My guest today is Ravi Gupta. Ravi spent a decade in private equity at KKR before joining Instacart as their first CFO and COO. He navigated them through a critical moment in their history and returned to investing in 2019 as a partner at Sequoia. Our discussion gets to the heart of what it means to build and invest in great businesses, and we talk a lot about the personal side of the journey, which tends to get overlooked. Please enjoy this great conversation with Ravi Gupta.
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[00:02:34] - [First question] - Why it’s important to keep the main thing the main thing
[00:04:59] - His first exposure to this idea; How Will You Measure Your Life
[00:07:50] - Thoughts on the conflict of the main thing for a business and a person
[00:11:45] - The most painful episode of enacting this philosophy at Instacart
[00:16:13] - How this concept has manifested in his life as an investor at Sequoia
[00:19:16] - Amazon’s 14 leadership principles vs. his concept of focus
[00:21:55] - What good main things share in common and their attributes; Frank Slootman Episode
[00:24:48] - Whether or not the feedback loop for things that work are very short
[00:26:04] - The nature of joy and competitiveness in company culture
[00:29:01] - How he assesses the depth that motivation runs through people and companies
[00:32:43] - Analysis of his own motivations in life
[00:35:34] - Differences and shortcomings of virtuous and vicious motivators
[00:37:15] - How to accurately figure out someones motivators in a short period of time
[00:40:22] - Being Demanding and Supportive; Why these words pair so well together
[00:45:55] - What he’s looking for in companies given all of the ideas discussed so far
[00:51:11] - How his ideology manifests inside of Sequoia
[00:58:44] - What it’s like to mentor an apprentice and how to do it well
[01:02:40] - Adjusting behaviors to meet current markets where they’re at
[01:06:13] - Defining what a great product is
[01:07:56] - What he did to turn around Instacart by narrowing their focus
[01:12:28] - The things that most drove the switchover at Instacart
[01:14:53] - The k