Episode 7
The Cost of Trusting Your Gut with Chris Gray
Jason Lee sits down with Chris Gray — marketer, co-founder of Red Palm, and Front Row Dad — to unpack the decision logic couldn't make, and the alignment work that made his gut trustworthy in the first place. Chris shares how he moves from head to body before reacting, why joy is the most…
Chapters
- 00:00:00 — Welcome to The Living Question
- 00:00:47 — The decision logic couldn't make
- 00:07:00 — Keeping someone the numbers said to cut
- 00:08:10 — Why joy is the most vulnerable emotion
- 00:12:30 — Catching unconscious reactions at home
- 00:17:45 — AI as a spiritual guide
- 00:20:17 — When surrender becomes another framework
- 00:26:50 — Selling confidence while Google rewrites the rules
- 00:33:27 — How leading from the head once protected him
- 00:38:33 — Chris's living question: learning to feel
Show notes
Jason Lee sits down with Chris Gray — marketer, co-founder of Red Palm, and Front Row Dad — to unpack the decision logic couldn't make, and the alignment work that made his gut trustworthy in the first place. Chris shares how he moves from head to body before reacting, why joy is the most vulnerable emotion, how he built AI "spiritual guides" shaped by the Bhagavad Gita, the Bible, Eckhart Tolle, and Richard Rohr — and the moment one of those agents showed him that turning surrender into a framework was just his ego grabbing the wheel. They dig into faith moves versus good moves, why the peace that goes beyond understanding requires forfeiting your right to understand, why clients are ultimately buying confidence, and how the state you decide in determines the quality of the action. Chris closes with his current living question: what does it actually look like to feel your feelings, when you've spent a lifetime equating feeling with weakness?
Chapters:
- (00:00:00) - Welcome to The Living Question
- (00:00:47) - The decision logic couldn't make
- (00:07:00) - Keeping someone the numbers said to cut
- (00:08:10) - Why joy is the most vulnerable emotion
- (00:12:30) - Catching unconscious reactions at home
- (00:17:45) - AI as a spiritual guide
- (00:20:17) - When surrender becomes another framework
- (00:26:50) - Selling confidence while Google rewrites the rules
- (00:33:27) - How leading from the head once protected him
- (00:38:33) - Chris's living question: learning to feel
Links and Resources:
- Connect with Chris Gray @yochrisgray — Instagram, Facebook, LinkedIn
- Red Palm, Chris's marketing company for home service businesses: https://redpalm.us
- The Surrender Experiment by Michael Singer: https://www.amazon.com/Surrender-Experiment-Journey-Lifes-Perfection/dp/080414110X
- Front Row Dads: https://frontrowdads.com
About The Living Question
The Living Question is a long-form leadership and decisiom-making podcast hosted by Jason Lee for founders, CEOs, entrepreneurs, and leaders navigating high-stakes business transitions, entrepreneur burnout, and life decisions strategy alone cannot answer. Each episode slows down one real crossroads: selling a company, staying or leaving, scaling through burnout, rebuilding after success, choosing integrity over momentum, navigating a leadership transition, or redefining success when the old scoreboard stops working. With calm pressure and precise questions, Jason helps guests stop performing certainty and name the real decision, the hidden cost, and the version of themselves the choice requires. Grounded and unhurried, the show is not about doctrine, spiritual branding, or productivity hacks. Faith appears as lived discernment: the conviction you cannot un-know, alongside intuition, conscience, values, and self-trust. Together, these inner signals shape public choices in work, money, relationships, identity, purpose, and direction. If you are carrying a living question of your own, this is a place to borrow courage from people who have stood at the edge of reputation, momentum, and belonging—and still stayed with uncertainty long enough to choose a path they could actually live with.