Entrepreneurial Grit, Innovation, and Leadership Built Through Reinvention

Tim Hentchel’s remarkable journey, from washing dishes at 14 to co‑founding HotelPlanner, reveals a leader shaped by entrepreneurship, grit, and deep industry expertise. He shares how hands‑on hotel experience, paired with his Cornell education and passion for technology, sparked the idea to bootstrap a travel‑tech platform long before startups became mainstream. Tim describes how building HotelPlanner with co‑founder John Prince meant learning every job, securing world‑class talent, and staying relentlessly focused on product innovation and partner needs.

He reflects on the power of expertise, surrounding himself with leaders who understand hotels, technology, and operations inside and out. He speaks candidly about choosing battles wisely, protecting personal capital, and remaining humble in an industry where partnerships determine longevity. Tim shares insights on resilience through industry upheavals, global expansion to London and Singapore, and navigating crises from 9/11 to COVID, all while prioritizing reinvention and service.

His reflections highlight his belief in bootstrapping, equity ownership, and ensuring technology creates opportunity, not concentration, exemplified by his gig‑based, AI‑augmented call center designed to give agents a fair share of value.

Notable Quotes/Highlights

• "I always wanted to be an entrepreneur."
• "Be an expert, and act like one."
• "Choosing your battles wisely can define your career."
• "To stay relevant, you have to keep reinventing."
• "Do the fundamentals better every day."

Closing Reflection

Tim Hentchel’s story reminds us that entrepreneurship thrives on humility, discipline, and bold vision. His journey inspires every professional to stay curious, build real expertise, honor relationships, and push innovation forward, one thoughtful decision at a time.