Tennis: Grossman has played huge role in Tiburon Challenger’s growth
Dan Grossman of Tiburon majored in math at Yale University and earned an MBA from Stanford University before embarking on a successful career as a money manager. Today, he invests in tennis.
When the Tiburon Challenger finals take place on Sunday, the crowd will be watching from their seats at the intimate Kennedy-Grossman Stadium Court at Tiburon Peninsula Club.
Grossman and his wife, Cathy Kennedy, have been backing their hometown tennis tournament since its outset in 2003 and also support next week’s Solano Challenger and the annual collegiate Battle in the Bay in San Francisco.
“Dan was an integral part in the starting of the Challenger in Tiburon in 2003 and he was the reason we were able to get that tournament started,” said Steve Jackson, former tournament director from Nicasio. “I can’t thank him enough for what he’s done for tennis in Northern California and in particular Marin and San Francisco.”
With Jackson as the brainchild and Grossman as an early investor, the Tiburon Challenger now presented by Raymond James has established itself as the premiere event at its level, drawing pro players from throughout the world and sellout crowds. Sunday’s qualifying matches drew more spectators than some Challenger finals.
“It was Steve’s pie-in-the-sky kind of idea,” says Grossman. “I don’t think I even knew what a Challenger was. I suppose he twisted my arm … but I also just took it on faith that he could do it. I don’t think he was sure either.”
Grossman and Jackson combined resources to fly in Pete Sampras for an exhibition against Sam Querrey in the inaugural tournament, acing their first test promoting pro men’s tennis in Marin County.
“In that first year, we lost a lot of money,” said Grossman. “The first year I wouldn’t say was a financial success but it was a success getting people out to watch.”
After 10 years at Tiburon Peninsula Club, Jackson has been tennis director at California Tennis Club in San Francisco for the past 16 years. With Grossman’s backing, Jackson started The Battle in the Bay event for college players held each September.
To connect the dots between the two Bay Area Challenger events and college players, winners from The Battle in the Bay receive wildcards to the main draws in Tiburon and Solano.
“Dan has been a continuous supporter of Battle in the Bay, creating a pathway from collegiate tennis to professional tennis,” says Jackson. “This allows them to take that next step to try their skillset at the professional level.”
Grossman played No. 1 singles and No. 1 doubles at Yale for four years but didn’t return to the court seriously until 2013. Now at 72 years old, he’s captured four World championships and ranked No. 1 in the International Tennis Federation world ranking in 65s and 70s in four different years, including 2024. He’s also captained two Marin teams to USTA national titles.
Grossman just finished competing in the USTA Senior Men’s Clay Court Championships in Palm Beach Gardens, Fla. He teamed with Geoff Cykman of San Francisco to reach finals where they lost to Jan Bortner and Dane Petchul 6-4, 6-4. Grossman and Cykman did not drop a set until the final.
“He’s not just a supporter but also an actual player,” Jackson says of Grossman. “Just an overall person that you can go to to talk about tennis, and you know he’s always been there to support it, so I can’t say enough positive things about him.”
When he’s not sponsoring three Bay Area tennis events to the tune of $25,000 apiece or playing in tournaments, Grossman manages the No. 1 doubles team in the world. An investor to his core, Grossman noticed an aging singles player in Julio Peralta of Chile while watching a Challenger singles match and convinced him to focus on doubles.
Peralta initially played with Horacio Zeballos of Argentina, but due to the Chilean’s wrist injury, Zeballos now plays with Marcel Granollers. Grossman manages Zeballos and Granollers, helping strategize with the players and their coaches at all the Grand Slams and at least six ATP Masters 1000 tournaments each year. Before their conversions to doubles and rise to the top, Grossman helped support the players financially believing that his investments would pay off.
“It’s crazy,” says Grossman. “It’s sort of a labor of love. It’s a retirement labor of love really.”
Kennedy, captain of the Boyle Park 65 women’s team that is headed to USTA nationals, often travels with Grossman to the Grand Slam tournaments, and jokes that she’s visited every museum in Paris.
Grossman’s investments keep paying off with personal achievements and perks most tennis aficionados can only dream of.
“He’s doing what he loves,” says Kennedy. “He retired from an intense job that he was very focused on and he loved. And now he’s shifted and doing what his passion is.”
IF YOU GO
What: The $82,000 Tiburon Challenger presented by Raymond James is a tournament that’s part of the second-highest level of men’s professional tennis in the world.
When: Qualifying started on 9/29 with matches throughout the week; semifinals on Saturday; finals on Sunday
Where: Tiburon Peninsula Club
Who: Players rank from No. 151-250