My guest today is Dara Khosrowshahi, the CEO of Uber. Before Uber, Dara ran Expedia for thirteen years. We start with why he took this job in 2017, and a big part of that story is Daniel Ek, who told him that life is not about happiness, it is about impact.
We talk about what the chaos felt like on day one, and how his family leaving Iran when he was nine shaped the way he handles pressure today.
We spend most of our time on autonomous vehicles and Uber's role as the demand aggregator in a world of physical AI. Dara explains why Uber is a supply-led company, what it will take to win, and why he expects many winners in AVs rather than one.
We also discuss Uber's $10 billion in free cash flow, the push toward a single app for everything, and what he has learned from Allen & Co, Barry Diller and Reed Hastings.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com).
Timestamps:
(00:00:00) Welcome to Invest Like The Best
(00:02:29) Intro to Dara Khosrowshahi
(00:03:37) How Daniel Ek Convinced Dara to Take the Uber Job
(00:06:54) Bringing Order to Chaos
(00:09:20) Managing Stress as a Leader
(00:11:22) The Chip on His Shoulder
(00:12:53) Parenting Lessons
(00:17:01) Mandate for AI Adoption
(00:21:21) Uber's Role in Physical AI
(00:22:48) Winning the AV Demand Race
(00:27:41) Partnering vs. Competing with Waymo
(00:32:05) AV Success Unlocks New Markets
(00:35:09) Why Drones Haven't Arrived Yet
(00:36:27) Regional AV Rollout Differences
(00:37:35) Uber Eats International Winning Formula
(00:39:44) Key to Aggregating Supply Well
(00:44:34) Adding Hotels to Uber Platform
(00:50:46) Lessons in Marketing at Scale
(00:52:59) Apps vs. AI Agents in Seven Years
(00:54:08) What Dara Learned from Barry Diller
(00:56:52) What Dara Learned from Allen & Co
(01:00:09) Buybacks vs. Growth Investing
(01:04:17) Lessons from Reed Hastings
(01:05:49) The Kindest Thing
Guest is Lucy Sweet, a Staff Software engineer at Uber and the lead for the Kubernetes Node Lifecycle Working Group. Imagine trying to move millions of compute cores and thousands of microservices to a brand new platform. All without dropping a single user request, ride, or delivery. Sounds like an absolute logistical nightmare, right? Well, today we are sitting down with someone who actually lived to tell the tale Lucy. In this episode, we are diving deep into Uber's monumental infrastructure journey: moving away from their in-house system to Kubernetes. We'll be unpacking the reality of running at this scale, why it's always DNS and why building things for fun is worth it.
Do you have something cool to share? Some questions? Let us know:
- web: kubernetespodcast.com
- mail: kubernetespodcast@google.com
- twitter: @kubernetespod
- bluesky: @kubernetespodcast.com
News of the week Broadcom announced donating Velero to the CNCF Sandbox Level
KubeCon && CloudNativeCon Amsterdam 2026 Transparency report
Call for Proposals for KubeCon && CloudNativeCon North America 2026 closes May 31
OpenChoreo v1.0 CNCF Sandbox
Links from the interview Lucy on Linkedin
Lucy's website
[Article] Migrating Uber's Compute Platform to Kubernetes
[Lucy Video] Migrating 2 million CPU cores to Kubernetes
Up: Portable Microservices Ready for the Cloud
Peloton: Uber's Unified Resource Scheduler for Diverse Cluster Workloads
Odin: Uber's Stateful Platform
Uber Batch platform
Apache Mesos
Hyrum's Law
GKE Blue-Green nodepools
Node Lifecycle Working Group
Scaling Infrastructure Management with Grail
kubegpt.org
Osquery
Uber Careers
It’s become an annual tradition to have Uber CEO Dara Khosrowshahi join us in the studio when he comes to New York for Uber’s big Go-Get event every year. This year, the big news was that Uber's expanding into a much larger platform for travel, starting with hotel booking and services like personal shopping.
Uber is going so far as to call this an everything app, so I wanted to see how far Dara thinks everything actually goes — and whether he’s feeling pressure to own more of the user experience in a world where AI companies keep promising that their chatbots will book all the cars for you.
