This story appears in the November 2025 issue of Entrepreneur. Subscribe »
The founder was freaking out. He’d been trying to raise VC funds and finally landed a big investor meeting. The night before the pitch, he texted me: “If this doesn’t go well, I’ll never raise this money.”
I replied: “The stakes are lower than you think.”
He thought I was insulting him. I wasn’t. Instead, I was offering him a lifeline. Because in the topsy-turvy world of entrepreneurship, this is the only way to survive: You must develop a low-stakes mindset.
Here’s what I mean.
I’ve interviewed thousands of entrepreneurs, consulted with hundreds, and sit on many advisory boards. And I see this pattern repeatedly: Struggling entrepreneurs tend to have a high-stakes mindset — treating everything as a make-or-break moment, and believing that every action has dire consequences.
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As a result, they overthink major decisions. Hesitate longer. Move through the world anxiously.
By contrast, the most successful entrepreneurs think differently. They have a low-stakes mindset — it’s a kind of emotional detachment where everything is treated as a small part of a larger journey, and nothing is ever final.
This is a more rational way of looking at the world. Entrepreneurs often like to draw clean, simple, basic lines between things — assuming that A leads to Z, and that today’s decisions can determine a company’s future. But that’s not usually true! Everything we see, and everything we experience, is only one data point in a much larger and more complicated calculation. It is literally impossible to predict how one action will lead to one outcome.
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