The Early Lessons that Shaped Damon Woodward

Nicolas Bueno
3 min readFeb 5, 2021

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Every entrepreneur has his origin story, or at the very least a story about the business they’ve started in the industry in which they’ve made it big. For Damon Woodward, a real estate entrepreneur, the venture at hand was a Rent-to-Own business. Damon followed the advice that served him so well during his career and invested heavily into self-betterment; he started working with coaches, he was attending courses, and he picked up every morsel of knowledge that could have helped his endeavor.

That all seemed fine and well for a time; he figured he would be able to help people get homes while making a decent living if his service level remained high. The one thing Damon couldn’t have counted on was that the next seminar he would attend would be hosted by none other than Stefan Aarnio, whose philosophy was slightly different. The trip made Damon rethink the business model that he was putting together, and he hired Stefan Aarnio’s company to teach him how to flip houses instead.

Damon’s Rent-to-Own venture didn’t prove to be a success. What it did do, however, was allow Damon to learn about investing strategies. It allowed him to travel, and each real estate symposium was a new chance to meet other investors, learn from them, network, and eventually work together with them on numerous real estate projects.

As for the bare-bones business lessons, the one about buying, fixing, and then selling a property was much more valuable than anything he was trying to do with Rent-to-Own. This business strategy is something he recommends to beginners to this day, as it’s one of the easiest ways to teach someone who is new to real estate some fundamental skills.

Getting familiar with new skills is yet another lesson that’s been following Damon Woodward from his earliest days, even though he’s taken it up a notch or two these days. “I have spent over $100,000 on my personal development over the last few years and every time I put a dollar in I am pulling several dollars out,” he explains, adding, “Hiring a coach to work with one-on-one is very important if you want to succeed.” As for working in larger coaching groups, Damon thinks they’re better than nothing, but subpar when compared to working one-on-one with a coach.

Finally, Damon also had to learn a thing or two about running teams. Everything was happening quickly to him, so it didn’t take too long before he was in the position to have several teams work beneath him. In those cases, it’s incredibly important to structure the team properly; every position on the team needs to come with clear responsibilities so that the person who is filling the position does not doubt the role they have in the grand scheme of things.

“Managing people is one of the most difficult jobs out there and can be extremely complicated,” Damon says, adding, “Having a very clear structure of how the team operates is extremely important.” While the process to determine that every person matches their given position and that position itself is well defined is difficult, Damon understands that it’s crucial. Given how it’s one of the things that helped him build his business empire, it seems that it’s time and effort well-spent.

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Nicolas Bueno

Nicolas Bueno is the Content Manager at HighKey Agency.