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.

  1. 3d ago ·  Bonus

    Why Creator Marketing Won Cannes, with Tubi’s Cynthia Clevenger

    Creator marketing stole the show at Cannes Lions—and Tubi’s SVP of B2B Marketing Cynthia Clevenger is here to explain why. In this special-edition micro-episode from the 2026 Cannes Lions International Festival of Creativity, host Will Trowbridge sits down with Cynthia at the Tubi Cabana to unpack the biggest stories, creative risks, and culture-shaping campaigns marketers need to be paying attention to right now. They cover: Why creator marketing is the number one story coming out of Cannes Lions—and what every marketer needs to understand about creator-brand relationships How creators are giving brands unprecedented speed to market, helping them move quickly, remove red tape, and create content in the moment The Levi’s FIFA World Cup campaign and how it’s influencing culture, not just delivering impressions The bold B2B campaign “More Performance, Less Anxiety” and how Tubi is making performance marketing feel human, cheeky, and on-brand If you’re a B2B marketer, brand leader, media strategist, or creator looking to: Build faster, more trusting creator partnerships Connect performance marketing to real human behavior Take smarter, bolder creative risks in 2026 …this micro-episode is a must-watch. About Cynthia Clevenger: Cynthia Clevenger, SVP B2B Marketing at Tubi, is a B2B Marketing veteran with nearly two decades of experience working on both the agency and publisher sides of the industry. She has extensive knowledge in advanced measurement, programmatic and streaming. Clevenger currently leads all B2B Marketing efforts at Tubi, including go-to-market strategy, ad product marketing, sales enablement, branded entertainment, events and industry partnerships. During her time at Tubi, Cynthia has helped develop award-winning marketing campaigns resulting in 5x Cannes Lion awards, the prestigious Super Clio award and 5 Effies. 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.com Instagram: @SaylorAgency LinkedIn: https://www.linkedin.com/company/saylor-agency/

    5 min

  2. Jun 11

    The Death of Boring Ads: Inside Immersive Marketing with Sawhorse’s Nic Hill

    Nic Hill has spent the last decade helping brands evolve from traditional spots to immersive, interactive experiences. As co-founder and Chief Innovation Officer at Sawhorse, he’s worked with Walmart, Alo, and other major brands to build worlds on platforms like Roblox and Fortnite that audiences actually choose to spend time in. In this episode, Nic joins host Will Trowbridge to unpack how Sawhorse went from a scrappy production company to a leader in interactive marketing, why Gen Z audiences are forcing brands to rethink everything, and what it really takes to create branded experiences that feel like entertainment instead of ads. They get into the risks of going all‑in on a creative company, what metrics actually matter in immersive environments, and how AI fits into the future of production without replacing human storytelling. In this episode, we cover: 00:00 – Introduction & welcome 02:02 – From filmmaker to co‑founder and the pivot into interactive 04:20 – Early days of Sawhorse and landing bigger brand work 05:22 – The “this could work” moment and going all‑in on the company 09:12 – Why nothing can fully prepare you for entrepreneurship 09:49 – How Sawhorse became a leader in interactive marketing and gaming 11:00 – Why traditional entertainment marketing is being disrupted 13:00 – What immersive marketing really is (and why Nic hates most ads) 15:21 – Inside Walmart’s Roblox world and multi‑platform campaign strategy 17:34 – Being both innovation partner and ROI‑driven marketer for brands 18:43 – Defining success: KPIs, flywheels, and always‑on campaigns 24:30 – What Gen Z actually wants and how UGC communities “vote” on content 26:15 – Busting the “gamer = teenage boy in a basement” stereotype 26:28 – Gaming as mainstream behavior across every demographic 27:02 – How Sawhorse is thinking about AI in production 29:58 – Looking ahead: the future of immersive marketing and Sawhorse’s next chapter About Nic Hill: Nic Hill is the co-founder and Chief Innovation Officer at creative agency Sawhorse, where he leads award-winning branded content, gaming, and immersive marketing work for some of the world’s biggest brands. He’s also the co-host of Brands In Play, an immersive marketing podcast exploring how culture, technology, and play are reshaping the future of advertising. On the show, Nic interviews leaders from brands, platforms, and agencies about what’s next for consumer engagement. He’s passionate about the evolving marketing landscape and the role emerging technologies play in how audiences connect with 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.com Instagram: @SaylorAgency LinkedIn: https://www.linkedin.com/company/saylor-agency/

    33 min

  3. May 7

    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 & welcome 02:22 – Abby’s path from HR into entertainment and social 05:00 – Cold-calling her way into Degrassi and early digital fandom building 06:47 – Launching creator and content programs at CBC and Wattpad 08:57 – What Disney and Netflix taught Abby about creative culture 11:44 – How ideas move from concept to campaign at Disney 13:38 – The Percy Jackson billboard and the power of a big swing 15:20 – Building a global campaign across out-of-home and social 16:59 – The High School Musical TikTok stunt and reintroducing beloved IP 21:07 – Why all great marketing starts with human storytelling 25:00 – Fellow Kids and translating Gen Alpha and Gen Z culture 27:24 – What’s next, including Hannah Montana’s 20th anniversary About 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.com Instagram: @SaylorAgency LinkedIn: https://www.linkedin.com/company/saylor-agency/

    28 min

  4. Apr 2

    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

  5. 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

  6. 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

  7. 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

  8. 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
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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
    13
  • Rating
    Explicit
  • Copyright
    © Saylor
  • Show Website
    This Could Work

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