Doug Has Questions
Doug Has Questions is a podcast dedicated to thoughtful conversation that leads to better understanding, connection, and inspiration. Host Douglas Olerud draws on his life experience to explore the stories of the people he’s met along the way.
Episodes
32 episodes
Episode 32: Charlie DeWitt; A Life Built In Alaska
You can hear a whole era of Southeast Alaska in Charlie DeWitt’s voice: Salvation Army roots, moving from post to post, then landing in Haines and deciding it is home for good. Charlie walks us through the early days, from small boats and canne...
Episode 31: Lee Robinson; What If Your Detours Are The Point
Dropping a signed contract into a FedEx box and immediately searching “how to recall a package” is a special kind of panic, and it’s exactly where Lee Robinson found himself after agreeing to buy The Rusty Compass in Haines, Alaska. Lee’s journ...
Episode 30: Mike Machowiak; What Survival Teaches About Love And Faith
A home birth in a ham radio room on a Fairbanks-area homestead is only the opening scene of Mike Machowiak’s life, and it explains more than you’d think. Mike grew up around improvisation, cold mornings, and the kind of grit you don’t lea...
Episode 29: Harriet Brouillette; From Boarding Schools To Tribal Leadership In Southeast Alaska
A family story can be entertaining, but it can also explain why a community looks the way it does. Sitting down with Harriet Brouillette, lifelong Haines resident and Alaska Tribal Administrator of the Year, I hear how one family line str...
Episode 28: Tod Sebens; What If You Treated Your Life Like A List
Something is off about a guy who can casually mention getting lifted by a humpback whale and then move right along to the next story. Tod Stevens has spent decades stacking real adventures the hard way, through mechanical skill, odd jobs, and a...
Episode 27: John Svenson; A Mountaineer Artist Explains How Adventure Becomes A Life In Art
Denali is the easy part compared to the people. That’s one of the clearest lessons we pull from our conversation with John Svenson, a Haines, Alaska mountaineer and working artist whose life somehow spans Yosemite dirtbag years, Alaska state su...
Episode 26: Lee Heinmiller; A Lifelong Haines Local Explains How A Community Gets Built
A town can start with a big dream, but it survives on unglamorous details: heat that actually works, water that keeps running, and neighbors who show up when the plan falls apart. We talk with lifelong Haines resident Lee Heimiller, president o...
Episode 25: Sean Brownell; From Ski Bum To Heli Ski Pioneer In Southeast Alaska
A fishing boat flips in the dark in a 60-mph blow, and a 23-year-old stays calm enough to get everyone into a life raft. That same steady nerve shows up again and again in our conversation with Sean “Sean Dog” Brownell, a longtime Haines reside...
Episode 24: Stuart DeWitt; From Trapping Lines To Fishing Grounds In Southeast Alaska
He grew up in Haines, Alaska with a bike, a beach, and more wilderness than rules and it shaped everything that came after. My guest, longtime local Stuart DeWitt, walks me through the moments that built his edge: early hunting trips, learning ...
Episode 23: Kim Larson; Eight Kids, Nine Hours, Zero Quiet
A licensed daycare in a small town sounds simple until you hear what it actually demands: nine-hour days, strict ratios, constant trust from parents, and almost no margin for error. We sit down with Kim Larson, a longtime in-home child care pro...
Episode 22: Thom Andriesen; What Does A Small Town Owe Its Volunteers?
A Disney crew, a Gold Rush story, and a tiny Alaska town that had to pull off big-league logistics in the dead of winter. We’re joined by longtime Haines resident Tom Andriesen, a familiar face to anyone who’s spent time around town, and he wal...
Episode 21: Michael Marks; From Woodstock To Haines
A kid in Queens watches planes at LaGuardia, runs a small-time “slug” hustle on coin machines, and then gets stopped cold by a store owner and a furious mom. Years later, that same kid hitchhikes across America at 16, goes to Woodstock, and som...
