A Perspective

How Entrepreneurs and Gamblers Share a Common Optimism Bias.

Striking a Balance Between Optimism and Strategy

Shehraj Singh
2 min readDec 31, 2023

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Source: shehraj.com

I can’t help feeling a little tickled by the notion that entrepreneurs and gamblers might be cut from the same cloth.

When you throw the dice or lay your cards on the table, you’re betting on a win against the odds — not so different from launching a startup, right Every entrepreneur feels they’re bound for glory, much like a gambler convinced their luck will turn.

It’s this surprising connection, a shared optimism bias, that straddles the worlds of business and chance.

But hang on, why does this matter, you might wonder?

Well, it’s this very blind optimism that often leads entrepreneurs to innovate, push boundaries, and drive progress. At its core, entrepreneurship is a high-stakes game, requiring big bets on unproven ideas in markets that can be as unpredictable as a roll of the dice.

The trap, though, is when we start believing our hype without doing our homework.

  • A smart gambler knows the game, the odds, and when to fold.
  • A smart entrepreneur needs to know their market, competition, and when to pivot.

Seems straightforward, but you’d be surprised how many get swept up in the excitement and forget to count the cost till it’s too late.

It’s all about balancing optimism with informed decision-making. When you’re making your next business move, consider seeking advice, crunching the numbers, and planning for those ‘just in case’ scenarios.

A reality check now can save a whole lot of headaches later.

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