From House Hacking to 15,000 Units: The Move That Changed Everything

Real estate investing can be a rollercoaster. One day, you're up to your elbows in a broken toilet; the next, you're signing papers on a multi-million dollar deal. That's been my journey, anyway. I started with a single house, built up to 21 units, then one move that took me to 15,000. Here's how it happened.

My First Taste of Real Estate

My uncle was flipping houses in Scottsdale, before flipping was cool. He would bring me along to help out – fixing up duplexes and condos, then selling them for a $20k to $30k profit. I was making pretty good money for a 17-year-old and wanted to start doing my own deals, but my uncle gave me a reality check. “Ryan, you don’t have any money,” he said.

I had also been getting into aviation around the same time. My uncle had recently bought a small plane and would take me up with him when we weren’t swinging hammers. Since I didn’t have enough money to flip houses myself, I decided to pursue a career as a pilot.

Little did I know at the time this decision would later put me on the path to building more wealth through real estate than I ever would have through flipping houses.

Building My 21-Unit Portfolio

Fast forward to 2008-2009. I'm 25, and my career as an airline pilot was taking off. However, I still had the real estate bug I caught working with my uncle. At this time, the market was tanking, and properties in Arizona were being sold for half price. I had a little bit of money now, so I bought my first house for $110,000. It was a four-bedroom, and I rented out three rooms and lived in the fourth. Not only was my house being paid for, but I was cash-flowing $400 per month.

Pro Tip #1: When starting out, look for properties that can generate immediate cash flow. Even in challenging markets, these opportunities exist if you're willing to get creative.

Over the next five years, I hustled my way up to 21 units. I got scrappy - selling my car to buy a three-plex, talking a neighbor into seller financing for a four-plex. I was the maintenance guy, the property manager, the whole shebang. But I was about to hit a wall that would change everything.

It Was Time to Go All in

At 21 units, I was too small to hire a property manager but too big to handle everything myself. As an airline captain, I would finish a 10-hour flight only to see messages about clogged sinks and broken AC units. I would be on the other side of the world, trying to coordinate repairs and chase down rent checks. Something had to give.

That's when I stumbled upon Grant Cardone's YouTube videos about real estate investing. His success and strategies fascinated me. I knew if I could learn from someone doing big things, it would allow me to scale. I took a leap of faith. I left my job at the airline, moved to Miami, and started working for Grant as a salesperson in his office.

After I proved my worth in sales, I mentioned to Grant that I was actually a pilot. He didn’t believe me at first, but once I convinced him it was true, he made me his personal pilot while I continued working in the business between flights. This gave me more face time with Grant and opportunities to learn about real estate.

During one of our trips, I proudly pulled out my phone to show Grant my portfolio. I was expecting praise. Instead, he said, "Ryan, these deals are junk. If you have equity, sell them all." It was a gut punch, but he was right. These were older properties with low rents.

Pro Tip #2: Sometimes, the best move for long-term growth is to let go of what you've built. Be open to pivoting your strategy when better opportunities arise.

I sold everything. Grant had just bought 826 units in Nashville and let me buy in. I went from 100% owner of 21 units to a 2-3% owner of 826. It was a scary move, but it flipped my whole strategy upside down.

The Power of Scaling Up

Overnight, I went from managing everything myself to being a passive investor. No more showings or roof leaks. We had a crew handling leasing and maintenance. I could focus on strategy instead of day-to-day operations.

The benefits went beyond convenience. In large multifamily properties, when you increase rents and NOI (Net Operating Income), the property value skyrockets. With one to four-unit properties, the value is limited by comparable sales in the neighborhood.

We bought those Nashville properties for $63 million and sold them three years later for over $92 million. My $400k investment turned into $1.2 million. I became a millionaire without unclogging a single toilet.

I immediately reinvested that $1.2 million into another deal and have invested alongside Grant ever since. I am now a partner in nearly 15,000 units – something I had never even dreamed would be possible back when I was flipping houses with my uncle.

Pro Tip #3: Look for opportunities to partner or pool resources. This can give you access to deals and expertise that might be out of reach individually.

Inflation and rate hikes have created a difficult environment for most investors in today’s market. But it's also opened up opportunities for those who can move quickly on large deals. Debt is coming due on many properties, and owners are selling at attractive prices because refinancing doesn't make sense.

This is where partnerships shine. Average investors can pool their resources to acquire these deals. It opens up opportunities that may never be available by going alone.

Of course, partnering has its challenges. You're giving up some control and relying on others to make decisions. But if you choose the right group, you can minimize risks while maximizing returns.

A Call to Reflection

Looking back on this journey from that first house to being part of a 15,000-unit portfolio, I'm amazed at how far I've come. Starting small taught me valuable lessons, but it was the willingness to level up that truly transformed my portfolio.

If you're grinding it out with a small portfolio, keep at it. But always be on the lookout for ways to scale. Letting go of control and partnering with the right people is often the fastest way to grow. It sure was for me.

I encourage you to think about why you're investing in real estate. What are your long-term goals? Is active management right for you, or could you benefit from a more passive approach through partnerships?

It's not just about working harder—it's about working smarter. And sometimes, that means knowing when to go from being a big fish in a small pond to being part of something much, much bigger.