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Opinion
Tomaino: Silicon Valley is driven by soulless greed, citing Sequoia Capital
“My sentiment in a lot of Silicon Valley is that it's very, there, there's a lot of soulless greed, and just this desire to create these kind of you know, massive funds create massive attention, and I think, again, Sequoia is the best example of this, and 1789,…”
Nick Tomaino Oct 30, 2023 ▶ 1:07:55 Nick Tomaino: The Future of NFTs, What Will Happen with FTX & Who Should be Held to Account | E1076 · 20VC with Harry Stebbings
Opinion
Legal AI Is Overfunded but Harvey Is Positioned to Win
“Probably legal. I think there's, you know, there's just so many me too's in this category. Whereas I think that the winner is already in existence. I'm obviously biased, but I think Harvey is very well positioned because they have the widest distribution. And …”
Julien Bek Aug 24, 2026 ▶ 1:17:04 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Insight
Browder: Accept Sequoia or Founders Fund Over Double Valuation Term Sheets
“There's like the kingmaker firms that you should accept at any price. One example would be Founders Fund or Sequoia or people like that. And so if you get an offer from them at X and the offer from someone else is at two X, you should take their offer because …”
Josh Browder May 18, 2026 ▶ 49:42 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
Opinion
O'Driscoll: Sequoia's initial leadership transition to Botha was unsuccessful
“The transition, having made one transition to Roloff and having had to make another transition abruptly means the first transition wasn't that successful.”
Rory O'Driscoll Apr 9, 2026 ▶ 41:13 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Sequoia and top VCs announce misleading blended valuations
“The amount of Sequoia rounds where it's like, oh, you know, X raises money from square five billion. Trust me, Sequoia got in at one, but they just club it together and then announced the sum and then the latest valuation. And it's just very misleading.”
Harry Stebbings Apr 2, 2026 ▶ 35:57 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Opinion
Oren Zeev: Traditional mid-sized VC partnerships are in deep trouble
“If you are traditional five, six person partnership without anything Very, very, very unique and special in the friendship that you bring to the table, then yes, I think you are in trouble because it's almost like, you know, worse off. On one hand, you're not …”
Oren Zeev Feb 2, 2026 ▶ 35:01 Oren Zeev: Why AI Growth Expectations Are BS & Won't Last? Why GPs Shouldn't Tell LPs Their Strategy
Insight
A seed lead only taking pro rata in Series A signals failure
“I fully believe if they're like, hey, Sequoia led our seed, and I'm like, hey, are they doing your A, and they're like, Well, they're doing their pro rata. I'm like, this is not a good company. Like, objectively is not a good company.”
Max Altman Nov 21, 2025 ▶ 31:34 20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster
Insight
Cahn: Venture capital firms cannot 'king-make' startups with capital alone
“I don't believe in King making and that's maybe a controversial thing to say. I think one of the lessons, you know, you'd think like, oh, Sequoia should be able to King make companies and like, that's so great. And that would be, by the way, if that was true, …”
David Cahn Oct 27, 2025 ▶ 34:56 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2025
Lemkin: Shaun Maguire will leave Sequoia Capital in 2025
“I'll take the bet that he leaves this year.”
Jason Lemkin Jul 10, 2025 ▶ 1:00:14 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Opinion
Jack Zhang says only the top five VC firm brands matter
“Only the top five make the difference. So having Sequoia makes a big difference. Huge difference.”
Jack Zhang May 26, 2025 ▶ 1:29:37 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Opinion
O'Driscoll: Sequoia permanently cuts off LPs who stop re-upping
“And you know, because those guys do vindictive like no one else, that if you pull out, you're done forever.”
Rory O'Driscoll Apr 24, 2025 ▶ 38:32 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
Opinion
Frankel: Multi-stage VC firms have no incentive to matchmake for startups
“Sequoia will, it doesn't matter, by the way, I don't want to single out Sequoia here, but it doesn't matter if you take your check from Andreessen, Sequoia, Axel, you name them, right? They will never, they have no incentive to matchmake. They have no incentiv…”
David Frankel Oct 14, 2024 ▶ 1:17:17 David Frankel, MP @Founder Collective: Investing Lessons from Seeding Coupang, Pillpack & Suno|E1214 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Shaun Maguire: A non-Sequoia VC firm mandated backing female founders yearly
“There is a venture fund that I know very well. It is not Sequoia that, For a period of time had a policy that every investor was to boast to back at least one female founder per year.”
Shaun Maguire Aug 12, 2024 ▶ 47:37 Shaun Maguire: Why Iran is the World's Greatest Evil & Trump is the Only Hope for Peace | E1189 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Maguire: Multiple people tried to get me fired from Sequoia Capital
“Many, many different people tried to get me fired in many different ways.”
