The Perilous Art of Pivoting: When Change Becomes Risk

An article we liked from Thought Leader David Zhou:

The Danger of Pivots

Mike Maples Jr. once said that 90% of Floodgate's exit profits come from pivots.

Hell, 50% of my angel investments have pivoted from the idea I first invested in. Pivoting is a constant norm of the entrepreneurial ecosystem. Many investors know it'll happen. Great founders instinctually prepare for that possibility. Being married to the problem, not the solution is the direct reflection of what it means to prepare for pivots. By definition, Meriam Webster defines the word as:

pivot (n) - a usually marked change, especially an adjustment or modification made (as to a product, service, or strategy) in order to adapt or improve

As such, small feature improvements, changes and additions, even omissions rarely count as one. But a large product shift, where the core product is no longer the product you once sold, is one. In general, the common advice on the street is that you should embrace pivots, until you find product-market fit. But also knowing that you can always lose product-market fit, even after you obtain it. A pivot should either help you catch lightning in a bottle, or help you keep lightning in the bottle.

But that's not the purpose of me writing this piece. It's about the opposite. The quiet thing no one explicitly talks about when it comes to pivot. The TL;DR version is each time you pivot, you lose trust. You lose trust because you didn't have conviction in your product. You lose trust because you didn't have conviction on where the market will go. Hell, you lose trust because you didn't do what you said you were going to do. You were not a person of your word. You lose trust because you made someone else lose trust. Because of you, they looked stupid. To their peers. To their bosses. Sometimes to their friends.

Once you lose trust, it's really, really hard to get it back, if at all. In the age of information excess and product surplus, you won't have the time or the attention from your customers to rebuild that trust. They'll just move on to the next solution.

Slow Ventures' Yoni also recently tweeted:

Pivots almost never work:

You need an actually good idea. These are rare and hard to come up with in real time.
You need resources sufficient to test it. You've already spent much of the money you raised.
You need the energy and excitement to keep going RIGHT NOW. Struggling is exhausting and you've been struggling for a long time.

You don't your investors (or yourself) a pivot.

We make a deal about spending money to prove/disproven something. Once you've done that (even if the answer is "false") your obligation is done.

You held up your side of the bargain. pic.twitter.com/BuJ7tT5wbt

— yoni rechtman (@yrechtman) May 27, 2025

All of which are true. But many truly great companies, as we know them today, have gone through their pivots. The idea that put them on the billboard was...