One of the main jobs Ravi Gupta has as a partner at venture capital giant Sequoia Capital is to help founders see the difference between fantasy and reality. On this episode of The Knowledge Project, Gupta dives deep into a wide range of topics that will help you better understand the realities of success, decision-making, why it’s crucial to practice doing things you don’t want to do, the best advice he ever received, and the value of quality over quantity.
Gupta has served as a partner at Sequoia Capital since 2019. Prior to joining the world of venture capital, he served as the Chief Operating Officer and Chief Financial Officer for Instacart, and he also spent a decade working in private equity with KKR & Co.
Here are a few highlights from our conversation:
He said, “Listen, son, don’t have a work personality and a home personality. It’ll just tire you out. You don’t want to have to live two different lives.”
But anytime you go and study one, you realize that every business is fascinating if you’re willing to go down to the details—every single one. Any business that you want to go and learn about, if you go and learn the details, you will find it fascinating.
Don’t try to write about what you think someone else will think is interesting. Write about something that you actually care about.
It’s easier to follow your principles 100% of the time rather than 98% of the time, because you don’t know what 98% of the time to follow them.
The entire point of being a leader might be to go find two or three trajectory-changing people for the company, rather than all of the other things that make you feel like you’re making more linear forward progress.
If what it takes to be the best in the world at the thing that I’m doing is to lose some of those aspects that we’re talking about, then I don’t want it.
Guys, this is not gymnastics; [there are] no points for degree of difficulty. Let’s just get to the right answer; let’s go. If it’s hard, it’s hard; cool, but sometimes it’s not hard. Let’s just do the thing.
00:00 – Intro
00:38 – Gupta’s best advice
02:54 – Gupta’s upbringing and living in the shadow of his brother
06:20 – On success and parenting
13:35 – The second-order effects of “equality”
15:55 – On embracing reality
18:33 – How Gupta helps founders deal with reality
23:29 – What Gupta learned working in private equity
29:59 – Gupta’s best writing advice
33:42 – The key to success in any domain
37:19 – Gupta’s rules for success in life and work
41:02 – What’s still missing at Instacart
45:04 – Quality vs. quantity
51:48 – Business vs. family
55:20 – Can you be successful and have balance
01:01:59 – On keeping the main thing the main thing
01:09:39 – On hiring questions and scenarios
01:14:11 – How to be a great decision maker
01:22:21 – On structuring the day for success
01:25:30 – Short-term vs long-term decisions
01:33:54 – Common ways successful people ruin themselves
01:40:46 – How Gupta defines success