Kai Sato is a friend of the Ouimet Fund who started Caddieshack to Corner Office, a website and podcast which features successful business leaders who got their start as caddies. Kai was a caddie at prestigious Bel-Air Country Club while studying business at USC.

He is the founder of Kaizen Reserve, which serves as an investment advisor to family offices and corporations, helping align their existing assets with startups. He is also the founding partner of Vintage Capital Investments, which focuses on technology and media investments in sports.

Before his transition to venture capital, Kai cofounded FieldLevel, a social network dedicated to sports recruiting and participated as an entrepreneur in the inaugural Los Angeles Dodgers Accelerator. He works closely with accelerators across multiple industries and is also Hatch's Entrepreneur-In-Residence, actively mentoring its cohort companies.

Kai cares deeply about organizations like ours, helping disadvantaged youth through education. He created Caddyshack to Corner Office in part to teach young people about how golf can dramatically change their lives.

Claire Rogers grew up just down the road from Wannamoisett Country Club in East Providence, Rhode Island. Her golf-crazed family used to host players for the prestigious Northeast Amateur at Wannamoisett, including a future major champion who you’ll hear about in the episode.

She went on to attend Boston College for psychology, but eventually pivoted to golf content, interning at Golf Digest before being hired full-time as a social media coordinator in 2018. Since 2020, Claire has been with Golf.com, where she covers the biggest names and events from both the men’s and women’s professional tours.

Claire recently started a popular interview series called the Scoop, where she shares ice cream and chats golf with popular personalities from the game, including Max Homa, Nelly Korda, Brooks Koepka, Rose Zhang and Fred Couples.

Not only is Jerry York a Hockey Hall of Famer and the winningest coach in college hockey history, but he’s also one of the most well-respected and universally liked individuals in sports.

Coach York spent 50 years behind the bench at three different Division I schools, including 28 seasons at his alma mater, Boston College. He closed his illustrious coaching career with an NCAA record 1,123 victories to go along with five national championships.

He’s one of only three coaches in NCAA history to lead multiple programs to a national title. York lifted Bowling Green’s first national championship in 1984, then brought four titles to Boston College, including three in the span of five years from 2008 to 2012.

York was inducted into the Hockey Hall of Fame in 2019, becoming only the fifth NCAA coach to be inducted, and the first to coach exclusively at the college level. He’s also a member of the United States Hockey Hall of Fame and the BC Varsity Club Hall of Fame.

York grew up with nine siblings in Watertown and attended BC High before a standout hockey career at Boston College. He posted 134 points in his three varsity seasons, leading the Eagles to the 1965 Beanpot and a runner up finish in the NCAA Tournament that same year.