Small Bets, Big Returns

May 05, 2025

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I've been obsessing over this question lately:

Why do some people consistently stumble into big opportunities while others miss them completely?

After talking with dozens of successful founders, I've noticed a pattern: they're not necessarily smarter or more connected. They just make more small bets.

Last year, I made 14 tiny experiments:

  • Launched 3 micro-SaaS tools

  • Created 5 different content formats

  • Tested 4 different automation workflows

  • Explored 2 emerging AI platforms

Most failed. A few were mediocre. One exploded.

That single winner is now generating more revenue than my previous five years of careful planning combined.

Here's what I've learned: success in the AI age isn't about making perfect decisions. It's about increasing your surface area for luck.

The math is simple:

  • Small bets = More at-bats

  • More at-bats = Higher chance of hitting a home run

  • Small failures = Fast learning, minimal damage

One founder I know has a "Failure Friday" ritual. Every week, he launches something tiny that might fail. A new landing page. A different pricing model. An experimental feature.

Most weeks, nothing happens. But every few months, one of these small bets returns 100x.

This approach works especially well with AI tools because the cost of experimentation has collapsed. What used to take weeks now takes hours.

The secret isn't having better ideas—it's testing more ideas.

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So my challenge to you: What small bet could you make this week? Something quick, low-risk, but with potential upside?

Don't overthink it. Just ship it.

Remember: You don't need to be right most of the time. You just need to be right once.

What tiny experiment will you run this week?