The Owen Gifford Show

24 - Sean Connolly | The World Is Inherently Funny

Owen sits down with Denver comedian and host of the Intallerable podcast, Sean Connolly, for a conversation about stand-up comedy, podcasting, creative freedom, and why chasing success can sometimes get in the way of enjoying what you do. Sean shares what he's learned from producing nearly 250 podcast episodes, why connecting with guests matters more than preparing the perfect questions, and why creators shouldn't let social media analytics dictate their work. The two discuss the challenges of building a podcast from scratch, finding your comedic voice, and whether ordinary people make better podcast guests than celebrities. They also break down Denver sports, Carmelo Anthony's complicated legacy with Nuggets fans, Nikola Jokić's greatness, and why the solution to Idaho's problems might be making the state wider.

Owen and Sean also dive into their shared experiences with spinal fusion surgery, the challenges of turning personal suffering into comedy, and why spending time in nature might be essential to living a fulfilling life. They discuss psychedelics, Buddhism, Taoism, and the pursuit of enlightenment before exploring government conspiracies, media manipulation, and whether society is becoming increasingly disconnected from what really matters. The two debate Shane Gillis' recent controversies, Nathan Fielder's unusual approach to comedy, and the psychology behind Elizabeth Holmes and the Theranos scandal. Sean shares his approach to writing a joke every day, his thoughts on what makes a successful comedian, and why Denver's comedy scene has the potential to become something special. They close things out by discussing the need for more underground comedy shows and whether finding a venue is really as difficult as it seems.

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23 - Jake Tupitza | Kissing Babies and Shaking Hands

Owen sits down with Denver comedian Jake Tupitza for a conversation about stand-up comedy, creative freedom, the struggles of making money as a comedian, and whether being funny actually makes someone interesting. Jake talks about getting his start in comedy after moving to Denver, his early days performing in a rock band, and how he became involved in Denver's underground comedy scene. The two discuss the challenges of writing original material, finding your comedic voice, and whether new comedians should spend years developing their craft before posting their first sets online. They also get into the rise of social media comedians, why some of the biggest names in comedy struggle to deliver great specials, and whether performing for audiences who already love you can actually make you a worse comedian.

Owen and Jake also break down Nathan Fielder's latest movie, the bizarre personalities behind its story, and why an unexpected nude scene might be the strangest example of Chekhov's gun ever put on film. They debate whether the Beatles are overrated, why garage bands seem to be disappearing, and whether staring at the ceiling might be the secret to writing better jokes. Jake shares stories about performing at the Netflix is a Joke Festival competing in Denver's roast battle scene, and performing for a room full of drunk Australians. They close things out with Halloween costumes and Jake's potential presidential campaign built around shaking babies and kissing hands.

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22 - Jackson Omilian | All Roads Lead to Beer League

Owen sits down with comedian Jackson Omilian for a conversation about stand-up comedy, sports, growing up in small towns, and why bombing on stage might be the best way to keep your ego in check. The two break down the controversy surrounding Shane Gillis' SNL monologue and why Saturday Night Live might no longer be the path to becoming a great stand-up comedian. Jackson talks about getting his start in comedy in Fort Collins, bombing at his first open mic, and learning that making people laugh is a lot harder than it looks. They discuss the grind of writing jokes, finding your voice, building a reliable material, and why Denver has the potential to become one of the best comedy cities in the country. They also get into Boston sports fans, the Colorado Rockies' never-ending struggles, hockey rivalries, and why no matter how far you make it as an athlete, all roads eventually lead to beer league.

Owen and Jackson also talk about growing up near ski resorts, small-town bonfires, college drinking games, and why nobody seems to start garage bands anymore. They swap stories about Red Rocks concerts, getting way too drunk in college, and watching a girl throw up her way through an In-N-Out drive-thru. The conversation takes a turn into Idaho's stranger residents, Mormon basketball coaches, overpriced mountain towns, and an encounter with elk that had Owen's girlfriend questioning whether they were going to survive their hike. They close things out with conspiracy theories about Antarctica, the moon landing, the absurdity of sending billionaires to the bottom of the ocean with a video game controller, and why spending ten years getting good at comedy might still be worth it.

