696: Jamie Left a Nike Exec Job to Bootstrap A Drinkware Brand - Now It's On Track For Seven Figures

Jamie spent over 20 years in corporate America, including a stint as a Nike executive, before a barbecue accident changed everything. Hosting friends and family in Park City after a near-perfect day outdoors, he tripped and sent a tray of drinks flying over everyone. That clumsy moment sparked two ideas at once: a better, genuinely leak-proof product, and a brand built around the outdoor-lifestyle-and-moments-of-pause philosophy he and his wife Michelle wanted to live by. He funded SMMT Outdoor entirely himself, went all in from day one, and spent nearly two years and 50 prototypes getting the product right.

In this episode, Jamie is refreshingly honest about the unglamorous middle of the journey - the weeks with one or two orders, the pivot away from the category he launched in, the agency burns, and what it actually feels like to go from leading teams of teams at a billion-dollar company to being a solo operator with one contractor.

What you'll learn in this interview:

The barbecue accident that sparked the whole brand - and why Jamie built SMMT around an emotional "active days and moments of pause" philosophy, not just a product spec

Why he launched in bags first, then pivoted to drinkware after 18 months and 50 prototypes - and how that detour taught him the business he actually needed to learn

The reality of the early days: weeks with one or two orders, days of "crickets," and the humbling gap between corporate experience and blank-page entrepreneurship

Why he chose to bootstrap with only family capital - keeping the cap table simple, feeling the pain of his own money, and buying himself the freedom to make long-term decisions

The "rocking chair test" he uses for big life and business decisions - fast-forwarding to age 80 and asking what he'd regret not doing

Why he deliberately built for a sustainable family business rather than a unicorn - and his case for why a $10-20M brand is a huge win nobody talks about enough

The Thanksgiving dinner spent refreshing Shopify to see if the drinkware launch would work - and why 25 sales on day one felt enormous

The exact equation he obsessed over instead of chasing revenue: customer lifetime value over CAC - and why he attacked the numerator first through bundles, pairs, and a 980-unit limited edition program

How a $15 personalisation upsell, print-on-demand art drops, and a rethought checkout experience quietly built margin and average order value