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Assertion Supported
Levine: Sequoia's seed deals in Airbnb and Dropbox are history's best
“Two of the best deals of all time were seeds by Sequoia. I think an initial almost 600,000 dollar investment in Airbnb and a million dollar investment in Dropbox to get very large ownership positions.”
Daniel Levine Nov 12, 2020 ▶ 29:27 20VC: Accel's Dan Levine on The Current State of Seed & Series A, The Rise of Pre-Emptive Rounds, Solo Capitalists and Multi-Stage Funds Entering Seed & Market, People and Product; What To Prioritise?
Opinion
Botha: Investors Taking Public Credit for Startup Success Is Misplaced
“I find it misplaced when investors crow about the success of a company as though they were the ones who were in the trenches every day. I think investors can have a big influence sometimes for the better in the outcome of a company. But there's a reason we hav…”
Roelof Botha Oct 26, 2020 ▶ 36:25 20VC: Sequoia's Roelof Botha on His Biggest Lessons Working Alongside Don Valentine, Mike Moritz and Doug Leone, Leading Sequoia's US Business and What Sequoia Do To Retain Their Edge at the Top & The Crucible Moments That Define Startup Success
Insight
Botha: Startups Face Only One to Three Truly Critical Decisions Yearly
“There are many decisions every day that a company gets to make that are somewhat tactical in nature, and often they're reversible decisions, so they don't matter as much in the sense that it's better to try something, and if it doesn't work a couple weeks late…”
Roelof Botha Oct 26, 2020 ▶ 29:51 20VC: Sequoia's Roelof Botha on His Biggest Lessons Working Alongside Don Valentine, Mike Moritz and Doug Leone, Leading Sequoia's US Business and What Sequoia Do To Retain Their Edge at the Top & The Crucible Moments That Define Startup Success
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
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
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
Disclosure
Hartz: Eventbrite took Sequoia's Series A despite the lowest valuation
“In the case of Eventbrite, our Series A was actually the lowest price term sheet, but having that trust and knowing his brainpower and prowess in building companies, it became a very easy choice for us”
Kevin Hartz Aug 31, 2020 ▶ 32:45 20VC: SPACs. What Are They? Why Now? How Do They Change The Venture Landscape? Are They Better Than IPOs & Direct Listings? How Should Founders Think About Them? Kevin Hartz & Troy Steckenrider @ A*
Disclosure
Summit Peak tracks follow-on investments from top VC brands like Benchmark
“Look, I would be bullshitting you to say that it's not important to us. Those brand names do matter, whether that's Benchmark Capital, Andreessen Horowitz, Sequoia Capital. They are great funds, and they're great investors at various stages, and you want to se…”
Apurva Mehta Aug 17, 2020 ▶ 29:27 20VC: Why Entrepreneurs Care Less About Firm Brand at Seed, How LPs Should Think About GP Commit & How The World of LPs and Fundraising Will Change Post COVID with Apurva Mehta, Managing Partner @ Summit Peak Investments
Opinion
Ittycheria: Roelof Botha listens instead of dominating board conversations
“I found in many other companies, the largest investor always feels like they have the bully pulpit. They talk the most and they dominate the board conversations. Roloff was very different. He spoke very little. He listened very hard. And when he spoke, he had …”
Dev Ittycheria Aug 10, 2020 ▶ 28:35 20VC: MongoDB CEO, Dev Ittycheria on Why Sometimes You Have To Be Inefficient To Be Effective, The 2 Different Types of Decisions and How Great Leaders Respond To Each & Why Value To Overhead Ratio Is The Metric To Use When Selecting Investors
Disclosure
Schalit: Sequoia's Jim Goetz convinced Dashlane to raise equity over debt
“You know, we had just raised a thirty million round of debt with no plan on taking equity, and in the meeting, Jim made me see the opportunity I was potentially missing by not considering an investment from Sequoia, and he convinced me in that meeting to rethi…”
Emmanuel Schalit Dec 6, 2019 ▶ 32:30 20VC: Why Raising A Mega-Round Makes Your Life Harder Not Easier, Why Your Board Is Not Your Boss and Lessons on Successful Board Management & The Biggest Breakpoints in Company Scaling with Emmanuel Schalit, Founder & CEO @ Dashlane
Disclosure
Sequoia historically made the mistake of being too greedy on ownership
“I think one of the mistakes we made historically was to be a little bit too greedy, quite frankly, on ownership.”
