Dara Khosrowshahi, Bill Gurley, Brad Gerstner, & Jason Calacanis on Uber's growth and future | E1878
This Week in Startups
Jason Calacanis
4.2 • 1.4K Ratings
🗓️ 12 January 2024
⏱️ 75 minutes
🧾️ Download transcript
Summary
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.
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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
*
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
Transcript
Click on a timestamp to play from that location
| 0:00.0 | Hey Dara, how are you? |
| 0:01.3 | I'm doing great, how about you? |
| 0:03.7 | Pretty great, looks like I'm stuck on another pod |
| 0:07.0 | with two lunatics. |
| 0:08.6 | I don't know what happened here. |
| 0:09.6 | I was asking about this. |
| 0:10.9 | This is a real thing now. It's amazing. It's an experiment. It's an experiment. |
| 0:14.9 | It's an experiment. It's just a couple guys. |
| 0:19.7 | It's like it's a thing that Bill, the girlian you are is an experiment. I love it. |
| 0:25.0 | This week in startups is brought to you by |
| 0:28.0 | Gusto is easy online payroll, benefits, and HR built for modern small businesses. |
| 0:35.4 | Get three months free when you run your first payroll at gusto.com slash twist. |
| 0:40.6 | The paintbrush loan is the earliest startup financing on the internet. |
| 0:44.0 | No pitch deck, no business plan, and no warm intros. |
| 0:48.0 | Plus you get to keep your equity. |
| 0:50.0 | Visit get paintbrush.com to see if you qualify for a $50,000 startup loan in less than two minutes. |
| 0:57.0 | And, Squarespace, turn your idea into a new website. |
| 1:01.5 | Go to Squarespace.com slash Twist for a free trial. |
| 1:05.0 | When you're ready to launch, use offer code Twist to save 10% off your first purchase of a website or domain. |
| 1:11.0 | All right, everybody, welcome back to this week |
| 1:14.1 | and startup slash BG squared. |
| 1:16.3 | It's a little bit of an experiment we're doing here last week. |
... |
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