In this conversation, I dive deep with Brent Bowers on the systems, delegation strategies, and mindset shifts that allowed him to go from overwhelmed Army officer to building a scalable land-investing business supported by simple processes and smart hiring. His journey is full of hard-earned lessons about cash flow, data, virtual assistants, tech tools, and how to move from the operator seat into true ownership. If you’re an investor who knows you’re capable of more but your current structure is holding you back, this is a story you’ll want to hear.
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Hello everyone. I’m glad you’re here today. Get ready for insights to help you scale, systemize, and create more freedom. Let’s jump in. Thank you for being here with me today.
I’m happy to be here. Thanks for having me.
For those who may not be familiar with your work, can you share a snapshot of your real estate journey, what your business looks like today, and how you landed on land investing as your focus?
I started in 2007. I got my real estate license. I always wanted to be in real estate and bought my first rental property, held it through 2008 and 2009. I joined the Army in 2009 because real estate investing was difficult for me at that point, and I took a break during deployments to Afghanistan.
Stationed in Germany, then back to the United States in 2013. I bought another rental in 2013, another in 2014, and then in 2015 my wife and I had our first baby. I needed to get out of the military and be home more often. I was preparing for my third combat deployment but couldn’t leave because these rentals were costing me money. I had six at the time. I looked at what other people were doing. I wholesaled houses and made money to pay for college courses. Then I heard a podcast with someone talking about flipping vacant land and doubling his money overnight. I decided to try it and started mailing people on the tax delinquent list.
So that’s what drew you to land investing as a strategy. You weren’t cash flowing in other strategies and needed cash flow, and land investing looked like it would get you there.
Yes. I was making a couple hundred dollars a month over the mortgage payment. Some houses were vacant after evictions. If my mortgage was $750 and I was getting $1,000, repairs like water heaters, air conditioners, roof leaks, and septic failures wiped out profit for years. Land was different. This person was buying parcels for a couple hundred and selling them for a thousand. I was earning about $60,000 a year in the military and working 80-hour weeks, deployed, with little sleep.
I mailed the tax delinquent list of landowners. I sent them a handwritten postcard. I bought many properties with it. It said: “My name is Brent. I’d love to buy your land if you’re interested in an all-cash, fair price offer. Call or text me.” My phone started ringing. I bought the first parcel of land for $285. I was scared and unsure how to comp it. I sold it a few days later for $5,000.
That must have gotten you hooked.
It felt like winning the lottery because I had never made $5,000 in a few days. I hired a VA from Upwork to help me scrub my next list. I thought I couldn’t mail the same list again, which was wrong. I got another tax delinquent list. They would fax pages to me in 2015. They were difficult to read. My VA, Joanne, who I still work with today, spent weeks converting 600 pages into 600 parcels of land. Then I could mail them. Thank goodness for a virtual assistant.
You started off like most real estate investors, putting in the labor. As you continued to evolve this, what systems or processes made it scalable over time?
Over time, I used a program I call my CRM. First, I pull data directly from a data source. I don’t care if it’s tax delinquent, probate, or inheritance. I follow a rule: what can I delete, automate, and delegate? Complexity kills businesses. It’s easy to accumulate complexity. On my accounting call today, we worked on making things easier with one system rather than multiple.
I start with Redfin to see where land is selling. I don’t want to create demand; I want to fill demand. Then I pull a list from a software program. For $25 a month I can pull landowners in the areas where I saw demand. Once I pull the data, I upload it into the CRM. It mails people. They can call me back. It tracks where everyone is in the process, shows how much we can pay, and includes maps. I send offer letters. If they accept, I make a profit. It’s a numbers game. Buying land is like dating. The closing is the marriage, then you never have to see each other again. That was similar to my first marriage in the Army because you’re gone a year at a time.
You were serving full time in the Army while scaling this. What helped you keep it going with limited time?
Having Joanna as my virtual assistant, and hiring a partner in Colorado Springs where I did most of the land deals. I also did some wholesaling, but land was the most profitable. We think we should do everything in business, but we should focus on what makes money. I didn’t know that at the time.
I hired someone to answer phone calls because during field training we couldn’t have cell phones. Calls were missed and marketing dollars wasted. She got a percentage of profit on deals she closed. She was good at sales. I didn’t have all the skills or ability. I shared my vision with her and with Joanna.
Now I have an office manager who runs the company. She tracked her last seven days of tasks. We uploaded everything into ChatGPT, which suggested what to eliminate, delegate, automate, and even recommended hiring her an assistant.
I see this constantly—service providers who miss calls and lose money because they won’t hire a VA. And I love how you’re using ChatGPT. Many investors underutilize it. Often our office managers need an assistant to handle their bottom 80% so they can do their top 20%.
If you’re using ChatGPT only as a search tool, you’re missing out. I have a mobile home park I bought months ago. I’m stabilizing it. My property manager still collects cash. I needed better reporting: income per unit, expenses per unit, electricity, water, bill-back amounts. I explained it to ChatGPT as if speaking to the property manager. It built a Google Sheet for plug-and-play use. Then it asked if I wanted instructions and created them. I treat ChatGPT with respect. It’s amazing what you can accomplish. Ask it to interview you about your business. Mine knows about my office manager, our land training process, and references it accurately.
Is there more? Any other tools or automations that anchor your workflows today?
