This Week in Startups is brought to you by…

Gusto is easy online payroll, benefits, and HR built for modern small businesses. 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

The Paintbrush Loan is the earliest startup financing on the internet. No pitch deck, no business plan, no minimum time in business, and no warm intros. Plus, you get to keep your equity. Visit http://www.getpaintbrush.com to see if you qualify for a $50K startup loan in less than 2 minutes.

Squarespace. Turn your idea into a new website! Go to https://www.Squarespace.com/twist for a free trial. When you’re ready to launch, use offer code TWIST to save 10% off your first purchase of a website or domain.

*

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

*

Check out Uber: https://www.uber.com

*

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