Pat Grady Jul 1, 2019 ▶ 9:10 20VC: Sequoia's Pat Grady on What Sequoia Is Focused On Today, How Sequoia Think About Investment Decision-Making Processes & Why It Is Important To Trade A Few Points of Efficiency for Culture When It Comes To Attribution
Disclosure
Sequoia replaced individual partner names with 'Team Sequoia' in its CRM
“In one fell swoop, we actually changed all of the names in the database from individuals to the singular name Team Sequoia, and the point is that every prospect we're talking with, every company with whom we're in business today, they don't belong to an indivi…”
Pat Grady Jul 1, 2019 ▶ 14:04 20VC: Sequoia's Pat Grady on What Sequoia Is Focused On Today, How Sequoia Think About Investment Decision-Making Processes & Why It Is Important To Trade A Few Points of Efficiency for Culture When It Comes To Attribution
Disclosure
Qualtrics was Sequoia's most expensive software deal at the time
“That was a scary investment for us because at the time it was the most expensive price we had ever paid for a software company.”
Pat Grady Jul 1, 2019 ▶ 23:50 20VC: Sequoia's Pat Grady on What Sequoia Is Focused On Today, How Sequoia Think About Investment Decision-Making Processes & Why It Is Important To Trade A Few Points of Efficiency for Culture When It Comes To Attribution
Disclosure
Collin Reference-Checked Sequoia's Brian Schreier With 90% of His Portfolio CEOs
“When I chose Brian, Brian is actually one of the only investors during our series B that I didn't know much before. And so I hadn't built a relationship with him. And so I knew it was very important to understand if we would work well together. So I think I to…”
Mathilde Collin May 24, 2019 ▶ 25:54 20VC: Front's Mathilde Collin on Why Discipline Is More Important Than Vision, The Right Way To Approach Investor Updates and Director Reports & How To Effectively Structure 1-1s
Assertion Contradicted
Sequoia Capital Invests More Money Outside California Than Inside
“Today, Sequoia, and many of the other venture firms, they invest more money outside of California than inside of it”
Chris Olsen Apr 23, 2018 ▶ 10:13 20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learnings The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne
Opinion
Abrams: Top VC brand signaling matters much less than people pretend
“The idea that, that being a Sequoia company is going to be this huge advantage in terms of the branding, there's a lot of great investors these days that have great reputations, so chances are, if you have a bunch of Competitors. They probably have great names…”
Jonathan Abrams Aug 25, 2017 ▶ 18:23 20VC: Nuzzel's Jonathan Abrams on Why The Top VCs Do Not Have A PlayBook For Startup Success, Why Most Boards Are Not Successful & Why He Is Bored Of Hearing "I Fell Into VC"
Insight
Lemkin: Pitching founders outside the SaaStr community was a waste of time
“What I quickly learned is meeting with founders that weren't Part of the Sastra community, even back in a few years ago, was a complete waste of my time. I was completely undifferentiated as an investor. They didn't know who I was. Why not just go to Sequoia o…”
Jason Lemkin Mar 20, 2017 ▶ 3:56 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
Insight
Grady: Private equity financial modeling skills can hinder venture capitalists
“In a funny way, the skills that I learned there hurt me here, which might sound counterintuitive. But the skills that I learned there were things like building financial models, and being able to build a financial model is a very good way to break down a busin…”
Pat Grady Mar 13, 2017 ▶ 3:38 20VC: Sequoia Partner, Pat Grady on Why Data Is The New Oil, Why We Will See The Return of The Apprenticeship Model in VC & The Defining Characteristics of The Next Generation of Great Software
Assertion Partly supported
O'Driscoll: Kleiner and Sequoia paid nearly $100M post-money for pre-revenue Google
“The single most successful venture investment in the last probably 20 years was done in 1999, and it was done at an absurd valuation. That's Google. Kleiner and Sequoia paid almost a hundred posts for a pre-revenue company There was doing a search engine in 19…”
Rory O'Driscoll Nov 28, 2016 ▶ 8:35 20VC: Why Market Is More Important Than Team, The 4 Key Roles of A Board Member & Why Founders Get Market Sizing So Wrong with Rory O'Driscoll, Founding Partner @ Scale Venture Partners
Opinion
Small VC funds succeed by avoiding direct competition with Tier-1 firms
“The nice thing I like about some of these small funds is that they don't compete in their sector, in their geography, in their states. They don't compete with Sequoia and Excel, benchmark, and increase. So they are dominant. They will never lose to them becaus…”
