Ryan’s journey into real estate began not with a lifelong passion, but with a Google search. Frustrated by the corporate grind of a large real estate firm, Ryan, a finance major, decided to forge his own path. That initial search for “best businesses to start” led him to real estate, and a subsequent search for “best cities to invest” pointed him toward Tampa, Florida.
A decade later, Ryan has built an impressive mix of portfolio of over 43 units and remodeled close to 100 units, a mix of long-term rentals and flips, with a growing focus on new construction. He recently sat down with LendingOne to share how he got started, the challenges he’s faced, and the surprising lessons he’s learned along the way.
From Corporate Finance to Full-Time Investor
Ryan’s first real estate deal was a foreclosure in Hudson, Florida, purchased in 2014 for $50,000. He went in with a partner and his parents, who had recently retired to Florida. That initial investment, a rental property, was the first domino in a long chain of successful projects.
“Once I did it and cash-out refinanced, I just kind of never stopped doing it,” Ryan explained.
While the financial return was a key motivator at first—he worked in finance until 2019, focused on building enough income to leave his W-2 job—his passion for the work quickly became the primary driver. He finds deep satisfaction in the physical transformation of a property, a feeling that many people don’t see when they only focus on the financial aspect of being a landlord.
“I’ve taken dumps, gutted them to the ground, taken every floor joist out of a 100-year-old home, elevated the ceilings, and put beams in,” Ryan said. “It’s an awesome experience to see this change.”
Now, his goals have shifted from simply building wealth to enjoying the process, especially with his recent focus on new construction. “It’s not financially motivated anymore,” he shared. “As long as I enjoy it, that’s what matters.”
The Hands-On Approach to Building
While his career was in finance, Ryan grew up with a stepdad who was a talented handyman. This early exposure to construction work, coupled with a job at a commercial development company, gave him a fundamental understanding of building. However, his real construction education came from doing the work himself.
Tired of the headaches that came with hiring general contractors, Ryan decided to take on a large addition on his own, pulling a homeowner’s permit to learn the process firsthand. This experience, combined with a little help from the internet and a retired plumber he met at Home Depot, became his real-world classroom.
He learned to “reverse engineer” the process, starting with smaller remodels and gradually taking on more complex projects. By asking questions, paying attention to the details, and learning from the tradespeople he worked with, he built a deep understanding of building codes and construction practices.
Lessons Learned: Challenges and Breakthroughs
Ryan has faced his share of hurdles over the last decade. Early on, the biggest challenges were securing capital and dealing with the stringent requirements of traditional lenders like Fannie Mae. These limitations forced him to be disciplined, only pursuing deals that were “home runs.”
The turning point came when a friend referred him to LendingOne. “I just remember not believing them when they were like, ‘Yeah, you’re done with underwriting,'” he said of his first experience with the company. The speed and ease of the process were a stark contrast to his past experiences.
Beyond financing, two specific projects were particularly transformative for Ryan. The first was a triplex he bought in 2019 in Clearwater, Florida, that was in terrible shape. “There was a trash can…in the roof, pouring through the downstairs,” he recalled. The extensive remodel was grueling, but it taught him that no challenge was insurmountable. “Everything after that is easier now,” he said.
The second lesson came from a project where he got caught doing work without a permit. The experience, while frustrating, taught him the ins and outs of Florida’s strict building codes and the importance of following the proper protocols. “Everything was easy after that,” he said, as it demystified a process he had previously feared.
The Network and the Mindset
Ryan’s success is a testament to the power of a solid network and a focused mindset. From the very beginning, his support system was instrumental. His mother served as his first partner and a steadfast source of encouragement. Later, his wife, Anna, played a crucial role by managing their properties, freeing Ryan to concentrate on sourcing new deals and overseeing construction. Ryan also points to the BiggerPockets podcast and his friend, Aiji, as vital resources. It was Aiji who first introduced him to LendingOne, and Ryan considers him one of the most brilliant and hardworking business minds he’s ever encountered.
When asked for three pieces of advice for new investors, Ryan shared a mix of practical and philosophical insights:
- Get good with your numbers. Don’t be overly optimistic and force a deal. The numbers are what they are.
- Don’t be afraid. While real estate is hard, so is every other profession if you want to be good at it. The biggest gains come from tackling challenging projects.
- Take a long-term view. Ryan believes many people have a short-sighted view of the market, focusing on the anomaly of recent years rather than the consistent, long-term growth of real estate.
As he looks to the future, Ryan is focused on continuing to build his portfolio of long-term rentals, with a few flips and new construction projects sprinkled in each year. He and his wife, who manages their properties, have a system in place that allows them to live in Charlotte, North Carolina, while still operating their successful business in Florida.
For Ryan, real estate investing is not just about the numbers; it’s about the creativity, the problem-solving, and the deep satisfaction of bringing something old and forgotten back to life.