Links:
Uber adds hotels to its app in big travel swing | The Verge
Uber CEO Dara Khosrowshahi is okay with reinventing the bus | Decoder
I have to be honest, AI will replace jobs at Uber | Diary of a CEO
The DoorDash problem | Decoder
Airbnb CEO Brian Chesky wants to build the everything app | Decoder
Booking and Priceline chief wants you to yell at bots, not humans | Decoder
Subscribe to The Verge to access the ad-free version of Decoder!
Credits:
Decoder is a production of The Verge and part of the Vox Media Podcast Network.
Decoder is produced by Kate Cox and Nick Statt; this episode was edited by Xander Adams. Our editorial director is Kevin McShane.
The Decoder music is by Breakmaster Cylinder.
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Emil Michael is the Under Secretary of War for Research and Engineering at the Pentagon. Michael joins Big Technology to discuss how AI is transforming the Department of War, from targeting systems to drone warfare to cyber defense. Tune in to hear his account of why the Pentagon designated Anthropic a supply chain risk, what actually happened in the contract negotiations, and whether the decision was wise. We also cover how the military's Maven Smart System works in practice, what the U.S. learned from drone warfare in Ukraine and Iran, and whether the Pentagon Pizza Index is credible. Hit play for one of the most candid conversations you'll hear about AI and national security.
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Emil Michael went from scaling Uber across 600 cities to rewiring the world's largest military.
In the midst of the Pentagon-Silicon Valley debate, the now U.S. Under Secretary of Defense for Research and Engineering opens up about what a real partnership demands from both sides.
He also shares how he's built three new entry points for defense tech companies, and why America's military is called the "Department of War" again.
Guest: Emil Michael, U.S. Under Secretary of Defense for Research and Engineering
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This conversation with Emil Michael, undersecretary of defense for research and engineering and acting director of the Defense Innovation Unit, was recorded at the a16z American Dynamism Summit in Washington, D.C. Michael walks through how he inherited a department running 14 undefined technology priorities, cut them to six, and made applied AI number one. He also gives the first detailed account of why commercial AI contracts written under the previous administration created a vendor-lock crisis that put active military operations at risk.
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Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
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(0:00) The Besties welcome Under Secretary of War Emil Michael
(2:30) US war with Iran: Bigger picture and why now?
(13:16) Trump's new approach to warfare, AI, drones, rules of engagement
(28:39) Israel's role in the conflict, relationship with the US, Iron Beam
(37:24) Oil prices, Trump's maritime insurance play
(41:19) Pentagon vs Anthropic: Why Anthropic was labeled a supply-chain risk
(1:02:03) How to value Anthropic after its supply chain risk designation
(1:11:14) State of the US defense supply chain, the defense tech industry, DARPA, and China's military
Follow Emil Michael:
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https://x.com/emilmichael
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Intro Music Credit:
https://rb.gy/tppkzl
https://x.com/yung_spielburg
Intro Video Credit:
https://x.com/TheZachEffect
Referenced in the show:
https://x.com/chamath/status/2029584905831891069
https://polymarket.com/event/us-forces-enter-iran-by
https://polymarket.com/event/will-the-iranian-regime-fall-by-the-end-of-2026
https://x.com/chamath/status/2029416079781736844
https://x.com/USWREMichael/status/2029539950962626734
https://x.com/addyosmani/status/2029372736267805081
https://github.com/googleworkspace/cli
https://x.com/chamath/status/2029634071966666964
https://www.lloyds.com/about-lloyds/history/lloyds-buildings
https://www.bloomberg.com/news/articles/2026-03-05/pentagon-says-it-s-told-anthropic-the-firm-is-supply-chain-risk
https://www.bloomberg.com/news/articles/2026-03-03/anthropic-nears-20-billion-revenue-run-rate-amid-pentagon-feud
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
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Today’s arms race looks a little different from those of the past. Under the Trump administration, the US Department of War (DoW) is deploying generative AI to millions of employees in order to maintain a strategic edge over our global adversaries. Sarah Guo and Elad Gil sit down with Emil Michael, the Under Secretary of War for Research and Engineering of the United States, to discuss the radical technological transformation of the US military. Emil outlines the architecture and launch of GenAI.mil, a DoW internal AI platform powered by Gemini and Grok that reached over one million unique users in its first 30 days. He also highlights critical technology priorities for national security, including hypersonics, direct energy, and autonomous drone swarms. Together, they also explore the urgent need to rebuild the American defense industrial base and end dependency on foreign supply chains for critical materials, as well as how Emil is recruiting the next generation of “fixer-builder” workers to serve their country in government.
