Fixing Underperforming Businesses, Crafting Equity Deals, and Reclaiming Time with Casey Cavell

Agency Journey

“In today's day and age people are scared to be measured. But your athletes, they love it because that's how they grew up. How do you know who are the best players on the team? You look at the box score, you look at the stat sheet. So I like bringing a sports mentality to everything I do.”

Casey Cavell is a serial entrepreneur. He’s built a $40,000,000 portfolio from a $9,000 investment by founding, buying, or investing in dozens of small businesses over the last two decades.

He also has personal experience with the kind of burnout that results from the business growing and relying too heavily on one person.

Which is why he now focuses on helping companies simplify, focus, and get the business owner out of the day-to-day.

This episode of Agency Journey will be perfect if you’re an entrepreneur thinking about investing in and increasing the value of other businesses; bringing in A-players; and mindfully delegating tasks until you’re left working on what you do best and love most.

Episode Insights:

💡 How Casey found underperforming businesses to acquire, and how he turned them into more systematic, process-driven organizations

💡 Buying businesses outright vs coming in as an investor

💡 Structuring equity/profit-sharing deals with clients—including earning trust with a 90-day initial engagement

💡 How to prevent burnout by delegating tasks, hiring A-players, and removing reliance on the owner

💡 The specific tasks entrepreneurs should delegate first

💡 Defining what you want your business to do for your life

Resourced Mentioned:

📚 Casey’s consulting business

📚 Casey’s LinkedIn

📚 The Dugout CEO podcast

📚 The Friday Drive newsletter

📚 Books: Good to Great; Rich Dad Poor Dad; The E-Myth

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