Shaun Maguire Aug 12, 2024 ▶ 43:13 Shaun Maguire: Why Iran is the World's Greatest Evil & Trump is the Only Hope for Peace | E1189 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Maguire: Climate activists targeted Sequoia over Doug Leone's Trump support
“In my Sequoia inbox, the last 12 hours probably 20 Like climate people have emailed most Sequoia partners saying that like Doug Leone is problematic for supporting Trump and that Trump has anti-climate positions and they don't know how they can support, like h…”
Shaun Maguire Aug 12, 2024 ▶ 43:34 Shaun Maguire: Why Iran is the World's Greatest Evil & Trump is the Only Hope for Peace | E1189 · 20VC with Harry Stebbings
Opinion
Cahn: Current AI Products Are Not Yet Showing Strong Value Creation
“The burden to deliver value is very, very high in business. And we're not seeing that so strongly in AI yet.”
David Cahn Aug 5, 2024 ▶ 20:17 David Cahn: Why Servers, Steel and Power Are the Pillars Powering the Future of AI | E1186 · 20VC with Harry Stebbings
Prediction Open · timeframe Aug 2034
Cahn: ChatGPT Is Now a $3.4 Billion Revenue Business
“Definitely OpenAI. I mean, OpenAI has a brand, it has consumer distribution, it has product market fit with ChatGBT, which is a 3.4 billion dollar revenue business now. I think ChatGBT will definitely be around. Yeah, I think a bunch of the others will too for…”
David Cahn Aug 5, 2024 ▶ 1:11:13 David Cahn: Why Servers, Steel and Power Are the Pillars Powering the Future of AI | E1186 · 20VC with Harry Stebbings
Insight
Cahn: Founders Should Offer Up to 5% Equity for Transformational Hires
“I tell founders all the time, if you find someone who's going to transform your business, give them five percent of the company. Now I say that it's an extreme statement. Maybe it's four percent, maybe it's three percent. But I think we get very married to lik…”
David Cahn Aug 5, 2024 ▶ 1:09:58 David Cahn: Why Servers, Steel and Power Are the Pillars Powering the Future of AI | E1186 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Asparouhov: Founders Fund outperformed Sequoia, a16z, and Benchmark with fewer debacles
“If I were to look over the past sort of five years, I think generally the Founders Fund decision making has led to Generally superior returns and also less gaffes in various ways, whether it's the, you know, sort of FTX type, you know, sort of fraud debacles, …”
Delian Asparouhov Jul 29, 2024 ▶ 32:46 Delian Asparouhov: Inside the Walls of Founders Fund: What the World Does Not See | E1183 · 20VC with Harry Stebbings
Disclosure
Grady: Sequoia rejected a $5B buyout for a now-struggling portfolio company
“There's one in our portfolio now that I'm not going to name, but we had an offer from somebody to buy the company for almost five billion dollars. We own just north of 20%. That would have been a huge home run. Now the company looks like it is, ah, kind of not…”
Pat Grady Jul 8, 2024 ▶ 48:59 Pat Grady: Sequoia Partner on Investing Lessons from Doug Leone, Roelof Botha and Alfred Lin | E1174 · 20VC with Harry Stebbings
Assertion Supported
Grady: 10 years of Sequoia data shows consensus doesn't drive startup outcomes
“So we have actual data on this going back to 20 14 where we started recording the votes numerically on every single investment. So we have about 10 years worth, which believe it or not is not conclusive because there are so few outliers that have emerged even …”
Pat Grady Jul 8, 2024 ▶ 1:04:04 Pat Grady: Sequoia Partner on Investing Lessons from Doug Leone, Roelof Botha and Alfred Lin | E1174 · 20VC with Harry Stebbings
Opinion
Eyal: Andreessen Horowitz and Sequoia have become BlackRocks for startups
“And that's part of the challenge with what's happened today within the, what I call the institutionalization of VC, where Andreessen and Sequoia have become such big funds, the investment managers you know, the multiple targets are different. The RR targets ha…”
Avi Eyal Jul 3, 2024 ▶ 14:14 Avi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173 · 20VC with Harry Stebbings
Disclosure
Stebbings: Hot seed rounds raised by executive founders consistently underperformed
“I looked at the seeds, and I looked at those that haven't really worked, and all of those that haven't really worked have often been head of product at Twitter, head of product at Twitch, head of product at amazing company, the hottest of hot seed rounds with …”
Harry Stebbings Nov 21, 2022 ▶ 7:07 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Opinion
Stebbings: Sequoia is the only major multi-stage VC honoring portfolio conflicts
“I think the only big multistage fund that does care and honor it really well is Sequoia.”
