After earning his MBA at Duke University, Rod Santomassimo switched from consulting to becoming a commercial property broker — to be his own boss without a limit on his earnings potential. But he didn’t expect it would let him combine his lacrosse coaching skills and book writing with broker tips.
Four decades later, he said being a broker is a lot like playing Division I lacrosse in college before coaching the sport in graduate school: To succeed at both requires “a complete commitment to constant improvement.”
This philosophy, Santomassimo said, has helped him make a living not only as a commercial real estate broker but also as a business strategist for brokerage firms and now the owner of a firm that coaches dealmakers to help them survive and thrive in the competitive business. He’s the author of several books about how to be a better broker, including “Brokers Who Dominate,” his first and one he says still sells 16 years after publication.
His approach has attracted a clientele that includes Bob Knakal, the New York City investment sales broker who led JLL’s private capital group in the market for the past six years. Knakal is widely regarded as one of New York’s most prolific sellers of office properties, having been responsible for deals involving 2,252 buildings and over $21 billion in sales.
Santomassimo said the crux of his program is straightforward. It’s centered on teaching brokers eight main traits. To succeed, he said, brokers need to be disciplined, oriented to the client, assertive, team-oriented, entrepreneurial, have a sizable market presence and an industry and geographic focus and navigate their careers themselves.
“We approach all of our coaching clients as if they are CEOs,” he said in an interview. “And we address the sales, marketing, operations, finance, and even human resources aspects of scaling their business. While most are challenged in sales or prospecting, others are trying to build a team, while others need better approaches to stand out from their competitors.”
With the commercial property market seemingly poised to rebound later this year, he said, he is ramping up efforts to recruit new brokers to coach. But Santomassimo acknowledges he’s doing so as the number of commercial property brokers, or his customers, is shrinking, especially at larger brokerages.
Marcus & Millichap recently said its number of investment sales and financing professionals dropped 6.4% to 1,783 at year-end 2023. That represents a drop of more than 120 brokers. In 2023, the number of commercial members of the National Realtors Association represented 2%, or just over 31,000, of the group’s overall 1,554,604 members. Commercial members accounted for 3% of total NAR membership in 2020, 2021 and 2022, according to data from the association.
Santomassimo said his overall prospect list is shrinking as people leave the industry. He estimated the number of commercial real estate brokers in the U.S. is around 100,000 when you include those who also dabble in residential. “And don’t be surprised if next year, in the next two years, the number goes down to 75,000,” he said.
Still, Santomassimo is used to expanding during tough times. He launched Massimo Group in Cary, North Carolina, near Raleigh at the height of the Great Recession in mid-2008. Santomassimo said he picked the company moniker that aligns with his surname, following a focus group where someone recommended “Massimo.” It’s an Italian name that means the most, best or maximum.
As he seeks to expand, Santomassimo said he has clients in every state and some as far away as Australia. Texas, Florida, New York and California are “great targets” because they have the highest numbers of commercial brokerages.
Santomassimo’s first coaching gig was in 1986-1987 as an assistant coach for the Duke men’s lacrosse team while studying for his MBA. He became a coach after he played on the Washington & Lee University team during his undergrad days. Some of the traits that he teaches brokers — such as having the tenacity to overcome adversity — have been honed during his college lacrosse career and in the years after playing club lacrosse.
“I am a chronic asthmatic and legally blind in my right eye. Not a formula for a Division I athlete,” Santomassimo said. “While we do implement new approaches to finding and winning exclusives, it still requires a complete command of the fundamentals. Without that foundation, you can’t grow.”
He got into the brokerage business despite telling his father, the late Jim Santomassimo, years ago, “Dad I love you, but I will never be in commercial real estate.”
When he started his firm, Rod Santomassimo was a solo coach. Now, he directs the business and has a team of 32 coaches who teach brokers methods to break out of the pack and make more money from commissions. He’s had 2,500 brokers use his program and said he’s coached a total of “easily over 4,200” brokers when live events, speeches, conferences and consulting jobs are added to the number.
Knakal, who already was experiencing success as an investment sales broker in New York City when he signed to have Santomassimo coach him 12 years ago, said his “income has, in some years, tripled from what it was” before Santomassimo started coaching him.
“Working with Rod Santomassimo and the Massimo Group has changed my life,” Knakal said in an email. “I had never heard of a ‘broker coach,’ but then thought to myself, Michael Jordan has a coach, Tiger Woods has a coach, Olympic athletes have coaches, why not give it a try?”
Having a broker coach, Knakal said, “provides another layer of discipline to our practice and exposes us to best practices being implemented across North America,” which can help him do more deals. Santomassimo has included Knakal in two of his books, “Brokers Who Dominate” and “Dominators of Commercial Real Estate.”
Knakal is the only broker Santomassimo still coaches personally, and they talk each Saturday morning. “Working with Rod allows me to be in that position,” Knakal said. “If you are not being coached, you are leaving hundreds of thousands, or millions, of dollars on the table.”
Santomassimo said he offered Knakal advice on how to manage his time better to ramp up his business.
“One specific approach was for him to get off the ‘transaction treadmill’ as we refer to it and start allocating time to work on his business as well as in it,” Santomassimo said. While Knakal “is a deal machine,” the executive “wanted to create a same level of income while working less time. We ended up making a lot more in less time.”
Rod Santomassimo (Massimo Group)
Despite having no initial interest in going into commercial real estate, Santomassimo did just that after quitting his consulting job at Arthur Andersen, where he said he was the “low man in a totem pole.”
He moved to Tampa and quickly found out what commercial property brokers did when he landed a job with Bruce Lauer, who co-founded CLW Real Estate Services Group in Tampa, Florida, in 1988. The firm now is part of Cushman & Wakefield, where Lauer is a vice chairman.
“The first week of the job, Travelers Insurance came in and said, ‘We need someone to run around the country who knows leases and knows numbers,'” Santomassimo said. “And Bruce looked at me and said, ‘That’s your guy.’ So that’s what I did. I traveled to Southeast United States, working with the Travelers Insurance company on office expansions, contractions, relocations, understanding what the tenant improvements were.”
After that, Santomassimo started his own brokerage, worked in a law firm and for a telecom company before joining Sperry Van Ness in 2005. At Sperry Van Ness, he developed an expansion plan and orchestrated franchise operations for the international commercial real estate company. He also led education and training programs within the company.
He left Sperry Van Ness in 2008, during the Great Recession, and launched Massimo Group.
“There were no jobs, so I thought, ‘Why don’t you just become a coach and we’ll figure it out?’ And my wife agreed,” Santomassimo said. “Eventually someone said, ‘Yes, I’ll let you coach me,” Santomassimo said.
As for what’s next, Santomassimo said lacrosse, which he only stopped playing recently, will be part of the mix.
“I’ll add my two loves, right? I’ll end up coaching lacrosse, which I’ve done in the past,” he said. “I’ll coach junior lacrosse or something. As I start to take a little more time away from the office, that’d be the next thing I do.”