Is bigger really better in real estate? Not always. Meet Dave, an investor who built a thriving real estate investing business without moving to a major city. Instead, he focused on small markets, simple strategies, and mentorship that actually works.

In this interview, Dave shares:

• Why real mentorship saves years of trial and error
• How keeping it simple can multiply your results
• Why small markets can be more profitable than big cities
• His $72,000 first deal (and what it taught him)
• Dave’s no-fluff advice for new investors

Meet Dave

Everything around us seems to be getting more complicated—real estate included. With increasing regulations, stricter financial requirements, and rapidly evolving technology flooding us with endless data, it’s easy to feel overwhelmed. Despite these challenges, the opportunities in real estate are abundant. The question is: How do you grow a successful business while cutting through the noise?

Meet Dave, an investor who built and scaled his real estate company, even expanding into larger markets with major rehab projects. But along the way, he learned a crucial lesson: bigger isn’t always better. If you want to simplify your real estate business while making serious money in small markets, this interview is packed with insights you won’t want to miss.

Real Mentorship: No Hype, Just Real Work

When Dave joined the Freedom Mentor apprentice program, he wasn't some lifelong real estate expert. He was a merchant mariner with no experience in contracts, closings, or comps—just a deep drive to build something of his own. Today, he's a full-time investor, turning consistent profits in a market many would overlook: his hometown.

Before Freedom Mentor, Dave was drowning in real estate advice online, most of it promising riches with little effort.

"I’m watching videos and thinking, ‘This can’t be real. Nobody gets rich this fast.’ It all seemed too easy. I was looking for someone who actually told the truth."

That’s when his dad sent him a link to Phil’s YouTube channel. Within weeks, Dave had signed up for Freedom Mentor. What stood out? The honesty.

"You said, ‘This isn’t going to be easy. You’re going to deal with tough stuff and feel uncomfortable.’ That’s when I knew—this guy’s for real."

Profit-Sharing: A Win-Win Mindset

Some might balk at sharing profits in a mentorship program, but for Dave, it made sense from day one.

"I didn’t have much money to start with. This wasn’t like buying a franchise with huge upfront costs. I looked at it like paying tuition as I went."

Instead of debt, Dave saw opportunity and access to a level of experience that would’ve taken decades to figure out alone.

"My dad and I said, ‘It’s like a college education—but without the loans.’ It was a good deal."

Deal Highlights: That First Big Win

Dave's favorite deal? His first one. It was messy, scary, and transformative.

"It was tough for me, mostly because of the mental and emotional side of it. I had to go out and get a hard money loan—had to beg, borrow, and steal. And I remember going through everything, just scared to death.  But the important part was I was doing it."

But when it sold, Dave walked away with a $72,000 check.

"I still have that check at my desk. I can’t throw it away. Once I sold that property and got that check, a light bulb really went off. This is the real deal."

Small Market, Big Advantage

After graduating from the program, Dave considered relocating to a larger market by the beach. But a heart-to-heart with Phil changed his mind.

"I learned a lot of valuable lessons about trying to break into a big market versus working a smaller one. Phil told me, "You're crazy, you have a phenomenal market. Stay in the small place." He was right."

Instead of scaling up by chasing volume in larger competitive markets, Dave doubled down on simplicity and speed in a smaller, overlooked market—his own backyard.

"That first deal was five minutes from my house. Small market versus big market? I’m choosing small markets all day, every day."

Keeping It Simple: Multiply Simplicity

Dave lives by a single mantra written on the whiteboard behind his desk: Multiply simplicity.

"The fundamentals I learned on day one are still what I use now. Can I write the deal down on a napkin and have it make sense? If yes, great. If it’s complicated math that doesn’t add up, I walk away."

He also stays lean when it comes to renovations, preferring the wholetail model: light repairs, fast flips, and minimal contractor headaches.

"What I really narrowed down on is a model Brian talks about—the wholetail—how to not to do too much rehab. I learned that from you guys. It’s something I see every single day; people spending too much money, buying into what I call the "rehab myth." I think you even have a video called The Rehab Myth. It’s about finding the middle path between being a wholesaler and a rehabber. Instead of thinking, Let me just rehab every house, it's What does the market want? That mindset has helped me do a lot more deals and turn properties around much faster."

