Dane Atkinson has lived just about every version of the founder story.

He started his first company at 18. He’s been the CEO of Squarespace in its early years. He’s founded and exited multiple companies, including SumAll. He’s raised roughly $750 million across his career. He’s built businesses that employed thousands of people and created billions in equity value.

And about half of his companies didn’t work. That’s what makes this conversation different.

In this episode of Not Another Podcast, Dane and I talk about the part of founding that almost never gets discussed honestly: the psychological weight founders put on themselves, and how that weight quietly distorts decision-making, relationships, and even mental health.

We get into the illusion of obligation. The feeling that you owe investors, employees, family, or the “story” you sold an outcome you may not actually control. Dane shares deeply personal stories from early failures, from companies that raised tens of millions of dollars and struggled, and from moments where he spent years trying to “make things right” for others, only to realize how much of that pressure existed only in his own head.

In this episode, we cover:

• Why founders often overestimate how much they owe investors and how that guilt hurts decision-making
• The “obligation trap” and how it keeps founders stuck on paths that no longer make sense
• How claiming product-market fit too early can socially lock you into the wrong future
• What Dane learned from losing friends-and-family money early in his career
• Why failure is the real education founders never get taught
• How boards actually exert power, and how founders can reframe that dynamic
• The role of anxiety, ADHD, and imposter syndrome in founder behavior
• How nearly dying reshaped Dane’s view on ownership, leadership, and what actually matters

This isn’t a hype episode. It’s a perspective episode. And it’s one every long-term founder should hear.