This Could Work

Saylor

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. 1D AGO

    The Evolution of Internet Creativity with Nick Borenstein (General Manager, The Webby Awards)

    Nick Borenstein has dedicated his career to celebrating the best of the internet. As the General Manager of The Webby Awards, he oversees the most prestigious and competitive awards for digital creativity, honoring everyone from independent creators to global brands. In this episode, Nick joins Will Trowbridge to discuss what it actually takes to win a Webby and how the internet's creative bar is shifting. They dive deep into his own experience winning for the hit podcast Missing Richard Simmons, the messy but authentic state of human creativity in 2026, the rise of unhinged brand campaigns like Nutter Butter, and how AI is acting as a tool rather than a crutch in the landscape of digital art. In this episode, we cover:  00:00 – Introduction & Welcome 02:22 – Nick's journey to winning a Webby for Missing Richard Simmons  05:43 – Will’s experience winning for Netflix’s Dressing Funny  06:47 – What it takes to win a Webby (and why it doesn't cost $30 million)  09:00 – The Webby Awards judging process  09:38 – How AI is shaping the 2026 Webby Awards and creative workflows  12:17 – The state of creativity in 2026: Is the bar getting lower?  16:08 – Unhinged marketing and the demand for authentic content  17:50 – Why creators are the last bastion of trust on the internet  25:20 – Top tips for submitting and winning a Webby Award About Nick Borenstein: Nick Borenstein is an award-winning producer, filmmaker, and content executive who currently serves as the General Manager of The Webby Awards. In this role, he leads strategic development, partnerships, and industry relations to champion creative excellence and innovation across the internet. Before taking the helm at the Webbys, his diverse background spanning film, television, and audio yielded notable credits such as the Emmy-nominated series AKA Wyatt Cenac and the Webby-winning podcast Missing Richard Simmons. About This Could Work:  This Could Work, hosted by Saylor CEO Will Trowbridge, celebrates creative risk-taking and the people reshaping the future of brands. Follow Saylor:  Website: www.sayloragency.com Instagram: @SaylorAgency LinkedIn: https://www.linkedin.com/company/saylor-agency/

    30 min

  2. MAR 12

    The New Frontier of Fandom with Monica Austin (SVP & CMO, Blizzard)

    Monica Austin has built her career by following her curiosity into the heart of shifting industries. As the current SVP and Chief Marketing Officer at Blizzard, she oversees global marketing for iconic franchises like World of Warcraft, Diablo, and Overwatch. In this episode, Monica joins Will Trobridge to discuss her journey from traditional entertainment to Silicon Valley giants. They dive deep into the culture of Netflix, the early days of Instagram, and how Blizzard continues to foster one of the most passionate communities in the world. In this episode, we cover: 00:00 – Introduction  05:00 – From the UTA Mailroom to SVP 12:00 – Leaving Fox for Facebook 18:00 – The early days of Instagram 25:00 – The "Sink or Swim" culture of Netflix and scaling during the Stranger Things era 35:00 – Turning Calm into the "Nike of Mental Health" during the 2020 election 45:00 – Why gaming is the new comic book and the future of Blizzard About Monica Austin: Monica Austin is a seasoned marketing executive who has led teams at some of the most influential organizations in the world, including Blizzard, Calm, Netflix, Fox, and Facebook. About This Could Work: This Could Work, hosted by Saylor CEO Will Trowbridge, celebrates creative risk taking and the people reshaping the future of brands. Follow Saylor: Website: www.sayloragency.com Instagram: @SaylorAgency LinkedIn: https://www.linkedin.com/company/saylor-agency/

    34 min

  3. FEB 26

    The Indie Agency Era: How Indie Agency News Became a Home for the Industry’s New Power Players

    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.

    23 min

  4. FEB 12

    Fandoms, Chaos & Free TV: How Tubi Became a Social Powerhouse

    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.

    37 min

  5. 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

  6. 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

  7. 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

  8. 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

  9. 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

  10. 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
    10
  • Rating
    Explicit
  • Copyright
    © Saylor
  • Show Website
    This Could Work