Cabot Haggin Reflects on Sayre, Life Lessons, and Career Pathways

Cabot Haggin has many insights to share from his 13 years at Sayre School. Undoubtedly one of the most important lessons is this:

“Sayre offers students the opportunity to find their true passion and truly develop as a person. Don’t be afraid to step outside your comfort zone and embrace everything Sayre has to offer.”

As a student, athlete, volunteer, and leader, Cabot excelled in the classroom, on the basketball court, on the baseball field, and in the community. After graduation from college, he charted multiple courses in professional sports, horse racing, and beverage distribution before settling into what he expects will be a long-term career in financial planning.

Currently a wealth management advisor for LexInvest Wealth Advisors, Cabot reflects on how Sayre helped him explore various avenues as a student, setting him up for future success.

A natural choice and a great fit

Cabot started at Sayre as a kindergartner. The school was a natural choice, since Cabot’s father Louis and older brother Lee (class of ’08) had both attended. He soon realized why Sayre had been such a great fit for family members.

As a PK12 school, Sayre is rather unique, Cabot observes. Students grow up together, forming deep and lasting bonds. Teachers and staff have the opportunity to build long-term relationships with students and families, fostering trust and understanding. 

Plus, the school’s emphasis on responsible citizenship and social engagement prepares students to be active wherever they go after graduation. “All the opportunities on how to act as part of the community – it’s a skill you can’t be taught,” he says. 

As a legacy student, Cabot had big shoes to fill. But he forged his own paths, playing both baseball and basketball and getting involved in the Philanthropic Society. At commencement, he earned the rare distinction of receiving both the Optima Award and the Headmasters’ Award. 

College close to home

After graduating from Sayre in 2011, Cabot attended the University of Kentucky, where he lived on campus. Despite being a townie, he discovered an environment that felt distinct from his childhood. 

Much like Sayre, UK is a separate, self-contained community within Lexington, with its own culture, events, traditions, and social norms.

Living with a former Sayre classmate (Jamison Sutherland ‘11) and attending Spartan games kept Cabot connected to the school. “It was like continuing a chapter from Sayre, just in a new setting,” he says.

Sports, horse-betting, and beverages

Cabot earned a degree in business administration, and then he took an internship with the PGA of America. Rubbing elbows with the likes of Tiger Woods and Phil Mickelson, he helped to run the PGA Championship at Whistling Straits in 2015. 

Returning to Lexington in 2016, he then worked as sales manager for AmTote International, the largest pari-mutuel betting platform facilitator in North America, which processes more than $15 billion in wagers annually. The work took him to South Korea, London, Paris, and every province in Canada.

After four years of travel and experience in business development and government relations, Cabot relocated to Nashville, Tennessee, where he took an opportunity to serve as chief of staff for Hand Family Companies. The company is an industry-leading, multi-state beverage distributor. As chief of staff, Cabot assisted the president with day-to-day operations and long-term strategic planning. 

Settling into a career 

After three years in Nashville, Cabot set a course for home in January 2023, but to work in a different industry. 

“I had a conversation with my father (Louis Haggin) about my future career path and was extremely fortunate that timing worked out. This new opportunity offered me the chance to both learn and work with my father as he contemplated winding down his career, and I’m so thankful timing was on our side,” he says.

Cabot spoke with his then-fiancé Peyton, now his wife, and she was open to relocation. They moved to Lexington, where Cabot now works alongside his father and three other partners and has settled into his life-long career. 

Staying in touch

The personal connections Cabot forged at Sayre have remained strong, demonstrated by the fact that fellow Sayre alumnus Reid Freeman (’12) just served as the officiant at his wedding. 

“One thing I feel so fortunate about, I still see my teachers around town, and they still care so deeply about how you are doing,” he shares. “The faculty and staff at Sayre are so invested in the student’s success and that relationship truly never ends.”

Cabot’s connection with Sayre has evolved over the years from coaching Lower School students in Future Spartans as a high schooler to now attending games and watching his own coaches' kids play for the Spartans. He enjoys reconnecting with fellow alumni at events like the 2024 state championship football game, where students from one alma mater (Sayre) played in the stadium of his other alma mater (UK).

Advice for current students

Cabot encourages current Sayre students to live in the moment, embracing every opportunity and appreciating the support system the school provides. 

He also encourages students to stay in touch with Sayre’s faculty and staff after graduation. “The faculty, staff, and alumni care so deeply about the student body,” he says. “Continue to check in after graduation because just as they wanted you to succeed in every way as a student, they can’t wait to see what you accomplish as alumni.”