What does it really take to build wealth, freedom, and balance in life? In this interview, Scott shares his powerful story of starting in a corporate career, discovering real estate investing, and proving that you can have both time AND money.

With Phil and Brian from Freedom Mentor, Scott opens up about:

• Balancing a corporate job with real estate investing
• Why mentorship accelerated his success
• Lessons learned from his first subject-to deal
• The shift into short-term rentals as a long-term wealth strategy
• Managing multiple streams of income while raising five kids
• Practical advice for new investors on building skills, managing priorities, and staying consistent

This conversation is packed with wisdom, real-world examples, and encouragement for anyone considering real estate as a path to freedom.

Real Estate, Freedom, and Building a Life by Design

Many people believe you can’t have both time and money—you must choose one or the other. Scott’s journey proves otherwise. In this candid interview with Phil and Brian from Freedom Mentor, Scott shares how he balanced a corporate career with real estate investing, built multiple streams of income, and discovered that success is less about quick wins and more about discipline, patience, and intentional design.

Transition from Corporate to Real Estate

Phil: What I recall as being very unique and special was that you already had a good career in sales. When you started doing this, you weren’t immediately jumping at the opportunity to quit your nine-to-five and go full time. Tell us a little bit more about what that transition ended up being like—not only while you were in the program, but then after you graduated.

Scott: Yeah, you nailed it. I had a pretty good career, but I reached a point where I felt like my values and the company’s values, as I climbed the corporate ladder, were at odds with one another. It wasn’t that the company did anything wrong, it’s just how business is conducted in a big company.

I realized I needed to be able to say “no” in an environment where those values conflicted. That’s what I was seeking: the ability to say no. And Phil, this may surprise you—I still have a corporate job even now. We’ve simply expanded our streams of income through real estate, both during the program and after. It’s been a decade of building a real estate career. And if you stay at it, a decade is a good amount of time. You can get a lot done in ten years.

The Power of a Decade

Phil: We often overestimate what we can accomplish in one year and underestimate what we can accomplish in ten. When you said ten years is a good amount of time, tell us—where do you stand now versus where you thought you’d be?

Scott: It’s interesting. I went into all of this with a goal board that had “own a long-term rental” on it. That goal sat there for five or ten years. We have five kids, so during all the years of raising them, that itch persisted. I read a few books, did some research, and every sign pointed to the idea that you need to get good at house flipping before diving into rentals.

Flipping helps from a sourcing perspective and builds an understanding of foundational basics in real estate that can be applied elsewhere. Phil, I still don’t own a long-term rental. And that’s because I’ve learned so much along the way. At the very beginning of my journey, the plan was to build a long-term rental portfolio. But honestly, that never happened. Instead, it’s been all the zigs and zags we encounter when diving deeply into an area. That’s exactly what we did—followed the path, learned along the way, and built something different than originally planned.

Why Keep a Job While Investing in Real Estate?

Phil: Take us inside the mind of Scott and why you kept a job while being a real estate investor.

Scott: Very quickly, I subscribed to the philosophy of multiple streams of income. That became very attractive. We haven’t reached a point where we don’t want more—we want to continue to grow, to learn, and to expand. Another thing is, as you get good at skills and at an industry, you don’t have to devote as much attention to keeping it going. Something you’ve always said is that success comes to the people who just keep at it over a long period of time.

When we first signed up, you could look through our deals and see the range of success we had. A lot of our deals were narrow wins by our standards, and that’s pretty common. What seems like a great win at first often turns out to be just an okay win. Interestingly, after I left the program, I got my best deals—and I was doing fewer of them. My margins widened, and flipping became easier.

Quality Over Quantity

We were never the people who wanted to do 50 deals in a year. We see people like that, but I’d rather figure out which seven deals out of those 50 netted the most profit. Those are the deals I do now. I’d much rather focus on the seven most profitable deals and leave the other 43 to someone else—someone willing to chase volume and manage huge overhead. In the meantime, what we’ve built is a house-flipping business that works exactly that way: lean, profitable, and sustainable. Beyond flipping, we’ve also expanded into other real estate streams of income. For us, vacation rentals have become a key focus, and that’s where much of our energy goes today.

The Value of a Slower Path

Phil: What’s it been like to have a slower path to success? What does that feel like now?

