Podcast
Doug Has Questions
Hosted by Douglas · EN
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.
17episodes
Episodes
Newest firstAll episodes
Episode 28: Tod Sebens; What If You Treated Your Life Like A List
Yesterday01:36:10Tap to summarizeSend us Fan MailSomething 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.
Transcribe →Episode 27: John Svenson; A Mountaineer Artist Explains How Adventure Becomes A Life In Art
1w ago02:24:49Tap to summarizeSend us Fan MailDenali 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.
Transcribe →Episode 26: Lee Heinmiller; A Lifelong Haines Local Explains How A Community Gets Built
2w ago02:48:09Tap to summarizeSend us Fan MailA 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.
Transcribe →Episode 25: Sean Brownell; From Ski Bum To Heli Ski Pioneer In Southeast Alaska
3w ago01:56:59Tap to summarizeSend us Fan MailA 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?
Transcribe →Episode 24: Stuart DeWitt; From Trapping Lines To Fishing Grounds In Southeast Alaska
4w ago02:31:22Tap to summarizeSend us Fan MailHe 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?
Transcribe →Episode 23: Kim Larson; Eight Kids, Nine Hours, Zero Quiet
Apr 3002:21:02Tap to summarizeSend us Fan MailA 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.
Transcribe →Episode 22: Thom Andriesen; What Does A Small Town Owe Its Volunteers?
Apr 2302:15:35Tap to summarizeSend us Fan MailA 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?
Transcribe →Episode 21: Michael Marks; From Woodstock To Haines
Apr 1601:39:58Tap to summarizeSend us Fan MailA 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.
Transcribe →Episode 20: Charlotte Olerud; What We Owe The People Who Stay
Apr 902:33:49Tap to summarizeSend us Fan MailOne 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?
Transcribe →Episode 19: Aaron Davidman; A Director Explains Why American Solitaire Is About Community Over Fear
Apr 201:46:38Tap to summarizeSend us Fan MailA 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.
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