EPISODE · Mar 11, 2026 · 30 MIN
Trevor Dudeck on World-Building Brands & Maximizing Customer LTV Through Entertainment
from The Entrepreneur's Logbook: Lessons from Growing Businesses · host Zachary Bernard
In this episode of The Entrepreneur’s Logbook, Zachary speaks with Trevor Dudeck, founder of Lemonade, a full-service advertising agency built on the bold philosophy that “advertising should feel more like entertainment.” Trevor and Zach dive into the biggest stumbles and hard-won lessons of scaling an agency, from the pitfalls of chasing unicorn hires who promise to solve every problem but often leave gaps in sales and finance, to the power of bringing on an operations consultant who evolved into a game-changing COO. Along the way, Trevor shares how he and his team learned to balance custom and productized services, build repeatable offerings, and create decision frameworks that turn one-off hires into strategic, sustainable growth drivers. The conversation then shifts to Lemonade’s signature entertainment-first approach: the Story 360 model. Trevor breaks down how brands can think of themselves as media companies, borrow storytelling tactics from film and gaming, and craft programs that feel more like binge-worthy series than forgettable ads. He offers three concrete takeaways for entrepreneurs ready to experiment with entertainment-driven marketing: flip your campaign planning with “entertainment thinking,” treat every channel as programming that competes for viewers’ attention, and start small. By the end of the episode, you’ll have a clear roadmap for transforming product pitches into immersive experiences that captivate and convert over the long term. Timestamps Lessons on Hiring “Unicorn” Employees – 00:02:00 2. Bringing in an Operations Consultant and Building Processes – 00:06:00 3. Moving from All-Custom Work to Productized, Repeatable Services – 00:07:00 4. Shifting from Traditional Ads to Entertainment-Driven Marketing – 00:08:50 5. Introducing the Story360 Framework for Multi-Channel Campaigns – 00:15:00 Connect with Trevor https://www.lemonadetheagency.com/ https://www.linkedin.com/in/trevordudeck/ Sponsored by We Feature You PR - Helping entrepreneurs build thought leadership through strategic podcast placements and launching their own shows. Ready to amplify your voice? Get in touch today. Subscribe & Review: If you enjoyed this episode, please subscribe and leave a review on your favorite podcast platform! Chapters (00:00:00) - The Entrepreneur's Lockbook Podcast(00:01:22) - What Would I Do Different If I Had To Start My Company Again(00:08:51) - Lemonade: The Shift From Advertising to Entertainment-(00:17:58) - The Story360: Exploring the Entertainment Dimension(00:25:23) - How To Win in an Entertainment World(00:29:24) - PODCAST: Trevor Dudak
What this episode covers
In this episode of The Entrepreneur’s Logbook, Zachary speaks with Trevor Dudeck, founder of Lemonade, a full-service advertising agency built on the bold philosophy that “advertising should feel more like entertainment.” Trevor and Zach dive into the biggest stumbles and hard-won lessons of scaling an agency, from the pitfalls of chasing unicorn hires who promise to solve every problem but often leave gaps in sales and finance, to the power of bringing on an operations consultant who evolved into a game-changing COO. Along the way, Trevor shares how he and his team learned to balance custom and productized services, build repeatable offerings, and create decision frameworks that turn one-off hires into strategic, sustainable growth drivers. The conversation then shifts to Lemonade’s signature entertainment-first approach: the Story 360 model. Trevor breaks down how brands can think of themselves as media companies, borrow storytelling tactics from film and gaming, and craft programs that feel more like binge-worthy series than forgettable ads. He offers three concrete takeaways for entrepreneurs ready to experiment with entertainment-driven marketing: flip your campaign planning with “entertainment thinking,” treat every channel as programming that competes for viewers’ attention, and start small. By the end of the episode, you’ll have a clear roadmap for transforming product pitches into immersive experiences that captivate and convert over the long term. Timestamps Lessons on Hiring “Unicorn” Employees – 00:02:00 2. Bringing in an Operations Consultant and Building Processes – 00:06:00 3. Moving from All-Custom Work to Productized, Repeatable Services – 00:07:00 4. Shifting from Traditional Ads to Entertainment-Driven Marketing – 00:08:50 5. Introducing the Story360 Framework for Multi-Channel Campaigns – 00:15:00 Connect with Trevor https://www.lemonadetheagency.com/ https://www.linkedin.com/in/trevordudeck/ Sponsored by We Feature You PR - Helping entrepreneurs build thought leadership through strategic podcast placements and launching their own shows. Ready to amplify your voice? Get in touch today. Subscribe & Review: If you enjoyed this episode, please subscribe and leave a review on your favorite podcast platform!
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Trevor Dudeck on World-Building Brands & Maximizing Customer LTV Through Entertainment
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