This Could Work

Saylor
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This Could Work is a podcast where we celebrate creative risk taking and the people shaping the future of brands Host Will Trowbridge, founder of creative agency Saylor, sits down with founders and creatives to explore the real stories behind big leaps — no fluff, just the highs, lows, and everything in between.

Episodes

  1. JAN 29

    Kevin Prince Turned Viral Thinking Into a Creative Empire, Launching The Very First Drone Show Agency

    “You have to be a little bit crazy to start your own business and think ‘this could work.’”  Kevin Prince has quite literally done it *all* in Hollywood. From cutting his teeth as an NBC Page to building a career in entertainment marketing at CBS News, Netflix, Gawker, Showtime, and more.  Now, as a 360 creative marketing executive and co-founder of Heads In The Sky (the very first creative drone show agency), he’s sharing what he’s learned from his biggest swings and misses. This Could Work, hosted by Saylor CEO Will Trowbridge, celebrates creative risk taking and the people reshaping the future of brands.

    24 min

  2. 2025-12-18

    How Walt Disney World Imagineer Michael Hundgen Landed Everyone’s Dream Job

    If you’ve been waiting for a sign from the universe before taking that big career leap, let Michael Hundgen’s story be it.  Former Survivor producer turned VP of Creative at Walt Disney Imagineering, Michael Hundgen joins This Could Work to share his unconventional journey and explain how trusting his gut led him to the most inspiring work of his career.  This Could Work, hosted by Saylor CEO Will Trowbridge, celebrates creative risk taking and the people reshaping the future of brands.

    33 min

  3. 2025-12-04

    How Creatorpreneur Jayde I. Powell Turned Her LinkedIn Presence Into a Full-Time Business

    Former marketing executive Jayde I. Powell joins This Could Work to share the story behind one of the boldest moves in her career: walking away from a full-time role to bet completely on herself as a creator. In this episode, Jayde talks candidly about what it really feels like to leave the safety of a steady job, how she knew it was time to make the leap, and the mindset shifts that helped her step into a fully creative life on her own terms. If you’re a marketer, social strategist, or creative sitting on the edge of a big decision, this conversation is for you. This Could Work, hosted by Will Trowbridge, celebrates creative risk taking and the people reshaping the future of brands.

    33 min

  4. 2025-11-20

    From Netflix to Worthi: How Myles Worthington Built an Award-Winning Agency

    Myles Worthington, founder of Worthi, joins host Will Trowbridge to share the truly wild story of how he left his career at Netflix behind in order to launch his own agency. Worthi, a full-service marketing, creative and communications agency, works to help brands connect with underestimated audiences.  This Could Work is a podcast where we celebrate creative risk taking and the people shaping the future of brands. Host Will Trowbridge, founder of creative agency Saylor, sits down with founders and creatives to explore the real stories behind big leaps — no fluff, just the highs, lows, and everything in between.

    38 min

  5. 2025-11-12

    Giant Spoon’s Marc Simons

    Marc Simons, co-founder of Giant Spoon, joins the pod for the inaugural episode of This Could Work to discuss taking a giant leap into entrepreneurship and what his agency learned through the pandemic and beyond. This Could Work is a podcast where we celebrate creative risk taking and the people shaping the future of brands. Host Will Trowbridge, founder of creative agency Saylor, sits down with founders and creatives to explore the real stories behind big leaps — no fluff, just the highs, lows, and everything in between.

    31 min

  6. SEASON 1, EPISODE 1 TRAILER

    Coming soon... This Could Work

    This Could Work is a podcast about bold ideas and the people crazy enough to chase them. Host Will Trowbridge, founder of creative agency Saylor, sits down with founders and creatives to explore the real stories behind big leaps — no fluff, just the highs, lows, and everything in between.

    1 min

Trailer

About

This Could Work is a podcast where we celebrate creative risk taking and the people shaping the future of brands Host Will Trowbridge, founder of creative agency Saylor, sits down with founders and creatives to explore the real stories behind big leaps — no fluff, just the highs, lows, and everything in between.

Information

  • Creator
    Saylor
  • Years Active
    2025 - 2026
  • Episodes
    6
  • Rating
    Explicit
  • Copyright
    © Saylor
  • Show Website
    This Could Work