The Boss Frog of Maui: The Story of Founder Phil Kasper

A lot of people are called “boss” but only Phil Kasper has the distinction of being the “Boss Frog” of Maui. Kasper is the Founder and Owner of Boss Frog’s, with stores on Maui, Kaua‘i and the Big Island, and operator of the country’s finest snorkel boat, the Calypso.

Over lunch at Mala Ocean Tavern, Kasper explains that his story isn’t one of overnight success. “Everything happened incrementally,” he tells me. “I came here on my boat in 1987,” his first catamaran, the Frog Man. “There was never a business plan. Every day I tried to focus on what I needed to do to have a successful day.”

His entrepreneurial spirit shone at an early age. “I started a Thrifty Car Rental franchise in California when I was 26. Ten years later I closed it. I moved to San Diego with the intention of opening a body shop, since I knew a lot of friends making good money at it. But I was laid up for three months with ruptured discs in my back. Lying on the couch gave me time to think about what I really wanted to do with my life.”

On a boat trip to Molokini, Kasper thought, “this is the life for me.” Shortly thereafter, Kasper invested most of his savings on a shell of a catamaran—the future Frog Man—in Santa Barbara, moved it to Ventura and had a friend finish building it there.

Once finished, he found a captain to sail the vessel to Maui. “The trip was my first,” says Kasper. “It was cold and wet for five days, then we hit the tropics. Hurricane Hova threatened us for five days and then turned away at the last minute. When we got to Maui, I had $50 in my pocket, and my son Chris and I stayed on the boat for about a week.”

Mosquitos drove Phil and Chris from the boat and they rented a garage off of Lahainaluna. “I worked on the Frogman (from a Paul Simon song), during the day. At night, I waited tables. It took about a year to get all the necessary permits and captain’s license.”

The maiden commercial voyage was in 1988. Says Kasper, “It had one rider, complimentary I might add!” 

Kasper started noticing that SCUBA tours were doing quite well and hired an instructor. Business improved. They grew the tours to 16 passengers per trip three times a week. Then they moved from Ka‘anapali to Ma‘alaea so they could start serving the Molokini market. Along the way, Kasper took note of how many people rented their equipment beforehand and decided to offer rentals themselves, opening their first store in Lahaina. “We named it Boss Frog’s because that had become my nickname.”

Thirty years of focusing on having a “successful day” and Boss Frog’s now has 14 stores on three islands—ten on Maui, three on Kaua‘i and one in Kona on the Big Island. The star of the business, however, is the Calypso, a state-of-the-art snorkel tour boat that is the culmination of all Kasper’s education and experience. “The Calypso is the premiere snorkeling catamaran in America,” says Kasper. “It was constructed on O‘ahu, and took five years to design and build. It holds 149 passengers, it has a glass-bottom viewing area, water slides, jumping off points and freshwater showers. 

In spite of all this success, Kasper still is constantly re-evaluating. They’ve even added bikes, electric bikes and shave ice in the Lahaina store. But don’t expect Kasper to stop there. He still thinks “this is the life” and loves sharing his joy with others.

“I didn’t come here to get rich. I wanted to surf, dive and show people the magic of the ocean.”

Oh, he’s done that, alright.

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[This story appears in print in the October-December 2019 issues of This Week Maui.]

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