Harry Stebbings Sep 12, 2022 ▶ 14:39 Will Quist: Why 95% of Venture Capital is Not Really “Venture Capital” | 20VC #924 · 20VC with Harry Stebbings
Opinion
Doug Leone: High-velocity VCs cannot provide genuine company-building support
“You cannot do what we do if you're investing in five deals a week. There's no way to do that.”
Doug Leone Feb 23, 2022 ▶ 4:36 The Tiger Global Memo: From Sequoia Capital to Benchmark and Thrive: The World's Best on the Rise of Tiger Global
Assertion Not checkable as stated
Gurley: Claims of Disrupting Traditional Venture Capital Have Been Proven False
“I think this whole notion that you're going to disrupt and fundamentally take over the business has just been proven false over and over again. AngelList is awesome, but it's not 20% of the industry, you know. Andreessen said, we're going to completely, you kn…”
Bill Gurley Dec 6, 2021 ▶ 43:52 20VC: Bill Gurley and Michael Eisenberg on The First Signs of an Impending Bust, What Happens with a Market Crash, How Do Public Markets Impact Private Valuations & The Biggest Lessons from 20 Years Investing in Venture
Opinion
Leone: Fast-paced funds doing five deals a week cannot build companies
“Product market fit is yours. We do everything else. You cannot do what we do if you're investing in five deals a week. There's no way to do that.”
Doug Leone Sep 14, 2021 ▶ 21:25 20VC: Sequoia's Doug Leone on What Has Been Instrumental To Scaling Sequoia Over Generations, How Sequoia Think About International Expansion and What They Learned From China and India & Why When You Lose Pre-Seed You Become Private Equity
Opinion
Vrionis: Sequoia's global, multi-stage success is an anomaly others cannot replicate
“Look, I think Sequoia is an anomaly. Operating a VC firm the way they have on a global basis, it's unbelievable. I think a lot of firms are trying to emulate that, and I'm not so sure others can pull it off.”
John Vrionis Dec 9, 2019 ▶ 18:35 20VC: Unusual Ventures' John Vrionis on Why We Need To Raise The Bar In Venture, Why Taking Multi-Stage Money At Seed Is Not In The Best Interest of Founders & Why To Be The Best, You Have To Specialise To Be The Best
Insight
Wand: Startup boards overweight top VCs' opinions based on brand, not merit
“Usually, if there is a partner from a top fund, there is a tendency to give overweight to his idea and decision point, where it's not substantiated by the merit of his idea, but just rather from the fact that he came from Sequoia, he came from Benchmark, he ca…”
Assaf Wand Jan 18, 2019 ▶ 11:21 20VC: Why Every Company Looks One Round Earlier Than It Should Be, Why Investors Don't Understand Term Sheet Psyche & How The Brand Behind The Investor Can Overweight The Attention Their Opinion Is Given with Assaf Wand, Founder & CEO @ Hippo
Opinion
Roger Dickey compares LPing in Sequoia or Andreessen to a mutual fund
“Like if you can LP with Sequoia Greylock, Kleiner, Andreessen, you're probably going to get your money back. You know, that's almost like a mutual fund.”
Roger Dickey Sep 29, 2017 ▶ 19:19 20VC: If You Do Not Like VCs, You Have Not Worked With a Good One, How Andreesen Have Added The Same Level of Value As A Co-Founder, Why Market Is The First Thing To Consider When Angel Investing & Why Series A Is A Hiring Decision with Roger Dickey, Foun
Insight
Bek: Arrogance in founders can be acceptable if tied to a spike
“If you look at founders you like versus founders who make money as a two by two matrix your job is to figure out in which part of the quadrant we make money. And he used to tell that to many of our partners. And it's not because you don't like the founder that…”
Julien Bek Aug 24, 2026 ▶ 40:01 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Prediction Open · timeframe Aug 2031
Bek: Next trillion-dollar company will be software masquerading as services
“So the prediction was that the next trillion dollar company will be a software company that masquerades as a service business. It's very important the masquerading because they cannot be a service company.”
Julien Bek Aug 24, 2026 ▶ 1:06:57 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Insight
Shaun Maguire: Judgment outweighs IQ and political quotient outweighs EQ
“His argument is that judgment is actually more important than IQ, and PQ is more important than EQ.”
Julien Bek Aug 24, 2026 ▶ 52:24 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Assertion Not checkable as stated
Bek Claims He Has Never Lost a Deal While at Sequoia
“So I never lost a deal an investment in my time at Sequoia, but I've lost investments before.”
