Douglas Layman

Cues and Views

Douglas Layman, Bend, Oregon entrepreneur and explorer, in brief.

December 12, 2025
3 Minutes
Douglas Layman

Home: Bend, OR and Cabo San Lucas, Mexico.  Age: Old enough to know better, young enough to do it anyway.  Birthplace: Syracuse, NY.  Profession: Entrepreneur, investor, occasional grown-up. Title: Retired CEO.  Alma mater: Oregon State University (BS); Georgetown University (MBA).

Current project: Learning to dance and just competed in my first dance competition.  Recent recognition: My tech company made the Inc. 500 list twice.  Latest contribution to others: Helping a friend navigate the chaos of starting a business and an active life at the same time. What’s been your big (or biggest leap)? Selling my business to pursue a life built around passion, movement, and adventure.  Hobbies: Skiing, kiteboarding, hiking (with gorillas), mountain biking, meditation, fine dining, and game night with friends.  Recent travel or adventure: Scuba diving in the Greek Islands.  Last book read: Klara and the Sun, by Kazuo Ishiguro.

Moral compass: Does the decision feel honest, respect people, and can I stand behind it tomorrow without cringing?  How do you define a perfect friendship? Trust, emotional openness, and the kind of vulnerability that lets both people be fully themselves.  What is your greatest joy? Shared moments of connection.  What natural talent have you neglected? Comedy.  I briefly did stand-up.  What occupation, other than your own, do you most admire? Social workers.  What is at the top of your bucket list? Scuba diving in the Galápagos Islands.  How do you relieve stress? A long hike, a bike ride, pickleball game, or even just wandering a new trail.  What ingredient is essential to your perfect vacation? A focus, something that gives the adventure a heartbeat.

Besides your parents, who has had the greatest influence on your life? My grandmother.  She taught me a lot. What’s the best advice you received growing up? Figure out what you’re passionate about and learn everything you can in that direction, the rest will work itself out. What’s the best advice you received in your career? Stay ready so you don’t have to get ready. What is your go-to source of news and information? The New York Times and The Economist. What company or organization do you most admire? Patagonia.  What personal circumstance has had the greatest influence on your life? Selling my company and choosing to step off the traditional career ladder completely reshaped my life.

What is your big idea?

Build a national adventure and wellness festival.

What change would you like to see in the world? People listening to each other with more curiosity and less defensiveness.  What message do you want to send out into the world? Live boldly, stay curious, and don’t wait for perfect conditions to start anything.  Life opens up when you let new experiences shape you.  What mega-trend most excites you? The rise of location-independent living and experiential lifestyles.  What mega-trend most concerns you? Being hyper-connected online but emotionally disconnected in real life.

What title would you choose for the movie about your life? How Did I End Up Here?  Who would you like to spend an evening with, in heaven? My grandmother, no hesitation.  As a kid, what did you first want to be when you grew up? An explorer.  After your loved ones, what object would you first save from your burning home? My travel journals.  How would you choose to spend tomorrow, if you knew it was your last day on earth? Outside, with the people I love, doing something simple and unforgettable.  What advice would you give your younger self? Relax.  You don’t need to sprint through life like it’s a limited-time sale.  Take chances earlier, trust yourself more, and stop acting like you need it all figured out by Tuesday.  What period in your life would you do differently, if you could? My late thirties.  Great time, terrible strategy.

Personal mission: To live boldly, stay curious, and build a life driven by connection, adventure, and meaningful experiences.  Personal motto: Another day, another chance to excel.  Favorite quote: “In the middle of every difficulty lies opportunity” (Albert Einstein).  Desired epitaph: He lived fully, loved deeply, and never stopped exploring.

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