The Value of Listening

One unique part of the program that Dave leaned into was group coaching.

"There were so many times I would get on a coaching call, and if I just sat there and listened, my answer would come out through somebody else. Especially early on, when I had no experience, I’d just hop on, listen, and soak it all in. It’s like getting experience without doing the deals. You’re not in the deal, but you’re like a bystander. You get to see inside the operating room, so to speak."

He still uses techniques shared on those calls years later.

"Some of the negotiation lines Brian taught, I still use them today, five years later."

Advice for Aspiring Investors

As someone who's walked the path from uncertainty to financial independence, Dave doesn’t sugarcoat what it takes to succeed.

"Freedom Mentor is not for someone looking for a free ride. You’ve got to put in the work. If you think you're going to get rich quick or that it's going to be easy—just forget about it. Go find something else. You’ll eventually figure out that doesn’t exist anyway."

For him, success started with humility and a willingness to follow the process.

"You have to put your ego aside and realize, I don’t know anything, and these guys are experts. Then just listen and do what they tell you."

He recalls a pivotal moment from his first deal:

"Phil kept saying, ‘Just get it under contract.’ I kept saying, ‘Yeah, but what about—’, He just said, ‘Get it under contract, then message me.’ So that’s what I did. Sometimes, you just can’t get too far ahead of yourself. You’ve got to be coachable. If you have good mentors and coaching, they’re not going to steer you wrong."

And when you’re facing deals that aren’t small, Dave says it’s better to take things step by step, with someone experienced guiding the way.

"Sometimes, especially when you’re doing the kinds of deals we were doing (which aren’t small), it’s better to take baby steps. In the beginning, you’re nervous, scared, and overwhelmed. It really helps to have someone say, ‘Do this. Come back to me. Let’s talk. Let’s go through the next steps’."

Why a Mentor Saves More Than Just Money

Some aspiring investors hesitate to invest in mentorship, thinking they can bootstrap their way through YouTube videos and free forums. Dave’s advice? Don’t mistake access to information for experience.

"The big hack with hiring a mentor is time. What we learned would’ve taken me 10 or 20 years to figure out on my own. What you gain is real experience. Not textbook hypotheticals but the real deal. That is what’s going to prepare you to make better offers, close deals faster, get creative in helping sellers in ways others can’t, and even try new marketing channels."

And perhaps the most important takeaway?

"What’s really important to me is taking care of sellers. We're in a business where people are often in compromised situations. You could lie, cheat, or take advantage—but being a local person who truly takes care of someone has become my purpose. I take great pride in that."

"When you're climbing the ladder to success, don't step on others to get there. Uplift them. Help others. Be a good person and it’ll come back to you in ways you can’t even predict."

Multiply Simplicity, Multiply Success

Dave wasn’t looking for shortcuts, hype, or get-rich-quick schemes. He wanted real experience, knowing that true success would require effort, persistence, and the right guidance. That’s exactly what he found at Freedom Mentor: a system that provided support, structure, and expert coaching to help him scale his business and achieve tremendous profits. But along with financial success, Dave discovered an even greater lesson: multiplying simplicity leads to multiplying results. Keeping things simple allowed him to refine his strategy, make smarter deals, and maintain consistency in his business.

Small Market Advantage

If there’s one thing to take away from Dave’s story, it’s this: Big money can be made in small markets with the right formula. If you’re ready to build a profitable real estate business, you need the right strategy and the right vehicle to get there. That’s where creative real estate and Freedom Mentor come in. With industry-leading training, proprietary techniques, and world-class mentorship, Freedom Mentor equips aspiring investors with everything they need to close profitable deals—consistently and successfully—no matter the market cycle.

Every Successful Creative Real Estate Investor Has a Mentor

Are you ready to simplify, multiply, and take control of your financial future? Apply to our apprentice program today, and let our expert team mentor, coach, and guide you toward real estate success: Freedom Mentor Apprentice Program.

If you have questions for us, text FREEDOM to 305-315-8030 or post a comment below.