DiscoverInvest Like the Best with Patrick O'ShaughnessyRavi Gupta - Focus - [Invest Like the Best, EP.289]
Ravi Gupta - Focus - [Invest Like the Best, EP.289]

Ravi Gupta - Focus - [Invest Like the Best, EP.289]

Update: 2022-08-09


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.


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




This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.




Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at




Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit


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.


Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.


Follow us on Twitter: @patrick_oshag | @JoinColossus


Show Notes

[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 kindest thing anyone has ever done for him

In Channel
Download from Google Play
Download from App Store








Sleep Timer


End of Episode

5 Minutes

10 Minutes

15 Minutes

30 Minutes

45 Minutes

60 Minutes

120 Minutes

Ravi Gupta - Focus - [Invest Like the Best, EP.289]

Ravi Gupta - Focus - [Invest Like the Best, EP.289]