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Ryan’s library · My current thinking

Ownership & Independence

What should owning a business make possible for the person taking the risk and the people counting on them?

Updated November 1, 2026

What do I want to own my time for?

When I look at my calendar on Sunday, I can usually tell how much independence I actually have. I can own the whole company and still have a week someone else has decided for me. I can also have a coaching conversation on that calendar that I’d choose to have even if I could take the afternoon off. Those are two very different ways to spend the same hour.

I want a business that gives me a say in that choice. That takes cash flow I can count on, value that holds up when I step away, and people who can make good decisions while I’m gone. What makes all that work worth doing is what we get to do with the freedom. In my case, I want to spend years helping owners I care about make decisions they feel good about.

Jump to the books and conversations ↓

What does the next dollar have to do?

At Imaging Path, I could see an opportunity to reinvest a dollar that my dad saw as income our family had earned. We were looking at the same bank balance. We hadn’t separated what the company owed us for doing our jobs from what it could afford to pay us as owners.

I’d put three numbers on paper today. What would it cost to pay someone else to do my job? How much cash does the company need to keep its promises? What could come home to my family after that? Those answers give me a much better basis for deciding whether to hire, invest or take a distribution.

See the Owner’s Playbook

Who can make the call when I’m away?

Jack Stack gave me a practical way to look at independence. If a manager knows what a rush order will cost, understands what the customer needs and has the authority to decide, my phone can stay in my pocket. The customer gets an answer and the manager gets to exercise judgment. That’s part of what I mean by impact.

In Small Giants, Bo Burlingham follows owners who chose what they wanted their companies to be good at. I like reading it alongside Jack’s story. Bo raises the question of what is worth building. Jack gives me a way to think about who gets to build it with me.

Hear Jack and me talk about the numbers · Find Small Giants

Would hiring a general manager give you your evenings back?

Suppose you want to be home by dinner three nights a week. Paying a general manager will use cash you could otherwise take home. The hire buys back your evenings only if that person also gets the authority to handle the calls that keep you late. I’d put the hours, the cost and the decisions you’re willing to hand over on the same page. Then you can decide whether the trade is worth it to you.

Try the Owner’s Scorecard · PDF ↗

Which work would I choose to keep?

One thing I loved at Imaging Path was listening to a book or a podcast on the drive in and being able to try an idea that day. I could talk to the team, change an offer, see what happened to proposals or sales, and learn something. When Kim interviewed me for episode 500, that was part of owning a company I remembered with real affection.

I think about that when an owner tells me they want to work less. Which parts of the week would they gladly give away? Which parts would they miss? If I build a company that can run without me, I can still choose to be there for the work I love. I can also give someone else real authority without taking it back the first time they make a different call. That’s the freedom I want on both sides of the table.

Hear Kim ask me what I loved about owning a business · Why I chose to work with 150 owners

Books from my library

Other podcasts and interviews

  • Naval Ravikant with Nivi · How to Get Rich ↗

    Naval and Nivi talk about the difference between earning for the hours you work and owning an asset. For someone who both owns a company and works in it every day, that distinction is worth hearing.

  • Jack Stack · The SRC Story ↗

    Stack tells the story from inside Springfield Remanufacturing. Watch for what employees needed to understand about the business they had taken responsibility for.

From my podcast