The Diary Of A CEO with Steven Bartlett Uber CEO: At Uber, If You Don’t Perform, You’re Out! Uber Was Losing $3b A Year
Feb 23, 2026
01:43:21
Uber CEO Dara Khosrowshahi reveals the future of driverless cars, how he led Uber’s financial turnaround, his family’s escape from Iran in 1978, and the truth about AI, automation, and job loss!
Dara Khosrowshahi is the CEO of Uber and successfully transformed the company from losing $3 billion a year to generating over $9 billion in free cash flow. He previously served as CEO of Expedia for over a decade, scaling the company into a global leader in online travel.
He explains:
◼️The "wartime" leadership strategy he used to save Uber from collapse
◼️Why telling the uncomfortable truth is the only way to scale a company
◼️His undercover experience as a driver and why it changed the app
◼️Why 80% of jobs face total disruption from AI automation by 2035
◼️The truth about autonomous vehicles and banning humans from driving
(00:00) Intro
(03:32) Why Escaping Iran Rewired My Appetite For Risk
(10:15) The Brutal Truth About Raising Kids In An Uncertain World
(16:50) Do Engineers Make Better CEOs — Or Miss What Really Matters?
(18:09) How To Choose The Few People Truly Worth Betting On
(19:16) The X-Factor That Turns Good Employees Into Game Changers
(20:51) Why Rejection Is The Price Of Building Something That Matters
(26:46) How To See Industry Shifts Before They’re Obvious
(32:51) The Jevons Paradox: Why More Efficiency Can Mean More Consumption
(39:47) Why Transparency As A CEO Builds Power — Not Weakness
(46:52) Can You Turn A Comfortable Culture Into A Hungry One?
(49:42) Ads
(51:10) The Advice Young People Need Before It’s Too Late
(57:36) How To Build A Culture That Improves Every Single Week
(01:01:53) Why Most Teams Fail At Goals — And How To Fix It
(01:06:56) What Happens When Strategy And Values Fall Out Of Sync
(01:13:53) How AI Is Changing Our Company — And The Moves We’re Making Now
(01:18:52) Why 90% Of Our Engineers Use AI — And What That Signals
(01:23:43) Will AI Replace 9.5 Million Uber Drivers — Or Reinvent The Job?
(01:35:05) The Most Important Advice For Thriving In An AI-Driven Future
Enjoyed the episode? Share this link and earn points for every referral - redeem them for exclusive prizes: https://doac-perks.com
Follow Dara:
X - https://link.thediaryofaceo.com/8IAzCZd
YouTube (Uber) - https://link.thediaryofaceo.com/7dRAeeV
Instagram (Uber) - https://link.thediaryofaceo.com/CtQISla
The Diary Of A CEO:
◼️Join DOAC circle here - https://doaccircle.com/
◼️Buy The Diary Of A CEO book here - https://smarturl.it/DOACbook
◼️The 1% Diary is back - limited time only: https://bit.ly/3YFbJbt
◼️The Diary Of A CEO Conversation Cards (Second Edition): https://g2ul0.app.link/f31dsUttKKb
◼️Get email updates - https://bit.ly/diary-of-a-ceo-yt
◼️Follow Steven - https://g2ul0.app.link/gnGqL4IsKKb
Sponsors:
WHOOP: https://JOIN.WHOOP.COM/CEO for one month free
Shopify - https://shopify.com/bartlett
Wispr: Get started with 14 days of Wispr Flow for free at https://wisprflow.ai/steven
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theexperienceplus.substack.com
Dara Khosrowshahi is the CEO of Uber and successfully transformed the company from losing $3 billion a year to generating over $9 billion in free cash flow. He previously served as CEO of Expedia for over a decade, scaling the company into a global leader in online travel.
He explains:
◼️The "wartime" leadership strategy he used to save Uber from collapse
◼️Why telling the uncomfortable truth is the only way to scale a company
◼️His undercover experience as a driver and why it changed the app
◼️Why 80% of jobs face total disruption from AI automation by 2035
◼️The truth about autonomous vehicles and banning humans from driving
(00:00) Intro
(03:32) Why Escaping Iran Rewired My Appetite For Risk
(10:15) The Brutal Truth About Raising Kids In An Uncertain World
(16:50) Do Engineers Make Better CEOs — Or Miss What Really Matters?
(18:09) How To Choose The Few People Truly Worth Betting On
(19:16) The X-Factor That Turns Good Employees Into Game Changers
(20:51) Why Rejection Is The Price Of Building Something That Matters
(26:46) How To See Industry Shifts Before They’re Obvious
(32:51) The Jevons Paradox: Why More Efficiency Can Mean More Consumption
(39:47) Why Transparency As A CEO Builds Power — Not Weakness
(46:52) Can You Turn A Comfortable Culture Into A Hungry One?
(49:42) Ads
(51:10) The Advice Young People Need Before It’s Too Late
(57:36) How To Build A Culture That Improves Every Single Week
(01:01:53) Why Most Teams Fail At Goals — And How To Fix It
(01:06:56) What Happens When Strategy And Values Fall Out Of Sync
(01:13:53) How AI Is Changing Our Company — And The Moves We’re Making Now
(01:18:52) Why 90% Of Our Engineers Use AI — And What That Signals
(01:23:43) Will AI Replace 9.5 Million Uber Drivers — Or Reinvent The Job?
(01:35:05) The Most Important Advice For Thriving In An AI-Driven Future
Enjoyed the episode? Share this link and earn points for every referral - redeem them for exclusive prizes: https://doac-perks.com
Follow Dara:
X - https://link.thediaryofaceo.com/8IAzCZd
YouTube (Uber) - https://link.thediaryofaceo.com/7dRAeeV
Instagram (Uber) - https://link.thediaryofaceo.com/CtQISla
The Diary Of A CEO:
◼️Join DOAC circle here - https://doaccircle.com/
◼️Buy The Diary Of A CEO book here - https://smarturl.it/DOACbook
◼️The 1% Diary is back - limited time only: https://bit.ly/3YFbJbt
◼️The Diary Of A CEO Conversation Cards (Second Edition): https://g2ul0.app.link/f31dsUttKKb
◼️Get email updates - https://bit.ly/diary-of-a-ceo-yt
◼️Follow Steven - https://g2ul0.app.link/gnGqL4IsKKb
Sponsors:
WHOOP: https://JOIN.WHOOP.COM/CEO for one month free
Shopify - https://shopify.com/bartlett
Wispr: Get started with 14 days of Wispr Flow for free at https://wisprflow.ai/steven
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theexperienceplus.substack.com