After serving as a lieutenant in the Army’s 8th Infantry Division and then spending twenty years in finance (mostly in Manhattan), Tayloe Dameron and his wife Suzy moved back to Virginia to start Upper Shirley Vineyards. Just 30 minutes outside of Richmond on a bend in the James River, their historic home and equestrian farm set the perfect backdrop for weddings, events, or just watching the sunset from the back porch with a glass of petit verdot. We catch up with Tayloe for this week's 3 Questions.

If you weren't running a vineyard, what would you be doing?

If I were not doing this, honestly I’d be searching for something that looked a lot like this. That is, I would be looking for a business to make Upper Shirley relevant, self-sustaining, and an open space for a generation or more. My wife Suzy and I are very committed to that goal. I would build another road where I could get farming and hospitality to have a head on collision.

What advice would you give your 20 year old self?

My advice to my 20-year-old self would be to wear sunscreen. That turned from cliche to real for me. Fortunately, my introduction to melanoma turned out to be a minor fender bender as opposed to a fatal crash. I’m very lucky. Beyond that, the question rings of what regrets I have. I really have none. I have been extremely lucky take a giant bite out of the apple. I would like to think that I’ve made the most of my opportunities given that it was not obvious that I was prepared to meet any of them.

What is your idea of perfect happiness?

My idea of happiness.... Opening a bottle of our wine and playing the video in my head of grape growing: leaf pulling, shoot thinning, green harvest, lab tests, and more lab tests. Getting it right is the happiest ending ever scripted.

Find out more about Upper Shirley Vineyards here. Shop our collection of casual shirts here. Photos by Kate Magee.

June 25, 2018 — Jason Deitz