Scott: Well, I think if you skip the steps, you pay for it down the road—and you could pay with bigger numbers. There’s always some interest associated with that shortcut. For us, the slower path has meant wisdom. You become a different person—the kind of person who can handle the new environment you’re in. That’s why people who win the lottery often lose their money within three to five years. They haven’t become the person who’s earned the right to manage those resources.. When you earn the right through mistakes, through learning skills, and through persistence, you tend to retain what you’ve built—and ultimately gain more.

Why Freedom Mentor?

Brian: What brought you across Freedom Mentor? Why choose to work with us?

Scott: I was at a crossroads. Like many people, I had developed some level of self-confidence and thought, “I can go after this on my own.” But I believed I could do it faster and skip a lot of steps if I had an experienced person walking alongside me. That’s where the model made sense. I looked at it and said, “Okay, if I can get an experienced person alongside me, instead of it taking ten years to reach this phase, maybe it’ll take me two or three years—or whatever the pickup is.” So I was willing to pay the price for that advantage.

The Critical Role of Mentorship

Brian: How important do you think the mentor was to what you’ve achieved?

Scott: I think it was critical. If I rewind the clock and limit my answer to your question, I’d say it was extremely helpful. The hardest part is when the learning curve is steepest—knowing exactly which path is right and which eight other paths are wrong. Those wrong paths are out there, whether they’re misguided “common sense” or advice from everyone else.

Having a mentor helped me cut through the noise. It gave me clarity on what to do and what not to do. That became the foundation—the rules I used moving forward. The biggest advantage was during those first eight to ten deals. That’s when mentorship mattered most. It helped me get rid of bad habits and avoid misguided common sense that wasn’t true. After that, things got easier. But without that guidance early on, I would’ve wasted time, money, and energy chasing the wrong strategies.

Unexpected Benefits of Freedom Mentor

Phil: Were there any other situations that, as a result of Freedom Mentor, you were surprised by—benefits you didn’t expect going in?

Scott: I’ve been out for six years now. During that time, I’ve made close friendships through Freedom Mentor and continue to stay in touch with those individuals. We’ve learned from each other, grown together, and supported one another as we’ve continued our journeys. That continuation of relationships and ongoing learning was an unexpected benefit—100 percent. And it wasn’t just from the coaches. It came from other people who had one thing in common: we all made it through the process. That means we all crossed the hurdles, and that shared experience created bonds that have been very rewarding. Honestly, that benefit wouldn’t be obvious to someone just starting today. They have to climb the mountain first. But once you’ve been around long enough, you see the value of those relationships.

How Deals Were Funded

Brian: Shifting gears just a little, Scott—when it came to the deals you did, how did you get most of them funded?

Scott: I had money in the bank that helped me early on when I was more serial—doing a deal, closing it, then moving on to the next. For the first year, I self-funded. Oddly enough, my boss got let go and became a hard money lender for me on a couple of deals. Then I found a local bank, and that relationship has been very fruitful. Honestly, I don’t see many other people leveraging local banks, but maybe I’m just lucky because I’ve got one right here in my pocket. For me, the local bank became the answer and it was really good money. The terms are generous, the interest rate is super low, and now we have the relationship backed by all the other properties we own. It’s sorted out beautifully.

A Deal That Stands Out

Phil: Do you have a favorite story or a favorite deal that you remember, something that really sticks out?

Scott: I don’t know that I have one single deal that stands out above all the rest. But I’ll tell you, when it finally clicked for me how to do a subject-to deal—that was special. If you can pull off a subject-to, everything else feels easy compared to that. I was lucky enough to have a coach guiding me through the process. It’s incredibly empowering when you complete a complicated deal you didn’t think you could do. At first, it almost feels like a myth—like nobody really gets these deals done. And then you do one. All the elements align, you close it at a UPS store, and you walk out thinking, I just did one of these things. The level of complexity in that first subject-to deal made it the most special for me.

Advice for New Freedom Mentor Students

Brian: If you had it to do over again, in the midst of all you’ve learned, what would you advise someone considering Freedom Mentor today? What would you do differently, and how would you help point them in the right direction?

