Exit On Your Own Terms

That’s exactly why I sat down with Jamie Waldren—author of Exit on Your Own Terms—to unpack what real succession planning looks like.

Questions We Tackled:

• When should you actually start planning your exit?
• What’s the first step if you’re starting from zero?
• Why do most founders only think about exiting when a buyer shows up?
• How does your exit vision impact the type of buyer you choose?
• What makes succession planning harder for sub-$10M MSPs?
• Where do things go wrong without a plan?

Key Insights (Don’t Miss These):

An exit needs a Succession Plan like a road trip needs a Map
You can do one without the other, but you’ll probably get lost.

Start earlier than you think
1–3 years minimum. 3–5 years is ideal.

Work backward from your life—not your valuation
Your retirement goals should drive your deal structure.

Owner dependency kills value
If all key relationships run through you, buyers get nervous.

~50% of exits are forced
Death, disability, or unexpected events—planning isn’t optional.

ESOPs are underrated (especially < $10M MSPs)
A powerful, tax-efficient way to reward loyal teams.

Your plan determines your buyer
PE vs strategic vs employees vs family—this isn’t random.

One Action to Take Today:

Ask yourself:
“Who is the right next owner of my business—and what does my life look like after?” That single question changes everything.

If you’re an MSP founder thinking about an exit in the next 3–5 years, this episode is a must-listen.

Happy to share the episode—just drop a comment or DM.