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Chapters:
00:00 – Cold Open
00:00 – Emil Michael Introduction
00:58 – Emil’s Role at the Department of War
05:22 – Innovation Priorities for the DoW
08:27 – Shift Toward Autonomous Defense Technologies
10:41 – Identifying Common Needs Across the DoW
12:02 – Architecting GenAI.mil
13:48 – Applied AI Initiatives at the DoW
15:57 – The Future of Warfare
17:55 – Recruiting for DoW
19:33 – Arsenal of Freedom Tour
22:25 – Opportunities for Entrepreneurs at DoW
25:49 – Speeding Up and Scaling DoW Initiatives
28:37 – Innovation in Defense Tech
30:00 – Change Management in Government
32:09 – Rebuilding the Defense Industrial Base
37:27 – Initiatives and Opportunities at the Office of Strategic Capital
41:41 – Lessons from Emil’s Government Experience
44:30 – Conclusion
We're bringing you a special episode of On With Kara Swisher! Kara sits down with Uber CEO Dara Khosrowshahi to dig into how applied artificial intelligence works at scale.
At Uber, AI powers everything from pricing, routing, and customer service to autonomous vehicles and sidewalk robots that deliver food. It has partnered with more than 20 autonomous vehicle manufacturers, and it’s moving aggressively into robotaxis. And although it may take many decades, Khosrowshahi believes society may eventually decide humans aren’t safe enough to be trusted behind the wheel. Kara and Dara discuss what this all means for jobs, congestion, climate and Uber’s business model.
This conversation was recorded live at the Johns Hopkins University Bloomberg Center as part of its Discovery Series on artificial intelligence.
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Kara sits down with Uber CEO Dara Khosrowshahi to dig into how applied artificial intelligence works at scale.
At Uber, AI powers everything from pricing, routing, and customer service to autonomous vehicles and sidewalk robots that deliver food. It has partnered with more than 20 autonomous vehicle manufacturers, and it’s moving aggressively into robotaxis. And although it may take many decades, Khosrowshahi believes society may eventually decide humans aren’t safe enough to be trusted behind the wheel. Kara and Dara discuss what this all means for jobs, congestion, climate and Uber’s business model.
This conversation was recorded live at the Johns Hopkins University Bloomberg Center as part of its Discovery Series on artificial intelligence.
Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher.
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(0:00) Introducing Uber CEO Dara Khosrowshahi
(0:59) Uber's self-driving business: partnerships, market size, LiDAR vs computer vision, safety, distribution
(8:14) How self-driving impacts Uber's business model over time
(13:30) Other forms of transportation Uber could provide
(16:09) $20B stock buyback plan vs. investing in R&D and acquisitions, future of food
(21:03) Dara's pitch to Elon for bringing Tesla Robotaxis into Uber's network
(22:31) How Uber thinks about driver job displacement from self-driving
Thanks to our partners for making this happen!
Solana - Solana is the high performance network powering internet capital markets, payments, and crypto applications. Connect with investors, crypto founders, and entrepreneurs at Solana's global flagship event during Abu Dhabi Finance Week & F1: https://solana.com/breakpoint
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Google Cloud - The next generation of unicorns is building on Google Cloud's industry-leading, fully integrated AI stack: infrastructure, platform, models, agents, and data. https://cloud.google.com/
IREN - IREN AI Cloud, powered by NVIDIA GPUs, provides the scale, performance, and reliability to accelerate your AI journey. https://iren.com/
Oracle - Step into the future of enterprise productivity at Oracle AI Experience Live. https://www.oracle.com/artificial-intelligence/data-ai-events/
Circle - The America-based company behind USDC — a fully-reserved, enterprise-grade stablecoin at the core of the emerging internet financial system. https://www.circle.com/
BVNK - Building stablecoin-powered financial infrastructure that helps businesses send, store, and spend value instantly, anywhere in the world. https://www.bvnk.com/
Polymarket: https://www.polymarket.com/
Follow Dara:
https://x.com/dkhos
Follow the besties:
https://x.com/chamath
https://x.com/Jason
https://x.com/DavidSacks
https://x.com/friedberg
Follow on X:
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Follow on Instagram:
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Intro Music Credit:
https://rb.gy/tppkzl
https://x.com/yung_spielburg
Bozoma Saint John’s story isn’t just about leading the world’s biggest brands - it’s about surviving unimaginable loss, breaking every “career rule,” and redefining what success really means. In today's episode of CEO Diaries, the former Netflix and Apple CMO reveals why she quit chasing work-life balance, why being selfish saved her, and how personal tragedy shaped her path to the top.
