I Gave Away Too Much Money
I Gave Away Too Much Money
How can business owners improve their money mindset for growth?
I’ve listened to podcasts and spoken with many real estate investors, and it seems like most people have a healthier relationship with money than I did, at least initially.
I grew up without much money, the middle child of seven, in a mobile home in rural Wisconsin. It was a great family, but I was always aware that we couldn’t afford certain things. If I asked my dad for a video game or something, the answer was often, “No, there’s no money.” That sense of lack stayed with me and motivated many of my actions, especially when I first started out.
I have three kids now, and the idea of telling them, “We can’t afford that,” doesn’t sit well with me. I’ve always felt a responsibility, not just for myself but for my kids. I don’t want them to feel the way I did growing up.
That motivation was perhaps negative in the beginning, but I’ve since added layers of gratitude for the childhood I had. I started working young—shoveling snow in Wisconsin for $10—and that entrepreneurial drive never left me.
Now that I have some stability, I’ve told my wife, “We could stop for a while, and we’d still be fine.” But now it’s about growth: How can I feed more people? How can I challenge myself? How can I push myself out of my comfort zone again? When I started doing bigger real estate deals and talking to millionaires and banks, it stopped feeling scary or challenging. But I thrive in high-stakes, high-stress environments, and I always want to put myself back in that pressure cooker.
What steps help business owners set and achieve bigger goals?
The best people I connected with had a similar mindset: they understood that success is an ever-shifting benchmark. When I first started, like many real estate investors, I had a goal of making $10,000 a month. I thought I’d be satisfied when I reached it, but once you hit that milestone, you realize there’s so much more to life and business than you initially knew.
When I worked a nine-to-five job, my days felt mundane—wake up, go to work, get paid a fixed amount. If I needed more money, I just worked more hours. I had blinders on to all the creativity and opportunities happening around me. But as a business owner, once you achieve that first financial goal, the question becomes, "What’s next?"
For me, I wanted the freedom to work from anywhere with just my laptop. Then I got even more ambitious. One day, I was driving on the northbound 75 freeway in Dallas, where you get an amazing view of the city skyline. I remember thinking, "I want to change that skyline. I want to build something that I can point to and say, ‘That’s mine.’"
That thought changed how I approached my business. You don’t get to that level by flipping $10,000 or $20,000 properties. You have to take big steps every year. Even if I never make it, I’d rather have a vision that pushes me to take big steps because if your vision is small, your steps will be small too.
How can self-examination help business owners make better decisions?
Not everyone is spiritual, but I follow a simple process of self-examination in every area of my life. Whether it's deciding how to respond to my wife or how to handle my child throwing a fit, I apply the same process to business decisions.
For example, if I’m considering taking on a high-risk deal, I ask myself what’s motivating me. If the risk could significantly impact my business or family, I try to understand if I'm only focusing on the upside. Am I making a decision driven by greed?
This self-examination helps me understand my motivations, and it varies day to day. I've even turned down deals because I was having a bad day. It sounds odd, but in my business, where we do a lot of deals, losing a few here and there isn’t a big issue.
I make sure to check myself, often adding prayer or meditation to get clarity. I ask if my actions are driven by ego or if they truly serve my family. While business decisions are often straightforward, especially in real estate, I rely on this process to evaluate deals beyond the numbers. It's easy to analyze—what we’re buying, the comps, market days, and our buyer's list. But beyond the data, I also look at my risk tolerance, making sure I'm not overconfident because I just closed a big deal.
This process has yielded great results, even when the answers are hard to accept. Sometimes, I have to walk away from deals with huge upsides because I know my motivation is greed or something else that won’t serve me in the long run.
Why should entrepreneurs see mistakes as learning opportunities?
I don't really view any decisions I've made as "bad." Instead, I see them as learning experiences, many of which were necessary. One example is when I first brought an investor into a real estate deal. As an entrepreneur, you often start with no track record, making the cost of capital high. My first investor put in $15,000, which generated $95,000 in revenue—$25,000 to $35,000 in cash and $60,000 on notes. While it felt like a lot to pay him over five or six years, without his support, I might not have taken that first step.
Though I had no real estate experience at the time, that investment allowed me to try new things without risking my family’s financial stability. The investor became a mentor and introduced me to more opportunities, including a key partner for my development company. Even though it was a gut check when my accountant laid out the numbers, I realized I learned more from that experience than I could have from expensive coaching. I made money, gained a mentor, and built valuable relationships.
Another lesson came from a partnership that I entered into without being as selective as I should have been. We were flipping properties and had great success until a disagreement arose over access to funds. My partner insisted on being the only one with access to the business account. That situation taught me to trust my instincts and to always have clear expectations and strong operating agreements in place.
Although it was uncomfortable, and I had some tough conversations, I learned the importance of having everything clearly outlined in partnerships—how decisions are made, who has access to accounts, and setting expectations upfront. Despite the tension, we still made money from that deal, but the experience was a valuable lesson in how to structure future partnerships.
What are the benefits of joining a mastermind for business growth?
For a long time, I put off spending money on big things, especially if someone was selling it to me. As a salesperson myself, I was wary. However, training my sales team helped me understand the value of these products. Whether selling land or anything else, the key is identifying if your product meets the needs of the person across the table.
When it comes to learning from a group like a mastermind, I realized that if you're looking to surround yourself with people who have exclusive knowledge, unique drive, and a willingness to invest in themselves, you generally find the right group. That’s not always the case—sometimes people just have money and want to be around others doing things, but that's rare.
I’ve also been part of free masterminds, and you know what happens there? Nothing. If you're not investing capital, you're usually not investing your time or effort either. As an industry leader, I take pride in staying at the cutting edge with new tech and strategies. I’m generous with knowledge, but I don’t want to broadcast industry secrets to just anyone.
In a paid mastermind, there's reciprocity. People exchange valuable insights and ideas. Additionally, building community is one of the first things you should do in your business. In the masterminds I’ve paid for, I’ve found people who are willing to partner on deals. For example, if I meet someone who operates in Tennessee and I find a seller there, I can easily hand off the deal, make money in the middle, and know the deal will be handled well.
That network is everything. It’s hard to overstate how important it is, especially when you’re trying to move from having a successful business to an extremely successful one.
*This interview has been edited and condensed for clarity.*
