Jacksonville Real Producers ~ Tobin Bossola | March 2025

The Drive to Thrive

By Zachary Cohen | Photos By The Real Estateographers

When Tobin Bossola decided to leave his stable, salaried job at Home Depot in 2006, he was taking a leap of faith into a career that promised more flexibility and potential. The long hours and all-consuming nature of his role as a Home Depot Store Manager didn’t align with the life he envisioned, and so, he turned to real estate.

“My wife and I were planning to have kids, and I didn’t want to be married to the job,” Tobin recalls. “I started exploring options, and real estate stood out. It was an exciting time in the market, and I thought it would provide the flexibility I wanted for my family.”

That leap of faith into real estate, however, coincided with one of the most turbulent periods in the industry’s history.

A Rocky Start

After leaving Home Depot, where he had spent five years, Tobin entered real estate just as the market began to unravel. He joined Vanguard, drawn by the brokerage’s forward-thinking approach to lead generation.

“My team leader at Vanguard Realty was ahead of his time,” Tobin explains. “He had invested in SEO and owned about 20 domains, generating hundreds of leads monthly. That gave me something to work with as I started out.”

Despite these tools, Tobin’s first year was challenging. He had only one closing in 2006. By 2007, he had found his rhythm, but when the market bottomed out in 2008, the challenges escalated.

“Our first child was born in December 2007, and for the next five months, I didn’t have a single closing,” Tobin recalls. “We were burning through savings, and I started to feel doubt creep in. I even began teaching myself to code and stayed up late doing online surveys to earn a little extra money.”

While money was tight, there was a silver lining. “I got to be really involved in the early part of my daughter’s life,” Tobin says. “But I knew I had to find a way to make real estate work.”

A Strategic Pivot

Determined to carve out a sustainable niche, Tobin immersed himself in the foreclosure market. He began doing Broker Price Opinions (BPOs), completing over 1,000 in 2009 and 2010.

“BPOs were a great way to stay busy, make some money, and learn the market,” Tobin explains. “They also led to a few foreclosure listings, which became a turning point.”

When Coldwell Banker was purchased by his brokerage, Tobin joined their foreclosure team, and his career took off.

“I took over an account and grew it exponentially. For five years, I was deeply immersed in foreclosures, and that experience gave me a huge number of listings and a large book of business, especially with investors.”

Even as Tobin thrived in the foreclosure space, he maintained a diverse business model. “I knew the foreclosure market wouldn’t last forever, so I kept working on other parts of my business,” he says.

“That decision made a big difference when the market shifted again.”

Business Today

Nineteen years later, Tobin is still with Coldwell Banker Vanguard Realty, working as a solo agent. In 2023, he had his best year yet, closing nearly $24 million in volume with over 55 transactions. He followed that with a $8 million, 24-transaction year in a down market in 2024.

“My business thrives on personal connections,” Tobin says. “I’ve developed a script I’ve memorized so I can focus on looking people in the eye and really connecting with them.”

Tobin attributes his success to three key principles: doing BPOs to gain market knowledge, creating work lists to stay accountable, and staying organized. “Organization is huge,” he emphasizes. “It’s what keeps everything moving smoothly.”

Outside of real estate, Tobin’s life revolves around his family. He and his wife, Rachel, have three children: Lily (17), Amelia (13), and Myles (10). Rachel, a part-time pediatric nurse, works three days a week, while Tobin takes on a hands-on role at home.

“I’m up every day helping my kids get ready for school, making breakfast, and packing lunches,” Tobin says. “Being present for my family is just as important to me as my career.”

Tobin’s past experiences also influence his personal life. A former cook with a degree in environmental horticulture, he enjoys preparing meals for his family and tending to their garden. “We grow some of our own food and compost — it’s something we enjoy doing together,” he says.

Tobin hopes to leave a legacy defined by being a good husband and father, as well as a professional who was deeply committed to his clients.

“One of the things that separates me from other REALTORS® is how driven I am,” he says. “I wake up every day ready to exercise, get organized, and get to work.”