This Could Work
This Could Work

This Could Work

Saylor

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Episodes

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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.

Recent Episodes

How to Hook Audiences on Social with Disney’s Abby Ho (VP of Digital & Social)
MAY 7, 2026
How to Hook Audiences on Social with Disney’s Abby Ho (VP of Digital & Social)
Abby Ho has built her career at the intersection of fandom, social, and storytelling. As VP of Digital & Social at Disney Branded Television, she leads campaigns that help fans discover, connect with, and stay engaged with some of the most beloved franchises in the world, including Percy Jackson, Bluey, and Mickey Mouse Clubhouse.In this episode, Abby joins Will Trowbridge to share how she went from HR to shaping digital strategy for major entertainment brands. They discuss the creative differences between Disney and Netflix, why the best campaigns are built around human behavior, how Percy Jackson became a global social and out-of-home moment, and why she launched her “Fellow Kids” newsletter to translate youth culture to the masses.In this episode, we cover:00:00 – Introduction & welcome02:22 – Abby’s path from HR into entertainment and social05:00 – Cold-calling her way into Degrassi and early digital fandom building06:47 – Launching creator and content programs at CBC and Wattpad08:57 – What Disney and Netflix taught Abby about creative culture11:44 – How ideas move from concept to campaign at Disney13:38 – The Percy Jackson billboard and the power of a big swing15:20 – Building a global campaign across out-of-home and social16:59 – The High School Musical TikTok stunt and reintroducing beloved IP21:07 – Why all great marketing starts with human storytelling25:00 – Fellow Kids and translating Gen Alpha and Gen Z culture27:24 – What’s next, including Hannah Montana’s 20th anniversaryAbout Abby Ho:Abby Ho is the VP of Digital & Social at Disney Branded Television, where she leads fan engagement strategy across franchises including Percy Jackson, Bluey, and Mickey Mouse Clubhouse. She has held senior roles at Netflix, Wattpad, and CBC, building a career around fandom, audience development, and culturally resonant storytelling. She is also the author of Fellow Kids, a newsletter focused on decoding Gen Alpha and Gen Z culture for marketers and brands.About This Could Work: This Could Work, a Webby-award winning podcast hosted by Saylor CEO Will Trowbridge, celebrates creative risk-taking and the people reshaping the future of brands. Follow Saylor: Website: www.sayloragency.comInstagram: @SaylorAgencyLinkedIn: https://www.linkedin.com/company/saylor-agency/
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28 MIN
The Evolution of Internet Creativity with Nick Borenstein (General Manager, The Webby Awards)
APR 2, 2026
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 & Welcome02:22 – 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 AwardAbout 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.comInstagram: @SaylorAgencyLinkedIn: https://www.linkedin.com/company/saylor-agency/
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29 MIN
 The New Frontier of Fandom with Monica Austin (SVP & CMO, Blizzard)
MAR 12, 2026
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34 MIN