Leadership Dynamics and Cultural Impact

My guest today is Jason Droege, a venture partner at Benchmark. Jason’s had a long entrepreneurial career, which most recently culminated in building and leading Uber Eats. He joined Uber in 2014 with a blank piece of paper to grow the business beyond ride sharing. Within six years, he found product market fit with food delivery, refined the service, and scaled Uber Eats to a global $20 billion GMV run rate. Our conversation pulls out the most important lessons learned during that period and how Jason now employs them in his role at Benchmark. Please enjoy this great conversation with Jason Droege.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

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Show Notes

[00:02:52] - [First question] - What it was like at a high level building Uber Eats

[00:07:38] - How he would structure entrepreneurial incentives on a platform like Uber for a new leader or team attempting to build on top of it

[00:10:17] - What he learned about selecting competitive frontiers and mistakes made while building Uber Eats

[00:15:17] - Things that Uber Eats got most right that he’s proud of 

[00:18:16] - Constructive mistakes that taught him a lot from his time with Uber Eats

[00:20:36] - What made India such a competitive environment 

[00:26:13] - What improved the most in his playbook for launching in a new city

[00:27:14] - Defining what best means in this competitive sector  

[00:29:01] - Dealing with suppliers in different categories and finding an ideal balance

[00:32:09] - When monogamy between the buyer and supplier matters and when it doesn’t in a marketplace 

[00:36:12] - Defining what founder market fit is and being “fingertippy”

[00:37:29] - His views on the relationships between leaders of businesses and their cultures

[00:40:26] - Why Uber believed in him more than he did 

[00:41:40] - What he learned about marketing to suppliers specifically 

[00:45:18] - Differing views he has on the concept of failure  

[00:47:31] - Thoughts about ideas versus execution and the relative importance of the two

[00:49:10] - Effectively measuring opportunity cost and using it in decision making  

[00:58:56] - The most interesting things he’s learned from his time as a partner at Benchmark

[01:00:15] - The kindest thing anyone has ever done for him