In The Trenches (Steve Divitkos) vs Think Like an Owner
Which operator podcast earns the post-close slot?
In The Trenches (Steve Divitkos)
A 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.
Free · Free 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.
- 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
- 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
Verified Jul 11, 2026 · Full review →
Think Like an Owner
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.
Free · Free on all podcast platforms; 297 episodes as of early 2026, publishing about twice weekly.
- 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
- 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
Verified Jul 11, 2026 · Full review →
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.