Team USA Gesmer Triumphs in Return of Regatta for Entrepreneurship
BOSTON—July 22, 2026—Team USA Gesmer put on a magic act aboard J/46 Vanish at the 2026 Regatta for Entrepreneurship, disappearing down the course to win this year’s Founders Cup, with Team UK Christopher Ward Watches doing its best to keep time.
In front of a spectator crowd of nearly 130 guests aboard Northern Lights on Boston Harbor, the Team USA Gesmer, aboard J/46 Vanish, demonstrated impressive course handling and composure in shifty wind conditions.
Both boats started well, with Vanish and Team UK Christopher Ward’s More Cowbell powering up and jockeying for position before the Flux Marine start boat. But the variability and strength of the wind was the deciding factor on the day.
Led by skipper Bill Jacobson, the Vanish crew showcased a precision that took them around the course consistently, clinical in the way they navigated the large gusts to extend on More Cowbell, driven by skipper Bill Starr. Vanish was able to keep momentum through the gusts, with Jacobson driving efficiently through the changing conditions. Local knowledge of the impact of the wind through the buildings was key to this race, as well as familiarity with the commercial traffic maneuvering around the busy working harbor.
Sail inventory plays a huge factor in racing, where the right sail choice can impact speed and positioning, and a miscalculation can not only cost the win but put the sail at risk of shredding. Each sail supports a precise threshold of wind, and because of the wild shifts, the choice in this contest was tricky. Too light a sail, and a boat gets overpowered in the gusts; too heavy, and it gets bogged down in the lighter wind.
Both teams were tested, struggling to choose the right sail wardrobe against a wildly inconsistent wind, oscillating between 8 and 22 knots throughout the race.
“We were slow in the lulls,” Starr said, “and we were overpowered in the breeze. (Jacobson) was able to drive through the changing conditions better, and kept momentum through the gusts. They were able to anticipate and adjust, so they got lifted while we got driven down.”
Team UK Christopher Ward came in scrappy, with four Sealanders (youth 12-24) aboard, while Team USA Gesmer represented with an experienced crew of veterans who race each week in the same waters.
“Our Sealanders learned a great deal on the day, how it takes time to on the water together to compete in challenging conditions,” said Starr. “The Team USA crew gave us a proper show on how to do it well.”
Team UK Christopher Ward skipper Starr, also founder of Sealander Sailing Academy, kicked off the awards ceremony on Rowes Wharf after the race.
“First and foremost, I’d like to thank Bill (Jacobson), who came out and showed me his boat. I was soundly beaten,” said Starr, shaking Jacobson’s hand. “But it was fun.”
From the podium, Christopher Ward Watches CFO Joseph Keech congratulated Jacobson as he awarded him the Sealander GMT watch for his efforts as the winning skipper.
“I am told I have to challenge you for next year,” Keech said to applause and cheers from the gathered crowd of sponsors and friends, who had enjoyed conversation, food and drinks, cruising on the Northern Lights and watching the race unfold.
“Challenge accepted,” Jacobson said. “Bill, thank you for putting this on, you’ve brought energy, you’ve brought excitement, you’ve brought many kids into the sport, and it’s really something very nice for Boston Harbor. We are more than pleased to participate.”
Defender Team USA took the Founders Cup, first awarded in 2016 to winner Gesmer Updegrove, followed in 2017 by Bowen Advisors, Starboard CFO in 2018, and the Nexxus Group in 2019. This is the first regatta since the pandemic, and the first year the race has seen a repeat team come to victory, with Team USA Gesmer retaining its defender title.
“The Founders Cup, this is the fifth time it’s been awarded,” Starr told the crowd. “Every person who sails on the boat has their name on the cup, because no skipper is good without a crew. We’re out there trying to train as many sailors as we can.”
“Gesmer could not be happier or more proud to hold on to this trophy,” said entrepreneur-in-residence and partner Steve Snyder. “The Vanish crew did a wonderful job as defender, and we look forward to defending again on Aug. 5, 2027.”
Sealander No. 10 Aidan Swiger, joined by No. 11 Charlie Greenwood, thanked sponsors Gesmer Updegrove,Christopher Ward Watches, BBSI, Evolve Currency Management, Learning Syndicate, Metal Fuels, Flux Marine, and Starboard CFO for their support of the Regatta and the Sealander program.
“We just wanted to truly thank all the sponsors for allowing us to have this amazing opportunity, to be able to sail out in Boston Harbor on a big boat and be able to have a great time out here,” he said. “We hope you will continue to support Sealander until we get to Sealander 1,000.”
About the Regatta
The Regatta for Entrepreneurship is an invitational annual sailing regatta on Boston Harbor, bringing together local growth companies and service providers to raise money to support the youth of Sealander Sailing Academy. Sealander provides coastal sail training and racing opportunities for youth 14 to 24 regardless of socioeconomic background, skill level, or physical ability.
