Lexington, Kentucky T–00 DAYS · First episodes September 15, 2026

TheStartup Conversation

Real talks about the leap — from the people who made it.

A podcast about the jump

They had the salary, the mortgage, the safe path. They left anyway.

Honest conversations with people who walked away from good jobs — with real obligations on the line — to build something of their own. Hosted by a guy still deciding whether to make the jump himself.

The trailer is live.

Two minutes on who's behind the mic, why this show exists, and the question nobody answers: everybody tells you how to leave a bad job — nobody tells you when to leave a good one. First three full episodes drop Tuesday, September 15.

Trailer · Live Now

Every conversation follows the Startup Sequence — six stages, from the day job they left to the life they built. Same structure, every guest. So you can compare one leap to the next.

  1. T–02 Pre-flight Life before: the job, the paycheck, the person they were.
  2. T–01 Ignition The catalyst. What finally caused the jump?
  3. T–00 Liftoff The leap itself: the runway math, the spouse conversation, the first days out.
  4. T+01 Max Q The moment of maximum pressure — when the whole thing nearly came apart.
  5. T+02 Stage Separation What they had to let go of to keep climbing.
  6. T+03 Orbit & Debrief Life now — and what they'd say to someone still on the launchpad.
"I have the good job. The one you're not supposed to walk away from. This show is me asking the people who did."

— Your host, still on the launchpad

Read the whole story

You made a leap worth talking about?

We're booking Season 1 now — main street, not Silicon Valley. If you left a real livelihood, with real obligations, to build something of your own, we want the honest version.

Be a guest