends the analogy into 1D, 2D, and 3D chess in creator monetization. | |
| Scaling Contrarian Thinking and Fighting Corporate Monopolies | 4 | 5 | 1 | 1 | Codie outlines her thesis that attention is the ultimate commodity and discusses her upcoming book fighting corporate conglomerate monopolies. Alex agrees, underscoring the vital community role of independent local businesses. | |
| Analyzing YouTube Growth and Narrative Resonance | 5 | 5 | 1 | 1 | Alex quizzes Codie on her rapid YouTube subscriber growth from 3.5k to over 400k in eight months. Codie explains the dual value of verifiable industry track record and shifting narrative focus strictly onto the viewer's problems. | |
| Portfolio Metrics, Team Structure, and Leadership Growth | 5 | 5 | 1 | 1 | Codie reviews her 24-business, $50 million revenue portfolio and candidly discusses her shortcomings in day-to-day management. Alex shares personal parallels regarding executive standards, missed deadlines, and vision casting. | |
| Hot Takes: Angel Investing, Suffer in Silence, and Mental Masturbation | 5 | 5 | 2 | 2 | Alex presents several of Codie's contrarian tweets on angel investing, suffering in silence, and mental masturbation. Codie explains why angel investing is reckless for early capital and Alex adds his own decision to fund internal projects instead. |
Statements from this episode (32)
Sanchez: Finance Culture Stifles Curiosity by Equating Uncertainty with Low Intelligence
“Most people in finance, you know, there's almost like a downside to being curious. People think, well, your intelligence must be lacking because you don't have all the answers, and that's how a lot of financial people think.”
Sanchez bought her first business, a Phoenix laundromat, for $100,000
“The first technically boring business I bought was a laundromat. That was a laundromat that we bought for a 100,000 bucks, give or take... Phoenix, Arizona. So did about 67, 68,000 dollars in profit.”
Sanchez: Buying a very small business is effectively buying a job
“And what I don't think people realize is that's buying a job. You're buying a job when you buy a company that small. And those types of deals exist all around this country. They're everywhere.”
Sanchez: Mastering dealmaking creates billionaires, while mastering budgeting does not
“But if you master budgeting, that does not make a billionaire. If you master deal making, that makes billionaires.”
Sanchez: Inexperienced negotiators ruin deals by failing to use silence
“And the pros know the beauty of silence. And I think that's the biggest thing people mess up in the beginning is they talk themselves out of a deal.”
Sanchez: Professional dealmakers prioritize controlling terms over price
“The pro knows that you want control of the terms, not the price always.”
Sanchez argues gyms have a tough business model due to customer density
“Gyms are a hard business. Think about it. The more people that are in your gym, what do you feel? Not happy about it. You're like, I can't use the machine. It's kind of a tough business model.”
Sanchez: First seller-financed acquisition yielded five-figure payout in month one
“So I started getting a check that was, you know, a five figure check the first month that I closed the deal from taking over this business and running it.”
Sanchez: Lost $50K personal check and wrote off multi-million dollar fund deals
“Like, you know, I've written a check for 50,000 dollars and lost that completely. We had multi-million dollar deals that we had to write off completely when I was at the fund, thankfully.”
Sanchez: Boring businesses fail less frequently than startups if sized properly
“It's just harder to have happen in these boring businesses if you do it right and you size them right, I think, than if you do a startup.”
Sanchez: The best company starters typically make poor operators
“And the best starters typically aren't the best operators.”
Sanchez: Candidates who solve problems mid-interview make the best operators
“If they start solving your problems, they're, it's a really good indicator that they're a good operator.”
Sanchez says she will never hire anyone who supports quiet quitting
“I'll never hire somebody who believes in quiet quitting or would ever do that.”
Codie Sanchez predicts a double-dip recession with rising inflation
“Well, I think we're in the first part of a recession. That'll probably be a double-dip recession and we'll actually see inflation come back up again. That's my assertion.”
Sanchez says ATMs are a terrible business with tiny profit margins
“ATMs, terrible margin business, not into it. One to three percent. These businesses typically just, you cannot collect enough of them to get enough income on them. Plus money's going away.”
Sanchez: A good boring business needs 15% to 50% margins
“So I would say a good boring business is 15 to 50, 15 to 50% margins. 50 would be like really good. 15 would be like, okay, we've got a healthy business within lots of characteristics. One to three is awful.”
Sanchez: MrBeast's Feastables is now a $100M company
“The Feastables, the chocolates or whatever that Mr. Beast has done, when they originally told me about that, I was like, oh God, that's an awful business. Who eats like a whole chocolate bar anyway? And now it's like a hundred million dollar company, which is …”
Sanchez: Reese Witherspoon sold Hello Sunshine for $900 million
“Reese Witherspoon just sold the business for nine hundred million dollars, her Hello Sunshine company.”
Sanchez: Reese Witherspoon's net worth is an order of magnitude higher than Brad Pitt's
“Reese Witherspoon is worth more than Brad Pitt at an order of magnitude.”
Sanchez predicts Dwayne Johnson's tequila earns less than Witherspoon's media company
“The Rock will probably make less money on Terra Mana than Reese Witherspoon did on Hello Sunshine.”
Sanchez: Contrarian Thinking generates 60M to 70M views per month
“Right now we have three million followers and we do 60 or seventy million views a month.”
Sanchez: Conglomerates own 25% of US local businesses and stores
“25% of construction stores, grocery stores, coffee shops, just about everything you can think of in the US is owned by giant conglomerates.”
Lieberman: Sanchez grew from 3,500 to 409K YouTube subscribers in eight months
“March meaning eight months ago.
I don't guess.
20,000 or something.
3500.
Today you're right around 409,000 subscribers on YouTube.”
Sanchez: Creators should build real-world experience before giving online advice
“You don't always have to be an expert, but like, you should try to do a few things before you try to talk about doing things.”
Sanchez's portfolio of 24 small businesses generates $50 million in revenue
“Well, they do about fifty million in revenue.”
Sanchez: Media business operates with fewer than 10 employees
“Well, inside the boring businesses a lot you know, hundreds, hundreds inside of the media company, very few, you know, less than 10.”
Sanchez: Media business will eventually overtake portfolio cash flow
“Still the boring businesses, but I'm, if we keep it this trajectory and I don't buy more boring businesses, the media company will definitely take over at some point.”
Sanchez: Angel investing is dumb for 99.9% of people
“I think angel investing is dumb for your first dollars. You're going to lose 80% of your takes. So I still think angel investing is dumb for 99.9% of people. Don't play a game where you bet on other people's ability before you've bet enough on your own and sta…”
Lieberman: Reallocating all angel investing capital to personal side projects
“I've learned in the last year that I hate angel investing. So actually my strategy has changed to, I'm just going to take all the money that I had your mark to put in angel investing. And I'm just going to use it to bet on side projects that I'm building mysel…”
Lieberman: Not having detractors means accepting bad business trade-offs
“If you don't get anyone to dislike you, It probably means that you're accepting trade-offs that probably aren't worth accepting in a business.”
Sanchez: Small business market will trend downward over 6 to 12 months
“I'd probably wait another six or 12 months and see what goes down. I'd like to spend a bunch of time learning about this stuff that I think is going to be super impacted. So for me, it would be like, I would learn deal making. I would learn to buy boring busin…”