Alex Bangash Jul 20, 2016 ▶ 20:37 20VC: Why The Whole Industry Is Backward Looking, The Best Funds Are Entrepreneur Led and Venture Is All About Access with Alex Bangash, Founder @ Trusted Insight
Prediction Not checkable as stated
Kim predicts only 1-2 of Cendana's 18 funds will reach Sequoia status
“I would say that to be realistic, maybe one or two out of You know, the 18 plus funds that we work with may ultimately emerge in that category”
Michael Kim Jul 6, 2016 ▶ 15:44 20VC: What It Takes To Raise A VC Fund & Investing in First Time Fund Managers with Michael Kim @ Cendana Capital
Prediction Not checkable as stated
Bek: VC funds will collaborate more on hardware and physical AI deals
“In, in hardware now, for instance, which is like the new thing, right, that's consensus physical AI the time to get validation is just a lot longer, and so you have to invest early, hoping that those companies can get through those phases of experimentation an…”
Julien Bek Aug 24, 2026 ▶ 12:26 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Disclosure
Bek Partners With Two to Three Founders Annually, Targeting 20 Boards
“In your career, you can make 20 investments. Some people do more than that. That's just not my style. I partner with two, three founders a year, and so in my career, I can expect to do basically be on the board of 20 companies. I'm not going to short myself. I…”
Julien Bek Aug 24, 2026 ▶ 13:49 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Opinion
Bek: Dean Meyer is Sequoia's top deal sourcer
“Time and time again, if I have to pick, I'll pick Dean Meyer, my partner who sits in Tel Aviv, but basically lives on plane. He's just a phenomenal human being. He was a professional football player for multiple years. He, so he has the competitive juices of m…”
Julien Bek Aug 24, 2026 ▶ 15:40 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Assertion Not checkable as stated
Bek: Sequoia has only executed tranche rounds a handful of times
“First, I've only seen that happen a handful of times, and I think that's probably giving us too much credit.”
Julien Bek Aug 24, 2026 ▶ 22:37 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Insight
Bek: Reference checks only work when asking outlier performers to judge talent
“You want to ask exceptional people if someone is exceptional, not good enough people, and that's often the problem with references.”
Julien Bek Aug 24, 2026 ▶ 48:08 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Disclosure
Bek Uncovered a Fraudulent Founder for the First Time in 2026
“I remember this year is the first year I uncovered a fraudulent founder”
Julien Bek Aug 24, 2026 ▶ 37:24 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Assertion Partly supported
Sequoia Won Citadel Securities Deal Through Partner's College Relationship
“Constantine Bueller my partner Helped us lead the investment in Citadel Securities, Ken Griffin's company. They had never taken outside capital. The reason we were able to invest is Constantine built a relationship with Ken since he was a student. He had been …”
Julien Bek Aug 24, 2026 ▶ 7:24 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Opinion
Bek: Luciana Lixandru is Sequoia's best company picker
“That one's easy. Luciana Alessandro my partner who actually Brought me into Sequoia. We worked together at Excel before, so I've worked with Luciana for most of my career now. She, you know, when I met her, she had just invested in Deliveroo then she did Frame…”
Julien Bek Aug 24, 2026 ▶ 16:37 Inside Sequoia's Investment Committee | How the SpaceX & Citadel Deals Went Down | Julien Bek
Assertion Supported
Stebbings: Sequoia leads funding for Valar Atomics at a $6 billion valuation
“Valar Atomics triples to six billion dollar prices Sequoia bets on nuclear for AI. It's a three-year-old small modular reactor company raised at two billion, now Sequoia leading around at six.”
Harry Stebbings Aug 5, 2026 ▶ 39:11 Leo Aschenbrenner's Situational Awareness Blows Up | Moonshot AI Raises $3.5B at $35B
Assertion Supported
Stebbings: Chai Discovery raised $400M at $3.8B valuation
“Four hundred million at a 3.8 billion dollar valuation led by Index, Kleiner, Sequoia, Dimension.”
Harry Stebbings Jul 16, 2026 ▶ 1:07:24 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Disclosure
Matan Grinberg Dropped Out of PhD to Pitch Sequoia Partnership
“There was so much momentum, I'm, you know, I, he answered my email, we got along well, I met the co-founder the next day, and I was like, you know what, fuck it. Dropped out, sent him a screenshot, and he was like, alright, you have a meeting with the Sequoia …”
Matan Grinberg Jun 13, 2026 ▶ 55:31 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Accel and Sequoia raised $4B and $7B AI growth funds
“Excel adds four billion leaders fund to follow into hot AI growth rounds. Sequoia four days ago raises seven billion dollar growth round growth fund.”
