My First Million · Episode Brief
I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson
Andrew Wilkinson ranks business models by desirability and the list is more honest than anything you'll find in a business school curriculum.
Andrew Wilkinson has built Tiny — a portfolio of small, profitable internet businesses — by being ruthlessly selective about what he acquires and avoids. This episode is essentially the operating thesis made explicit: here are the business models worth pursuing, here are the ones that look attractive but destroy you, and here's how to tell the difference before you're three years in.
The ranking format is a useful compression mechanism. Wilkinson places agencies near the bottom not because they can't be profitable but because they're people-intensive in ways that prevent leverage — every new client is a new management problem. Restaurants and retail are in the same bucket. SaaS and content sit higher because they have the structural property that makes a business worth owning: the ability to generate revenue while you sleep.
His real estate framing is more nuanced than the usual debate. His point isn't that real estate is bad but that most people who pursue it are buying a second job, not a passive asset — the management overhead is invisible in the underwriting and visible in year two.
The 'courage to be disliked' thread is Wilkinson at his most personal. His argument is that most people build businesses to be liked — by employees, by customers, by the market — and that this orientation is incompatible with the decisions that produce outsized returns. The best operators, in his telling, are willing to make moves that disappoint people in service of a thesis they believe in. Tiny's portfolio construction is his proof of concept for this position.
Key Ideas
- →Wilkinson's business model hierarchy: SaaS and content businesses sit at the top because they generate revenue without adding headcount; agencies and restaurants sit at the bottom because every dollar of growth adds management complexity.
- →The real estate trap: most people buying rental property are underwriting passive income but purchasing a second job — the management overhead is invisible in the pro forma.
- →The 'courage to be disliked' principle: building for approval leads to a different set of decisions than building for returns, and most founders are optimizing for the wrong thing.
- →Tiny's acquisition model is a version of private equity without the leverage — buy good businesses at fair prices, leave management in place, collect cash flow.
- →Wilkinson's take on agencies: they can be profitable, but the ceiling is low and the floor is unstable — the moment you lose a client, your overhead doesn't adjust with it.
Worth Remembering
Wilkinson walking through the full business model ranking with Shaan pushing back on each category — the back-and-forth makes the framework sharper than a monologue would.
The moment Wilkinson explains why he passed on a restaurant investment that looked great on paper, and the real reason had nothing to do with the numbers.
His account of building Tiny's portfolio with the explicit goal of never managing anything himself — and what that constraint forced him to learn about deal selection.
The courage to be disliked segment: Wilkinson being unusually direct about the social cost of the decisions that built his portfolio.