Welcome to "The Rollercoaster," a podcast where host Tyler Hall interviews successful entrepreneurs, CEOs, business leaders, and startup founders about the highs and lows of startup life. Join Tyler as he gets real about the challenges and triumphs of building a business from the ground up, and learn how these successful leaders have navigated the rollercoaster ride of entrepreneurship. Whether you're a seasoned entrepreneur or just starting out on your business journey, "The Rollercoaster" has something for you. Tune in for valuable insights and practical tips on succeeding as a startup business leader.
Welcome to "The Rollercoaster," a podcast where host Tyler Hall interviews successful entrepreneurs, CEOs, business leaders, and startup founders about the highs and lows of startup life. Join Tyler as he gets real about the challenges and triumphs of building a business from the ground up, and learn how these successful leaders have navigated the rollercoaster ride of entrepreneurship. Whether you're a seasoned entrepreneur or just starting out on your business journey, "The Rollercoaster" has something for you. Tune in for valuable insights and practical tips on succeeding as a startup business leader.
In this episode of The Roller Coaster Podcast, I sat down with Billy McFarland, yes, that Billy, the mastermind behind the Fyre Festival. But this isn’t a story of excuses or spin. It’s an unfiltered, emotional conversation about ambition, delusion, and the high cost of chasing validation at any cost.
Billy opens up about the exact moment he lied to an investor, the deep regret that still keeps him awake at night, and what it felt like to lose everything, freedom, reputation, and trust. We talk about solitary confinement, broken relationships, redemption, and the hard lessons learned inside federal prison.
But we also talk about what’s next. Billy’s stepping into a new chapter, owning his past, paying restitution, and building a product focused on what he does best: getting attention.
This episode isn’t about defending a scandal. It’s about humanising the person behind it, and what happens when the world watches you fall. If you’ve ever made a mistake, felt the weight of your choices, or wondered what true redemption looks like, this one’s for you.
Listen now.
Key Moments:
0:00 The Call That Changed Everything
2:49 The Moral Weight of Betrayal
5:48 The Lies That Made It Worse
10:21 The Arrest Timeline
16:54 His Take on the Netflix Doc
20:57 Clearing Up the Bahamas Rumour
24:01 Prison Surprises
30:00 The Darkest Days Behind Bars
34:02 Who Stayed, Who Left
37:36 COVID in Prison: Ice Cubes & Strip Searches
40:15 Redemption, Responsibility & Rebuilding Trust
Guest Info:
IG: @pyrtbilly (https://www.instagram.com/pyrtbilly/?hl=en)
X: @pyrtbilly (https://x.com/pyrtbilly?lang=en)