Episode 8 - Are You Working ON or IN Your Business?

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? Using Oodle’s long-running offsite rhythm as the backdrop, they break down how stepping away from daily execution creates space for alignment, strategic thinking, and better decision-making.They cover how their offsites have evolved over the years, what preparation looks like, how to spot when you’ve become the bottleneck in your own business, and why intentional time away can be one of the best investments you make as a business owner. Along the way, they mix in stories from past offsites, lessons from hard pivots, and the frameworks they use to keep the business moving forward.Chapters00:01 Intro, working on vs. in your business01:09 What offsites are and why they matter03:14 What Oodle offsites actually look like06:28 How they prepare and gather leadership input09:23 Early offsites, tactical work, and the shift to strategy12:51 Asking, “If we started today, would we build this business the same way?”14:00 Offsites as alignment and board-meeting time15:00 How to tell if you’re stuck working in the business18:35 Why true offsites need zero distractions20:27 The “seesaw” framework and removing yourself as the bottleneck22:15 Family, tax write-offs, and why they avoid turning offsites into vacations26:15 The artifacts and strategic documents that come out of offsites27:56 Most memorable and most impactful offsite stories34:14 Planning 3 years out, even when tactics change fast37:00 Final takeaway, when to change structure and create space to work on the business