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Sachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He’s been in product for over 25 years (at Google, Palm, Flywheel, and now Uber). He is known for his “extreme dogfooding” ethos—personally completing almost a thousand Uber driving and delivery trips to sharpen his product insight and user empathy—and his “ship, ship, ship” mantra, which drives rapid iteration across Uber’s global teams.
What you will learn:
1. Dogfooding at scale
2. “Ship, ship, ship” as a cultural mantra
3. Obsession with inputs over outputs
4. Uber’s hybrid marketplace vision for autonomy
5. How Uber changed its culture to focus on profitability
6. What to do when data says “no” but your gut says “yes”
7. Career advice: maximize cycles
8. AI as a research assistant, not an oracle
9. Uber rider etiquette tips
—
Brought to you by:
• Paragon—Ship every SaaS integration your customers want
• Stripe—Financial infrastructure to grow your revenue
• Coda—The all-in-one collaborative workspace
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Where to find Sachin Kansal:
• LinkedIn: https://www.linkedin.com/in/sachinkansal/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Sachin’s background
(05:00) Dogfooding in practice
(11:24) Empathy and understanding drivers
(20:18) Balancing metrics and user experience
(22:04) Operationalizing dogfooding
(24:26) Challenges and solutions in dogfooding
(29:49) The motto: “ship, ship, ship”
(36:37) Product announcements and live demos
(40:49) Career advice for product managers
(43:51) The evolution of product management with AI
(46:55) Collaboration between engineers and product managers
(49:36) Uber’s vision for self-driving cars
(55:59) Uber’s path to profitability
(01:01:58) Balancing data and gut decisions
(01:07:21) AI tools in product management
(01:10:14) Failure corner
(01:13:48) Lightning round and final thoughts
—
Referenced:
• Uber: https://www.uber.com/
• Oracle: https://www.oracle.com/
• Snowflake: https://www.snowflake.com/en/
• Fivetran: https://go.fivetran.com/
• Uber for Business: https://www.uber.com/us/en/business
• McDonald’s: https://www.mcdonalds.com/
• Domino’s: https://www.dominos.com
• PalmPilot: https://en.wikipedia.org/wiki/PalmPilot
• Praveen Neppalli Naga on LinkedIn: https://www.linkedin.com/in/pneppalli/
• May Mobility: https://maymobility.com/
• Uber strikes deal with May Mobility to deploy ‘thousands’ of robotaxis: https://www.theverge.com/news/659563/uber-may-mobility-autonomous-ridehail-partnership
• Waymo: https://waymo.com/
• WeRide: https://www.weride.ai/
• Uber and Avride Announce Autonomous Delivery and Mobility Partnership: https://investor.uber.com/news-events/news/press-release-details/2024/Uber-and-Avride-Announce-Autonomous-Delivery-and-Mobility-Partnership/default.aspx
• Dara Khosrowshahi on X: https://x.com/dkhos
• Uber Elevate: https://www.uber.com/us/en/elevate/vision/
• Uber AV: https://www.uber.com/us/en/autonomous/
• Uber Reserve: https://www.uber.com/us/en/ride/how-it-works/reserve/
• Uber for teens: https://www.uber.com/us/en/ride/teens/
• Flywheel: https://www.flywheel.com/
• ChatGPT: https://chatgpt.com/
• Gemini: https://gemini.google.com/app
• NotebookLM: https://notebooklm.google/
• Behind the product: NotebookLM | Raiza Martin (Senior Product Manager, AI @ Google Labs): https://www.lennysnewsletter.com/p/googles-notebooklm-raiza-martin
• BlackBerry: https://en.wikipedia.org/wiki/BlackBerry
• Peaky Blinders on Netflix: https://www.netflix.com/title/80002479
• Deep research: https://openai.com/index/introducing-deep-research/
—
Recommended books:
• Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies: https://www.amazon.com/Blitzscaling-Lightning-Fast-Building-Massively-Companies/dp/1524761419
• Nobody Wants to Read Your Sh*t: Why That Is And What You Can Do About It: https://www.amazon.com/Nobody-Wants-Read-Your-Sh-ebook/dp/B01GZ1TJBI
• Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648537
• Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281
• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Today, I’m talking with Uber CEO Dara Khosrowshahi. We recorded this conversation on the same day Uber announced a big set of product updates, including new options for shared rides. Dara was in New York for all that, so he came to our studio and we did this one together, which always makes for a great episode.
