Pursuit of Passion

It’s a well-worn cliche, but the “serial entrepreneur” moniker is truly fitting for Randy Kaplan, whose most current venture is his role as founder and CEO of Sandee, a startup focused on cataloging and rating every beach in the world. It’s not a modest goal, but it’s typical for Kaplan.
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Life's a Beach - A serial entrepreneur, Randy Kaplan grew up in Southfield and Birmingham before heading west to make his mark in multiple industries. // Courtesy of Randy Kaplan
Life’s a Beach – A serial entrepreneur, Randy Kaplan grew up in Southfield and Birmingham before heading west to make his mark in multiple industries. // Courtesy of Randy Kaplan

It’s a well-worn cliche, but the “serial entrepreneur” moniker is truly fitting for Randy Kaplan, whose most current venture is his role as founder and CEO of Sandee, a startup focused on cataloging and rating every beach in the world. It’s not a modest goal, but it’s typical for Kaplan.

“It’s been an enormous undertaking,” he says matter-of-factly, “but I like tackling and trying to solve large problems. And there was no definitive resource for the billion people a year who go to the beach.”

The business is the latest in a string of entrepreneurial pursuits driving the restless and peripatetic Kaplan, who readily concedes he’s been highly motivated since he was a small boy, growing up first in Southfield, and then Birmingham, where he attended Covington Middle School. “There was a stuttering issue and a bullying issue and, you know, that’s tough,” he reveals. “Many kids were just cruel the entire way through. I didn’t have a lot of friends. I couldn’t speak for a while. I couldn’t even go into a restaurant and order. I would ask my parents to order for me.”

Kaplan eventually overcame his stuttering with the help of a speech therapist — and a steely promise he made to himself. “All those kids who made fun of me, in my own mind I’d say it’s not going to impede me, and one day I’ll show them,” he says resolutely. “I was incredibly motivated. I think I was just born with a drive to be curious, identify problems, and try to solve them. And I’ve learned, over the years, to pursue things you’re passionate about.”

Kaplan moved on to Detroit Country Day for the ninth grade. “I wasn’t a great athlete there, and the athletes were the most popular kids, and it bothered me,” he admits. “Again, I just didn’t have the confidence. I mean, a lot of sports is skill and confidence, and I certainly didn’t have those.”

But he excelled in the classroom, and an economics course Kaplan took during his sophomore year proved to be a significant milestone. “Don Corwin taught the class, and I loved Mr. Corwin and the class, got 100 percent, and it changed my life,” he says. “Was that a seminal moment for me to know that I wanted a career in business? The answer is yes.”

One day the class took a field trip to a large public company, ending their tour in the office of the CEO. “I asked if I could sit in his chair,” Kaplan remembers, laughing. “So, I sat down at this big desk, I’m looking out at this beautiful view, and I said to myself, I’m going to be a CEO one day and run a big company — and that was another seminal moment for me.”

He graduated from Country Day with honors and  headed to the University of Michigan in Ann Arbor, where he continued to excel as a student and launched his entrepreneurial career.

“I thought, I’m going try my hand at T-shirts,” Kaplan says. “I took $400 of my bar mitzvah money, came up with a design, and ordered 100 shirts. Cost me five bucks each, and I was selling them for $12. Doing door-to-door soliciting isn’t permitted in the dorms, so I’d get kicked out and leave through the front door, go right back in through the back door, and go to another floor.”

Northwestern Law School was the next stop for Kaplan, where his grades were excellent, as usual, but his focus was significantly compromised. “I never wanted to be a lawyer,” he admits, “and I never wanted to go to law school.”

Which explains, in large part, why Kaplan spent his first year out of law school cycling through two jobs in Los Angeles before landing a third as a tax associate for a law firm. “It was the last thing I wanted to do,” he concedes, but the experience proved to be a catalyst for his next big idea.

“When my law career got off to a terrible start, I decided to try to make the transition into business, and I came up with something very different and very unique — writing incredibly detailed and unique letters to CEOs, asking for informational interviews, not a job. I knew that writing a letter asking for a job, the CEO would never get it.”

Kaplan wrote 300 letters, and says each took five hours to compose.

“There was no Google then, so I used LexisNexis,” he says. “I would do this late at night at my office. I printed out every article going back 20 years on everyone I wanted to meet. I highlighted all of the jobs they’d had and all of the quotes they’d given, so each letter was unique. I had stacks of paper 5 to 6 inches high, (and) 15 to 20 piles at one time. I was very persistent with these letters, and I got 80 meetings with (people like) the CEOs of Disney, Marriott, every studio in town, and others.”

