I started investing in real estate in 1996 with nothing but hustle and a library card.
No family money. No connections. No algorithm feeding me off-market deals at 3 a.m. Just me, a beat-up Ford, and the willingness to knock on doors until someone said yes.
I was a landscaper. A broke one. The kind of broke where you're choosing between gas money and groceries. But I'd read enough books to know that real estate was how regular people built real wealth — not stocks, not crypto, not some get-rich-quick scheme. Buildings. Apartments. Cash flow.
So I bought my first property. A small multifamily in Brockton, Massachusetts. I had no idea what I was doing. I learned plumbing from YouTube before YouTube existed (it was called "calling your uncle and hoping he picked up"). I learned tenant management by making every mistake in the book — and then some.
But I figured it out. And once I figured it out, I couldn't stop.
The Journey
Bought my first multifamily property in Brockton, MA. Had barely enough for the down payment. Learned everything the hard way.
Scaled to dozens of units across Massachusetts. Discovered the power of value-add investing — buy underperforming buildings, fix them up, raise rents, build equity. Rinse and repeat.
Founded RE Mentor to teach other people what I'd learned. Started with small workshops. Turns out, a lot of people wanted to know how a landscaper built a real estate portfolio.
Expanded into syndication and larger deals. Published Multi-Family Millions — it became the go-to book for apartment investors. RE Mentor grew into a national education company.
While everyone panicked during the financial crisis, I bought. Hard. Properties at 40 cents on the dollar. Those acquisitions became some of the best-performing assets in the portfolio. Lesson learned: move when others freeze.
Scaled to 10,000+ units across 27 markets. Built teams, raised capital, ran a machine. RE Mentor helped thousands of students close their first deals — and their fiftieth.
Stepped down as CEO of RE Mentor after 22 years. The industry was changing. AI was reshaping everything. Time for the next chapter.
Launched Deal Makers Society — a community for real estate investors built on everything I've learned. Plus a newsletter, a podcast, AI tools, and a whole lot of straight talk. This is what I was meant to do.
What I Care About Now
Four things dominate my days (besides my kids, who come first):
Real Estate. Thirty years in, I'm still doing deals. Still finding opportunities. The market in 2026 is wide open for small investors — and I'm going to keep showing people how to take advantage of it.
Artificial Intelligence. AI is the great equalizer. The tools that used to cost institutional investors millions are now available to anyone with a laptop. I use AI every single day — to analyze deals, to build businesses, to create content. If you're not using AI in your investing, you're already behind.
Self-Improvement. The deal you do is only as good as the person doing it. I'm up at 4:45 AM every morning — priming, sauna, cold plunge, weights, cardio. It's not about being tough. It's about being sharp enough to make good decisions all day long.
Longevity. What's the point of building wealth if you're not around to enjoy it? I'm obsessed with the science of living longer and better — cold exposure, metabolic health, sleep optimization, the works. Building an empire means nothing if your body gives out at 60.
Why I'm Doing This
I could have walked away. Retired to a beach somewhere. But I've got kids who need to see what building something looks like. And I've got a community — you — that I'm not ready to walk away from.
The game is rigged against regular investors. The banks know it. The institutions know it. The information that moves markets has been locked behind expensive networks and country club handshakes for decades.
I'm here to change that. No paywalls. No pitches disguised as paragraphs. Just the same intel the big guys hoard, delivered to people who actually buy buildings.
Welcome. Let's build something.
— David