If you’ve been listening to Decoder recently, you know that I’m very curious about how service apps like Uber will handle things like AI agents. Dara had a lot of thoughts there. There’s a lot in this one, and Dara didn’t hold back. I think you’re going to like it.
Links:
Uber’s new bus-like feature is nearly 50 percent cheaper than UberX | Verge
An interview with Dara Khosrowshahi | Stratechery
Uber preps for Waymo’s robotaxi launch in Atlanta | Verge
Uber ends year in the black for the first time ever | Verge
Uber’s not out of the woods yet | Verge
UberX Share brings carpooling back to NYC and eight other cities | Verge
Uber CEO vows to be ‘hardcore’ about costs, slow hiring | Verge
Transcript
Credits:
Decoder is a production of The Verge and part of the Vox Media Podcast Network.
Our producers are Kate Cox and Nick Statt. Our editor is Ursa Wright.
The Decoder music is by Breakmaster Cylinder.
Learn more about your ad choices. Visit podcastchoices.com/adchoices
Brian Tolkin is the Head of Product @ Opendoor where he has spent the last 6 years and is responsible for product strategy and product and design teams. Before Opendoor, Brian spent an incredible 5 years at Uber through their wildest growth periods.
In Today's Episode with Brian Tolkin:
03:53 Brian's Journey at Uber: Launching China Pool
05:07 Product Lessons from Uber's China Launch
08:22 The Role of a PM in a Pre vs. Post AI World
10:16 Product Development Process in an AI World
17:43 The Importance of Simplification in Product Management
19:21 OKRs and Prioritization in Product Management
23:12 The Importance of Feedback Loops in Product Development
23:38 Evaluating Product Changes: User Adaptation vs. Bad Decisions
25:00 Balancing Gut Instinct and Data in Product Leadership
25:38 The Role of Simplicity in Product Design
27:02 Consensus vs. Dictatorial Product Leadership
27:54 Hiring for the Best Product Teams
31:33 How to do Effective Sprint Management
38:39 Quickfire Round: Insights and Advice
This week, the A.I. company Anthropic has Silicon Valley rethinking the timeline for artificial general intelligence. In addition to releasing a new safety policy, the company’s chief executive, Dario Amodei, laid out a vision of how A.I. could help cure cancer, mental illness and mitigate climate change in the near future. We consider his most surprising claims and what this means for the acceleration of the technology. Then, the Uber chief executive, Dara Khosrowshahi, joins us in the studio to discuss his company’s new partnership with Waymo, the autonomous vehicle company, and the future of that industry. And finally, leaked court documents reveal exactly how many TikTok videos you need to watch to get hooked on the app. So, Casey puts the number to the test.
