Leading from the front — with Sam Philbrook

Many children dream of growing up to become a police officer or a firefighter. Sam Philbrook said he couldn’t wait to become a soldier. Four generations of his family have served in the armed forces, and his goal was to join their ranks.

After 13 years in the Army, Philbrook found that the leadership and organizational skills he learned as an infantry officer transferred well into a new career in the financial services world.

Philbrook is managing director of Commonwealth Financial Group in Boston, where he is responsible for coaching and developing new financial advisors as well as serving a clientele of business owners and young families. He is a registered representative of and offers securities, investment advisory and financial planning services through MML Investors Services.

He was honored with one of Advisor Today’s 4 Under 40 awards for 2023 issued by the National Association of Insurance and Financial Advisors Sept. 20, 2023, and covering the time period between Aug. 31, 2022, and Aug. 31, 2023. 

To be considered, an advisor must be under 40 years old and a current NAIFA member. Candidates can self-nominate or be nominated by industry peers and are selected based on professional credentials, industry involvement, volunteerism and community involvement. The award is not an endorsement or indicative of the future performance of the financial adviser. MassMutual is a member firm and pays an annual fee to maintain its membership. MassMutual is not involved in the nomination or final selection process. A fee was paid for consideration.

Growing up in the coastal town of Marion, Mass., Philbrook was eager to follow his other family members into the service. He graduated from Norwich University, a small military college in Vermont, and entered the Army soon afterward.

“I began as an infantry officer and then graduated to a scout platoon leader, which is typically reserved for the No. 1 infantry lieutenant in the battalion,” he recalled. “I then went on to become a company executive officer for a headquarters company, which is the best [post for a] lieutenant after scout platoon leader. It’s a very diverse role with a lot of moving parts.”

From there, Philbrook became an operations officer, then was deployed to work intelligence in the Middle East, a role that he said is a unique path for an infantry officer.

“Typically, an intelligence officer is an intelligence officer, and an infantry officer is an infantry officer,” he said. “But the Army liked the way I thought about things. I could present data and talk the language of movement and maneuver as an infantry officer, but I also could look at a data feed and understand what the enemy was doing or trying to accomplish.”

After 11 months in the Middle East, Philbrook was redeployed to Macedonia when Russia invaded Ukraine, and he spent a month or two in that country.

When his military career was over, some friends suggested to Philbrook that he could earn a lot of money doing tech sales in Boston. But he soon found that was not the career for him. Another friend told Philbrook he might be better suited to a financial services career.

“I told him ‘I don’t know anything about the S&P 500, I don’t know anything about mutual funds, I am the least qualified person when it comes to financial planning,’” he said. “But he told me if you’re good at dealing with people, they’ll teach you the rest. And that is how I entered financial services.”

Philbrook soon found out that although he thought he was unqualified to work in financial services, the skills he obtained in the Army helped him in his new career.

“It comes down to leading from the front,” he said. “Selfless service is always doing the hard stuff. I’ve always said I will probably outwork everyone around me. This is the reason why I needed something entrepreneurial, because I do not work very well underneath someone when I’m going to outwork them. I will put the team on my back and move forward. If that means working 14-hour days or whatever it takes to get the job done, I will do that. Because that’s what you’re taught in the military. It’s that you will continue to think through different ways of achieving the objective, whatever the objective is.”

The best of both worlds

In his practice, Philbrook said he has the best of both worlds. He and his wife are living and raising their three children in his hometown of Marion, an hour’s drive from Boston. He travels to Boston three or four times a week to work in his office.

“My team and I do a lot of work with business owners and with families,” he said. “Our clients want to make sure that if anything happens, they don’t want to be a financial burden to their loved ones. They want to make sure they retire on time; they want to make sure they’ve saving money to the right areas.”

Philbrook said his philosophy about planning is rooted in the principles of protection, savings and growth.

“Are we protecting your income in the right way? Are we saving money to the right vehicles, and are we invested correctly? Our job is to pull our clients off the treadmill of life and help them financially plan by design, rather than by default.”

He said many clients are on the default path. “They’re pumping money into their 401(k) account, they’re putting money into savings and their fingers are crossed, thinking they really hope this all works out. Our job is to make sure they’re saving in the right area, they’re protected in the right way and they’re invested correctly.”

Leading by serving

Philbrook has always had a passion for serving others, and one of the most notable ways he spearheaded service was during the U.S. military’s withdrawal from Afghanistan in 2021, ending 20 years of U.S. military involvement in that country.

His unit was assisting in the evacuation of civilians from Afghanistan, most of whom fled with nothing but the clothes on their backs and their meager possessions stuffed into plastic bags. Philbrook’s birthday was approaching, so he made a social media post requesting that his family and friends donate supplies to the Afghan civilians in honor of his birthday. The request went viral and was shared by several influencers on Instagram. More than $82,000 worth of supplies were donated.

“It was hygiene products, flip-flops, hydration salts — Red Bull donated a pallet of energy drinks,” he said. “We had all these supplies shipped to us to distribute to the displaced population. So that one social media post ended up having a huge impact on those families who were sitting in hangars or on airport runways with nothing.”

Back home in Massachusetts, Philbrook realized he and his family lived in what he called “a kind of bubble.” He looked for a way they could help others and discovered an organization called the Friends of Jack Foundation, whose mission is to provide and support overlooked programs that enhance the physical, mental and emotional health and well-being of children across the South Coast region of Massachusetts and Rhode Island.

Commonwealth Financial Group’s founder started Rally 2 Give, with the goal of raising funds to benefit organizations in the Greater Boston area. Last year, the rally generated $500,000, $30,000 of which was donated to the Friends of Jack Foundation.

The rally attracts about 50 cars. The drivers race over a four-day period through southern New England up into Montreal, Canada, or Burlington, Vt.

“It’s all about an experience and bringing people together to network and enjoy each other’s presence,” Philbrook said. “You stop at a dinner venue, you go to a hotel, and you kind of do the same thing for three or four days throughout New England, up into Canada. All the cars have to raise money, so they reach out to their networks and activate their ambassadors or their communities to donate money, and it has snowballed.”

Between his family, his practice and his community activities, Philbrook leads a busy life. His guiding philosophy is “Time is your greatest asset.”

“You always want to acknowledge the fact that if everything is important, nothing is important,” he said. “There are four priorities I always have, which are: Focus on priorities, not emergencies. Get organized. Delegate, don’t detour. And I think the most important thing is to foster a culture of accountability and excellence in your practice, and if you’re leading a team, infuse that into your team.” 

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Susan Rupe is managing editor for InsuranceNewsNet. She formerly served as communications director for an insurance agents' association and was an award-winning newspaper reporter and editor. Contact her at [email protected].