The regatta format re-creates the match-racing style of America’s Cup golden days, with two Sealander yachts racing to win the prestigious Founders’ Cup. The sailing is guaranteed to be competitive. Team USA vs. Team UK. There is no second!
Special guests enjoy the race with friends and colleagues from the vantage point of the classic harbor cruise Northern Lights.
The Regatta Spectator Floating Party is the networking event of the summer, as 150 entrepreneurs and service providers are celebrated for their contributions to the Boston ecosystem aboard the classic yacht Northern Lights. PHOTO BY MATT STONE
Thank you to our Sponsors
We’d like to extend a special thank you to this year’s sponsors:
And our contributing sponsor Spinlock Limited
Past Regattas
REGATTA PRESS RELEASE
FOR IMMEDIATE RELEASE—JULY 16, 2026
CONTACT: Shelagh Braley, shelagh@mylifelist.org, 781-346-1429
Teams Raise Anchor for Return of Regatta for Entrepreneurship
BOSTON—The city’s excitement for the Tall Ships has hardly gone out with the tide, but the Regatta for Entrepreneurship will carry it forward in Boston Harbor Wednesday, July 22, 2026.
This exciting community event brings together high-profile founders of Boston growth companies to experience the on-water thrill of a competitive sailing race, connect with peers and partners, and support the next generation of Boston’s innovation leaders.
This year’s gathering, the first regatta since the pandemic, takes on a spirited twist provided by two premier sailing teams, Gesmer Team USA vs. Christopher Ward Watches Team UK.
Metal Fuels CEO and startup veteran Bill Jacobson will take the helm for Gesmer Team USA. Jacobson, the founder of Workbar, also serves on the board of directors for Courageous Sailing, whose mission is to transform lives through sailing programs that inspire learning, personal growth, and leadership.
“It’s an honor to represent the home team,” said Jacobson. “Boston has an incredible entrepreneurial community, and we’re excited to compete while supporting organizations that help develop the next generation of entrepreneurs, leaders, and sailors.”
“We’re going head-to-head yachting for the first time, USA against the UK,” said Christopher Ward Watches Team UK skipper Bill Starr, managing director at Starboard Services and founder of Sealander Sailing Academy. “We’ve shifted the format to make it more competitive. This is old-fashioned America’s Cup-style racing at its best. It’s going to be quite a challenge, but we’re up to it. We’re going to try to put on the best show we can.”
The regatta gathers more than 130 members of Boston’s tech community: a tightknit collection of founders, friends, and sponsors who support growth and want to celebrate it. Sponsors include Gesmer Updegrove (winner 2016), Christopher Ward Watches, The Learning Syndicate, Evolve Currency Management, BBSI, Starboard Services(winner 2018), Metal Fuels, and Flux Marine. Other past winners include Bowen Advisors (2017) and The Nexxus Group (2019).
“This regatta creates a special opportunity to celebrate our growth companies and those that support them. Events like this energize our already vibrant community,” said Regatta Commodore Steve Snyder, partner and entrepreneur-in-residence at Gesmer Updegrove LLP. “These are the friends we choose to build our businesses with.”
The event sets off at 11:30 a.m. on Wednesday, July 22 when guests board the Northern Lights from 60 Rowes Wharf, behind the Boston Harbor Hotel. They will be treated to lunch, entertainment, and a special Christopher Ward Watches exhibition shop while the course is set. Competition begins at 1 p.m. for the two race boats: Beneteau First 40.7 More Cowbell for Christopher Ward Team UK and the J/46 Vanish for Gesmer Team USA. The Northern Lights will disembark at approximately 3 p.m.
The post-race awards presentation will be held at 60 Rowes Wharf. Racers will pose for photos, and the winning team will begin its yearlong bragging rights, hoisting the much-envied Founders Cup. The winning skipper will receive a Christopher Ward Sealander watch.
But no trophy is worth more than the gift of knowledge delivered to the next generation of business builders through the work of Sealander Sailing Academy. Funds raised by the Regatta provide youth 14-24 with a summer of healthy recreation away from their phones, big-boat safety and racing instruction, and team-based leadership development.
“Challenges that require curiosity, discipline, and mastering complexity: These are the experiences that build growth mind-set,” said Maura Collins, director of student experience at Sealander Sailing. “We want to make those experiences happen for the greatest number of kids, to support their future success.”
“Our goal in creating the Regatta back in 2016 was to strengthen Boston’s tech ecosystem while supporting future leaders,” said Snyder. “A decade later, we are so proud to see how far we’ve come.”
“There’s nothing better than having 130-plus members of Boston’s tech community together on the water,” Snyder said. “It’s an opportunity to create real value and have fun, in service to the next generation of business leaders.”
Please direct any questions to Bill Starr, 310-717-6953 or Shelagh Braley, 781-346-1429.
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