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In The Trenches (Steve Divitkos) vs Think Like an Owner

Side by Side

In The Trenches (Steve Divitkos) and Think Like an Owner, attribute by attribute
AttributeIn The TrenchesThink Like an Owner
What It IsA podcast about the part after the wire: Steve Divitkos, a former searcher CEO who bought, ran, and exited the software company he acquired, interviews SMB CEOs and operators on hiring, boards, systems, decision-making, and the psychological load of ownership.Alex Bridgeman's interview podcast on how ambitious CEOs grow great companies, with heavy coverage of search, small-company acquisition, and the operators and investors around them; roughly two episodes a week and nearly 300 episodes since 2018.
CategoryPodcasts & YouTubePodcasts & YouTube
Pricing ModelFreeFree
What It CostsFree on all podcast platforms; roughly two episodes a month since 2021, with 141 episodes as of April 2026. The host also publishes companion essays and invests in searchers through his own firm.Free on all podcast platforms; 297 episodes as of early 2026, publishing about twice weekly.
Best ForSearchers under LOI and owners in their first years post-close; it fills the operator-content gap that the deal-focused shows leave openSearchers and new owners who want operator and investor perspectives beyond deal mechanics, including hiring, systems, and growth after the acquisition
Where It FitsLearn & Choose Your Path, Operate & Grow the BusinessLearn & Choose Your Path, Operate & Grow the Business
Our VerdictQueue it the week you sign an LOI; it is the best free preparation for the job you are actually buying.Add it to the rotation for the operating half of the journey; it pairs naturally with In The Trenches once a deal is in sight.
Pros
  • Rare, sustained focus on operating after the acquisition rather than deal hunting
  • Host credibility: he searched, bought, ran, and exited before becoming an investor in searchers
  • Long-form depth (episodes run about an hour) with a consistent cadence since 2021
  • Deep archive of operator and investor conversations relevant before and after an acquisition
  • Active cadence (about two episodes weekly) with recent 2026 episodes confirmed
  • The host invests in the space, which keeps guest quality high
Cons
  • Deal sourcing and screening are not the point; listen elsewhere for the buy side
  • Roughly twice-monthly cadence is a slower drip than the deal-a-week shows
  • Public rating volume is small, so platform ratings are a thin signal
  • Coverage is broader than searcher-specific mechanics; deal-process detail is lighter than the deal-teardown shows
  • The host's investing activity means guests often come from his own network, so perspectives can cluster

Our take

Choose In The Trenches for depth on the owner's chair itself: a former searcher CEO on decisions, boards, and the psychological load, at a deliberate twice-monthly pace.

Choose Think Like an Owner for breadth and cadence: twice-weekly conversations across operators and investors, strongest when you want range rather than a single operator's lens.