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EP 04 May 20, 2026 Wingfoot & Sebonack, New York

Country Club Hook-ups at Wingfoot & Sebonack

Chris Roach, CEO of Porter Road, joins the pod to share his experiences touring a few courses located on the Great Peconic Bay on Long Island. It's an intimate trip with a very good friend, but they made it a family trip around golf. Unfortunately, his golf game ruined one of his golf experiences, but that's golf!

Guest
Chris Roach
Destination
Wingfoot & Sebonack, New York
Location
NY

The Setup

Chris Roach — CEO of Porter Road — joins the pod to break down a intimate trip to two legendary courses on Long Island’s Great Peconic Bay. What started as a buddy trip evolved into a family-centered golf experience with his very good friend, blending serious golf with off-course moments.

The Format

Wingfoot and Sebonack back-to-back — two very different country club experiences. Chris walks us through how they structured the days around family time, tee times, and the expectations that come with visiting clubs of this caliber.

The Hot Takes

  • Wingfoot vs. Sebonack: which one lived up to the hype
  • The reality of a “family trip” where golf is the main event
  • How your golf game can derail the experience — and why it shouldn’t
  • The Long Island country club scene from an outsider’s perspective

The Run-It-Back

Chris breaks down whether this format scales beyond a two-person crew, and what he’d change (or keep) for the next version of this trip.