The podcast episodes explore the idea of missed opportunities through various lenses, including personal reflection on past decisions, the perspective of venture capitalists who passed on promising investments, and the story of a NASCAR driver whose career did not reach its full potential.

In the episode Tan France asks about missed opportunities, the hosts of the "Handsome" podcast discuss opportunities not taken and how they can shape one's life journey. Similarly, in Issa Rae thinks a little delusion goes a long way, the actor and creator reflects on forks in the road and missed opportunities, such as not studying abroad in Paris, and how those experiences have impacted her perspective.

The topic of missed opportunities is also explored from an investor's point of view in episodes like Investor Stories 342: Why I Passed and Investor Stories 335: Why I Passed, where venture capitalists share stories about startups they decided not to invest in, only to see those companies go on to great success.

Finally, the episode 535 - Casey Atwood: The Career I Don't Talk About delves into the story of a NASCAR driver whose career did not reach its full potential, providing a personal account of the regrets and lessons learned from missed opportunities.