Scott: The acquisition of skills should be the goal. It’s easy to get wrapped up in the dollars and cents, but if you focus on acquiring skills, leaning into discomfort, and following the guidance you’re given, that leads to success. The money will take care of itself. I often got the behaviors and the outcomes backwards. If you put the behaviors first, the outcomes become the least of your concerns. You’ll get good outcomes but only if you get the behaviors straight first.

Constructing a Life of Time and Money

Phil: There’s real power in maintaining your day job while you’re building those behaviors. You’ve got something to fall back on, something to help fund and run this thing. Because the reality is, you didn’t find a bunch of motivated sellers for free—there’s money involved. So tell us a little bit more about the value of keeping that job.

Scott: All these streams of income feed each other. Sometimes one’s doing better, sometimes another needs a little help, and sometimes they’re all doing well—that’s great too. But ultimately, having multiple streams of income provides stability. I’ve mentioned before, we have five kids. With five kids, things happen. Some are expected, like Christmas, which costs money. Others are unexpected. Either way, having those streams of income makes it possible to handle life’s ups and downs.

Choosing Balance Over Burnout

We reached a point where we said, “We’re going to want more. Why can’t we just have it all?” And the truth is—we could. I don’t work 80-hour weeks. That’s not my vibe. In fact, we take a lot of time off and go on wonderful trips. My mom used to tell me when I was a kid, “You can’t have money and time. You have to pick one.” I don’t believe that. In fact, I told her recently, “Mom, that’s false. You can have both, you just have to construct that life.”

The key is living by the rules that make it possible. That means eliminating distractions like the silly interruptions from your phone or anything else that pulls you away from your goals. Ultimately, yes, you can have both time and money. It’s about designing your life intentionally, building streams of income, and protecting your time.

Managing Multiple Streams of Income

Brian: Scott, when you started out, you didn’t leave your corporate job, but you wanted that option. After doing this for a time, you determined that multiple streams of income were possible—and managing them has been important. How has that developed for you, and what’s your outlook now after several years?

Scott: We can emphasize different aspects of the business when it’s “go time.” For instance, during COVID, two things clearly happened. First, right after COVID hit, there were six months where nobody wanted to stay at a vacation rental. Then suddenly, demand exploded and it was gangbusters for a time. At the same time, there was a ton of appreciation in the real estate market. So we thought, “Let’s acquire what we can a little more aggressively here.” You put your foot on the pedal when conditions are favorable.

Managing Market Cycles

Things are different now. We’re much more selective in what we add to our vacation rental portfolio in this higher interest rate environment and more mature market. As for house flipping, we’ve changed our approach. We’re not doing as many rehab deals; instead, we’re doing more wholesales. That’s market-specific. We’re less aggressive in taking down deals we might have pursued four or five years ago. Through it all, we’ve had W2 income coming along in the background. That stability allows us to adjust, emphasize, or de-emphasize different streams of income depending on the market cycle.

Managing Time

Phil: Any tips on how someone manages a life like yours, with so many things going on?

Scott: You need to know what you want. Part of that decision-making is deciding what you are not going to do. I say “no” to a lot of things, and I choose those “nos” in advance so that when they come, it’s an easy decision—I’ve already made it. The less important things are hard nos. If it’s not a hard yes, it’s a hard no. We say no often so that we have time for the important things.

Focused Learning with Freedom Mentor

Phil: I’ve asked others in the past who have worked with us what their experience was like with the Freedom Mentor Team and our program. What would it be for you?

Scott: I got focused learning in a way that showed me the right paths to take each individual step of the way. It wasn’t an overwhelming fire hose of 30 things I had to do. Instead, it was: What do I have to do tomorrow? Then I could go do it, come back, ask the same question again, and the next step was there. That’s exactly what I needed. Otherwise, the next step would have been choosing between an array of 20 different options—and oftentimes not making the right decision. That leads to discouragement and getting off the path. Freedom Mentor kept me focused, clear, and moving forward.

Every Successful Real Estate Investor Has a Mentor

If there’s one theme that runs through Scott’s entire journey, it’s the power of mentorship. Having someone experienced to guide you through the steepest learning curves, help you avoid costly mistakes, and keep you focused on the right next step can make all the difference. Freedom Mentor provided that clarity and support. If you're looking to achieve both time and money, apply to the Apprentice Program here: Freedom Mentor Apprentice Program.

Questions for us, text FREEDOM to 305-315-8030 or post a comment below.