Guest:
Dara Khosrowshahi, chief executive of Uber
Additional Reading:
Dario Amodei’s Essay “Machines of Loving Grace”
TikTok Executives Know About App’s Effect on Teens, Lawsuit Documents Allege
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JM Nickels is a Senior Director of Product Management at Uber. Previously, he was Head of Product for Commercialization at Waymo and led product teams at DoorDash. JM is also a coach and advisor focused on conscious leadership. In our conversation, we discuss:
• How to sharpen your vision and strategy skills
• What “conscious leadership” means and how to practice it
• Practical techniques for managing stress
• The power of soft skills and emotional intelligence in product leadership
• Lessons from working at Uber, Waymo, and DoorDash
• Keys to living a successful and fulfilling life
• Much more
—
Brought to you by:
• Pendo—The only all-in-one product experience platform for any type of application
• The Enterprise Ready Conference — For B2B leaders building enterprise SaaS
• Vanta—Automate compliance. Simplify security
—
Find the transcript at: https://www.lennysnewsletter.com/p/becoming-a-conscious-leader-john-mark-nickels
—
Where to find John Mark Nickels:
• X: https://x.com/nickelsjm
• LinkedIn: https://www.linkedin.com/in/jmnickels/
• Website: https://www.rhythmofbeing.com/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Introduction to JM
(02:02) Conscious leadership explained
(03:41) The power of soft skills
(07:34) Navigating Uber’s evolution
(12:41) Embracing emotions and inner work
(21:46) Crafting strategy and vision
(41:16) Balancing vision and execution
(46:13) Lessons from DoorDash, Uber, and Waymo
(52:32) The future of autonomous ride-hailing
(55:18) Contrarian corner: Embracing emotions in the workplace
(59:47) Keys to a fulfilling life
(01:04:45) Taking responsibility and agency
(01:07:29) Lightning round and final thoughts
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Scott Gorlick was employee #99 at Uber. Over 6 years, Scott built Uber in Atlanta and helped the company scale from 10 cities to $10B in revenue. Scott is also a prolific angel investor having written early checks into Lime and Standard Cognition to name a few.
In Today's Episode with Scott Gorlick We Discuss:
1. The Driver Acquisition Playbook: Scaling to 1M Drivers
How did Uber acquire 1M drivers? What was the playbook?
What worked? What did not work?
How much of a role did driver-to-driver referral payments have in driver acquisition?
What did Lyft do on the driver acquisition side that Uber should have done?
What did the retention look like for drivers on a 30, 60 and 90 day period?
2. The City Expansion Playbook:
What was the expansion playbook that Uber used for new cities?
What worked in ramping demand in a new city? What did not work?
How much of a role did promotions and discounting play? Lessons from them?
Why did Uber often let Lyft launch in a new market first? What was the benefit of this?
How did Scott see the maturation rate change with new markets opening? How fast did each subsequent market reach profitability?
3. Travis Kalanick and What Uber Could Have Been:
How would Uber be different today if Travis was still in charge?
What are the biggest mistakes that Dara has made with their M&A strategy?
What are some of Scott's biggest leadership lessons from working with Travis?
How did Travis create such strong followership and cult around him?
What were the single biggest management mistakes made by Travis?
Dara Khosrowshahi runs one of the most complicated businesses in the world, Uber. Since taking over in 2017 Dara has led the company to profitability against all odds. In this episode, we touch on a number of things including Uber’s position on the future of Autonomous Vehicles (AVs), the challenges that were overcome in making Uber profitable, and some of the operating principles that have stuck with Dara since his days at Expedia.
(00:00) Intro
(01:49) Uber's Economic Resilience and Consumer Trends
(04:40) The Future of Autonomous Vehicles
(14:27) Strategic Decisions and the Advanced Technologies Group
(31:01) Uber's Expansion and Competitive Landscape
(38:01) Living in the Suburbs: Practical Insights
(39:23) Cultural Reset at Uber: A Necessity
(42:39) Operational Efficiency: Lessons from Uber
(46:56) Global Adaptations: Uber's Local Innovations
(48:58) Leadership and Mentorship: Personal Reflections
(51:32) Career Path: From Finance to CEO
(01:00:14) The Importance of Constructive Conflict
(01:04:47) Long-term Strategy and Board Governance
(01:07:07) The Impact of Uber: A Global Perspective
(01:08:54) Conclusion and Farewell
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
Tap follow and enable notifications to stay ahead of the game.
