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.

Ouimet Scholar and Westford native Morgan Smith is one of the most accomplished young amateur golfers in Massachusetts, and the Smith family is synonymous with golf.

Morgan’s dad Phil is a former Massachusetts Mid-Amateur champion and both of her younger sisters are talented players, including Molly who plays collegiately at Division I Central Florida. Morgan grew up playing at Vesper Country Club in Tyngsboro and eventually began playing and working in the pro shop at Mount Pleasant Golf Club in Lowell.

Morgan’s accomplishments as a golfer and a student earned her a spot on the Division I women’s golf team at Georgetown University in Washington, D.C. She was recently named BIG EAST Freshman of the Year after finishing second overall for the Hoyas in her first-ever BIG EAST Championship.

Morgan is the two-time defending champion of the New England Women’s Amateur, and won her first Massachusetts Women’s Amateur in dramatic fashion back in 2022. She has lofty goals for what she aims to accomplish in the future both on and off the golf course.

There is no one who has been more supportive, more passionate, and more dedicated to the Francis Ouimet Scholarship Fund than Dick Connolly.

Dick started caddying as an eight-year-old at Woburn Country Club and earned a Ouimet Scholarship to attend Holy Cross, where he captained the golf team before beginning a remarkable professional career.

He spent nearly 60 years in the financial services industry, becoming one of the most successful and respected advisors in the country. Exactly a week after this year’s Ouimet Banquet in late March, Dick officially retired as Managing Partner of The Connolly Group at Morgan Stanley.

One of his clients was Arnold Palmer, who became a dear friend and a passionate supporter of the Ouimet Fund. Dick was instrumental in expanding the Annual Banquet in 1997, an event in which Palmer was the first recipient of the Ouimet Award for Lifelong Contributions to Golf.

Dick and his wife of 43 years, Ann Marie, are the largest benefactors in the history of The Fund, and the Connolly’s have made a lifetime commitment to countless other charitable causes locally, nationally and abroad.

Dick’s philanthropic efforts are perhaps only topped by his modesty and his storytelling, and we hope you enjoy our second conversation with Mr. Ouimet Fund.

Dave Wilson spent a decade as a successful golf professional and now works as a career consultant for the PGA of America, helping to better the lives and careers of PGA Professionals.

The son of Irish parents, Dave grew up in Quincy, MA and began caddying at Wollaston Golf Club in middle school. He continued his loops at Wollaston throughout his time attending BC High before earning a Ouimet Scholarship. His college choice was Penn State, graduating from its PGM program in 2012.

Wilson’s career as a PGA professional has taken him to some of the most prestigious golf courses both nationally and beyond, including Spyglass Hill in Pebble Beach, Shinnecock Hills on Long Island, Cape Kidnappers in New Zealand, The Country Club in Brookline, Hole in the Wall in Naples, Florida, Somerset Hills in New Jersey, and eventually Hyannisport on the Cape, where he was the head pro beginning in 2018.

Dave has served as a board member for The Fund for the last three years and is a member of the Club Relations Committee. We’re extremely grateful for his dedication as a mentor in the game of golf, and for his promotion of our life-changing scholarship opportunities to young men and women in Massachusetts.

Jennifer Misiaszek is a Program Manager for the Boston Parks and Recreation department. Jenn has worked for the city for eleven years, and has been the Ouimet Fund’s “go to” partner and contact through her oversight of the Boston Parks and Recreation Caddie Scholars Program – where each year, more than 100 young men and women work at either Franklin Park or George Wright golf courses.

Through working in this program, young people become eligible to apply for a Ouimet Scholarship (as one of the prerequisites is two years of golf employment at a Massachusetts golf course). The program was founded in 1996 and over the nearly 30 years, has experienced great success and growth due to the efforts of people like Jenn along the way. In that time, $2,510,000 in need based awards have gone to 181 young men and women who participated in the Caddie Scholars Program at Franklin Park and George Wright.

Jenn grew up in Boston and is a graduate of UMass Boston, where, as a standout athlete, she played both softball and basketball. Growing up as an athlete and now having two children, Brayden and Madison (both of whom participate in many sports), Jenn has been moved by having once been the person on the fields and courts, playing in tournaments organized by the City – and now she is the person organizing them.

Glenn Kelly is the Head Golf Professional at Woods Hole Golf Club in Falmouth, Massachusetts, a Ouimet Alumnus, and a lifelong supporter of the Ouimet Fund and its mission. For decades, Glenn has led Woods Hole’s successful caddie program, and has guided more than 50 young men and women to Ouimet Scholarships totaling in excess of $300,000 in awards. For his decades of dedication and effort, Glenn received The Fund’s 2023 Golf Professional of the Year award.

Glenn grew up in Pembroke, Massachusetts and grew up working at Pembroke Country Club. Glenn’s love for the game of golf would lead to a celebrated career, as he joined Woods Hole Golf Club in 1985 as Assistant Golf Professional to legendary Head Pro Dutch Wessner. Glenn was promoted to Head Golf Professional at Woods Hole the following year, and has been staple in the Club’s community ever since.

Glenn has been deeply involved with the Cape Cod chapter of the PGA, and during his career has served as District Director and was elected to the prestigious Quarter Century Club of the PGA.