Uploaded August 2026 | Updated September 2026, 2 weeks ago
Andrew Macdonald (Mac) is the longest-serving employee at Uber. Today, he is the President and COO. No one on the planet has spent more time mastering ride-sharing than Mac. Uber now does 300M rides per week, has 200M users, and is one of the most recognised brands on the planet. Mac never does interviews and so this was a rare look behind the scenes at the Uber machine.
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Timestamps:
00:00 Intro
01:51 How Andrew Retains Execution Drive While Being Liked
03:07 Where Andrew Has Been Wrong: Resisting Membership Longer Than He Should
06:32 The Most Efficient Dollar at Uber: Why Membership Beats Price Incentives
08:34 Why Uber One Is Not Yet Amazon Prime
10:08 New Revenue Lines: The Innovator's Dilemma at $250B Scale
11:54 How Uber Incubates New Businesses From Inside a Giant
18:33 Waymo vs Uber
23:56 The China Exit
34:09 Uber Blew Its AI Budget in 4 Months
36:49 The Real AI ROI Question
39:32 How to Budget for AI When Usage Is Vertical and Unpredictable
43:44 Will Uber Have More or Less Employees in 5 Years?
45:44 Should Enterprises Fear Frontier Model Providers?
51:00 How Uber Is Using AI Agents Internally
57:25 Andrew Now Running Uber Eats Directly: The Three-Sided Marketplace Problem
59:45 Why Uber Eats Is Not #1 in the US
01:02:29 Quick-Fire Round
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Subscribe on Spotify:
open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466
Subscribe on Apple Podcasts:
podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465
Follow Harry Stebbings on X:
twitter.com/HarryStebbings
Follow Andrew Macdonald on X:
twitter.com/andrewgordonmac
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tiktok.com/@20vc_tok
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Subscribe to our Newsletter:
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#20vc #harrystebbings #andrewmacdonald #uber #traviskalanick #ai #ubereats #doordash #waymo
Andrew Macdonald (Mac) is the longest-serving employee at Uber. Today, he is the President and COO. No one on the planet has spent more time mastering ride-sharing than Mac. Uber now does 300M rides per week, has 200M users, and is one of the most recognised brands on the planet. Mac never does interviews and so this was a rare look behind the scenes at the Uber machine.
-----------------------------------------------
Timestamps:
00:00 Intro
01:51 How Andrew Retains Execution Drive While Being Liked
03:07 Where Andrew Has Been Wrong: Resisting Membership Longer Than He Should
06:32 The Most Efficient Dollar at Uber: Why Membership Beats Price Incentives
08:34 Why Uber One Is Not Yet Amazon Prime
10:08 New Revenue Lines: The Innovator's Dilemma at $250B Scale
11:54 How Uber Incubates New Businesses From Inside a Giant
18:33 Waymo vs Uber
23:56 The China Exit
34:09 Uber Blew Its AI Budget in 4 Months
36:49 The Real AI ROI Question
39:32 How to Budget for AI When Usage Is Vertical and Unpredictable
43:44 Will Uber Have More or Less Employees in 5 Years?
45:44 Should Enterprises Fear Frontier Model Providers?
51:00 How Uber Is Using AI Agents Internally
57:25 Andrew Now Running Uber Eats Directly: The Three-Sided Marketplace Problem
59:45 Why Uber Eats Is Not #1 in the US
01:02:29 Quick-Fire Round
----------------------------------------------------------------------------------------------
Subscribe on Spotify:
open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466
Subscribe on Apple Podcasts:
podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465
Follow Harry Stebbings on X:
twitter.com/HarryStebbings
Follow Andrew Macdonald on X:
twitter.com/andrewgordonmac
Follow 20VC on Instagram:
instagram.com/20vchq
Follow 20VC on TikTok:
tiktok.com/@20vc_tok
Visit our Website:
20vc.com
Subscribe to our Newsletter:
thetwentyminutevc.com/contact
-----------------------------------------------
#20vc #harrystebbings #andrewmacdonald #uber #traviskalanick #ai #ubereats #doordash #waymo
