The asymmetric upside of being positive

by Dalton Caldwell12/21/2023

Many of us that are regular users of social media know that the snarkiest and most negative takes get the most engagement. This can train us to optimize for pointing out all of the problems with things in the world in hopes of being rewarded for it.

But this type of worldview doesn’t help founders building startups. The problems with any new startup are usually obvious and numerous, but you have to balance that with seeing the upside of making it work.

In this episode of Dalton and Michael, we’ll discuss the best ways for founders and aspiring founders to think about weighing optimism and pessimism in their day-to-day lives.


  • Dalton Caldwell

    Dalton is Managing Director, Architect and Group Partner at YC. He was the cofounder and CEO of imeem (acquired by MySpace in 2009), and the cofounder and CEO of