Episode 8 - Are You Working ON or IN Your Business?
Published Apr 15, 2026 · 37 min
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Summary
In this episode of the Not Brothers Podcast, Mark and Ryan dig into one of the most important questions for entrepreneurs: are you working in your business, or on it?
Chapters
- 00:01 — Intro, working on vs. in your business
- 01:09 — What offsites are and why they matter
- 03:14 — What Oodle offsites actually look like
- 06:28 — How they prepare and gather leadership input
- 09:23 — Early offsites, tactical work, and the shift to strategy
- 12:51 — Asking, “If we started today, would we build this business the same way?”
- 14:00 — Offsites as alignment and board-meeting time
- 15:00 — How to tell if you’re stuck working in the business
- 18:35 — Why true offsites need zero distractions
- 20:27 — The “seesaw” framework and removing yourself as the bottleneck
- 22:15 — Family, tax write-offs, and why they avoid turning offsites into vacations
- 26:15 — The artifacts and strategic documents that come out of offsites
- 27:56 — Most memorable and most impactful offsite stories
- 34:14 — Planning 3 years out, even when tactics change fast
- 37:00 — Final takeaway, when to change structure and create space to work on the business