Dara Khosrowshahi, Bill Gurley, Brad Gerstner, & Jason Calacanis on Uber's growth and future | E1878
This Week in Startups
Introduction
The hosts introduce the guest Dara Khosrowshahi, CEO of Uber, and discuss the success of their previous episode and their intention to learn from a business operator at scale.
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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!
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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
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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
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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
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X:
LinkedIn:
https://www.linkedin.com/in/jasoncalacanis
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Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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Check out Jason’s suite of newsletters: https://substack.com/@calacanis
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Follow TWiST:
Substack: https://twistartups.substack.com
Twitter: https://twitter.com/TWiStartups
YouTube: https://www.youtube.com/thisweekin
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Subscribe to the Founder University Podcast: https://www.founder.university/podcast
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