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21 - Owen Gifford | I’m So Tired of Impending Doom

Owen sits down for a solo episode about chasing your dreams, moving goalposts, and why more people need to measure success as moving towards something rather than achieving it. Twenty-one episodes into the podcast and four years into stand-up, Owen reflects on performing at Comedy Works, why success never seems to feel like enough, and how quickly the next goal replaces the one you spent years trying to reach. He talks about returning to his hometown in Idaho, feeling misunderstood by people who knew an older version of him, choosing comedy and podcasting over a more traditional career, and why failing upward might be the only real way to figure out what you’re supposed to be doing with your life.

Owen also breaks down the constant sense of impending doom that seems to follow every generation, from the Cold War to Y2K to 2012 to the pandemic and now artificial intelligence. He talks about AI doomsday predictions, robot boxing, BattleBots, jailbreaking a toaster, social media taking over everyday life, rising costs, and why he refuses to spend his life afraid of whatever apocalypse is supposedly coming next. He closes things out with a trip back to Idaho involving a skunk living under his parents’ porch, an exterminator sharing way too much information, and why ordering a McDouble would be significantly worse if McDonald’s told you the cow’s name.

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20 - Jacob Humphries | The World Is Absurd, Bring a Rotisserie Chicken to the Movies

Owen sits down with comedian Jacob Humphries for a conversation about marijuana, movies, comedy, and trying to stay sane in a rapidly changing world. Jacob talks about accidentally becoming a part-time marijuana influencer, and growing up in South Carolina after being born in England. The two break down their obsession with going to the movies, why theater subscription services might be one of the best deals left in America, why you can sneak absurd amounts of food into theaters now, and the people who somehow still think it’s acceptable to talk or use their phones during a film. Jacob also talks about working at the Denver Comedy Underground, and getting to watch some of the best comedians in the country develop their material up close.

The conversation goes deeper into stand-up comedy, AI, money, the government and the strange direction the world seems to be heading. Owen and Jacob talk about Rory Scovel improvising material that eventually makes it into his specials, Josh Johnson’s ability to constantly produce topical comedy, the evolution of Joe Rogan, billionaires and the pursuit of endless wealth, and their concerns about how artificial intelligence is changing everyday life. They close things out by talking about working around professional comedians, bombing at open mics, building new material one small piece at a time, and why sticking with comedy long enough to actually get good might be the most important part of the process.

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20 - Jacob Humphries | The World Is Absurd, Bring a Rotisserie Chicken to the Movies

Owen sits down with comedian Jacob Humphries for a conversation about marijuana, movies, comedy, and trying to stay sane in a rapidly changing world. Jacob talks about accidentally becoming a part-time marijuana influencer, and growing up in South Carolina after being born in England. The two break down their obsession with going to the movies, why theater subscription services might be one of the best deals left in America, why you can sneak absurd amounts of food into theaters now, and the people who somehow still think it’s acceptable to talk or use their phones during a film. Jacob also talks about working at the Denver Comedy Underground, and getting to watch some of the best comedians in the country develop their material up close.

The conversation goes deeper into stand-up comedy, AI, money, the government and the strange direction the world seems to be heading. Owen and Jacob talk about Rory Scovel improvising material that eventually makes it into his specials, Josh Johnson’s ability to constantly produce topical comedy, the evolution of Joe Rogan, billionaires and the pursuit of endless wealth, and their concerns about how artificial intelligence is changing everyday life. They close things out by talking about working around professional comedians, bombing at open mics, building new material one small piece at a time, and why sticking with comedy long enough to actually get good might be the most important part of the process.

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19 - Max Madorsky | Living in Thailand as a Professional Muay Thai Fighter

Owen sits down with comedian and professional Muay Thai fighter Max Madorsky for a conversation about fighting, comedy, Thailand, and what happens when you spend most of your life training to throw the perfect kick. Max talks about growing up at nearly 300 pounds, getting bullied as a kid, and discovering Muay Thai at 14 after deciding he needed to learn how to defend himself. He shares how a promise with a friend headed to Iraq helped motivate him to lose weight, how competitive Pokémon somehow played a role in the journey, and how he eventually went from an overweight teenager in Idaho to fighting professionally in Thailand. Max breaks down the art of eight limbs, cutting massive amounts of weight before fights, the difference between Muay Thai and MMA, and why getting punched with a four-ounce glove is a very different experience from getting hit with a boxing glove.

