Podcast
On this episode of Landowner Insider, I sat down with entrepreneur Jake Brydon to talk about how he’s built and grown businesses across roofing, software, branded apparel, ranching, and real estate. None of it, by his own account, started with a business plan. It started with him trying to solve a problem for himself and realizing other people had the same problem.
From One Guy to $55 Million in Roofing
Jake started Heritage Roofing with just himself and a couple of his brothers. Today it’s grown to roughly 80 sales reps across Texas and around $55 million in annual revenue. This past year, he brought on a private equity partner, Tritium out of Austin, selling 75 percent of the business while staying on as CEO.
His read on private equity might surprise people who assume it means getting bought out and pushed aside. In his experience, a serious private equity partner isn’t trying to cut costs and walk away, they’re trying to grow the business bigger than the original owner could alone. As he put it, most people selling to private equity aren’t big enough yet for a firm to make money by cutting them apart; the money is made by helping them double, triple, or quadruple in size.
Solving Real Problems Instead of Chasing Ideas
Jake was direct about how little of this was planned. The apparel company, the software company, the roofing business itself, all of it started because something didn’t exist the way he wanted it to, and he built it for his own use before realizing there was a real market for it. That’s also how he thinks about scalable business in general: find a real, specific problem, solve it well, and the opportunity to build a business around it tends to follow.
Building and Selling RoofLink
Heritage’s back office software, RoofLink, is a good example. Jake and his cousin built it to solve their own operational headaches, not to sell it. It worked so well that Heritage went from about 30 million in revenue with 17 people in the corporate office to 55 million in revenue with only seven. Eventually his cousin, who understood the software market, told him AI was about to devalue software as a service and that the time to sell was now, not after another year of growth. Jake wanted to hold out for a higher valuation; his cousin talked him out of trying to time the market. They sold at 11 times revenue. Multiples in that space have since dropped to a fraction of that. His takeaway: don’t assume you can time a market that’s already historically inflated.
Culture, Sales Teams, and Why People Stay
A lot of Jake’s growth strategy comes down to how he treats his sales team. Straight-commission sales reps can sell for anyone, so the challenge is building a culture worth staying for even when a competitor advertises a higher commission percentage. Heritage’s top reps make $700,000 to $800,000 a year in commissions, in part because of incentives beyond the paycheck itself, an annual boat given to a top performer, watches earned through performance, and consistent investment in the team. As Jake put it, that law of reciprocity tends to pay for itself: good investment in good people almost always comes back around.
Lessons From Failure and Bad Investments
Not everything worked. Jake mentioned a genetics company investment that simply didn’t pan out, money that’s gone for good. But he draws a clear line between a bad investment and a real failure: as long as you understand why something didn’t work and adjust, it’s not a failure, it’s tuition. That mindset shows up in how he talks with his own kids about competition and setbacks.
Debt, Cash Flow, and Real Estate for Regular People
Some of the most practical advice in this conversation was aimed at everyday buyers, not entrepreneurs. Jake’s take: real estate rarely goes to zero, which makes it fundamentally safer than stocks or crypto, but people often expect it to cash flow every month the way a paycheck does, and that’s not always realistic. For someone without a lot of capital, his advice was straightforward: buy less house than you’re approved for, live in it, buy a second modest property and rent it out, pay down the note aggressively, and only then repeat the process. Growing wealth through real estate is less about finding the perfect deal and more about personal spending discipline.
He was also blunt about the risks of pulling equity back out of an appreciating property to buy another one, a strategy that worked well when rates were low and rents kept rising, and that’s caught a lot of investors off guard as property taxes, insurance, and interest rates climbed faster than rents did.
Why Ranch Ownership Still Matters to Him
Jake’s ranches, including Aguinaldo in Rock Springs, didn’t start as an investment thesis so much as a recruiting tool, a way to give his sales team something worth working for that a competitor couldn’t easily offer. Over time it became something more: a place his team and clients genuinely want to be, and in his view, part of what made his roofing and software exits possible in the first place, even though it doesn’t show up as a line item with a clean return.
His advice to anyone considering a ranch purchase mirrors what I tell my own clients: don’t buy a ranch unless you can afford it and would be happy owning it in five years, because if the market shifts, that ranch becomes your vacation, not a flip.
Building ProSwag
Jake’s apparel company, ProSwag, followed the same pattern as everything else. He was spending a quarter million dollars a year outfitting his sales team in name-brand gear at retail prices, effectively paying full price and still having someone else’s logo dominate the placement. After a supplier declined to sell him wholesale volume, he built his own line instead. What started as one shirt for his own crew turned into a full B2B apparel business built around speed, in-house inventory, and making custom branded gear easy for other business owners to order the same way he wished he could.
Watch the Full Episode
This article is based on my conversation with Jake Brydon on Landowner Insider.
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