Episode 20: Charlotte Olerud; What We Owe The People Who Stay
One decision, one returned phone call, one job opening in a tiny Southeast Alaska town and a whole family history gets rerouted. I’m sitting down with my mom, Charlotte Olerud, to capture the stories people have been asking for for years: growi...
Episode 19: Aaron Davidman; A Director Explains Why American Solitaire Is About Community Over Fear
A gun store in Alaska. A filmmaker from Berkeley. A quiet movie about a noisy country. We talk with director writer producer Aaron Davidman about American Solitaire and the long road from early theater mentors to a feature film built for real c...
Episode 18: Jimmy Yoakum; What If Policing Started With Grace Instead Of Force
A police chief doesn’t just arrive in a town like Haines, Alaska with a clean slate. Every choice gets remembered, every interaction becomes part of the story, and trust is earned one conversation at a time. That’s why I wanted to sit down with...
Episode 17: Rashah McChesney; From Texas To Alaska: Building Trust Through Local Journalism
A local newspaper can feel quaint until you see the bill: thousands per month just to print, plus a supply chain that depends on flights, couriers, and weather. We sit down with Rashah McChesney, owner and publisher of the Chilkat Valley News, ...
Episode 16: Tom Wayes; Chasing Lines, Building Gear, Racing Rocks: The Relentless Pursuit Of Flow
A 400-foot ski hill in Pennsylvania shouldn’t produce a heli-ski guide who opens Alaskan lines, designs technical gear, and races a 900-horse rock car at 140 on dirt—but here we are. We sit down with guide and multi-sport athlete Tom Wayes to t...
Episode 15: Al Badgley; From Baytown To Haines: A Life Of Service
A cabin burns to the ground on a winter night without phones. A young volunteer watches a ragtag crew of neighbors save what they can and decides to spend the next three decades running toward the worst moments in people’s lives. That’s the hin...
Episode 14: Travis Kukull; What If A Restaurant Could Feed A Town’s Soul?
A slice of fresh bread on a Sunday night can shape a life. Travis joins us to share how those early kitchen memories, a scientist father’s quiet example, and a teenage “pop-up” at home set him on a winding path from Shoreline to Maui, New York,...
Episode 13: Reba Hylton; How A Tourism Director Balances Growth, Wildlife, And Community Needs
A love story to place doesn’t always start pretty. For Reba Hylton, it began with a mother who worked fields and fought racism, a softball swing that opened college doors, and a gut feeling that life had to be wilder. Alaska answered. Reba lear...
Episode 12: Dr. Marnie Hartman; What If Your Hardest Struggles Become Your Superpower?
What if the hardest things you’ve lived through could become your superpower? We sit down with Dr. Marnie Hartman—physical therapist, yoga teacher, author, and death doula—whose life moved from the precision of competitive gymnastics to the int...
Episode 11: Bill Thomas; A Veteran’s Journey Through Alaska, War, And Public Service
A life can hold multitudes, and Bill Thomas’ story proves it. Born and raised in Haines with deep Tlingit roots, Bill carries us from Main Street memories and Chilkat dancers to the hot ramp at Bien Hoa, where a young crew chief learned to keep...
Episode 10 Lilly Boron; From Off-Grid Alaska To The Superintendent’s Office
A World War II tent. A Yamaha piano hauled off a swaying dock. Five bears on the playground. A cancer diagnosis delivered in a plastic-lined hallway. And a small town that kept showing up. This conversation with superintendent Lilly Boron is a ...
Episode 9: Joe Hamilton; Hard Work, Human Connection, And A Warranty That Built A Brand
What turns a humble birding shop into a global optics leader? A leap of faith, a relentless work ethic, and a belief that service beats slogans. Sitting down at Vortex HQ with CEO Joe Hamilton, we trace the arc from a dentist-turned-retailer to...
Episode 8: Cesre McQuaid: A Counselor’s Journey Through Trauma, Faith, And Community Healing
What if healing starts with a simple truth: your body already knows the way? Licensed counselor Cesre McQuaid joins us to share how a life-altering NICU crisis awakened her faith, redirected her career, and taught her the power of real-time sup...