How an Athlete-Turned-Actor-Turned-Entrepreneur Built a $30M Bourbon Trail Hotel

·55 min·5 clips

Will Hardy reveals how his $12 million hotel dream became a $30 million fight for survival.

Host Zach Buzicruz interviews Will Hardy, the creative entrepreneur behind the Trail Hotel in Bardstown, Kentucky. Hardy begins by recounting his high school audition for 'Grease,' where he secretly tried out and landed the lead role of Danny Zuko, defying his jock persona. After a brief acting career in Los Angeles, he moved to Atlanta, where a TV show inspired him to start flipping houses with only $100. He built a business flipping 50-60 homes before the 2008 crisis hit. Simultaneously, he suffered a spontaneous pneumothorax, requiring lung surgery and leaving him bedridden. As banks called loans due, he nearly lost everything, dwindling his savings to $5,000. To survive, he took a roofing sales job, becoming a top performer within months. With a partner, he re-entered real estate by wholesaling 27 townhouses in a risky 48-hour deal involving a clown costume to attract buyers. This led to flipping 800 homes over seven years through his company, Investor Network. Years later, experiencing burnout and anxiety, Hardy sold all his properties and short-term rentals. While on vacation in Antigua, he received a text about an abandoned 1970s Holiday Inn in Bardstown. He placed an offer sight-unseen, envisioning a boutique hotel. The project, initially budgeted at $12 million, escalated to $30 million, requiring historic tax credits and bank financing. Hardy convinced the bank to keep it unbranded, partnering with Schulte Hospitality for management. The Trail Hotel opened 12 weeks prior, featuring a steakhouse, speakeasy, bourbon library, and recovery room with IV therapy. Hardy explains the 'Bourbon Butler' service, which curates personalized distillery tours, positioning Bardstown as the 'Napa Valley of the South' for bourbon. He also discusses moving his family to Bardstown, where his wife opened a boutique, Caden Lake, and he launched a cocktail bar, Liam Ash. Additionally, Hardy produced a biopic on Milton Hershey, starring Finn Wittrock, set for release in 2026. The episode concludes with Hardy emphasizing the vulnerability and resilience required in entrepreneurship.

As heard by us

A $12 million project becomes a $30 million look at optimism, confidence, and founder endurance.

A $12 million project swelling into a $30 million project gives the episode its business backbone, but the real pull is the temperament behind it.

Read the full review in PlayNext →

Why you'd press play

You get the messy leap from a $12 million plan to a $30 million hospitality project.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Behind the Stays