Comment by maxnevermind

Many founders do try serial pivots until the money's gone. An entrepreneur shutting down cleanly with half the runway still in the bank would be seen by future potential funders as a net positive. It's worse to grind through all the money trying increasingly extreme pivots away from the original.

It takes maturity and decisiveness to recognize when a startup's core idea isn't going to work. In cases where any pivot wide enough to get into different lane is essentially a whole other business, it's often better to just shut down. Even if the last desperate pivot starts to work, you often have some team members and investors who aren't a good fit for the new focus and, worse, the 'new' business that's finally starting to work is almost out of money and the cap table is messed up. It's usually better to shut it down and reboot cleanly.

Founders who've successfully raised millions and executed well are usually quite fundable, even if their first startup didn't work out. Sometimes the timing is wrong or the market evolves differently. The key is how well you think, execute and communicate through both the windup and the wind down.

I feel like pivoting got unwarranted hype in the 2010s or so, possibly because Slack was an outlier in how successful they were.

Major pivoting is almost always a really bad idea. (I admit I'm doing a bit of weaseling using the "major" qualifier, but when I searched for examples online, a lot of the ones that came back weren't major pivots, just slight refinements of focus to find better product market fit). Pivoting usually carries a lot of baggage - better to just give the money back and start afresh most of the time.

He might not have had that choice. Investors can put money into a bank account, and just as easily take it out. This is what happened in the 2000 dotbomb.