It would be prescient, if not a tad presumptuous, to say that Sarah Chaisson knew from the jump that hitching her career wagon to Anthony Lamacchia’s rising star was the right stratagem. After all, she was just starting out as a kindergarten and first grade teacher, something she loved. Suddenly becoming a glorified assistant in a new real estate business, rejecting a classroom to instead work in a spare bedroom, might have seemed a reach to outsiders.
But Chaisson was an insider, for even as an adolescent schoolmate of Lamacchia’s she recognized his drive, persistence and absolute faith in himself, and her instincts were spot on. As the first-ever employee of what is now the multi-state Lamacchia Companies, she has risen to senior vice president of finance for all of them. Maybe pivoting from teaching was logic-driven after all.
Now celebrating year 20 with Lamacchia, Chaisson strolled down memory lane with RISMedia, detailing the two decades of professional growth with the force of nature that is Anthony Lamacchia, who also provided perspective. Their early years growing up blocks apart in Watertown, Massachusetts, informed all that would come later.
The roots run deep for both, now 44, with parents who provided guidance while insisting on discipline. Chaisson’s dad was the town’s chief of police, while Lamacchia’s owned a landscaping business where Anthony worked regularly from a young age.
“Sarah was always a friendly, warm and very smart girl growing up,” says Lamacchia. “There would be times we would start participating in stupid things, or I would say something off color, and she’d correct me. And 30 years later that still happens! Sometimes she’ll roll her eyes at me. She’s very methodical, very thoughtful, very caring.
“Her dad’s 80 now. I’m good friends with him, and he was very old-school. That was her upbringing. Even though she was an only child and was spoiled in some ways, they were very strict with her in other ways. I think some of her growing up in a structured environment has boded well for our company and her working with me.”
While Chaisson enjoyed the longtime friendship as well, she never imagined in its formative years that they might eventually join forces professionally. She expected that Anthony would eventually take over the landscaping business, and besides, she was charting a path of her own. She’d graduated college and was onto a master’s degree in education while starting her career as a teacher. Fate intervened when Lamacchia, busy launching a real estate business, asked her to work with him part-time, which quickly became full-time.
“I knew it was the kind of opportunity that I couldn’t pass by,” she says. “I knew Anthony was always going to be successful. I had nothing to lose because I could always go back to teaching if it didn’t work out. I was 24 and thought, let’s just take a chance and see where it goes. And honestly, it was one of the best decisions I’ve ever made.”
Of course success was not instantaneous.
“We actually started in a spare bedroom in Anthony’s house,” she says. “Pretty comical. Most people would be like, ‘That’s so bizarre.’ But it wasn’t weird at all. We had it set up with a bed on one side and a table on the other side. It was so laid back. I would go to work every day in a sweatshirt. At the beginning we were like, is this even going to work?
“I started out as a receptionist and worked my way up to office manager, director of operations and vice president of finance, and now I handle the finances for all of the Lamacchia companies.”
As for Lamacchia, did he feel any apprehension or angst yanking Chaisson away from her new career as a teacher? Not one bit.
“I didn’t feel any guilt because I knew that she would make dramatically more money with me,” he says. “And that has happened…she would’ve done great (as a teacher), but she was capable of significantly more. And I knew that I needed someone who was good at all things but also someone who would be incredibly loyal to me.
“You can’t hire people off the street that you just meet and get the same level of loyalty that you’re going to get from someone you grew up two streets away from and were friends with when you were nine years old. That’s just never going to happen. I knew I needed that one person I could depend on for loyalty. She’s as loyal to me as a family member.”
It is a true family affair in some regards, adds Chaisson. “Anthony’s wife, Nicole, works here as well. She’s our finance coordinator. She and I have also been best friends since middle school. We used to dance together, and we all hung out in high school, college and after. So it’s been fun.”
While recognizing Chaisson’s human qualities early on, Lamacchia admits he had no idea 20 years ago whether she would be able to keep up with his incredible pace and insistence on building the business 24/7.
“At that time, I didn’t,” he says. “I needed help and she did everything. I would do two to three listing appointments a day, four to five days a week. I did that for three years straight. I was running a television ad that said if I don’t sell your home in 70 days, I’ll buy it. My phone was ringing off the hook because at that time homes weren’t selling. I never, ever would’ve stood a chance doing as much business as I did if Sarah wasn’t in the office all day, every day.
“It was a solid three years at that level. The year before wasn’t at that level, and the year toward the end when I started training people wasn’t at that level, but that three-year period from about 2007 to 2010 was really when I mastered the sales process and learned the business from the ground up, and she helped me every single day.”
Luckily for Chaisson, as the years went by and her roles grew more corporate, she was able to carve out more free time in her life. With husband E.J. she has 14-year-old twins, a boy, Jackson, and girl, Riley, who are both hockey players, so mom and dad spend lots of nights and weekends at the ice rinks. In whatever spare time is left, Chaisson enjoys being outdoors, especially at the beach, and with old friends.
Spectacular company growth
Lamacchia Companies now has 75 full-time employees and about 750 real estate agents, making Chaisson especially proud that she was the very first hire. She certainly could never have known what the future held those days working out of the spare bedroom. But she recognized for sure that Lamacchia had special qualities, not just in business but as a person.
“He was always a workaholic,” she recalls. “At a young age he was working with his dad at the landscaping company. He would be in high school with a pager. Customers would call him throughout the day. He would go to a pay phone, put money in, call them back and after school go meet up with them and work. So I always knew that no matter what he did, he was going to be successful.
“He’s one of the most inspiring people that I know. He makes you want to be a better person and do great things, and his energy is super-contagious. I’m thankful for the opportunity that I’ve had with him. He’s also very caring, not just inside of work, but outside of work. If there’s something going on with someone’s family member here you’re not just a number.
“Anthony gets to know you. He reaches out to people all the time, so he’s not just some big corporate boss. Everyone has his cellphone number and is welcome to call him anytime. He expects a lot out of you, which is good. I don’t look at him like a friend when I’m here though. I look at him as the owner and leave our personal relationship out of it. He has a massive opportunity to do even bigger things as a very well known person in the industry now.”
Lamacchia is equally thankful to have convinced Chaisson to take that leap of faith 20 years ago, as he recognized her special qualities early on as well.
So…will there be another 20 years for Chaisson?
“I hope so,” says Chaisson. “I don’t think I could retire. I’d be bored. My husband loves my career, but he works where he can be done in a few years and wants to retire. I’m like, well, I’m not retiring, so we’ll need to figure something out.”
Not surprisingly, Lamacchia is more succinct, stating firmly that “Sarah and I will work together for the rest of our lives, no matter what. There’s no question about that.”
To view a video tribute featuring Chaisson, go here.
