Billionaire Fireside Chat: Jeff Hoffman, Priceline/Booking.com Founding Team & Airport Check-In Kiosk Creator

In this episode of the Capital Raiser Show, Richard C. Wilson sits down with Jeff Hoffman—serial entrepreneur and Billioanire, Priceline.com/Booking.com founding team member, inventor of the airport check-in kiosk, Grammy and Emmy winner, and chairman of the Global Entrepreneurship Network. Out of 275+ events and 2,000+ speakers, Jeff has been rated the single best speaker to ever hit the Family Office Club stage—and you're about to hear why.

Jeff unpacks the mindset shift that changed everything for him: real leaders don't create followers, they create other leaders. He shares how stepping out of the way, serving his team (including literally picking up a 20-year-old's dry cleaning), and obsessing over operational focus—"if it doesn't sell more hotel rooms, don't do it"—helped scale Priceline/Booking.com into a global giant. Jeff explains how to avoid being "blinded by your own brilliance," including the lesson he learned from Sam Walton: stop listening to experts and start listening to your customer (the "farmers").

He also dives into defining success and failure upfront on a single sheet of paper, wiring money back to investors when metrics showed they wouldn't hit the mark, and why most founders completely mishandle investor relations by only calling when they need cash. On the culture side, Jeff shows how you keep a team so engaged that nobody quits—by knowing exactly why each person comes to work (like buying a mom a house) and tying their personal goals to the company mission. He challenges the "grind 24/7" culture, arguing instead for working smart, automating ruthlessly, and reserving the all-nighters for the rare moments that truly matter.

Jeff closes with his work at the Global Entrepreneurship Network (200 countries) and World Youth Horizons, redefining entrepreneurship as self-determination and teaching people—especially youth—how to design their own future instead of depending on anyone else. If you care about scaling a business, leading people well, raising capital intelligently, and living a life that actually aligns with your values, this conversation is a masterclass.

To meet investors in person and plug into our ecosystem, visit https://familyoffices.com/. Our investor club offers 30 nationwide events a year, 10,000 registered investors, and 40 proprietary AI tools to help you raise capital and grow your platform.