The OLIPOP Strategy for Category Disruption

Mark Lester and David Lester are brothers who have turned a shared history of high-level brand strategy into a family legacy of innovation. David is the co-founder of OLIPOP, the prebiotic soda that has fundamentally changed the beverage landscape by blending gut-health science with the nostalgia of a classic cola. Mark, co-founder of the consultancy Squint, has spent his career at R/GA and We Are Pi shaping the strategic direction of global icons like Nike and Samsung. Together, they represent a unique bridge between the rigor of global brand building and the intuition required to launch a category-defining startup. What You’ll Learn in This Episode The hidden strategy of finding category value in plain sight How to break only one rule really hard to drive innovation Lessons from building a billion-dollar brand using global marketing rigor Why the discovery channel of the retail store still beats direct-to-consumer The unique dynamic of using brotherly advice to jump into the entrepreneurial unknown Episode Chapters (00:00) Intro (01:24) Growing up in Northern England with entrepreneurial roots (04:28) The Nashville hike that launched a business partnership (06:59) Concepts for innovation and the "break one rule" mantra (12:29) The philosophy of Squint and finding hidden value (15:15) Managing the shift from family connection to business collaboration (18:02) Navigating the pivot from D2C back to retail discovery (24:48) Lessons in building brands for scale from the very beginning (28:11) Brands that make the Lester brothers smile About David Lester and Mark Lester David Lester is the co-founder of OLIPOP, the prebiotic soda brand that has achieved over half a billion dollars in sales by blending gut-health benefits with classic nostalgia. Before turning his focus to functional beverages, David spent a decade in global innovation and marketing at Diageo, working across three continents to master the discipline of consumer goods. Mark Lester is the co-founder and Chief Strategy Officer of Squint, a strategic brand consultancy that helps global icons like Nike and Netflix unlock hidden value. With a background at R/GA and We Are Pi, Mark brings twenty years of big-brand experience to the challenge of category disruption. What Brands Have Made David and Mark Smile Recently? The brothers recently shared a smile over the enduring power of brand nostalgia and personality. Mark is energized by the intelligent copywriting of David protein bars and the experience-led branding of Duolingo, while David finds joy in the community-built legacy of Atlanta's Octane Coffee and the timeless playfulness of Nintendo. Resources & Links Connect with David and Mark on LinkedIn. Learn more about Squint and OLIPOP. Listen & Support the Show Watch or listen on Apple Podcasts, Spotify, YouTube, Amazon/Audible, TuneIn, and iHeart. Rate and review on Apple Podcasts and Spotify to help others find the show. Share this episode — email a friend or colleague this episode. Sign up for my free Story Strategies newsletter for branding and storytelling tips. On Brand is a part of the Marketing Podcast Network. Until next week, I’ll see you on the Internet! Learn more about your ad choices. Visit megaphone.fm/adchoices

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The OLIPOP Strategy for Category Disruption is an episode from On Brand with Nick Westergaard by Nick Westergaard.

This episode is 34:35 long.

This episode was published on Apr 20, 2026.

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