Could Be Worse

Matt Osterman
  • 5.0 (3)
  • ENTREPRENEURSHIP
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Could Be Worse: Big Ideas, Midwest Grit, and Just Enough Self-Deprecation.Could be Worse with Matt Osterman is a journey into the stories of working creators, filmmakers, artists, and entrepreneurs between the coasts. Sometimes hilarious, often aspirational, always valuable. Join as we uncover successes, failures, and insights on building, creating, and thriving in flyover country. This series is for anyone building or creating and appreciates the power of not waiting for permission.

  1. Discovering Rosario Dawson, Winning Over Burt Reynolds, and Embarrassing Yourself in Front of Spike Lee with Van Hayden

    04/04/2025

    Discovering Rosario Dawson, Winning Over Burt Reynolds, and Embarrassing Yourself in Front of Spike Lee with Van Hayden

    What actually goes into running a movie set? In this episode, we sit down with a legendary first assistant director whose resume reads like a film studies syllabus. From humble beginnings in Minnesota to working with huge directors on big sets, this conversation spans unforgettable set stories, navigating chaos with diplomacy, and the real unsung roles that bring movies to life. He shares how a random sidewalk encounter led to casting Rosario Dawson, what it was like being fired mid-show (and why it wasn't his fault), and why ADs are the most pointed-at crew members in the biz. If you've ever wondered what "making your days" means, this one's for you.

    47 min
  2. Navigating the Creator Economy: Authenticity, Burnout & Building Community with OnlyAubss

    03/25/2025

    Navigating the Creator Economy: Authenticity, Burnout & Building Community with OnlyAubss

    What does it take to build a social media following while staying true to yourself? In this episode, we sit down with Aubrey Regner (@OnlyAubss), a Minnesota-based content creator who shares her journey from making Disney videos to capturing the heart of the Upper Midwest with her fresh perspective. We dive into the realities of influencer life, including brand deals, navigating passive-aggressive culture, and the struggle to balance content creation with a 9-to-5 job. 🔹 How she grew her following after moving to Minnesota 🔹 The challenges of working with brands while staying authentic 🔹 Minnesota’s underrated food and music scenes 🔹 Balancing a full-time job with content creation 🔹 The real impact of social media on friendships and mental health 📲 Follow OnlyAubss on Tik Tok: https://www.tiktok.com/@onlyaubss and on Instagram: https://www.instagram.com/onlyaubss/ 🎧 Subscribe for more deep dives into creative careers, social media, and storytelling! #contentcreator #minnesota #socialmedia

    37 min
  3. Championing Indie Film & Creative Growth in MN with Andrew Peterson

    03/12/2025

    Championing Indie Film & Creative Growth in MN with Andrew Peterson

    In this episode, Matt sits down with Andrew Peterson, a filmmaker, producer, and advocate for independent artists. Andrew shares his journey from location manager to executive director at FilmNorth, highlighting his experiences working with iconic filmmakers like David Lynch and his time at Sundance. They discuss the evolving film industry, the power of storytelling, and the importance of empowering underrepresented voices in media. Andrew also shares insights on festival strategy, building creative careers, and how Minnesota can become a hub for independent filmmaking. 🎬 Don't miss this inspiring conversation about resilience, mentorship, and fighting for the underdog in the world of film. Learn more about FilmNorth at: https://filmnorth.org

    52 min
  4. Filmmaking, Finance, and Existentialism with Dave Ash

    02/26/2025

    Filmmaking, Finance, and Existentialism with Dave Ash

    How do you balance a career in corporate finance with a passion for filmmaking? David Ash—writer, director, and creator of Incompleteness—shares his journey from writing screenplays in Excel to producing an award-winning TV series. We dive into the creative process, the challenges of indie filmmaking, and the philosophical ideas behind his work, including determinism, AI, and the evolving tv and film industry. 🔹 The surprising way he outlines scripts (Excel?!) 🔹 Why he left Hollywood behind to create on his own terms 🔹 The deep existential themes of Incompleteness 🔹 Navigating Minnesota’s indie film scene and the industry’s shifting landscape 🔹 AI, free will, and the future of storytelling 📺 Watch Incompleteness trailer: https://incompletenesstheseries.com/

    44 min
  5. Designing Games, Scoring Films, & Rewriting the Rules with Charlie McCarron

    02/10/2025

    Designing Games, Scoring Films, & Rewriting the Rules with Charlie McCarron

    In this episode, host Matt Osterman sits down with Minnesota film composer and board game designer Charlie McCarron to discuss the intersection of music, storytelling, and game design. Charlie shares his journey from aspiring filmmaker to composer and how his love for problem-solving led him to board game creation. They explore the challenges of composing for film, the intricacies of designing engaging board games, and the parallels between both creative fields. Plus, Charlie talks about his latest projects, including his new game "Chroma Zone" and his work on the Minnesota Wild’s orchestral theme. Tune in for a deep dive into creativity, collaboration, and the art of making interactive experiences!

