Control the Business Game and Build What Lasts with Josh Payne

What really drives founders — is it passion, obsession, or hidden insecurity?

In this episode, we dive deep into the mind of an entrepreneur who built and sold a company for a massive exit and is now reshaping what success actually means.

You’ll hear the raw truth about chasing billion-dollar dreams, why “enough” is never really enough, and how founders can avoid burning themselves out on the startup treadmill. From the birth of seed-strapping to the culture clash between obsession and balance, this conversation uncovers the unfiltered realities behind building companies that last.

We also explore powerful lessons on timing exits, staying in the game when the odds are stacked against you, and redefining fulfillment beyond external validation. 

Tune in to discover why staying in the game might just be the ultimate founder advantage.

Key Topics:

-Redefining success and knowing when enough is enough

-The rise of seed strapping and capital efficient growth

-Obsession as both a strength and a dangerous fuel

-The importance of timing and resilience in the founder journey

-Balancing identity, fulfillment, and the realities of entrepreneurship

Quote  From The Episode: 

"You just have to ask yourself, when is enough enough?"

- Josh Payne

Timestamp:

[02:16]: When Is Enough… Enough? The Hidden Game Behind Startup Success

[11:10] AI, Obsession, and the Culture Clash Every Founder Faces

[20:19] The Dark Fuel Driving Founders—and Why It Burns Out Fast

[30:46] From Obsession to Ownership: The Real Rules of Delegation and Focus

[40:05] The 10-Year Grind, the Exit Gamble, and Why Timing Is Everything

[51:19] Stay in the Game: The Founder’s Real Secret to Winning

[1:05:36] Outro

Connect with - Josh Payne:

LinkedIn -  linkedin.com/in/jnpayne

Websites: medium.com/@jnpayne

Connect to Entrepreneurial-Excellence Podcast:

LinkedIn - https://www.linkedin.com/company/entrepreneurial-excellence-podcast

Youtube - http://www.youtube.com/@EntrepreneurialExcellencePod

TikTok - https://www.tiktok.com/@eepodcast24

Facebook - https://www.facebook.com/profile.php?id=61570329516959

Website - https://www.levy.company/entrepreneurial-excellence