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Episode Summary
You’re sitting at $1.5M in revenue and the question eating you alive is how to get to $1.7M. You’re answering the calls. You’re closing the place at night. You’re interviewing every new hire because nobody can do it as well as you. Casey Cavell sat in that exact chair, and looking back he says he was asking the wrong question. The right question was this: if I’m not here, would 1.5 still get done at an 8 out of 10? Because if it would, hire it out, leave the perfectionism on the table, and go open four more locations. Casey turned a $9,000 poker bankroll into a real estate roll-up, then built five baseball academies into a portfolio grossing $40M. We got into how a clear written plan made every hard call obvious. When to bring in partners. When to stop optimizing one location and start opening more. When to sell. The throughline is the iBD one. You can’t make a clean ownership decision without knowing what you actually want from the business and from the Milestone 1 — Time & Role Goals.
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## Top 10 Takeaways- Working in your business is just playing poker. You only get paid when you sit at the table.
- Buy what’s already underpriced or underperforming, then put your fix on top to capture the upside.
- Revenue cures problems faster than expense cuts, because you can’t shrink your way to value.
- If 8 out of 10 by someone else still hits the goal, your perfectionism is the constraint.
- Stop solving how to take 1.5 to 1.7. Start solving how to run five locations at 1.5 each.
- A written vision turns every hard call into a yes/no question against the plan.
- Pick a number of locations, a target valuation, and a role. The decisions get easy after that.
- The partners you need are the ones who fill the seats you don’t want to sit in.
- You will lose part of your identity when you exit. Plan for who you are after the title goes away.
- Business is what you do, not who you are. Otherwise the bad days will own you.
Sound Bites
“I realized that working in my business rather than working on my business was me playing poker because you could only make money if you played.” (@TBD) — Casey Cavell
“When I should have been thinking, 1.5 is good if I don’t have to be there anymore and I can hire other people to do the jobs I don’t want to do. And I can go start four more locations and do a couple million dollars a year in those four locations.” (@TBD) — Casey Cavell
“I would rather lose a million dollars and do it with friends that I really like to work with than make $10 million and be miserable and do it with people that I don’t trust, I don’t like.” (@TBD) — Casey Cavell
“You know where you want to go, you have a written plan on how you’re going to get there, and you have someone that’s going to help you stay on track.” (@TBD) — Casey Cavell
About This Episode
Casey Cavell is a former professional poker player who turned a $9,000 bankroll into a portfolio of real estate and baseball training academy franchises grossing over $40M in revenue. After exiting his operating businesses, he now coaches owners and athletes through his Dugout CEO podcast and advisory practice. His specialty is helping leaders clarify their vision, get out of the day-to-day, and build companies that serve the lives they actually want to live. His story is a tight match for the iBD throughline. A clear written plan plus the right partners turns every hard ownership decision into a yes/no question.
Resources Mentioned
- Casey Cavell — Free guides, newsletter, and the Dugout CEO podcast. — caseycavell.com
- The Dugout CEO Podcast — Casey’s podcast on leadership, business, and life through a baseball lens.
- D-BAT — The baseball/softball training franchise Casey installed at his original Atlanta location.
- Intentional Growth Starter Kit — Ryan’s free starter kit with the vision board, financial scorecard, and five-video case study series.
Connections
Phase + Module:
- Module 3 — Owner’s Playbook — The written plan and vision Casey kept coming back to
- Module 7 — Leadership Team — Bringing in partners to fill the seats he didn’t want to sit in
Milestones:
- Milestone 1 — Time & Role Goals — Casey’s clarity on the role he wanted (and didn’t want)
- Milestone 3 — Net Worth & Valuation Targets — Hitting the financial number that made the exit obvious
- Milestone 19 — Functional Leaders — The two partners who took ownership of operations and culture
- Milestone 25 — Operator Transition Plan — Casey’s eventual buyout and operator handoff
Concepts referenced:
- The Owner-Operator Trap™ — Burnout from being the only one who could do it 10 out of 10
- The Multiple & WACC — How Casey thought about cap rates on real estate and EBITDA multiples on the academies
- Independence by Design™ — Building a business that serves the life, not the other way around
- The One Thing — Casey’s coach pushing him to pick three priorities and cut the rest