Brian Tolkin is the Head of Product at Opendoor. Previously, he was one of the early employees at Uber, where he was instrumental in launching and growing UberPool, UberHop, and UberExpress and started one of the first product operations teams in tech. In our conversation, we dive into:
• How to enable product and ops to work well together
• How to run great product reviews
• How to make good decisions with limited data
• How he uses the jobs-to-be-done framework at Opendoor
• How to stay calm under pressure as a leader
• Wild stories from his time at Uber
• Challenges faced at Opendoor during the pandemic
• Much more
—
Brought to you by:
• Pendo—The only all-in-one product experience platform for any type of application
• Explo—Embed customer-facing analytics in your product
• Attio—The powerful, flexible CRM for fast-growing startups
—
Find the transcript and references at: https://www.lennysnewsletter.com/p/scaling-uber-and-opendoor-brian-tolkin
—
Where to find Brian Tolkin:
• X: https://x.com/briantolkin
• LinkedIn: https://www.linkedin.com/in/briantolkin/
—
Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
In this episode, we cover:
(00:00) Brian’s background
(02:14) Career beginnings at Uber
(02:49) Transitioning from product operations to product management
(06:47) Product and operations synergy
(10:00) Surge pricing at Uber
(12:18) Scaling challenges, and stories
(15:47) Opendoor and Covid adaptations
(25:38) Product reviews and Jobs to Be Done
(40:30) The challenges of A/B testing
(42:23) Increasing conviction in solutions
(44:33) Leveraging intuition in product decisions
(47:07) Partnering with Zillow
(52:55) Staying calm under pressure
(56:25) Finding the “kernel of truth” in product management
(01:00:21) Failure corner: Early days of Uber Pool
(01:06:11) Lightning round and final thoughts
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Great ideas are like electricity -- they snap into sharp focus and sprint from place to place. What's the best way to capture them? Bozoma Saint John, Chief Marketing Officer at Netflix, makes a compelling case to move away from an overreliance on data when making big decisions -- and calls on us all to tap into the power of our intuition and become creative trailblazers.
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Today’s show:
Dara Khosrowshahi joins Bill Gurley, Brad Gerstner, and Jason Calacanis to discuss his initial reservations about joining Uber and how he overcame them (14:57), the early magic of Uber that captivated investors (22:36), a deep dive into Uber's future plans (45:50), and much more!
*
Timestamps:
(0:00) Dara Khosrowshahi joins Bill Gurley, Brad Gerstner, & Jason Calacanis to discuss all things Uber
(2:41) Setting the stage for Uber entering 2024
(4:52) Untold parts of Uber's story
(09:38) Gusto - Get three months free when you run your first payroll at http://www.Gusto.com/twist
(11:38) Bill Gurley discusses Dara's selection as CEO
(14:57) Dara's initial reservations about joining Uber and how he overcame them
(20:57) Dara’s discomfort in the free-money environment of ZIRP
(21:43) Paintbrush - Visit http://www.getpaintbrush.com to see if you qualify for a $50K startup loan in less than 2 minutes
(22:36) Exploring the early magic of Uber that captivated investors
(26:27) How valuations impact founder mindset
(30:49) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/twist
(32:17) Discussing the relevance of secondaries in the near future
(35:02) Breaking down some Uber myths and Dara’s focus on drivers
(45:50) A deep dive into Uber's future plans
(51:31) Uber’s strategy with upselling as AI enters the conversation
(58:04) Bill Gurley on joining Zillow’s board and how innovation is needed in the real estate industry
(1:05:27) Brad Gerstner on markets
*
Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp
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Check out Uber: https://www.uber.com
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LINKS:
Silicon Valley clip referenced:
https://twitter.com/StephNass/status/1745132141652877788
*
Thanks to our partners:
(09:38) Gusto - Get three months free when you run your first payroll at http://www.Gusto.com/twist
*Gusto pricing shown in ad is based on pricing prior to March 2025
(21:43) Paintbrush - Visit http://www.getpaintbrush.com to see if you qualify for a $50K startup loan in less than 2 minutes
(30:49) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/twist
*
X:
https://twitter.com/Jason
https://twitter.com/dkhos
https://twitter.com/altcap
https://twitter.com/bgurley
LinkedIn:
https://www.linkedin.com/in/jasoncalacanis
*
Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
*
Check out Jason’s suite of newsletters: https://substack.com/@calacanis
*
Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
*
Subscribe to the Founder University Podcast: https://www.founder.university/podcast
Gergely Orosz is back for our annual year-end update on the tech market, writ large. How is hiring? Has AI really changed the game? What about that OpenAI fiasco?
