On the Relentless Pursuit Podcast, host Joe Adams interviews Will Hardy, a real estate entrepreneur and film producer who sold his company, moved back to Kentucky, and transformed an abandoned Holiday Inn in Bardstown into The Trail Hotel, a bourbon-centric boutique destination with 95 rooms, multiple bars, a restaurant, and a “bourbon butler” concierge.

Will describes a “dark night of the soul” at age 43 that he calls a “Divine interruption,” leading him into therapy, inner healing, and a more intentional second half of life. He shares childhood influences, performance-driven insecurity, body shame, and intense fasting that preceded back-to-back lung collapses during the 2008 crash, plus rebuilding through roofing sales and scaling a large Atlanta house-flipping business.

He discusses selling everything, relocating his family, and pursuing hope-filled filmmaking, including his upcoming film “Hershey,” and his podcast “Enter Up.”

This episode is for the man carrying pressure in silence… and for anyone who’s been forced to rebuild their life from scratch.

Connect with Will:

• Podcast: Enter Up

• Website: enteruptwithwill.com

• The Trail Hotel (Bardstown, KY)

00:00 Leap To Bourbon Country

01:24 Podcast Welcome And Guest Intro

02:57 Trail Hotel Vision

04:09 Divine Interruption Awakening

07:33 Midlife Battles And Burnout

08:15 Kentucky Roots And Sports

09:18 Finding Acting In High School

12:42 Grandfather Legacy Lessons

14:45 Doing The Inner Work

16:30 Proving Yourself Vow

21:12 Childhood Wounds And Body Shame

27:23 LA Leap And Real Estate Breakthrough

30:48 Faith Fear And Getting Moving

34:10 Enjoying The Journey

36:32 Fear and paralysis

37:21 Parenting against fear

38:46 Take the shot mindset

40:13 Leaving ministry and burnout

41:13 2008 crash and lung collapse

44:47 Roofing hustle comeback

46:34 Flipping boom and rentals

49:27 Dark night and sell it all

51:53 Buying the bourbon hotel

56:18 Hotel lessons in leadership

01:02:38 Why therapy now

01:08:41 Relentless pursuit and wrap

01:11:56 Healing in many lanes

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