“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
Powered By:
E092: The Influencer Marketing Playbook - with Lily Comba, Founder & CEO of Superbloom
Operators Titans E008: +$100M Path Nobody Wants: DUDE Wipes’ Sean Riley
