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Could Be Worse

Could Be Worse

By: Matt Osterman
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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.

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Art Economics Leadership Management & Leadership
Episodes
  • Discovering Rosario Dawson, Winning Over Burt Reynolds, and Embarrassing Yourself in Front of Spike Lee with Van Hayden
    Apr 4 2025

    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.

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    47 mins
  • Navigating the Creator Economy: Authenticity, Burnout & Building Community with OnlyAubss
    Mar 25 2025

    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

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    37 mins
  • Championing Indie Film & Creative Growth in MN with Andrew Peterson
    Mar 12 2025

    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

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    52 mins
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