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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:

https://twitter.com/Jason

https://twitter.com/dkhos

https://twitter.com/altcap

https://twitter.com/bgurley

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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Permabyte: Matt Winters - The Gift