Gesmer Updegrove was proud to once again support the Regatta for Entrepreneurship, bringing together founders, investors, business leaders, clients, and friends for an unforgettable day on Boston Harbor.
The 2026 Regatta marked the event’s return for the first time since the pandemic, welcoming nearly 130 guests aboard the Northern Lights to connect with Boston’s entrepreneurial community while watching Team USA Gesmer and Team UK Christopher Ward Watches compete for the Founders Cup.
And this year, Team USA Gesmer brought the Founders Cup home.
Aboard the J/46 Vanish, skipper Bill Jacobson and the Team USA Gesmer crew navigated challenging and rapidly changing conditions, with winds ranging from 8 to 22 knots. Their experience, teamwork, and ability to adapt ultimately carried the team to victory.
The win was particularly meaningful for Gesmer Updegrove. The firm won the inaugural Founders Cup in 2016, and 2026 marked the first time in the Regatta’s history that a previous champion returned to win again. As Gesmer Partner and Entrepreneur-in-Residence Steve Snyder shared, “Gesmer could not be happier or more proud to hold on to this trophy.”
But the Regatta has always been about much more than competition.
Since the event’s inception in 2016, Gesmer Updegrove has championed its mission of supporting entrepreneurship and creating opportunities for the next generation of leaders. That mission closely reflects our own. For 40 years, Gesmer has worked alongside entrepreneurs, emerging growth companies, technology ventures, and investors as they transform ideas into businesses and navigate the opportunities and challenges that come with growth.
This year’s sponsors helped extend that impact beyond the harbor. Together, their support funded 20 Sealander Sailing Academy scholarships and a $1,000 donation to Courageous Sailing on behalf of the Team USA Gesmer Vanish crew.
We are grateful to everyone who joined us, raced alongside us, sponsored the event, and helped make the day possible. Events like the Regatta remind us why Boston’s entrepreneurial ecosystem is so special: it is built on relationships, mentorship, collaboration, and a shared commitment to helping the next generation succeed.
We’re already looking forward to defending the Founders Cup in 2027.
Read the full recap on Sealander Sailing Academy’s website.
