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This Could Work

Author: 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.
8 Episodes
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Independent agencies aren’t the scrappy underdogs anymore—they’re the ones pushing the industry forward.In this episode, host Will Trowbridge sits down with Doug Zanger, founder and editor-in-chief of Indie Agency News, a member-first platform built as a true home for independent agencies across advertising, marketing, and production. They dig into how Indie Agency News is tapping into a real changing of the guard—from holding company dominance to hundreds of powerful indie shops—and what it means to create infrastructure that helps those agencies feel seen, supported, and connected.This Could Work, hosted by Saylor CEO Will Trowbridge, celebrates creative risk taking and the people reshaping the future of brands.
When your brand becomes a meme (in a good way) you know something’s working.In this episode, This Could Work host Will Trowbridge sits down with Celeste Roque, Head of Social at Tubi to unpack the bold, fandom-fueled strategy behind one of streaming’s most talked-about brands.From cultivating an unapologetically chaotic voice to tapping into hyper-niche communities, Tubi proves that when you truly understand your audience, engagement isn’t forced—it’s inevitable.Watch for stories from behind Tubi’s most viral moments, the strategy that fuels its fearless tone, and how a social-first mindset brought new life to free streaming.This Could Work, hosted by Saylor CEO Will Trowbridge, celebrates creative risk taking and the people reshaping the future of brands.
“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.
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.
 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.
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.
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.
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.
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