<p>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.</p><p>In this episode, Nick joins Will Trowbridge to discuss what it actually takes to win a Webby and how the internet&#39;s creative bar is shifting. They dive deep into his own experience winning for the hit podcast <em>Missing Richard Simmons</em>, 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.</p><p><strong>In this episode, we cover:</strong> </p><p>00:00 – Introduction &amp; Welcome</p><p>02:22 – Nick&#39;s journey to winning a Webby for <em>Missing Richard Simmons</em> </p><p>05:43 – Will’s experience winning for Netflix’s <em>Dressing Funny</em></p><p> 06:47 – What it takes to win a Webby (and why it doesn&#39;t cost $30 million) </p><p>09:00 – The Webby Awards judging process </p><p>09:38 – How AI is shaping the 2026 Webby Awards and creative workflows </p><p>12:17 – The state of creativity in 2026: Is the bar getting lower? </p><p>16:08 – Unhinged marketing and the demand for authentic content </p><p>17:50 – Why creators are the last bastion of trust on the internet </p><p>25:20 – Top tips for submitting and winning a Webby Award</p><p><strong>About Nick Borenstein:</strong></p><p>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.</p><p><strong>About This Could Work:</strong> </p><p>This Could Work, hosted by Saylor CEO Will Trowbridge, celebrates creative risk-taking and the people reshaping the future of brands.</p><p><strong>Follow Saylor: </strong></p><p>Website:<a href="http://www.sayloragency.com/"><u> www.sayloragency.com</u></a></p><p>Instagram:<a href="https://www.instagram.com/sayloragency"><u> @SaylorAgency</u></a></p><p>LinkedIn:<a href="https://www.linkedin.com/company/saylor-agency/"><u> https://www.linkedin.com/company/saylor-agency/</u></a></p><p><br></p>