SHOW / EPISODE

Connor Garnett: Leaving Banking for Pickleball, Yips That Got Him Traded, and Twoey Nation | S5 E5

Season 5 | Episode 5
1h 0m | Nov 5, 2026

In this episode, Connor sits down with Roscoe and Jared to walk through one of the most unlikely paths on tour, from hitting with Novak Djokovic at the US Open to clocking 92-hour weeks in banking. The conversation covers why he bet on pickleball, how he built a brand around his two-handed backhand, and what still stands between him and #1.


Connor opens up about the yips that took over his serve, cost him confidence on the sport’s biggest stages, and helped lead to his MLP trade out of Columbus. He breaks down how he won a bronze with Alix Truong in the middle of it, then rebuilt his mechanics from the ground up with help from an unlikely source: Bryson DeChambeau’s approach to the golf swing.


Connor also gets into the business side of the sport, including why he only needed to break even to leave banking, how his first Twoey hats landed right as he won the LA Open, and why investing in pickleball has put him in the rooms he used to sit silently in as an analyst. He gets honest about a slow start to the year, recommitting to training, and turning down a bonus because he didn’t feel he’d earned the #2 ranking.


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Timestamps:


1:05 — The Atlanta Run That Broke the #17 Curse


1:32 — Why the Work Finally Started Paying Off


2:24 — The Shy Kid From Bellevue


2:53 — 6 A.M. Practices and Brutal Tennis Punishments


3:36 — Pacing the Court With Novak at the US Open


4:11 — “You’re Late”: Novak’s First Words to Him


5:04 — How COVID Killed His Pro Tennis Plans


5:20 — The Forced Move That Led Him to Pickleball


5:48 — The US Open Connection Behind His First Game


7:19 — Silver in His First Pro Tournament


8:11 — Beating Hayden Patriquin and Wyatt Stoneman Right Out of the Gate


9:12 — Getting Humbled After Every Big Win


9:53 — Learning What Pro Pickleball Really Looks Like With Tyson McGuffin


11:16 — The Tyson Connection Nobody Knew About


12:11 — Just How Good Was He at Tennis?


13:35 — The Cutthroat World of Pro Warm-Up Partners


15:02 — Only Child Syndrome and the Coach Who Fixed It


16:17 — Winning on Sunday, Back at His Banking Job Monday


17:05 — The 92-Hour Work Week


18:11 — Why He Walked Away From Investment Banking


18:29 — The Childhood Racket-Stringing Hustle


19:23 — Why All He Needed Was to Break Even


20:02 — From Silent Analyst to Getting in on the Deals


20:28 — Why He Wrote for The Kitchen for Free


21:25 — When Men’s Singles Caught Fire


23:32 — The Atlanta Tournament That Changed Singles


24:44 — Why James Ignatowich Was So Electric


26:23 — The Worst Yips in Pro Pickleball History


26:51 — Winning Bronze With Alix Truong Through the Yips


27:32 — The Trade Out of Columbus


28:05 — Why Sports Expose Who You Really Are


29:04 — Rebuilding His Serve the Bryson DeChambeau Way


30:54 — The Clutch Second Serve That Made the Yips Worse


31:52 — Could the Yips Come Back?


33:26 — What Zverev’s Double Faults Can Teach You


34:10 — The Night Roscoe Forgot How to Hit a Backhand


36:15 — Saying Zero Words in a Three-Person Group Project


37:40 — Learning to Talk in a Room


38:58 — Taking on Your Weaknesses Head-On


39:12 — How the Shy Kid Became a Top Clinic Coach


41:13 — The Origin of the Twoey


42:13 — The Hat Drop That Hit at the Perfect Time


43:13 — The Free Hat Promise From Center Court


45:26 — Is Pickleball the New Golf?


45:39 — Katy Perry, Necker Island, and Where Pickleball Takes You


46:21 — What the Next Year Looks Like


47:41 — Locking Back In After a Business-Focused Year


48:05 — “You Either Got It or You Don’t”


49:19 — Warming Up the Mind Instead of the Body


50:22 — The Pro Pickleball Nickname Game


54:20 — Two Straight Hours of Dinking


55:14 — The Squat Stat Nobody Saw Coming


56:18 — Why He Passed on His #2 Bonus


56:55 — What’s Holding Him Back From #1


59:28 — Pickleball: Choose Your Own Adventure

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