“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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