Julien Bek Aug 24, 2026 ▶ 1:21:12 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Disclosure
Maguire Pushed Sequoia's SpaceX Investment After Partner Voted '1' in IC
“Credits to Sean when he brought in the SpaceX investment, We vote on companies. I think someone voted a one. Yeah. I've seen fours, of course. I've seen threes. Never seen a two. I didn't even know we could do one. I didn't even know it was on the scale. But w…”
Julien Bek Aug 24, 2026 ▶ 17:49 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Insight
Alfred Lin: Never mistake an outlier operator for an outlier founder
“Do not mistake an outlier operator for an outlier founder.”
Julien Bek Aug 24, 2026 ▶ 51:35 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Insight
Bek: Unanimously high IC ratings are dangerous because founders retrofit narratives
“First, if everyone's a seven or eight, Quite dangerous. Because look, founders know what we want to hear. The best founders are able to you know, retrofit the narrative that they think is going to land with investors, and that can be dangerous. So in, in those…”
Julien Bek Aug 24, 2026 ▶ 33:35 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Opinion
Cursor Is the Best AI Agent Startup Outside Sequoia's Portfolio
“It's probably cursor. One, they're in one of the most important markets. But second, where there was a lot of chatter around AI wrappers, they were the first company to really understand that you could post train models and actually be, go deeper into the stac…”
Julien Bek Aug 24, 2026 ▶ 1:18:55 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Disclosure
Bek: Sequoia will not back legacy services companies pivoting to AI
“I will not invest in one of those companies. For the following reason. I think you can make money in that business. The reality is I've only seen it in my career. The best companies are able to concentrate talent and you just not going to get frontier talent w…”
Julien Bek Aug 24, 2026 ▶ 1:14:38 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Insight
Stebbings: Top talent joins startups based heavily on VC brand signaling
“The amount of great operators who you're like, well, they wouldn't be, I'm so, I don't mean this rudely, dumb or naive enough to just join a company because of a VC. Do just join a company because of a VC. They'll go, oh, it's a Sequoia-backed company, oh, it'…”
Harry Stebbings Jun 20, 2026 ▶ 35:50 Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings
Opinion
Matan Grinberg: Founders should accept valuation discounts for Sequoia Capital
“So generally, yes. I mean, they're the best firm.”
Matan Grinberg Jun 13, 2026 ▶ 58:07 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Opinion
Rajaram: Moritz's Instacart investment was the top VC bet ever
“I think the best venture capital, I, someone asked me what's the best venture capital bets. I talk about a paradoxical one. I think it's Mike Moritz betting on Instacart. Why? Because he lost three hundred and seventy million on web van less than a decade ago.…”
Gokul Rajaram Mar 16, 2026 ▶ 47:11 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Opinion
Zeev: Top VC Funds Like Sequoia Have Zero Incentive to Inflate Paper Marks
“If you're a fund that's, let's, let's say Sequoia, for example, they know that they can raise any time, right? So they have zero motivation to inflate numbers. They have all the motivation in the world to show things as conservatively as possible, right? Becau…”
Oren Zeev Feb 2, 2026 ▶ 37:28 Oren Zeev: Why AI Growth Expectations Are BS & Won't Last? Why GPs Shouldn't Tell LPs Their Strategy
Assertion Not checkable as stated
Weinberg: Most enterprise customers do not know Sequoia or Andreessen Horowitz
“The vast majority of our customers don't know who Sequoia, A-sixteen, Z, or any of those people even are, right?”
Winston Weinberg Jan 19, 2026 ▶ 15:37 Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings
Assertion Open · timeframe Dec 2026
Stebbings: Multi-Billion Mega Seed Rounds Include Undisclosed Cheaper Tranches
“The one lesson that I've learned from a lot of these deals, whether it's Thinking Machines or this or some others, is that although it's 500 or five billion on the sticker price when it's announced, there's actually several rounds before that Sequoia and Andre…”
Harry Stebbings Dec 11, 2025 ▶ 37:48 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
Opinion
Founders should always accept an investment offer from Sequoia Capital
“I think it's really hard if you get Sequoia to offer you money and be on your cap table and have that amazing brand halo effect to not take it, and I think someone always should.”
Max Altman Nov 21, 2025 ▶ 49:08 20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster
Assertion Not publicly verifiable
Andreessen Horowitz led only two seed rounds for billion-dollar AI startups
“Of the first 40 of them, only one person had two lead checks, and that was Andreessen, and no one else had two, and if you look through the smattering, there are, you know, Green Oaks is in there, a lot of Gill's in there, but there's a lot of other random peo…”
Max Altman Nov 21, 2025 ▶ 29:12 20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster
Assertion Not checkable as stated
Cahn: AI infrastructure investment requires $840B in end-user revenue
“If you invest one hundred fifty billion in NVIDIA chips, that's about three hundred billion of data center investments. And to pay that back, the person using the compute needs to earn a 50% gross margin. So there's about six hundred billion of revenue that ne…”
David Cahn Oct 27, 2025 ▶ 3:20 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
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