    52 min
  6. From YouTube's Early Days to Working with Netflix, Justinsuperstar has Stories to Tell

    09/16/2024

    From YouTube's Early Days to Working with Netflix, Justinsuperstar has Stories to Tell

    Join us for a jam-packed conversation with Justinsuperstar, a creative force who has had a front row seat to the online video explosion. In this episode, Justin reflects on his early days of online content creation, getting fired from College Humor, being around for the creation of Vimeo, having the #1 app in the country, winning an Emmy, and how his journey evolved into becoming a serious documentary filmmaker.  Discover his thoughts on the importance of completing projects, the lessons learned from failures, and his unique perspective on navigating an ever-changing digital landscape. Don’t miss the rest of the discussion, where Justin talks about his time at YouTube, launching his own agency, and his current documentary project, 'Mom and Dad's Nipple Factory.' With over 20 years in the creative world, Justin shares the highs and lows of his career, offering invaluable advice for aspiring filmmakers and digital creators.

    56 min
  7. Exploring Cryptids and the Horror Genre with Anthony Cousins

    07/15/2024

    Exploring Cryptids and the Horror Genre with Anthony Cousins

    This week, we chat with Anthony Cousins, the director of the acclaimed short When Susurrus Stirs and the found footage horror film Frogman. Anthony has made waves in the indie horror genre with his film Frogman, a genuinely frightening tale shot in glorious low-res high-8 film. The film follows three friends in search of the Loveland Frogman who find out that he is more than just a local legend. Anthony takes us through his creative process, the importance of authenticity in lo-fi horror, and his fascination with cryptids like the Slide-Rock Bolter. We also cover the state of the film industry, the unique aspects of the horror genre, and Anthony’s opinions on AI. Hear about his lessons from life's setbacks and what’s next for his career, including the sequel Frogman 2. Connect with Us: https://www.instagram.com/propellant_podcast https://www.facebook.com/PropellantFilms https://www.tiktok.com/@propellantstudios Key Highlights: • Found Footage Horror: Insights into creating Frogman and the challenges of the shaky cam subgenre. • Cryptid Research: Anthony’s extensive knowledge of cryptids, including the Loveland Frogman. • Current Film Industry: Thoughts on the state of the film industry and the independent horror genre. • AI in Filmmaking: Anthony’s opinions on the impact of AI on the creative process. • Lessons from Setbacks: Personal experiences and lessons learned from setbacks in life. • Future Projects: Exciting details about the upcoming sequel, Frogman 2.

    58 min
  8. The Magic of Themed Entertainment & Immersive Storytelling with Chris Grap

    07/08/2024

    The Magic of Themed Entertainment & Immersive Storytelling with Chris Grap

    This week, we chat with Chris Grap, the Vice President of Experiential Entertainment at the Mall of America. Chris shares his journey from working on film sets in LA to creating immersive experiences at the largest mall in the United States. Discover how he collaborates with Nickelodeon Universe to expand the on-site theme park and his plans for an upcoming waterpark. Chris also discusses his passion for themed entertainment, his move back to Minneapolis, and his annual Toys for Tots fundraiser featuring a screening of the Star Wars Holiday Special. Key Highlights: • Innovating Themed Entertainment: Chris discusses his role at the Mall of America and how he pushes the boundaries of themed entertainment in a retail space. • Upcoming Waterpark: Chris shares exciting plans for a new waterpark at the Mall of America. • Film Industry Background: Stories from Chris’s time working on film sets in LA and his transition to Minneapolis.  • Annual Toys for Tots Fundraiser: Chris talks about organizing his yearly fundraiser, featuring a screening of the Star Wars Holiday Special. • Leaving LA: Chris’s decision to move back to Minneapolis and his experiences since returning. Connect with Us: https://www.instagram.com/propellant_podcast https://www.facebook.com/PropellantFilms https://www.tiktok.com/@propellantstudios

    1h 10m
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Ratings & Reviews

5
out of 5
3 Ratings

About

Could Be Worse: Big Ideas, Midwest Grit, and Just Enough Self-Deprecation.Could be Worse with Matt Osterman is a journey into the stories of working creators, filmmakers, artists, and entrepreneurs between the coasts. Sometimes hilarious, often aspirational, always valuable. Join as we uncover successes, failures, and insights on building, creating, and thriving in flyover country. This series is for anyone building or creating and appreciates the power of not waiting for permission.

Information

  • Creator
    Matt Osterman
  • Years Active
    2023 - 2025
  • Episodes
    31
  • Rating
    Explicit
  • Copyright
    © 2025 Propellant, LLC
  • Show Website
    Could Be Worse