Learning After Winning: The Hidden Trait of Great Entrepreneurs

Startup success is often credited to grit, timing, or a lucky pivot. But our new study suggests that what separates many successful entrepreneurs is not hustle; it is how they think. 
Some founders try things until something works (practice-based entrepreneurs). Others have a theory for why something should work, and they refine it with every step (theory-based entrepreneurs).  

The big takeaway from my research? Founders who keep questioning their assumptions - even after early wins - often perform better.

My paper, co-authored with researchers from MIT Sloan and the Rotman School of Management, builds a “Bayesian model” to simulate how founders make decisions under uncertainty. It compares those who update their thinking as they go with those who stick to fixed assumptions - tracking when they stop, push forward, or circle back - and how those choices shape outcomes.  

Many founders might stop once something works. Theory-driven entrepreneurs don’t. If a result is far better than expected, they don’t see it as the finish line; they see it as a clue. Maybe there’s more to uncover. Success becomes a reason to keep going.

You can see this mindset at work in founders like Jeff Bezos. Before launching Amazon, he had already helped build a successful online stock trading system for a hedge fund. But instead of stopping there, he pushed further - not because that strategy failed, but because its success signalled a bigger opportunity. Rather than sticking with what worked, he kept searching.  

And today, Amazon is far more than an online bookstore - it’s a $2.2 trillion business empire. 

At the heart of this mindset is a habit: constantly updating what you believe. Every result is a signal, not just a win or a loss. Theory-driven founders start with a working idea - and stay ready to revise it as new evidence rolls in.

That kind of thinking also makes it easier to revisit old ideas. Google’s founders, Larry Page and Sergey Brin, first built a search engine called Backrub at Stanford University. Their original plan was to license the tech to big portals like Yahoo!. When those deals went nowhere, they pivoted back to an earlier idea - launching their own search site. What looked like a fallback turned out to be the breakthrough.

If a past failure starts to look different under a new lens, theory-driven entrepreneurs like Page and Brin don’t hesitate to take another swing - something others may not even consider. 

Theory-driven founders treat advice as a way to sharpen their thinking - not just fix problems. They look for insight from people who know the space, using that input to refine how they see the market. Practice-based founders, by contrast, tend to ignore advice unless it offers a clear, immediate payoff. They focus on what worked last time, not what it reveals.  

Shoe retailer Zappos is a clear example of the former: it started with a drop-shipping model, where the seller takes orders but the manufacturer ships the product directly to the customer. But investor Tony Hsieh, who later became Zappos’ CEO, pushed for a shift to owning inventory. That change helped the company grow into one of the most successful e-commerce companies of its time, culminating in a $1.2 billion acquisition by Amazon in 2009. 

Some people naturally think this way, but the mindset can be taught. Just asking why you are stopping - and whether it is the right moment - can lead to better learning. Early success is not always proof you have nailed it; sometimes it’s a sign you should keep digging.

The paper’s impact goes well beyond academic theory. For investors and startup accelerators, it offers a way to spot different founder mindsets - and identify who’s more likely to succeed.

It also flips how we read founder behaviour. Going back to an old idea, testing beyond success, or seeking out advice might look like second-guessing - but it can actually signal deeper strategic thinking.

The model opens up new ways to teach entrepreneurship, too. Most training focuses on execution and pitching. This adds another layer: helping founders build, test, and sharpen the thinking behind their decisions.  

And for investors, it highlights rare but valuable patterns - like founders who keep searching after a win, pivot when the data shifts, and value advice that fits the market.  

In a world that celebrates instinct and hustle, this research offers a smarter take. The best entrepreneurs are not always the fastest or flashiest. They are the ones who treat success as a clue, failure as a signal, and every result as a chance to rethink what they believe.

Seen this way, entrepreneurship is not about trial and error - it is closer to running experiments. And with so much on the line, that shift in mindset could be what turns a good idea into a great company.