I have been in real estate long enough to know how easy it is to drift from the original reason you started. In this conversation, I sat down with an experienced investor who has been through multiple cycles, strategies, and shiny objects and ultimately found clarity by simplifying instead of adding more. We talk about mission-driven decision making, how to evaluate opportunities without emotion, why most investors are overwhelmed, and what it actually takes to build a real estate business that supports your life instead of consuming it. If you have multiple doors and still feel scattered, this conversation will challenge how you think about growth, deals, and freedom.
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Hi everybody. I’m excited today to have a great guest here with me. I want to set the stage and start with a simple question. Can you give us a quick overview of what you focus on in real estate today?
Thanks for having me on the show. I appreciate it. Our focus today is getting back to basics. We have been in this for 17 years now, and we have seen so many things in the real estate investment space. Wholesaling, construction, flips, rentals, Airbnb, and more. We are just getting back to basics. We did not get into real estate to become a guru or chase everything. The goal was to get involved with real estate, make investments that make money, nothing too crazy, nothing too difficult, and something that could have a return in a relatively short amount of time. Rinse and repeat. It is simple.
The real estate world is very large, and it is easy to get caught up in a hundred different rabbit holes. In reality, you end up becoming incredibly distant from why you were here in the first place. I think back to when I first got into real estate after reading Rich Dad Poor Dad in 2008. I got the email, went to the seminar, and went home to my wife and said this looks like another investment vehicle that could make money better than what we were doing in the stock market. That is where it all started. Very simple. Then I look back and think about how far we deviated from that over time.
That happens as things evolve. You have successfully operated across wholesaling, flipping, rentals, and new construction. How do you decide when to add a new strategy versus doubling down on what is already working?
Today it is a lot easier because we are past shiny object syndrome. If I log into Instagram, it feels like mental abuse because of all the distractions. So I try not to spend much time there. My approach now is that I only do two or three things. That is it. I am not interested in a lot of the other things I have done in the past unless it is a prime opportunity.
For almost a decade, we did a lot of new construction. The problem was that I became a builder. When I first learned about real estate investing with my wife, the idea was never to become a builder. Looking back, we learned a lot and I enjoyed it, but it was not part of the mission. There are things we enjoy that we are fine not doing because they are not part of the mission.
We reached a point where we were literally running a construction company and had to stop and say this is not what we signed up for. Nothing wrong with being a builder. Some people love it. That just is not me. If I ever do it again, it would be a one off, on the side, and in a location that is inspiring to go to. Building a house itself is not that inspiring. At the end of the day, it is four walls and a roof. Some are prettier than others, but that was never the goal.
What I love about that is how clearly mission plays into decision making. Especially for real estate investors, it is easy to see opportunity everywhere. But if you do not know why you are doing this, it becomes dangerous. How did your mission evolve and how did you come to realize its importance?
In the early days, it was easy to stay focused. I was working a full time job and buying properties, doing small remodels, and renting them out. This was long before BRRRR was a term. In 2012, we bought a house when the market was still bad. We tried to sell it, but no one was buying. It was on a small lake, so we decided to rent it short term. This was before Airbnb was mainstream. We were doing short term rentals before we even had language for it.
The property made a little money, which was the goal. If I am going to hold a property, it needs to make a little money. If I am going to flip it, it needs to make a little money. Nothing extreme. We were not trying to be Elon Musk. The issue came when we started seeing other opportunities.
Opportunity is a dangerous word. There are always opportunities everywhere. The question is whether the opportunity lines up with your mission. It is very easy to convince yourself it does when it does not. That is why I believe people need a coach. If you are not leaning on people who have experienced both highs and lows, it is easy to get knee deep into something that does not align with who you are or what you want.
That outside perspective matters. Coaches are not emotionally attached to the opportunity. They help you evaluate whether it is aligned or just a distraction.
I will give you a real example. I currently have an opportunity in Pittsburgh. The numbers look good, but I have never been there. Going into another market comes with problems. I already know the renovation budget could increase by 30 to 40 percent. The numbers still work, which makes it tempting. I reached out to contractors and will do one walkthrough. That will tell us quickly whether this is something we need to do or if it makes more sense to hand it off to someone else in that market.
Ten years ago, I would not have asked whether this was aligned with my mission. That is how investors get into trouble. They see a good opportunity and jump in without support or perspective. That is why some people end up in real estate even though it does not align with what they truly want.
We talk a lot about evaluating opportunities based on mission. What other systems help you decide which deals are worth pursuing?
It depends on the type of opportunity. For flips, people talk about 70 percent of ARV minus repairs. That sounds good, but it does not work for a lot of people because it is inaccurate. We had to refine our system. In our market, appreciation is flat or declining, so we look closer to 65 percent.
That 65 percent includes repairs, holding costs, and all financing. Not best case scenario financing, but worst case. If we think it will take five months, we underwrite nine or twelve. The formula needs to account for realistic risk. That only comes with experience.
I see this from the lending side as well. Deals take longer than expected. Holding costs add up. But good deals still exist if you run numbers correctly. You just have to work to find them.
I agree. Deals are not found anymore, they are created. Back in 2008 and 2009, deals were everywhere. Now, with hedge funds in the space, competition is real. Creating deals takes work. Negotiation matters, and understanding why a seller is selling matters even more.
Most people negotiate numbers without understanding needs. The need is rarely money. It is almost always emotional. Money is a byproduct of emotion. When you understand the emotional need, you can create real solutions.
This applies to relationships too. Trust matters. Trust is built by talking about what happens when things go wrong before they go wrong. Every mistake I have dealt with came from trusting someone based on what they knew instead of who they were.
Real estate is a business where mistakes can surface years later. When things break down, it is almost always bi directional. Both sides failed to communicate or set expectations.
We all go to seminars where everything is presented as perfect. No one sells what can go wrong. But that is what actually matters. You need to know how someone handles problems before you partner with them.
That is why I encourage hard conversations early. Talk about worst case scenarios. Most people will walk away from that conversation, and that is a good thing.
This applies to partnerships, bird dogging, cold calling, or anything else. Most people underestimate how hard the work actually is. Success rates are low. Rejection is constant. You have to be honest about whether that aligns with who you are.
I also believe in going deeper instead of broader. Listen to things multiple times. Read books slowly. Connect everything back to why you are doing this in the first place.
At the end of the day, there is always a sales side of the table and a risk side of the table. Sellers sell upside. Investors must protect downside. When relationships fail, it is usually because the downside was never fully discussed.
That is where clarity, alignment, and trust come from.