PLAN B: Rick DiPietro was forced into early retirement after suffering a series of injuries. Luckily, he was able to rely on a fiscally responsile back up plan he put in place years before just in case anything like this happened.


Rick DiPietro was living the dream after joining the New York Islanders as a first-round draft pick following a stunning year for Boston University. After several years with the team, he was offered an unprecedented 15-year contract. Even early on, DiPietro knew he’d have to start planning for his future.

“There’s only a finite amount of time where you’re going to be able to earn the money you’re earning, and you need to be smart with it,” DiPietro explains.

Early retirement

Two years after signing his groundbreaking contract with the Islanders, DiPietro suffered a string of injuries that kept him mostly benched for the next few years until he was released from his contract for an early retirement. Now he’s thankful he had a family that looked out for him when he was starting his financial life.

“I was fortunate to have a good support system around me, especially my mom and dad who took an active interest early,” DiPietro says. “We had a plan in place where, even if I wasn’t able to play until my late 30s, I’d be taken care of. My dad was involved very early on as far as what agent I hired, and as far as the people we entrusted with the money, we went through the entire interview process. And the best thing I ever did is marry a woman who is extremely fiscally responsible and keeps track of every penny we make.”

Financial lessons

Though DiPietro had planned ahead, he says he still made some of the financial mistakes a lot of pro athletes make.

“Now he’s focusing on setting his children up for success the way his family helped him.”

“A lot of us don’t know what the second act is going to be, and a lot of the bad investments we make are trying to set us up for that,” he explains. While DiPietro’s career is exceptional, the financial lessons he’s learned are things all young people should know.

“Most of the things you think you’ll enjoy spending money on aren’t worth it,” DiPietro says. His buying regrets include luxury cars and alpacas, so take it from someone who’s been there: material things aren’t everything.

If you’re going to spend money, DiPietro says, “Take a vacation, enjoy yourself.”

He also explains that he was making risky investments to set himself up for the future when his salary could be saved in more secure ways.

“I realized I was making enough money to take care of myself without having to do anything too risky,” DiPietro explains.

The second act

DiPietro turned his love of sports and commitment to hard work into a new career: sports talk show host.

“Our tagline was, ‘We’re going to do keep doing this until they make us stop,’” DiPietro laughs.

It’s been four years since DiPietro debuted, and there’s still no sign of him stopping. Now he’s focusing on setting his children up for success the way his family helped him.

“You have to teach them to respect money. You can’t have everything you want. I explain that I have to go to work to pay for the house, food, bills,” DiPietro says. His son is only three, but DiPietro thinks it’s never too early to start with financial literacy.

“It would be nice, in school, if they taught you how to be a grownup,” DiPietro says.