Doug Has Questions

Douglas

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.

  1. 3d ago

    Episode 31: Lee Robinson; What If Your Detours Are The Point

    Send us Fan Mail 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 journey to small-town business ownership is anything but linear: film photography in school darkrooms, newspaper assignments in the pre-digital era, a decade of whitewater rafting and outdoor guiding in Colorado, and even life on the road during the 1990s fiber optic boom negotiating right-of-way and crop damages with farmers. Every chapter looks unrelated until you zoom out and see the same throughline: curiosity, people, and learning by doing.  We talk about the harder part most “reinvention” stories skip: what it feels like to be capable but not confident, to enjoy students but still feel unsettled as a teacher, and to chase stability while craving adventure. Lee shares how he meets Darcy, how faith stays constant when the plan keeps changing, and how family decisions reshape career decisions. He’s candid about real estate during the 2007 to 2008 crash, the pressure of debt, and the realization that selling yourself is exhausting when you already doubt yourself.  Then the Alaska leap becomes real. Lee walks through espresso fundamentals, barista training, and why great coffee comes down to details like grind, pressure, extraction time, and milk microfoam. He also tells the unglamorous truth: the ferry move, living above the shop, the brutal first summer, and the moment COVID pulls him back into teaching, only to prove that doing two big jobs at 70% is a fast track to burnout. What emerges is a story about entrepreneurship, community, and building a warm “third place” where locals and travelers feel welcome.  If you like stories about career change, small business ownership, specialty coffee, moving to Alaska, and finding purpose without a perfect plan, hit subscribe, share this with a friend who’s at a crossroads, and leave a review. What’s the biggest leap you’ve taken, or the one you’re still debating?

    2h 14m

  2. Jun 18

    Episode 30: Mike Machowiak; What Survival Teaches About Love And Faith

    Send us Fan Mail  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 learn from a manual. From there, his family history stretches back to WWII Europe: the Polish underground, a POW camp and escape, Switzerland’s mountain culture, and the long, complicated ways trauma can echo into the next generation.  We follow Mike’s path through welding, shipyards, commercial diving, and the early, cowboy days of Dutch Harbor where marine work is equal parts skill and hazard. He breaks down what underwater welding actually looks like, why maritime refrigeration becomes his niche, and how the Bering Sea fishing boom changes everything. Then the story pivots to adventure on purpose: he and Martha buy a steel sailboat, build real offshore competence, and spend years sailing the Pacific, balancing the romance of the sea with the realities of risk, fatigue, and loss.  The most gripping chapter comes later with aviation. After Mike finally earns his pilot license, a fuel loss after departing Juneau forces a ditching in Lynn Canal. What follows is raw, specific, and unforgettable: cold water, hypothermia, rescue, and the medical decisions that save Martha’s life. If you care about Alaska, survival, seamanship, aviation safety, faith, and how people keep going after the worst day, this conversation stays with you.  Subscribe for more long-form stories, share this with someone who loves Alaska and hard-earned life lessons, and leave a review so more listeners can find the show. What part of Mike’s journey hit you the hardest?

    3h 14m

  3. Jun 11

    Episode 29: Harriet Brouillette; From Boarding Schools To Tribal Leadership In Southeast Alaska

    Send us Fan Mail  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 stretches from France to Louisiana to Southeast Alaska and then collides with some of the hardest chapters in Alaska Native history. The details are vivid: a grandmother sent to boarding school at age five, relatives lost to distant institutions, and the way paperwork and prejudice tried to rewrite identity. We also get practical about what tribal leadership looks like when it is not a slogan. Harriet talks about building stability at the Chilkoot Indian Association, leveraging funding to run programs, and using tools like 105(l) leases with the Department of the Interior. We dig into the difference between a sovereign tribal government and an ANCSA Native corporation, why some Southeast Alaska communities became “landless,” and what it takes to move landless legislation forward when the Tongass National Forest becomes the battleground. The conversation stays grounded in everyday life too: growing up at Three Mile without electricity, huge gardens, the realities of food security, and even a Prohibition-era potato still that helped families survive. We close on what it means to lead under scrutiny in a small town, why transparency matters, and what Harriet wants most for the future, including tank farm cleanup and a healthier path for the next generation. If this meant something to you, subscribe, share it with a friend, and leave a review. What part of Harriet’s story hit you the hardest?

