This Could Work

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/

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 SVP12:00 – Leaving Fox for Facebook18:00 – The early days of Instagram25:00 – The "Sink or Swim" culture of Netflix and scaling during the Stranger Things era35:00 – Turning Calm into the "Nike of Mental Health" during the 2020 election45:00 – Why gaming is the new comic book and the future of BlizzardAbout 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.comInstagram: @SaylorAgencyLinkedIn: https://www.linkedin.com/company/saylor-agency/

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.