This Losing Mindset Is Common Among Entrepreneurs — I’ve Interviewed Thousands of Them
Struggling entrepreneurs tend to fall victim to this fallacy.
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.
Related: This One Overlooked Habit Could Transform How You Lead, Connect and Grow Your Business
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.
For example, consider the founder I described. He struggled to get an investor meeting, finally got one, and then worried that he had only one shot at success. If he flopped, it would doom his company to failure.
But…is that definitely true? Of course not! Every situation has infinite possible outcomes. Absolutely anything could happen! We cannot be certain of any one path, which means it’s pointless to worry about taking the wrong one. A high-stakes mindset only hinders our ability to think clearly, take action, and react fast.
If you’re stuck in high-stakes thinking, here’s how to bring those stakes down. It’s a formula I use whenever I get stuck in imaginary stakes. And it goes like this:
Step 1: Start with your current scenario. For example, let’s imagine that you’re pitching an investor.
Step 2: Imagine things not going the way you wanted. For example, maybe the investor says no.
Step 3: Create three realistic positive outcomes from that. Show yourself, very logically, how something “bad” can lead to something good. Make some realistic assumptions!
Related: How Mindset Plays a Role in Your Entrepreneurial Success
For example… the investor might reject you, but they’ll also share an important insight that’ll help you refine your outreach. Or perhaps you’ll discover that you’ve been pitching the wrong kinds of investors all along. Or you might get feedback that prompts you to make massive changes to your business model, transforming your business in the process. Who knows!
Ultimately, this is all about control. We want things to work out clearly and perfectly, exactly the way we want them to, and we struggle when we cannot control the outcomes.
There’s good news here, though: There’s plenty you still can control! Because once something happens, you can control your response to it.
That’s exactly what happened to the founder who texted me. He went to that meeting, got rejected, but felt great about it anyway. The investor asked smart questions, took him seriously, and gave feedback that the founder took to heart. He’s now midway through raising his round — and he’s smarter, better, and more confident because of that first rejection.
Like I said: The stakes are much lower than you think.
P.S. Are you a regular reader of my column? Good news — you can get something like this every week, in your inbox! Subscribe to my newsletter at jasonfeifer.com/newsletter.
Related: The Mindset that Helped Me Start 5 Companies Before Age 30
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.
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