Ravi Gupta

Partner, Sequoia Capital · 1 appearance on the record.

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investorexecutiveoperator@GuptaRK22 ↗rkg.blog ↗

Ravi Gupta is a venture capitalist at Sequoia Capital focusing on growth-stage consumer, internet, and fintech investments. He previously served as the Chief Operating Officer and Chief Financial Officer of Instacart and worked for a decade at KKR.

14statements → 7claims → 5claims resolved → 40%fully supported → 4.07/5average certainty → 1.64/5average debate potential → ≈4.5/5argument clarity, estimated → 17said about them ↓

2 supported 1 partly supported 2 contradicted 1 not yet assessed 1 not checkable as stated how the 7 claims stand · each chip opens the sources

7 assertions · 1 opinion · 5 insights · 1 disclosure · every statement was checked. The predictions and assertions are the 7 claims: statements the public record can support or contradict. 5 are resolved, 1 is not yet assessed, and 1 names no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Ravi argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported

Gupta: Carl Eschenbach scaled VMware's revenue from $40 million to $6 billion

“Carl talk to you, who's scaled VMware from forty million in revenue to six billion.”

Ravi Gupta Sep 14, 2020 ▶ 16:55 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Their most notable contradicted claim

Assertion Contradicted

Gupta: Sequoia Capital requires unanimous partner approval for all investments

“This is reinforced by things like unanimous decision-making, which means we all need to be bought in when we decide to partner with a company.”

Ravi Gupta Sep 14, 2020 ▶ 16:34 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Expressed certainty vs assessment result

none yet certainty 1

none yet certainty 2

100% certainty 3

33% certainty 4

50% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

How they sound: speaking style how? →

253 words/min while actually speaking · 0 um and uh per 1k words

No argument clarity score for Ravi Gupta: no usable question→answer exchanges on raw tape (a fair score needs 8+). We do not score a sample that small. Roundtable and news formats yield far fewer direct exchanges than interviews. Their coarse estimate from 26 exchanges on the produced feed is ≈4.5/5, shown at half point precision because the sample is small and produced tape scores higher.

Measured by listening to 5,981 words across 1 episode, but every recording we have of Ravi Gupta is the aired feed, and an editor cleaned that audio before release. Some of the hesitation was cut before we ever heard it, so read these as floors: the true rates are at least this high. These are measurements of speaking style, not scores. How it's measured →

How the interview went all their pushback → series average →

Across 1 rated episode:

host pushback ▾ 2/10

pushed back at the host ▾ 2/10

setup questions received 35%

host pushback: the hardest questions Harry asked, tap to play ▶ 10:23“How do you think about the balance between filling seats, but also maintaining quality bar?” ▶ 30:53“So is it possible to be both? And why is it important in your mind to be both?”

when Ravi pushed back ▶ 4:47“I actually, I would tell you I agree with a part of it, and I don't agree with a part of it, but I bet if we go through it deeply, you and I will end up in the same place” ▶ 21:12“To be clear, I would imagine for the audience here that they need to know Sagar was being deeply sarcastic when he talked about my exceptional Excel modeling skills.”

What they said14 What others said17 Episodes1

Everything Ravi Gupta said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Assertion Contradicted

Gupta: Sequoia Capital requires unanimous partner approval for all investments

“This is reinforced by things like unanimous decision-making, which means we all need to be bought in when we decide to partner with a company.”

Assertion Not publicly verifiable

Gupta: Sequoia allows founders to choose which partner joins their board

“When entrepreneurs ask somebody at Sequoia, hey, if I work with Sequoia, who will my board member be? And the answer is always the same, which is whoever you want. You get to choose.”

Ravi Gupta Sep 14, 2020 ▶ 16:41 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Disclosure

Gupta: A Sequoia partner shared their 360 feedback with the entire partnership

“At Sequoia, one of our partners late last year shared their three 60 feedback with all of us at a partner meeting and then asked, can you help me get better on these?”

Ravi Gupta Sep 14, 2020 ▶ 25:22 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Insight

Gupta: Sequoia evaluates founders on trajectory (slope) rather than baseline (intercept)

“I think that when we talk about the people we like to invest in at Sequoia, we talk about investing in slope rather than intercept.”

Ravi Gupta Sep 14, 2020 ▶ 29:03 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Insight

Gupta: Any team evaluation short of 'enthusiastic rehire' is a no

“I think the question you've got to ask if you're building or evaluating your team is, would you enthusiastically rehire this person if given the chance, knowing everything you know? And I think the word enthusiastically is so important here because it removes …”

Ravi Gupta Sep 14, 2020 ▶ 6:55 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Opinion

Gupta: Stripe maintains its talent bar by enduring unfilled open roles

“I think that Stripe is absolutely inspirational on this topic. And I personally, I think they've done it the right way, which I think they are willing to deal with the pain of not filling a spot because they respect that spot so much that they're only going to…”

Ravi Gupta Sep 14, 2020 ▶ 10:35 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Assertion Contradicted

Gupta: Sequoia backed Stripe founders before they wrote any code

“At the time, Patrick and John at Stripe, when all they had was an idea and not a single line of code, because they were remarkable and they were daring.”

Ravi Gupta Sep 14, 2020 ▶ 15:32 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Assertion Partly supported

Gupta: Instacart lost $20 on every order during its early operations

“When we were losing 20 dollars on every order at Instacart, which we were at the beginning”

Ravi Gupta Sep 14, 2020 ▶ 31:44 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Insight

Gupta: Work provides more immediate feedback than parenting, distorting our priorities

“There's always a reason that you should stay late and work on something, because the impact that you'll make at work will be more visible for that next hour than the impact you'll make at home by the things you do with your kids, and it's more visible and tang…”

Ravi Gupta Sep 14, 2020 ▶ 34:37 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Insight

Gupta: VCs must remember companies exist for people's life's work

“Investors would be best served to remember that Companies do not exist for their pleasure. Companies exist for people to do their life's work. And when you do decide it's not for you, that it's not about proving that you're right.”

Ravi Gupta Sep 14, 2020 ▶ 37:37 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Assertion Supported

Gupta: Carl Eschenbach scaled VMware's revenue from $40 million to $6 billion

“Carl talk to you, who's scaled VMware from forty million in revenue to six billion.”

Assertion Not checkable as stated

Gupta: Instacart's execution stalled when attempting six priorities in one quarter

“And so I remember this time at Instacart where we had six company priorities in a quarter and a month into the quarter or halfway into the quarter, we weren't moving nearly as fast as we wanted on any of them.”

Ravi Gupta Sep 14, 2020 ▶ 18:07 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Insight

Gupta: A board member's goal is becoming the founder's first call

“I would tell you, I think the way I would articulate the goal for you is you should Seek out to build enough trust from the very beginning with a founder where you are their first call when things are good or when things are bad.”

Ravi Gupta Sep 14, 2020 ▶ 26:39 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

Assertion Supported

Gupta: Sequoia made a Series A investment in two 19-year-old founders

“And so with Samir and Runik, who are very young, I mean, I think we made our series A investment when they were both 19 years old.”

Ravi Gupta Sep 14, 2020 ▶ 29:49 20VC: Sequoia's Ravi Gupta on His Lessons From The Hyper-Growth of Instacart, The Key Question To Ask When Building or Evaluating Teams & The Importance of Investing In and Detecting Slopes Rather Than Intercepts

The other half of the tape: Ravi Gupta's own voice is left out of every number here. Other people bring the name up 17 times in 8 episodes on 20VC. every mention, with the transcript →

Who brings them up most Harry Stebbings 10 Miles Clements 6 Samir Vasavada 1