    2h 20m

  4. Jun 4

    Episode 28: Tod Sebens; What If You Treated Your Life Like A List

    Send us Fan Mail 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 stubborn willingness to try things most of us only talk about. We sit down and follow the thread from growing up between Virginia and California to joining the US Army as a marine diesel mechanic, including the pride of helping train the first woman to become a senior marine diesel mechanic in his track. From there, the conversation veers into the kind of lived history you can’t fake: basic training incidents that still haunt him, a cross-country breakdown that turns into a lesson in human kindness, and a surprising stint promoting country music shows that puts him face-to-face with famous performers in unfiltered backstage moments. Then Alaska takes over with Talkeetna bush life, small-town stories, and a six-month sail around Mexico where boat repairs pay the bills. We also get into the Haines years: starting Denali Boatworks, directing community theater, upgrading DMX stage lighting at the Chilkat Center, and doing special effects work on the film White Fang before heading south again. Tod’s Antarctica seasons with the National Science Foundation bring the scale up to eleven, from McMurdo to remote camps, deep ice cores, and the weird reality of color deprivation. Along the way, we talk risk, recovery, shark conservation, solo bicycle travel, side-scan sonar and ROV work, whale disentanglement, and the wake-up call of surviving sepsis and double pneumonia. If you like Alaska stories, Antarctica jobs, whale watching, hands-on trades, and travel that doesn’t gloss over the danger, this one is for you. Subscribe for more conversations like this, share it with a friend who loves a good true story, and leave a review with the moment that surprised you most.

    1h 36m

  5. May 28

    Episode 27: John Svenson; A Mountaineer Artist Explains How Adventure Becomes A Life In Art

    Send us Fan Mail 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 surveying by rope, high-altitude guiding, and a studio full of watercolor, fused glass, and beadwork. We talk in John’s Extreme Dreams Gallery as spring ramps up in Haines and the season starts to feel like controlled chaos.  John walks us through the long arc: growing up in Southern California, getting pulled north through Alaska Indian Arts, and finding mentors who taught him what real expedition travel looks like. From there we get into Denali guiding and the hidden job of leadership: team psychology, acclimatization, risk calls, and the moments when a guide has to protect the whole group from one person’s spiral. If you’re curious about Denali climbing, mountaineering training, or what guiding actually demands, this part is packed with real-world detail.  Then we shift into the art and the economics. John breaks down how an adventure life becomes subject matter, why galleries shape what artists can afford to make, and how glass art and watercolor each pull you in different directions. He also shares two deeply human threads: making memorial beads by fusing cremated remains into glass, and how surviving cancer reshaped his urgency around early screening and paying attention to timing. We wrap by talking about mentoring younger artists, what “mastery” really means, and why Haines still feels like one of the best places on earth to build a life.  If this conversation hits you, subscribe, share it with a friend who loves mountains or art, and leave us a review with your biggest takeaway.