We also talk in-depth about Gergely’s self-published book, The Software Engineer’s Guidebook, which has been four years in the making.
Join the discussion
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Featuring:
Gergely Orosz – Website, GitHub, LinkedIn, X
Jerod Santo – Website, GitHub, LinkedIn, Mastodon, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
Show Notes:
The Pragmatic Engineer Newsletter
The Software Engineer’s Guidebook
Anthropic
Something missing or broken? PRs welcome!
In this moment, the American businessperson and marketing executive, Bozoma Saint John discusses how to find your destiny. Bozoma says that too often people say that they just ‘fell into’ the job or industry they are in, when in fact she believes that this is destiny coming to find you and that we are constantly creating our destiny. She says that we underestimate the power of letting go of control (which is not the same as surrendering or giving up) as a way of opening up to different possibilities and routes to finding our destiny. As too often we bang our heads against closed doors, when instead there is an open door that is open on a different route. To realise this, she says we need to treat our powers of intuition like a muscle, ignoring external voices and opinions, training and growing your intuition to the point where you can have 100% faith in whatever it is telling you.
Listen to the full episode here - https://g2ul0.app.link/q9EARBxJ9Eb
Watch the Episodes On Youtube - https://www.youtube.com/c/%20TheDiaryOfACEO/videos
Bozoma:
https://www.bozomasaintjohn.com
https://www.instagram.com/badassboz/?hl=en
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Uber: hard to live with it, or without it. In this episode Kara grills CEO Dara Khosrowshahi on the company’s sky-high prices, high take rate, treatment of drivers/couriers, policies around safety and why oh why he is kind to his predecessor, Travis Kalanick.
Before and after the interview, Kara and Nayeema make sense of the power and problems of Uber, and discuss Lesbians Who Tech (a conference — not in general).
Note: Khosrowshahi discusses a 15% “take rate” in the United States, exclusive of commercial insurance expenses. Globally, the company reported a 29.3% “take rate” in Q2 of 2023 inclusive of these costs.
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In this episode, Steven sits down with the former CMO of Netflix and former Chief Brand Officer of Uber, Bozoma Saint John.
The first black woman to hold all of these (and many more) trailblazing roles, she is a legend of the corporate world. Born in Ghana in 1977, she moved to the U.S. at a young age. Saint John has held high-profile roles at companies like Apple, where she led global consumer marketing for iTunes and Apple Music, and Uber, where she was Chief Brand Officer. Saint John is widely recognized for her influence in the industry, her efforts to increase diversity in corporate America, and her engaging and unique public speaking style.
Some topics discussed in this episode:
The secrets that make Uber, Netflix and Apple so successful
How to stop getting the Sunday scaries
Is work-life balance a lie?
How to forge your own career
How to find your own identity in the workplace
Personal tragedy, loss, and emotional healing
How to sell anything
How to ask for help
Boz’s Book: https://www.amazon.com/Urgent-Life-Story-Love-Survival/
Follow Boz:
Twitter: https://twitter.com/badassboz
Instagram: https://www.instagram.com/badassboz
TikTok: https://www.tiktok.com/@badassboz
Website: https://www.bozomasaintjohn.com
Follow me:
https://beacons.ai/diaryofaceo
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Eric Schmidt, Angela Ahrendts, and Dara Khosrowshahi — three legendary culture-setters — sit down with host Bob Safian to discuss how they’ve built and rebuilt great cultures at Apple, Uber, Google and more. Recorded live at the Masters of Scale Summit in San Francisco, the conversation delivers surprising stories, and counterintuitive lessons on authenticity, making mistakes, and how to build a unique culture that’s right for your business.
Read a transcript of this episode: https://mastersofscale.com/
Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Brian McCullough and Chris Messina are starting a new, $15 million fund for pre-seed through Series A investments in AI companies. They've already raised money from Marc Andreessen, Chris Dixon, and Dennis Crowley and join Big Technology Podcast for a special episode where they share their strategy and the opportunity they're going after. At the core of this question is whether AI companies are worthy of investment or will just be subsumed by larger players. Stay tuned for the second half where we cover AI + Hollywood strikes and AI + warfare.
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