Will Dasco got demoted the summer he was a bartender on Cape Cod. Bartender down to server — a punishment, on paper.

He made more money, he was better at it, and it set the direction for the next decade.

A few years later he finished an accounting degree at Suffolk and had two comparable offers in hand: JP Morgan Chase and Hillstone Restaurant Group. He took the restaurant job. His family hated it. "I got a lot of stern talking-tos" — but finance didn't feel right in his core, and hospitality did.

What followed was ten years of saying yes to everything: Boston to Beverly Hills to San Francisco to Boca Raton to Orlando to Pompano Beach, where he was promoted to general manager a week after his 24th birthday. Then Miami, then Atlanta six weeks before the pandemic, then Denver. He saw more of the country in his twenties than most people see in a lifetime, one transfer at a time.

And then, just before 30, he hit the question that ends a lot of good runs: is this it?

IN THIS EPISODE

• The demotion that changed his trajectory, and why serving paid better than the bar anyway
• Turning down JP Morgan for Hillstone, and the conversations with family that followed
• Why saying yes to every transfer is the whole game in your twenties — "if you don't say yes, they'll move on to the next person"
• Becoming a GM at 24 and feeling the weight of it immediately
• Moving to Atlanta six weeks before the pandemic, and what that kind of isolation does to you
• The manager who gifted him a snowboard as a parting shot — and how falling down a mountain taught him to adjust in public
• The night he wrote a resignation letter, made himself a Negroni, drank it, and hit send with nothing lined up
• "I couldn't decide what was next until I decided that this wasn't it"
• Getting walked out ten days into a three-month notice, and how he thinks about that now
• Why he started Hospitality by Will, and the video about needing an hour of silence after a shift that went everywhere
• Chasing a viral moment and catching yourself doing it
• What AI genuinely can't replace — and the moment every one of us starts shouting "agent, agent, agent" into a phone tree
• Reader stories from the industry, including a guest locked out of their room at 3am with no clothes on

CONNECT WITH WILL DASCO
Instagram → https://instagram.com/hospitalitybywill

ABOUT CHECK-IN WITH BRYAN
Hosted by Bryan Fish, CEO of Reliance Hospitality — conversations with the owners, operators and creators shaping hospitality. On your side of the table.
Subscribe → https://www.youtube.com/@Check-InwithBryan
check out more at checkinwithbryan.com

Special thanks to our sponsors: Immedia, Regency Group, Avalon Risk Management, Arcstone Insurance Advisors, and Achilles HR.

Season 6 presenting partner: Immedia

Produced by RH Media Productions.

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