“What do you do when you stop winning?”

In this episode, Sean and Matt drop the highlight reel and talk candidly about what it actually feels like when a once high-flying brand stalls, hits flat revenue, or even starts shrinking.

They unpack why every business has a “natural size,” why top-line obsession is the laziest definition of winning, and how to think more clearly about margin compression, momentum, and your own financial security as a founder.

From redefining success beyond horsepower-style revenue numbers, to product, channel, and positioning pivots, to doing the brutal “Fog of War” cuts instead of slow bleeding out, this is a tactical, psychologically honest roadmap for operators trying to diagnose stalled growth and decide whether to push for the next level or intentionally right-size the business and finally take money off the table.

Chapters

00:00 – Cold open: what it feels like when winning stops

02:20 – Why this episode matters: growth stalls, failure, and the messy middle

04:06 – Defining “winning”: growth vs profit, lifestyle, and the natural size of a business

07:18 – Survival first: financial security, changing goals, and evolving definitions of success

12:51 – Diagnosing stalled growth: macro forces, misalignment, and internal blind spots

17:42 – Tactical vs strategic stalls: product, category limits, and being in the wrong vehicle

23:48 – Playing by the rules of the game: CAC, channels, and market realities

33:13 – Diversification as defense: why building on rented land is dangerous

39:00 – When winning tactics stop working: SEO hits, waves crashing, and preparing for stall-outs

44:00 – Operating paranoid: assuming stalls, diversifying early, and the tradeoff of leaving money on the table

50:00 – Changing the business: adding new product lines, multiple business units, and hedging inside your own brand

56:00 – Rented land warning: Facebook media, platform dependency, and why omnichannel is non-negotiable

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