    2h 25m

  6. May 21

    Episode 26: Lee Heinmiller; A Lifelong Haines Local Explains How A Community Gets Built

    Send us Fan Mail 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 of the Port Chilkoot Corporation, about the unlikely chain of events that helped turn Fort Stewart from a postwar military site into the heart of Port Chilkoot. Lee shares the inside story of veterans trying to buy surplus equipment, the scramble to finance a fort purchase, and what it meant to build a community in Southeast Alaska when money was tight and winter was not forgiving. From there, the conversation opens up into a deep, practical history of Haines and Tlingit cultural work through Alaska Indian Arts and the Chilkat Dancers. We get into how scouting, statehood-era promotion, and federal manpower training programs helped launch artists and carvers, and why the value of a totem pole is measured in hours, risk, and responsibility as much as dollars. Lee also tells stories about shipping major carvings, projects that ended up across the country, and the way cultural pride grew when public performance was not always welcomed. We also take on the question people argue about the most: Fort Stewart’s barracks buildings. Lee breaks down why “save it” can mean $30–$40 million, how landmark rules shape what’s even allowed, and why a seasonal tourism economy makes big redevelopment plans so hard to sustain. If you care about Haines Alaska history, Fort Stewart, Port Chilkoot, Alaska Native art, and what preservation looks like when budgets get real, this one is for you. Subscribe, share this with a friend who loves local history, and leave us a review telling us what part of Haines you want us to record next.

    2h 48m

  7. May 14

    Episode 25: Sean Brownell; From Ski Bum To Heli Ski Pioneer In Southeast Alaska

    Send us Fan Mail 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 resident and one of the old-guard voices in Alaska heli skiing. We go back to where his winter obsession starts, how the Juneau ski-bum years turn into early heli days, and why those rough beginnings eventually demand real avalanche education and professional guiding systems.  From there, the story widens into what it means to build a heli ski operation in Haines, Alaska over decades: weather windows, pricing by the run, loyal “core” clients, and the constant push and pull of permits, land ownership, and borough-managed maps. Sean talks candidly about competition between operators, how small boundary mistakes can change an entire run, and why he’d rather see a stable status quo than another round of high-drama rulemaking.  We also dig into Powdah Mountain, Sean’s DIY local ski hill built from a driveway, grooming, and a whole lot of sweat equity, plus the new Powdah Mountain Ski Club effort to get organized for insurance, fundraising, and grants. Add in homestead-scale gardens, cold-room food storage, and the “heli homestead” lifestyle, and you get a picture of adventure tourism that is grounded in community and day-to-day work, not just glossy footage.  If you care about backcountry skiing, heli skiing in Alaska, the economics of outdoor recreation, or how small towns manage big terrain, you’ll get plenty to chew on here. Subscribe, share this with a friend who loves the mountains, and leave us a review. What part of Sean Dog’s story hit you the hardest?

    1h 57m

  8. May 7

    Episode 24: Stuart DeWitt; From Trapping Lines To Fishing Grounds In Southeast Alaska

    Send us Fan Mail 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 to trap from old-school mentors, and the kind of outdoor freedom that turns into real capability when things go sideways. Then we get into the working life. Stuart shares what it really takes to survive in commercial fishing in Southeast Alaska, from gillnet salmon to Dungeness crab and halibut fishing under the IFQ quota system. We talk about why diversification matters, how risk decisions get made, and the wild chain of events that led to buying a 45-foot boat in Hawaii, building a cradle, barging it to Seattle, and driving it back north. It’s a masterclass in timing, relationships, mechanical problem-solving, and being prepared when luck shows up. We also don’t dodge the hard parts: viral encephalitis as a kid, the brutal reality of hospitals full of sick children, the politics of fisheries management, allocation pressure, hatchery economics, and what happens when prices crash. On the personal side, Stuart reflects on coaching youth basketball, building confidence through small wins, and what he hopes his kids remember about work ethic, reliability, and family. Subscribe for more conversations rooted in Haines and Southeast Alaska, share this with someone who loves fishing or small-town stories, and leave a review if it hits home. What’s the biggest risk you’ve taken that ended up changing your life?

    2h 31m
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Ratings & Reviews

5
out of 5
10 Ratings

About

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.

Information

  • Creator
    Douglas
  • Years Active
    2025 - 2026
  • Episodes
    31
  • Rating
    Explicit
  • Copyright
    © 2026 Doug Has Questions
  • Show Website
    Doug Has Questions

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