Cloudflare billionaire Matthew Prince accused of meddling in Vail board fight

American billionaire Matthew Prince, the co-founder and chief executive of internet security company Cloudflare, has been drawn into a boardroom fight at Vail Resorts Inc., after the ski company accused him of helping an activist investor choose candidates for its board.

In a filing with the U.S. Securities and Exchange Commission on Oct. 19, Vail said Prince introduced two of Oasis Management Co.'s four nominees to the hedge fund. Vail said Olympic ski champion Picabo Street, a friend of Prince's, consulted him about the nomination before he put her in touch with Oasis, and that venture capitalist Bryce Roberts, who called Prince "an old friend" in a 2021 post on X, also came to Oasis through him.

"Mr. Roberts and Ms. Street were introduced to Oasis approximately one week before their nominations," Vail said in the filing, adding that the connections were "raising questions regarding potential conflicts of interest."

Prince, who lives in Park City, Utah, has spent more than a year trying to buy Park City Mountain from Vail. He rejected the suggestion that he is behind the Oasis slate.

"Nope. I suggested several candidates to Oasis," Prince said in an email. "Beyond suggesting people I thought would be well-qualified, I had no influence over who Oasis put forward."

A hedge fund builds its stake

Oasis, a Hong Kong-based fund founded in 2002 by Seth Fischer, manages about $14 billion and is best known for activist campaigns at Japanese companies, including Toshiba, Kao and elevator maker Fujitec. It now owns about 3.43 million Vail shares, or roughly 9.6% of the company, up from 6.2% when it dropped its passive stance in a Sept. 16 filing.

On Oct. 13, Oasis asked shareholders to elect its four candidates: Street, who won super-G gold at the 1998 Winter Olympics and lives in Park City; Roberts, a Park City-based investor who co-founded O'Reilly AlphaTech Ventures; Robert Chapek, the former chief executive of Walt Disney Co.; and M. Ashton Hudson, a Florida investor. Even if all four win, they would hold a minority of seats on Vail's nine-member board.

The fund says Vail's guest experience has slipped, pointing to long lift lines, crowding and rising food prices. It cites a drop of about 12% in season pass sales for the coming winter and a fall in Vail's resort earnings before interest, taxes, depreciation and amortization to $745.7 million in the fiscal year ended July 31, from $844.1 million a year earlier. It also says the 2024-25 holiday strike by about 200 ski patrollers at Park City Mountain, which closed terrain and left skiers in long lines during the busiest weeks of the season, damaged Vail's ties with workers and mountain towns.

Vail, which owns or operates 42 mountain resorts, is backing its own slate of nine directors, led by Chief Executive Officer Rob Katz. It has not set a date for its annual meeting, which will be held online.

Prince's long campaign for Park City

Prince, 51, grew up in Park City and once worked there as an assistant ski instructor. He founded Cloudflare in 2009 with Michelle Zatlyn and Lee Holloway, and took it public on the New York Stock Exchange in 2019. He owns about 8% of Cloudflare and is worth about $7.5 billion. He and his wife, Tatiana, bought the Park Record, the town's 143-year-old newspaper, in 2023.

He confirmed in May 2025 that he had made an offer for Park City Mountain, a few months after the patrollers' strike. Vail turned it down. This year he said he would spend about $500 million on new lifts and snowmaking if he owned the resort, share profits with staff and give residents a stake. "The town should own part of the resort," he said in June.

Katz has said Vail has no plans to sell. The company runs the resort under a 300-year lease and has said it does not have the right to sell it.

Vail's filing sets out a string of Prince's public comments. On March 18, he described on X how he might get the resort, starting with "1. Find an activist to target Vail 2. Have them take over the Board." After Oasis named its candidates in September, he posted a clip from the 1980s television series "The A-Team" with the line "I love it when a plan comes together."

Oasis has hired proxy solicitor Innisfree M&A Inc. to win votes. Its latest filing dropped earlier language saying it might push for a review or sale of Vail or some of its resorts.