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. 6 DAYS AGO

    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
  2. 30 APR

    Episode 23: Kim Larson; Eight Kids, Nine Hours, Zero Quiet

    Send us Fan Mail 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 provider in Haines, Alaska, to trace how she got here and why her work has quietly held up families for decades. From Kansas roots to growing up in Anchorage, Kim’s path is full of grit, humor, and the kind of consistency that kids and communities depend on. Then the story turns. Kim walks us through the December 2020 storm and the Haines landslide that took her daughter Jenae. We talk about the chaos of those first hours, the community search, and the strange ways grief shows up later: songs that stop you cold, anniversaries you try to spend out of town, and the exhausting reality of living near reminders that never get fixed. Kim also shares how Jenae’s Playground came to life, turning love and loss into a space built for kids, joy, and memory. We also get practical and political about the child care shortage in rural Alaska: why home-based care can be more reliable than a center, how staffing rules can shut programs down overnight, and how a federal food reimbursement program can fail the “last provider standing” because nobody will travel to do an inspection. If you care about child care, community resilience, disaster recovery, and what real support looks like after trauma, this conversation stays with you. Subscribe, share this with a friend who needs it, and leave a review with your biggest takeaway.

    2h 21m
  3. 23 APR

    Episode 22: Thom Andriesen; What Does A Small Town Owe Its Volunteers?

    Send us Fan Mail 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 walks us through how White Fang ended up filming entirely in the Chilkat Valley and what it took to make it happen day to day. Tom shares the behind-the-scenes reality of movie production in Southeast Alaska, from scouting and paperwork to moving trailers, tents, restrooms, security, and keeping sets safe in remote locations like Chilkoot Lake and Nataga Creek. Along the way, we hear about meeting actors, housing animal trainers, and why film workflows looked so different in the 35mm era. We also zoom out into the fuller Haines story: growing up between Seattle and Alaska summers, his family’s Alaska-made art and gift shop hustle, and the fairgrounds accident at age 12 that led to 13 surgeries and later changed his career path after an engineering degree. Tom talks candidly about decades as a volunteer firefighter and EMT, the strain of middle-of-the-night calls, and why small towns depend on people who keep showing up. If you love Haines Alaska history, White Fang filming location stories, volunteer EMT life, or the real mechanics of tourism in Southeast Alaska, you’ll find a lot here. Subscribe for more local conversations, share this with a friend who loves Alaska stories, and leave a review if you want to help the show grow. What’s one moment in your life that changed everything without warning?

    2h 16m
  4. 16 APR

    Episode 21: Michael Marks; From Woodstock To Haines

    Send us Fan Mail 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 somehow ends up getting paid to draw Bert and Ernie for Sesame Street. Michael Marks’ story is one of those rare life arcs that connects real cultural history to the day-to-day work of building community, and it all lands in an unexpected place: Haines, Alaska. We talk through Michael’s path from art school and CalArts to commercial illustration, then into teaching and arts education programs funded through grants. From there, he becomes Santa Clarita’s first cultural arts coordinator and helps build concerts in parks, public art, festivals, and the unglamorous but essential systems that make events safe and possible. He also shares what it was like during the 1994 earthquake, when “arts department” gear like canopies, chairs, and supplies instantly turned into emergency response infrastructure. The conversation comes home to Haines: why he and his wife fell for Southeast Alaska, how fishing changed his idea of living well, and why he keeps saying yes to local boards and volunteer work. We dig into Elder Rock Lighthouse restoration and the push to open it to the public, plus the ongoing effort to keep the Chilkat Center active, from performances to a Steinway-focused concert, all while facing real challenges like travel logistics, film licensing costs, and even finding a piano tuner. Subscribe for more long-form conversations, share this with someone who loves arts and small-town stories, and leave a review so more listeners can find the show.

