Preston Rutherford, Cofounder of Chubbies, joins Drew and Michael to share how the brand went from the brink of bankruptcy to a nine-figure exit. They dive into the dangers of ROAS obsession, the shift to a 50/50 brand vs. performance strategy, aligning teams around contribution, and the hard lessons that turned Chubbies into a durable, beloved brand.

Think Black Friday prep starts in the fall? Think again. In this episode, Drew and Michael explain why Back to School is the ultimate test window for Q4 success. They break down four actionable strategies you can launch this summer to identify your most profitable customer segments, validate your creative, and lower acquisition costs—before the holiday rush drives up competition and ad prices.

Recorded on Memorial Day, Drew opens up about the top lessons he learned as a Navy intelligence officer - lessons that shape how he leads today. He and Michael also reflect on personal regrets, from family and risk-taking to life metrics that matter most.

After auditing hundreds of Shopify brands, Zak Cassady-Dorion has a clear message: You’re missing easy revenue. He joins Drew to reveal his retention-first approach, killer Klaviyo playbook, and why PostPilot is his secret weapon.

This week, Drew and Michael unpack the latest tariff relief and what it means for DTC operators, break down Zuck’s vision for Meta as a fully automated ad platform, and explore the tension between brand and performance marketing. Plus, a deep dive into Aviator Nation’s remarkable rise—from Venice Beach to Forbes’ richest list.

What really changes when your DTC brand scales from 10 to 120 people - remotely? Drew and Michael break down the systems, rituals, and mindset shifts that helped PostPilot grow fast without losing culture, speed, or clarity. From all-hands to offsites to decision frameworks, this is a behind-the-scenes look at scaling alignment in a distributed team.

Drew and Michael are joined by PostPilot’s Head of Finance, Daan Harmsen, to unpack what the latest eCommerce data reveals about consumer behavior and shifting market sentiment. They dive into lessons from past tariff disruptions and share practical strategies for leading through uncertainty—emphasizing transparency, adaptability, and keeping momentum when it matters most.

Performance marketing gets all the spend—but is it driving real growth? Bonobos CEO John Hutchison talks with Drew & Mike about how rebalancing the mix toward brand led to stronger revenue, better retention, and long-term customer loyalty. Plus, they dive into his leadership style, navigating culture during change, and what younger marketers should focus on today to someday run the brands they love.

Mike gives a full rundown of Shoptalk, from the Vegas suite party to the AI trends in DTC. Plus, the Nerds talk about Vera Bradley unloading Pura Vida for... only $1 million?