The Long Game with Michael Benson

Most great golfers entertain a momentary hope each time they tee up on a par 3—a hole in one. For Michael Benson, that hope came to fruition twice within four months a few years back when he was 65. Such a rare feat—after playing for decades and achieving an enviable 6 handicap—perhaps sums up Benson’s life thus far. Or, as the contradictory maxim goes, “It takes years to become an overnight success.”

Just as years of steady play led to his golfing milestones, each accomplishment along Benson’s journey has been the result of dedication and perseverance. Born and raised in Cleveland, Ohio, and the second of five children, he realized a significant goal as a teen when he attained the rank of Eagle Scout, a distinction earned by fewer than 2 percent of those who enter the scouting program. Notably, he received his badge from fellow Eagle Scout Neil Armstrong the year the astronaut walked on the moon.

Benson’s first jobs delivering newspapers and selling goods door to door for the Fuller Brush Co. were good indicators he was on a path to entrepreneurship. He credits his late father, a 38-year Proctor & Gamble executive, with teaching him the fundamentals of persuasive sales, as well as essential soft skills, which established the groundwork for his future success in business. “He told me, ‘When you go to the door, smile, look people right in the eye, and extend your hand,’” Benson recalls.

The senior Benson also teed up his son’s future happiness when he encouraged him to ask Shirley Simmons for a date in 1980. The two met in elementary school and were in each other’s orbit throughout high school but didn’t go out until after college, when Michael needed a plus-one for a company dance. Forty-five years of marriage, three sons, and six grandchildren later, Benson feels blessed to have their entire close-knit bunch in Naples, where the family put down roots in 2007. “If I need a grandfather hug, I just drive 20 minutes,” he says.

Benson studied sales and marketing at Miami University in Ohio and began selling life insurance right out of college. “After 10 years, my manager said, ‘Do something special and be better at it than anybody else,’ so I started a planned-giving consulting firm,” he says. That initial venture eventually led him to founding, co-founding, or co-investing in a half-dozen more financial-services companies, resulting in several billion dollars in assets under management or administration. One of those startups was the eponymous Benson Blackburn LLC, an insurance consultancy he launched in 1976 and sold in 2022, and for which he serves as managing partner.

On Par with the Best

One of Benson Blackburn’s clients is Best Buy founder Richard Schulze. During a round of golf, Benson asked Schulze how he started his business from his garage and grew it to a $50 billion company. Inspired by the tale, Benson persuaded the electronics retail magnate to share the narrative with his young team. “I already knew the story but, as a courtesy, thought I’d sit in,” Benson recounts. “After two hours, my mouth was dropping open because he really went in depth on everything it takes to grow an enterprise.”

Following Schulze’s motivating talk, it dawned on Benson that Naples was full of renowned entrepreneurs, Fortune 500 CEOs, and other highly successful individuals who had valuable information to share, including triumphs, failures, and lessons learned. With that in mind, he launched the NextGen Speaker Series in 2013—aimed at advancing leadership, mentorship, empowerment, and philanthropy—for the benefit of Naples’ career-minded businesspeople.

“I remember when Michael first created the NextGen Speaker Series, and I’m proud to have been a small part of its inception,” Schulze says. “It’s been a resounding success and an important initiative to bridge generations of leaders.”

Past speakers include Shelly and Ralph Stayer, owners of Johnsonville Foods; Reinhold Schmieding, founder of Arthrex; Michael Duke, retired president and CEO of Walmart; Janice Fields, former president of McDonald’s USA—who “started as a fry cook,” Benson notes; Jerri and David Hoffmann, founders of the Hoffmann Family of Companies; Angie Bastian, co-founder of Angie’s BoomChickaPop; Ellen Latham, co-founder of Orangetheory Fitness; Virginia Rometty, former president and CEO of IBM; Marillyn Hewson, former CEO of Lockheed Martin; and Patty and Jay Baker, philanthropists extraordinaire.

Since its inception, the invitation-only series, which runs annually in January, February, March, and April, has hosted 45 high-profile speakers for a total audience of 6,000. In lieu of a fee for speaking, NextGen donates $5,000 to the charity of each presenter’s choice; to date, the company has raised nearly $200,000 for local causes.

The Back Nine

On the threshold of his seventies, Benson ponders his legacy. He has long served in governance and leadership roles on numerous nonprofit boards—including the Immokalee Foundation, The Shelter for Abused Women & Children, David Lawrence Centers, and First Tee–Naples/Collier—and has helped raise millions of dollars for those organizations. “I’ve always liked fundraising best; it’s my sales background,” he remarks. The Bensons’ current philanthropic passion is health care, with Michael providing consulting services for NCH’s planned-giving campaign.

Michael and Shirley are passionate about their own health as well, visiting the Pritikin Longevity Center and working out with personal trainers. Benson exercises his mind with a collection of tomes aimed at enhancing personal growth. “Almost every book in my library is self-help because I figure it’s a lifelong process to learn how to be a better person,” he says.

Richard Schulze might contend his longtime pal has already accomplished that goal. “Michael has a true generosity of spirit, and I believe that is what drives him as an individual. He demonstrates that true leadership isn’t just about success, it’s about fostering meaningful connections, growing in service to the community, and sharing experiences that will ultimately help others grow and succeed,” Schulze says. “He’s also a wonderful friend, a committed family man, and a great golfer.”

On the links, Benson is dedicated to staying at the top of his game, dividing his frequent play between The Old Collier Golf Club, Royal Poinciana Golf Club, and Grey Oaks Country Club. When he’s not on the course, he’s exploring new business ventures, mining Naples for NextGen speakers, raising money for local charities, traveling the globe with Shirley (57 countries and counting), and collecting grandfather hugs. He affirms, “It’s the best time in life as long as we have our health.”

The Leader Board

NextGen speakers’ secrets to success can be found in their sage reflections:

“Perseverance pays.” –Richard Schulze, founder, Best Buy

“Create a product or service that doesn’t exist.” –Reinhold Schmieding, founder, Arthrex

“People want to be great; empower them to use their God-given talents.” –Ralph Stayer, owner, Johnsonville Foods

“The answer is never in your office.” –Robert J. Kohlhepp, former chair/CEO, Cintas Corp.

“Clock out and respect personal time.” –Glenn Hasse, founder, Ryt-way Industries LLC

“If you don’t ask, you will never get it.” –Michael Feuer, late co-founder, OfficeMax

“Take care of yourself physically and mentally.” –Thomas Monaghan, founder, Domino’s Pizza

“Prepare, prepare, prepare.” –George Tamke, former chair, FedEx, Kinko’s, and several other ventures

Story Credits:

Shot on location at The Old Collier Golf Club, Naples

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