How Caleb Coombe Built a Risk-Proof Business Model by 25

At just 25, Caleb Coombe is one of the youngest founding members of The Club but his clarity around building a reliable, asymmetric business would make you think he’s been doing this for decades. 

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He’s already building with the clarity and patience of someone with much more experience. From military service to engineering school to launching a home services business and exploring land development, Caleb is actively designing a path that minimizes the downside while keeping the upside wide open.

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From Engineering to Entrepreneurship

Caleb grew up with limited financial resources, which sparked his work ethic early on. He joined the military at 17 to help pay for college, then pursued a degree in mechanical engineering. But during his first co-op rotation, he had a moment of clarity: "There's no way this is going to be the rest of my life."

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That insight launched his journey into real estate, inspired by books like Rich Dad, Poor Dad. He bought his first properties while still in college. After graduating, he worked full-time as an engineer for six months before making a key pivot.

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“Paul really drilled into me the reliable side of the barbell,” he said. “I knew rentals gave some of that, but I couldn’t rely on them for monthly income. That’s when I started thinking differently.”

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Rapid Tree Care: The Reliable Side of the Barbell

This insight led to the launch of Rapid Tree Care - a home services company built entirely on a subcontractor model. Caleb found experienced crews who wanted more work, then created a system to generate leads and connect them with jobs. To the client, it looks like a full-service operation. Behind the scenes, it’s a lean system powered by pre-vetted crews and smart delegation.

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With zero equipment to maintain, no debt, and only insurance as a fixed cost, the business has virtually no overhead. In its first year, Rapid Tree Care earned 91 five-star reviews and generated 100 leads last month alone. Momentum is building - and Rapid Tree Care is just getting started.

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For Caleb, it’s one of the most asymmetric bets he’s made: reliable income, low risk, and massive upside potential.

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Real Estate with an Engineer’s Mind

Though his attention shifted to business building, real estate still has Caleb’s heart. He’s currently working on a minor subdivision deal, partnering with two local builders to structure a no-money-out-of-pocket arrangement.

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He has an active role managing due diligence, working with the township to make sure things are moving in the right direction, and driving momentum; but he’s done it without putting a dollar of his own money into the deal. If it falls apart, he’s only spent time. And at 25, time is still his most available currency.

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He’s not afraid to lean into what he doesn’t know because he’s surrounded by people who do. Instead of trying to be the expert at everything, Caleb builds teams that bring strengths he doesn’t need to own.

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Decision-Making shaped by the Barbell Strategy and CASE

He credits The Club’s frameworks, like the Barbell Strategy and CASE, for helping him approach deals this way. Whether it’s construction or operations, Caleb is constantly applying these frameworks to remove volatility and maximize the upside. 

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He now reads the terrain through the lens of the Barbell Strategy. When it comes to making a decision, he asks himself: “How can I take the downside off the table?”. As he mentions, “It's just setting things up in a way where you're not gonna get hurt if something bad happens, because bad things happen, a lot”.  

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CASE Framework (Collect, Analyze, Strategize, Execute) has also shaped Caleb’s decision-making. 

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For him, collecting data is key to making thoughtful, informed decisions instead of emotional ones. Having data allows him to step back, create mental space - what he calls “almost nothingness” - and let new and different ideas emerge. This is undoubtedly an excellent Case in Point for Receivership. 

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Redefining Success at 25

For Caleb, success comes down to one word: control - of his time, his energy, and the way he moves through his day.

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He’s focused on investing his most valuable currencies - time, energy, and relationships - in places that generate a return. Sometimes, that return is financial. Other times, it shows up in clarity, opportunities, or confidence in his decisions.

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Right now, things just feel aligned. He’s leaning into projects that matter, building with intention, and waking up every single day, even before his alarm, because he’s genuinely excited and motivated to do what he does. 

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That’s what wealth looks like to him, designing the life he wants one move at a time.

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