When Should You Quit? A 7-Time Founder on Pivoting, Failure & Finding Product-Market Fit

Entrepreneurs are constantly told to keep going.

But what happens when persistence becomes stubbornness?

Nuri Otus has built seven companies, experienced successful pivots, raised capital, shut down ideas that weren’t working, and is now building DUO, an AI-powered matchmaking platform.

In this conversation, we dig into how founders can recognize real market validation, why criticism can actually be incredibly valuable, how positioning affects whether a product gets traction, and the signals that tell you when it might finally be time to change direction.

Nuri also shares how an elevator conversation led to an investment from AOL, why DUO gained users almost immediately after launch, and why some of his best business lessons came directly from mistakes.

A very real conversation about entrepreneurship, product-market fit, marketing, and knowing when to keep pushing versus when to move on.