Damon Caldwell

Quick Facts:

  • Profit Strategy: Wholesale
  • Number of Units: 10
  • Personal Money Invested: $0
  • Amount Earned: $25,000
  • Prior Experience: Before working with Lance’s team, Damon had previously dabbled in wholesaling multifamily with some hurdles, which almost pushed him out of real estate, but luckily stuck with it with the help of one of his childhood friends and mentors.

Damon was a firefighter and EMT. He was put in danger daily — earning only $12/hour — and knew this life wasn’t sustainable for him. He started a family at 18 and now has five children. In the early days, he worked three jobs to make ends meet. But even later, as a firefighter, he couldn’t pay rent on time and fell behind on child support. Needless to say, this situation wasn’t empowering. He knew he had to make a change.

“Getting emergency calls at 3 and 4 in the morning is very stressful. Some people love to do it. Some people are not built for it. I knew I wanted something different for my family,” he shares.

He read “Quit Your Job in 19 Weeks or Less” and “Rich Dad, Poor Dad.” Those two books changed his life. They changed the trajectory of his future.

Damon’s Call to Adventure

He wanted to start a business but had no idea where to begin or what type of business he wanted to pursue. Through self-education, he realized real estate was very lucrative. He also learned it could be a safer investment than the stock market because you acquire a tangible asset in the process.

Plus, when he was younger, he watched his stepdad buy inexpensive properties, fix them up, and make a good profit. Damon decided to dive into real estate investing. He raves, “it was life-changing.”

Damon thought he might pursue a similar model but has moved away from that. He’s closed on multiple wholesale deals and is working on a buy-and-hold. He can’t count how many wholesale deals he’s done to date, but he did share an often-recounted story of starting the business wrong.

His First Big Lesson

A handful of years ago, before working with Lance’s team, he completed his first wholesale deal. The deal profited roughly $2000. However, he had to split that three ways because he needed help from other investors. Then the other shoe fell. Shortly after closing the first deal, a woman trying to wholesale her house sued him. There’s a more extended version of this story, but the outcome was unfortunate. He couldn’t attend the hearing because he worked at the fire department that day. The judge awarded her $5000. Damon realized he was in over his head. He thought he knew how to wholesale properly but realized he didn’t. He wanted to stop investing.

As luck would have it, he connected with a childhood friend (Jay Jemmerson) who was successfully wholesaling properties. This friend mentored him, and the two of them started working together. Damon got experience with wholesaling and a fix-and-flip. In the process, he gained skills in repairing and renovating properties.

Damon’s Vision

Sure, Damon wanted income to quit his job, support his wife and five children, and create generational wealth. But more than that, he has always cared about others. His passion is helping other people, including helping homeowners who are in rough spots. He becomes a problem-solver for others.

Damon Discovers His Gift

As Damon puts it, “figure out what you are good at and discover your gift to the world. This is my gift. Once you find your gift, the money flows. It comes to you, and then you’ll be able to take care of your bills, debts, and family.”

Damon’s gift is helping people by simplifying their challenges. He feels great joy when sellers tell him he has improved their lives. This is his passion and what warms his heart.

As an example, he recounts a specific story. Damon’s wife helped him with a single-family deal. They made $15K on it. “But it wasn’t about the money at that point. The man couldn’t walk the steps anymore. He was a hoarder. His wife was getting sick inside the home. I was able to help move that seller and his wife to an apartment. I put the deposit down for them with my own money. I paid for the moving crew. After this, he told me how much I blessed his life. Knowing that I became a problem-solver was warming to me.”

Being able to help them was a defining moment for him. He knew, at that moment, that this was what he was born to do. Damon explains, “this was how God wants me to move forward in my life and help people.”

Being successful with real estate investing has made Damon “more helpful.” He shares that “some people say money changes a person. I believe money makes you more of who you already are. Doing real estate investing has made me more helpful. It has made me want to give more and the ability to help more people.”

The Financial Vision for His Legacy

Lance teaches mindset tools. One of those is a vision board, which Damon has implemented beautifully. He has a list of his financial goals and pictures on his wall of everything he wants for himself and his family, down to minute details. He reads his list daily and visualizes the dreams on his board.

Damon describes it, “I want to live in a certain type of subdivision. The house will have a pool, and I will drive a luxury car. My family will have vacation homes in multiple states. My new goal is to have a private jet. In fact, I’ve been looking into getting my pilot’s license. I would like to get that within the next year. And a small yacht.” The specific target for his bank account is $100 million. With his passion and gift for helping others, it’s easy to believe those goals are within reach.

Creating a legacy is a big part of his vision. He wants to be able to gift each of his five children an apartment building when they graduate high school. He hopes each child will live in one unit, rent out the others, and learn how to manage multifamilies. He wants to change his family’s financial forecast.

Real Estate Changed His Life

Damon discovered that real estate gives him a vehicle to help others. But he also learned that real estate opens doors to meeting people willing to help him. It has allowed him to take advantage of more opportunities — and bigger ones. He loves that part.

Damon shared, “where I come from, people tell you what you can’t do. That plays on your mindset. You learn not to believe you can do great things. Once my mindset changed, I had the paradigm shift.”

He surprised himself by closing on a 10-unit apartment building. He marveled, “I did that! What else can I do? Doing that deal made me wonder more: what else can I do?”

What else can he do? Well, he wrote a book, “Getting a Better Focus: The Basics of Wholesaling Houses With Little or No Money Down.” He intends to shatter the myth that you must have money to get into real estate. He knows firsthand this isn’t true.

Lessons Learned

Sometimes you don’t get to do what you want to do. Instead, you do what you have to do. Damon describes one of his lessons, “if I could do it over, I would keep the majority of the properties that I wholesaled and hold on to them. That’s how generational wealth is created. That is how to leave behind something for my children and their children.” But when he was doing the wholesale deals, he didn’t have money to hold onto them.

In some cases, it would have only taken $500. Damon pursued wholesaling because that is what his financial situation would allow him to do. And throughout his wholesaling, he profited at least $100K — not too shabby!

Damon also learned that being in control of the deal is immensely important. He lost out on a $15K deal because he allowed other people to control his buyers. From this experience, Damon learned to take charge of making sure the downpayment happens promptly and getting all the boxes checked. He elaborates, “it was heartbreaking, but it made me sit back and realize I need to revisit Lance’s training. Regardless of how many deals you close, go through it again and follow his steps. Lance has the blueprint. Follow his blueprint. I’m going through the blueprint again to avoid more mistakes.”

His Advice

Damon says listening to the right people was critical in his path to success. “If someone has a vision and you see it working in their lives, follow them. Learn what not to do and what to do. Be a follower of the right people. Growing up, your parents always tell you to stop being a follower and be a leader. Well, how can I do that? I have to follow someone who is already great.”

He also encourages others to not be fearful. “Break through the terror barrier,” he advises. “Don’t stay in your comfort zone. Push yourself to elevate to the next level. Don’t let fear hold you back.” He tells others to “just go for it. Stop thinking about it. Stop second-guessing.”

And finally:

Find. Your. Gift.


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