The conversation goes deeper into Max’s years living and fighting in Thailand, including winning two fights by knockout six days apart, getting offered the opportunity to stay as a sponsored fighter, being hit by a car, and opening a weed dispensary after an injury kept him out of the ring. Max talks about the injuries that eventually pushed him toward retirement, tearing his bicep just as he was getting healthy again, and why he’s now planning a return to fighting. He also calls out potential opponents, explains why American Muay Thai still has some catching up to do, and talks about his plans to return to Boise and help coach fighters. Owen and Max close things out by breaking down the surprising similarities between stand-up comedy and fighting: putting in deliberate reps, checking your ego, learning to fail in practice, and understanding that bombing at an open mic isn’t so bad when you’ve already been knocked out on national television.

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18 - Zach Hopkins | The Waymos Train While You Sleep

Owen sits down with comedian Zach Hopkins for a conversation quickly spirals into true crime, artificial intelligence, scams, and whether anyone can actually tell what’s real on the internet anymore. They talk about the allegations surrounding comedian Reggie Watts, the Lindsay Clancy case, and a fake 49ers player who allegedly scammed women by convincing them he was a professional athlete. Zach shares the story of nearly falling for an FBI phone scam as a teenager, while Owen talks about watching elderly people slowly learn how impossible it’s becoming to distinguish AI-generated videos from reality. They get into AI influencers, fake casino ads, self-driving cars, and why the technology seems to be advancing faster than anyone knows what to do with it.

The conversation goes deeper into climate change, nuclear energy, Elon Musk, the prison planet theory, Buddhism, suffering, and why humans sometimes need to get punched in the face by consequences before they change. Owen and Zach also talk about indie movies breaking through Hollywood, seeing the same actors in every blockbuster, Gen Z’s strange relationship with sex and dating, growing up during the early days of iPhones and social media, and the people who somehow still post Snapchat stories. Owen gives five rules comedians should follow before posting stand-up clips online, shares his experience eating at a Michelin-star restaurant, and explains why an incredible meal can coexist with making a late-night quesadilla while smoking a joint. They close things out with Denver drivers, self-driving Waymos roaming the streets at night, and the realization that while everyone else is sleeping, AI is still out there training.

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17 - Luke Cole | Live Life Like You’re Collecting Stories

Owen sits down with comedian Luke Cole, known as The Dive Bar Shaman, just weeks after Luke made the big leap from Montana to Denver to pursue stand-up more seriously. Luke talks about leaving Missoula, driving hours across Montana just to get five minutes of stage time, and why moving to a bigger comedy scene felt like the necessary next step. They compare doing comedy in Montana and Denver, the strange amount of talent that came out of a tiny Montana scene, and why getting better sometimes means being willing to leave a comfortable life behind. Luke also shares how a chance encounter with a Bozeman comedian first got him into stand-up, his abandoned plan to make a coffee-table book about Montana dive bars, and what he's learned from throwing himself completely into comedy.

The conversation dives deeper into taking risks, collecting experiences, and why both Owen and Luke would rather build interesting lives than spend all their time worrying about money, careers, or what other people think. They talk about growing up playing sports, insane sports parents, social media, politics, the apocalypse, homelessness, and why nobody actually cares what you're doing as much as you think they do. Along the way, Luke tells stories about his crazy life. They also get into why stand-up never really has an end goal, the importance of actually doing the things you claim to care about, and Luke's philosophy that if nothing really matters, you might as well take some risks and build a life worth having stories about.

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16 - Dave Neering | Behind the Scenes of Managing a Comedy Club

Owen sits down with Denver comedian and comedy-club manager Dave Neering for a conversation about the work that happens behind the scenes of stand-up. Dave shares how he moved from Florida to Denver before ever performing comedy, started at Comedy Works running food and seating customers, and eventually became Wendy Curtis’s executive assistant. He talks about driving touring comedians around the city, accidentally ending up in a group text with Brian Callen and former mobster Sammy “The Bull” Gravano, and ultimately leaving Comedy Works before finding his current role as general manager and booker at Denver Comedy Underground. They also get into what it takes to recognize talent, working with agents, choosing comedians who can sell tickets, and the strange pressure of booking performers while still being new to stand-up himself.

The conversation dives deeper into Denver’s growing comedy scene, the difference between treating comedy as a business and protecting it as an art form, and why producing shows and creating content have become so important for comedians trying to build a career. Owen and Dave also talk about hiking on psychedelics, camping in the Great Sand Dunes, bears, moose, mountain lions, exotic pets, and traveling outside the United States. Along the way, they discuss meeting famous comedians, discovering Reggie Watts, why the best comedy often comes from difficult experiences, and whether doing stand-up simply because it is fun is reason enough to keep showing up.

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