    1hr 40min
  5. 9 APR

    Episode 20: Charlotte Olerud; What We Owe The People Who Stay

    Send us Fan Mail 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: growing up between Fort St. John and rural Minnesota, learning to work early, and watching my grandpa keep going after losing an arm in a brutal construction accident. These are the kinds of details that don’t show up in official records, but they explain everything about how a family thinks, survives, and loves. We follow the leap to Haines, Alaska in 1964, when “we’ll try it for nine months” turns into a lifetime. We talk about what small town Alaska used to feel like when freight arrived once a month, when catalogs mattered, and when community was the safety net. Mom shares what it was like teaching home economics and PE, helping start what became the Southeast Alaska State Fair, and then building a family business that grew into Alaska Sport Shop and Olerud's Market Center, plus the unexpected chapters like bringing Sears to town and stretching every dollar to keep it all afloat. Then we get to the moments that changed us: a house fire that forced a reset, the economic shock after the sawmill shutdown, and the high-stakes gamble of the commemorative Winchester rifle tied to the American Bald Eagle Foundation. Finally, we talk about the hardest turn, my dad’s 1987 accident and what decades of care giving really require, from rehab limits to daily pain to rebuilding a life around new constraints. It’s also a conversation about what remains: baking, quilting, passing skills to kids and grandkids, finding purpose, and counting blessings. If you connect with stories about resilience, care giving, entrepreneurship, and Haines Alaska community history, subscribe, share this with someone who needs it, and leave a review so more people can find the show. What family story do you wish you had recorded?

    2h 34m
  6. 2 APR

    Episode 19: Aaron Davidman; A Director Explains Why American Solitaire Is About Community Over Fear

    Send us Fan Mail 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 conversations, not talking points. We get into what shaped Aaron’s craft from intense conservatory training to learning how to direct, fund raise, market, and keep going when the first edit feels like a catastrophe. He shares how research trips and interviews about firearms and gun violence led him to a veteran-centered story focused on reintegration, moral weight, and the moments people hide behind a “fine” exterior. We also unpack why language matters in suicide prevention, including the shift toward saying “die by suicide,” and how loneliness can quietly push people toward harm. Then we go straight into the hard stuff: firearm safety, safe storage, training, background checks, straw purchases, and the trust gap that makes “common sense gun reform” so difficult. From the perspective of a working gun store owner, we talk about what can realistically happen at the counter, when to slow a transaction down, and why community screenings and post-film discussions can change behavior the way designated drivers changed drunk driving norms. Subscribe for more grounded conversations, share this with someone who wants nuance over noise, and leave a review with your biggest takeaway.

    1hr 47min
  7. 26 MAR

    Episode 18: Jimmy Yoakum; What If Policing Started With Grace Instead Of Force

    Send us Fan Mail 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 Haines Police Chief Jimmy Yoakum and let you hear the full arc, from where he comes from to how he plans to lead. Jimmy opens up about growing up in Tennessee, learning in junior high that he was adopted, and the complicated mix of curiosity and peace that comes with searching for biological family. From there we follow a career that spans ROTC, Army intelligence, the messy reality of post-9/11 activations, and decades in law enforcement during a period when policing culture, community expectations, and public scrutiny all changed fast. He also shares the surprising detour into teaching criminal justice, where phones and AI tools collide with student motivation and what “real learning” even means now. We get practical about what leadership looks like in the Haines Police Department today: body cameras and transparency, tightening report writing for courtroom credibility, reviewing policies and evidence procedures, improving communications tech, and building better intelligence ties to address narcotics and potential trafficking concerns in Southeast Alaska. Then the conversation turns personal again as Jimmy explains how faith informs his work, what “grace” means when you still have to enforce the law, and why he dreams of creating nature-based trauma retreats for veterans and first responders using dogs, horses, and the outdoors. Subscribe, share this with a friend in Haines or anywhere, and leave a review if this conversation gives you something to think about. What part of Jimmy’s story hit you the hardest?

    3h 2m
  8. 19 MAR

    Episode 17: Rashah McChesney; From Texas To Alaska: Building Trust Through Local Journalism

    Send us Fan Mail 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, to talk about what it really takes to keep community journalism alive in Haines, Alaska when the old ad-driven model is collapsing and every “easy” fix comes with trade-offs. Rashah shares her winding path from East Texas to Alaska, from music school to photojournalism, from a draining metro newsroom to the kind of small town reporting where you can actually close the loop with people. We get candid about student loans and higher education costs, why “objective journalism” is more practice than promise, and how trust breaks when communities stop engaging and only one side will talk. The conversation also goes straight at the modern media ecosystem: social media outrage, national cable incentives, and why local news gets unfairly blamed for the worst behavior of national platforms. Then we zoom in on the business decisions that decide whether a paper lives or dies: newsletters, subscriptions, community events, print frequency, and what happens to accountability when the watchdog disappears. If you care about local government transparency, civic engagement, and the future of small town newspapers, this one is for you. Subscribe, share with a friend who says “the media,” and leave a review with your take: what would make you support local journalism?

    3h 8m

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.

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