The CRM is a major one for land investors. I also like DataTree—excellent quality data at a low cost. I can skip trace buyers. If I don’t want to buy a parcel, I can see who bought land deals for cash in the last six months. If they bought under an LLC, they’re likely building and may want more soon. I call them: “I noticed you bought land on Parker Street. I have a parcel nearby. Interested?” That’s wholesaling land.
With Redfin, my data service, the data site, and the CRM, you can run an entire business. It’s about connecting land buyers with sellers.
You’ve mentioned data several times. Data allows informed decisions—buyers for wholesaling, income and expenses for the mobile home park, KPIs for systems. Have you always embraced data?
I think since about 2015. In college, the Army pulled me out of Afghanistan and sent me to college in 2013. That was the only way I returned to the United States. It was culture shock after Afghanistan and Germany.
It was a private school. My GI Bill covered part of the costs. I had to pay the rest. I needed to make money quickly. I didn’t know about land then, but foreclosures existed. I used data to find who had a Lis pendens—people behind on mortgage payments. I door-knocked. People thought I was the bank and came out armed. I would tell them I was a cash buyer and ask if they were open to selling. They would say no. I eventually left sticky notes. Someone responded. I used data to find cash buyers. I met one buyer and his title agent, who bought the second house from me. It was all data. Success leaves clues.
You were in a tight spot wanting to attend college near your parents. You had to make the money work. Often we avoid tight spots, but they push us to grow. When I moved to a new area, restarted my real estate business, and had three kids under six, I had to bring on a VA. It was transformational. It sounds like discomfort pushed you to new opportunities too.
We bought a ranch in Colorado in 2018. I had just left the Army. I wasn’t sure if I would succeed in real estate. I had $12,000 a month in land payments coming in from parcels that weren’t buildable or accessible. I sold them on payments because people love to own American land. That was my safety net.
We bought a 4,000-square-foot house with a barn, garages, and 58 acres for $465,000. I went from making $4,000 a month to living on $12,000 a month in payments. I wondered how I would pay for it. It was uncomfortable. But we did it. We still own that house and land. It’s another mountain. Once you climb it, you realize it wasn’t as hard as it felt. You adapt quickly.
I’d like to return to what you said about being a “who not how” person. Hiring a team is a leap for many. How did you decide what to delegate, and what lessons have you learned about hiring and leadership?
It’s easy to be the “who not how” when you’re me. I’m good at finding people with specific skills. Smart people often excel at one thing, and you partner with them.
I try to delegate everything except what I enjoy and can do endlessly—like podcasts and coaching. I don’t enjoy accounting calls. I hired that out. My battery drains when I do tasks I dislike.
I delegated mowing my grass. I enjoyed it, but it took two hours a week. Someone could do it for $50 a cut. My time is worth more, especially on profitable land deals. If I want to mow, I can mow my parents’ lawn.
There are also people you need to remove. I don’t track time sheets. I care about results. My office manager’s husband is a Delta pilot. She travels frequently. As long as she attends meetings and handles her responsibilities, I don’t mind.
You have a goal to buy back time for your family. What boundaries or systems protect that time as your business grows?
My assistant set boundaries in my calendar. It used to be open from 6 a.m. to 9 p.m. My wife got frustrated when I left dinner for calls. My assistant blocked off time—nothing before 10 a.m., nothing after 3 p.m. Those are times when the kids are home. I choose if something enters those blocks. I used to feel like I needed to work 12-hour days. It was a scarcity mindset.
We travel internationally full time. I used to keep my calendar open late into the night for U.S. calls. Now I limit that availability. We can control our time more than we think.
If you consolidate to one night a week for calls, everyone could meet within the same three-hour window. You’re likely answering similar questions.
Sometimes we can’t see improvements in our own world, but others can. With your team—your office manager and VAs—how do you support each other?
Kelly identifies things constantly. She used to come with many questions, but I now ask, “What do you think we should do?” She’s smart, educated, and capable. That question is powerful. My business coach recommends bringing three solutions, but I find simply asking for her judgment works well. We encourage personal development. Sometimes people outside our industry notice things we miss.
An accountant questioned what I paid for my note collection service. I explained the cost and how we charged buyers a fee. She recommended a better system. Her facial expression irritated me, but she was right. Ego is harmful in a team. My kids ask if I’m the boss. I tell them I don’t think of myself that way. I own the company, but the people I work with are essential. At one point I had 15 VAs, all reporting directly to me. It was overwhelming. I needed someone in charge of them.
That’s a lot. When I was an active real estate agent, I learned that someone can manage about five people directly. Beyond that it becomes too much. Even if those VAs are productive, you get pulled into the weeds.
It lasted about a year and a half. I nearly lost my mind.
As we wrap up, for investors stuck in the operator seat, you’ve shared wisdom about building a team, becoming a visionary, and doing what you do best. What is one action you recommend they take this week to move closer to being a business owner?
Track what you’re doing for the next couple of days in 30-minute sections. For me, accounting drained me. Podcasting energized me. In minutes I will sign for a closing where I’m selling a piece of land. I’ve almost automated that. My office manager is my notary, so she signs for me. After five days, assess the list and highlight what energizes you. Remove what drains you. I want my office manager handling payments. I dislike paying bills and want that automated.
If people want to reach out to you to learn more about land investing or your work, what’s the best way?
The land investing website. You can book a time on my calendar to talk about real estate or land deals. I take on one or two coaching clients a month. If you want resources, I’m happy to point you in the right direction.
Perfect, thank you so much.