Small Bets

What they built

Daniel Vassallo (@dvassallo) is the clearest example of the portfolio approach to indie business. Instead of betting everything on one product, he runs many small ones: ebooks, courses, a Twitter guide, consultations, and Small Bets, a paid community for people who want to make money outside a single risky venture. His whole philosophy is that a spread of small, uncorrelated income streams beats one big gamble, and he has the numbers to argue it.

How they did it

Vassallo spent eight years as a developer at Amazon before quitting in 2019 with no real plan and a public commitment to make it work on his own. He started selling a book on building products, then an SQL course, then his approach to Twitter, layering income streams rather than chasing scale. He posts his revenue openly, including a year-by-year breakdown of everything he has earned since going independent.

The numbers

• $620K in revenue across his products in 2024, about $51,667 a month, posted on X as part of a full self-employment history. source
• Small Bets made almost $500K in profit in 2024 excluding platform fees, which he shared when announcing the sale. source
• Sold Small Bets to Gumroad in April 2025 in a deal he valued at $3.6M, while staying on to run it. source

The takeaway is not the exit, it is the method. Vassallo built a five-figure monthly income from a stack of cheap, low-risk products, none of which needed to be a hit on its own.