Letter Campaign - Kaplan has met hundreds of famous people and politicians, including former U.S. Sen. Carl Levin. // Courtesy of Randy Kaplan
Letter Campaign – Kaplan has met hundreds of famous people and politicians, including former U.S. Sen. Carl Levin. // Courtesy of Randy Kaplan

That total includes the one that changed his life — with fellow Detroit native Eli Broad, the billionaire philanthropist who was at the helm of Sun America, his second Fortune 500 company.

“I did all the research on him and actually made a cheat sheet,” Kaplan says. “I had it laminated. Eli was scribbling the entire time during the meeting, and I wanted to make sure he saw the sheet. When he did, you could see his eyes widen. And then he basically said, We have this assistant to the chairman job here and it’s open.”

Not for long.

“On my 27th birthday I had an offer to be the assistant to the chairman, and now I was no longer practicing law,” Kaplan says. “I was basically an investment banker, the junior guy on a very senior team. I was there to put my head down and learn. (It was) very demanding, 80 hours a week, (but it was the) best job in the world that I could have.”

He left “the best job” before he turned 30, launching Akamai Technologies, a content delivery and security software company, with three partners. The dream of running his own business had finally been achieved, but Kaplan admits the timing of his departure from Sun America could have been better.

“Three months after I left,” he says sheepishly, “Eli sold the company for $18 billion and I lost out on a little over $2 million in stock options.”

Kaplan never looked back.

Akamai was a huge success, and went public in 1999. On its first day of trading on the Nasdaq exchange, the stock closed with an astounding 458 percent increase from its initial offering price — the fourth-largest first-day jump ever. 

With Wall Street still abuzz over Akamai, he quickly pivoted and started JUMP Investors, an entrepreneurial investment firm that has made more than 60 early to late-stage venture capital investments in the last 20-plus years. Ever the multitasker, he asserts Sandee is the main focus of his attention these days.

“It’s been my full-time job for seven years,” Kaplan says. “We’ve cataloged 94 categories with data for every beach in the world, with more than 50,000 beaches and 212 countries. Our trademark is (telling people) choose your beach, and you can go on our website and filter through all the categories that are important to you, whether you have young kids and you want food, a bathroom, and a shower, or you’re going on a romantic vacation and you want something quieter and less popular.”

While Kaplan is certainly busy enough with his current ventures, including Thrive Properties, a real estate investment firm, he’s perpetually on the lookout for fresh opportunities.

“I love learning about new companies, and it’s a great job to meet with all kinds of people who come in with new ideas and pitch me,” he says. “I learn a lot about things I know nothing about — technology and new products — and it’s fascinating and mentally stimulating.”

Kaplan, 52, who lives in Los Angeles with his family, is also finalizing the details of a podcast, with plans to interview guests from a wide array of diverse backgrounds.

“The podcast is really the culmination of 18 years of our summer intern program at JUMP, providing an incredible teaching experience for young, hardworking, and motivated students,” he says. “We advertise the opportunity to work in a venture capital firm and learn from somebody who’s been a successful entrepreneur. A lot of students want that on their resume, and now we get over 1,000 applications per year.”

Less than a quarter of the applicants qualify for an interview, and 36 end up getting a job.

“It’s a teaching internship, which is very important,” Kaplan says. “It means I spend 60 to 90 minutes a day with the interns, giving lessons on venture capital, entrepreneurship, private equity, (and) real estate. It’s a 12-week program. We have guest speakers every week — well-known CEOs, venture capitalists, (and) private equity people. We spend a tremendous amount of time on the intangibles — which I stress are, in many cases, equally or more important than the tangibles you learn.”

Near the very top of Kaplan’s intangibles list, not surprisingly, is the art of making an indelible impression in a job interview, which harkens back to the scorched-earth approach he took in the letter-writing campaign that led to his career-making job with Eli Broad at Sun America.

“I prepared for those interviews like it was a final exam,” he says proudly. “We’re hiring people now, and one of the first questions I ask in the interview or meeting is, What’s my dog’s name? Some people know it. Some people don’t.”

Kaplan pauses here, seeming to relish what feels like a well-rehearsed kicker: “For people who don’t know the answer, the interview is over,” he remarks. “No chance at a job.”

On the other hand, laminated cheat sheets are most assuredly allowed, even encouraged. And they may well assure the gig is a lock. 

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