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July 22, 2025 34 mins

What do you do after building one of the most iconic companies of our generation?


If you’re Ryan McKillen, one of Uber's EARLY employees, you buy the U.S. SailGP Team and dive headfirst into the high-tech, high-stakes world of professional sailboat racing.


In this episode of The Early Podcast, we go behind the scenes of US SailGP — the Formula 1 of the ocean — with Ryan and team driver Taylor Canfield.


We cover:

🚀 Why SailGP is F1 on water

🌎 How Ryan helped build a global race team

📊 30,000 data points per second per boat

🧠 Tactical mastery, physical endurance & wild stories from the water

💥 And yes — race day is still less intense than Travis Kalanick


Ryan and Taylor take us from rookie sailing lessons to racing at 60+ mph, with helicopters, AR graphics, and Olympic-level strategy — all while building a business around it.


Subscribe for more stories from the earliest builders behind iconic startups.


#startups #sailing #SailGP #Uber #sportsbusiness #earlyemployees #F1



00:00 From Uber to SailGP – Ryan’s Journey

01:12 Redefining Success After a Unicorn

02:31 First Sailing Lesson → Near Disaster

04:55 Obsession Turns Into Team Ownership

05:35 What Is SailGP? F1 on Water Explained

07:05 60 MPH Boats, Foils, and Flight

09:21 30,000 Data Points Per Second

11:14 Filming Races with Helicopters & AR

13:20 Turning the Team into a Real Business

14:11 Race Day vs. Travis Kalanick

15:40 Taylor Canfield’s Origin Story

18:45 World Championships & the America’s Cup Dream

22:00 Driving an F50 for the First Time

24:42 Race Day: Prep, Strategy & Execution

27:05 How the Races Actually Work

29:37 Wind, Intuition, and Real-Time Decisions

31:01 Safety Protocols & Crazy Stories

34:27 F1 Meets Ocean: Why This Sport Wins

36:00 Athleticism + Trigonometry at 60mph



🎙️ ABOUT THE SHOW:

The Early Podcast is where host Max Crowley, Uber’s #25 employee, sits down with the earliest builders behind today’s most iconic companies. No fluff, just the raw stories of what it’s like in the trenches when your startup could still fail tomorrow.


✅ Subscribe for more untold startup stories every week

✅ Like, comment & share if you know someone interested!

✅ Listen on Spotify, Apple, or anywhere you get your podcasts



Let’s go. 💥


🎧 Listen to the full episode:

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🚀 New episodes drop every Tuesday. Let’s build this together.


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