Jeff Hoffman has spent decades building companies and even more time putting himself in unfamiliar rooms all over the world. So when Jeff Hoffman sat down with Sean Kelly on the Digital Social Hour, the conversation naturally drifted toward the stories that don't fit neatly into a resume: the dinners, the detours, and the decision to stop saying no.
What starts as a conversation about travel opens into something bigger — a look at how one man turned a simple habit of saying yes into a six-year experiment that reshaped how he sees the world.
About Jeff Hoffman
Jeff Hoffman is an entrepreneur and co-founder of Priceline.com, with a career that spans multiple startups, public and private CEO roles, and a reputation as a keynote speaker who has addressed audiences in dozens of countries. His work has taken him well beyond the boardroom and into communities most business leaders never visit.
Over the past several years, Jeff Hoffman committed to saying yes to nearly every invitation and opportunity that came his way, a decision that sent him traveling to dozens of countries and sharing meals with strangers along the way. That willingness to step into the unknown has become a defining thread in how he talks about growth, curiosity, and connection.
What Jeff Hoffman and Sean Kelly Talked About
- Why Jeff Hoffman committed to sharing dinner with people in 50 different countries
- The life-changing moment in Cambodia that reshaped how he views the world
- What six straight years of saying yes to nearly everything taught him about growth
- How unscripted travel became a real classroom for lessons business school never taught
- Why saying yes to the unfamiliar builds a kind of resilience most people avoid
- The lessons in generosity and connection he picked up from strangers around the globe
- How curiosity and hospitality opened doors that ambition alone never could
Why This Conversation Matters
This is the kind of conversation the Digital Social Hour is built to have — trading the polished entrepreneur narrative for the messier, more human story underneath it. Jeff Hoffman's willingness to say yes for six straight years offers a real look at what happens when someone lets curiosity lead instead of caution.
▶ Watch the full episode on YouTube
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About Sean Kelly & the Digital Social Hour
Sean Kelly is an entrepreneur and the host of the Digital Social Hour, one of the fastest-growing interview podcasts in the world, where he sits down with entrepreneurs, athletes, creators, and cultural voices for candid, long-form conversations. The show draws over 100 million views a month across platforms. Explore more guest features on SeanKelly.io.
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