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Tim O’Shea '77

May 2022

All good with the O’Sheas. Our three adult children are finding their ways, the oldest Andrew in Philadelphia with wife Hannah and grandchild George. Middle child, daughter Tori has evolved from a teacher/coach to a finance/investment professional and seems to be on a good path personally and professionally here in Richmond, Virginia. Youngest son Riley is also in Richmond, will wed in June, uses data to facilitate corporate strategy, and is beginning to show signs of sharing his father’s stubborn obsessions. Great to have two of three here and the third traveling through frequently.

Kim and I will be married 40 years this June. (That felt weird to type.) She keeps busy with home redecorating (our daughter-in-law is a designer), preparing meals before evening study halls for at-risk students attending schools like Gilman here in Richmond, some church activities, pickleball/golf, and constantly demonstrating patience and flexibility as she adjusts to having her husband work from home.

Speaking of work, I sold my health analytics business to an HCM/software company in 2019, worked through a two-year integration transition, and am now a product leader in that technology company, all while knowing very little about software or basic product management. I am almost always the oldest guy in the Zoom room. I think I’ve figured out a way to go to a part-time advisory role sometime by the end of 2022, which will allow me to also continue advising startups in the health and benefits tech space. My goal is to stay busy without having a job. Working in a little more golf and travel will become a priority.

I can’t be at the reunion this year. But I reflect often on how lucky I was to attend Gilman. I think I learned to apply myself, take on challenges, and to enjoy some success and suffer in defeat there. More importantly, I think of the Gilman culture and role models we shared, starting of course with Mr. Finney, but so many others too. It’s really special to see guys like Tim Holley follow in their footsteps. I will always cherish my Gilman classmates and our experiences together.


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