Harry Stebbings Apr 23, 2026 ▶ 1:05:59 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Assertion Supported
Sequoia took a 25% stake in Klarna at a $100M valuation
“They took a 25% stake at a hundred million dollar valuation, right? Yeah, at a hundred million dollar valuation.”
Sebastian Siemiatkowski Feb 16, 2026 ▶ 44:45 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Open Evidence raised at $12B valuation led by Thrive and DST
“Open Evidence raises at twelve billion dollars, labbed by Thriving DST. It's a 12 x valuation step up to where they raised at a billion dollars from Sikora at the start of the year.”
Harry Stebbings Jan 29, 2026 ▶ 39:08 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2026
Cahn: Sequoia Targets Only One or Two AI Investments Per Year
“I don't need to find 10 investment opportunities this year. I'd like to find one or two investment opportunities a year that I really love.”
David Cahn Oct 27, 2025 ▶ 13:46 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Disclosure
Sequoia Capital invested in AI voice startup Sesame
“We just, I think today right before this podcast, we announced our investment in a company called Sesame, which is an AI voice company, an AI conversation company.”
David Cahn Oct 27, 2025 ▶ 1:10:50 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2030
Cahn: Sequoia will only invest in defense startups every couple years
“I mean, my objective, I probably invested in a dozen AI companies in my career. I hope to invest in 20 more. My objective is not to invest in 20 more defense companies throughout my career. I think it's going to be a very small handful of companies. Maybe we'l…”
David Cahn Oct 27, 2025 ▶ 1:06:50 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Opinion
Cahn: Sequoia's primary value to portfolio startups is talent recruiting
“I think that's the number one way that companies do benefit from having Sequoia on the cap table, is that, is talent and recruiting, and we can talk more about that, and I'm fascinated by recruiting, and recruiting dynamics, so I do think Sequoia helps with th…”
David Cahn Oct 27, 2025 ▶ 36:40 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Disclosure
Cahn: Led Sequoia's investment in Clay at $1B+ valuation after long pivot
“Sequoia invested at the Series A in, I think, 2019. The company spent three or four years in the wilderness really figuring it out. I look at Kareem, I think the man is, like, enlightened from this experience. Like, a super painful experience. Varun ended up j…”
David Cahn Oct 27, 2025 ▶ 43:51 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Insight
Cahn: Scaling $0 to $100M ARR signals true product-market fit in AI
“Everybody's on the internet and everybody wants to buy AI. So if you have something really good, it's going to get adopted really fast. And so I do think to the point of playing the game on the ground and adapting to what you see in the market, the biggest thi…”
David Cahn Oct 27, 2025 ▶ 41:14 Sequoia Partner, David Cahn on Who Wins in AI, Defence & The New $0–$100M Playbook · 20VC with Harry Stebbings
Assertion Partly supported
Stebbings: Gong has surpassed $400M ARR and a $7B valuation
“The company has raised over six hundred million dollars from some of the best, including Sequoia, Thrive, Salesforce, and more, and Gong has surpassed Four hundred million in ARR, and serves thousands of customers, including multiple Fortune hundreds, and is v…”
Harry Stebbings Sep 12, 2025 ▶ 0:17 20VC: Why AI SDRs are BS and Do Not Work | How to Use AI in Your Sales Team and Process to Win Today | What Skills Do All New Reps Need to Have in an AI First World with Amit Bendov, CEO @ Gong
Opinion
Deeter: Sequoia Capital Continues to Deliver Platinum-Level Investment Returns
“Quantitatively, I think that, you know, Sequoia continues to mint platinum records.”
Byron Deeter Aug 25, 2025 ▶ 1:18:18 BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
Insight
Rory O'Driscoll: The best time to buy is when nobody else is buying
“The time to buy is when everyone else is not buying, especially when, let's put it out there, you're just little old scale, and you're not Sequoia who came in afterwards.”
Rory O'Driscoll Aug 7, 2025 ▶ 45:45 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Disclosure
Halligan regrets early HubSpot secondary stock sale to Sequoia Capital
“When we did our round, it was Sequoia. Sequoia came to us and said, we'd like to buy some of your shares in retrospect. It's a horrible financial decision for me, but it was good at the time. And I saw, I forgot a couple million dollars worth of HubSpot shares…”
Brian Halligan Aug 7, 2025 ▶ 33:22 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Disclosure
G Squared bought Bolt at $20 per share before Sequoia paid $260
“I think it was like, 20 bucks a share or something, and Sequoia did it at two 60.”
Larry Aschebrook Jun 16, 2025 ▶ 1:32:21 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Assertion Not checkable as stated
Sequoia refused to invest in Airwallex until Tencent committed
“The deal was stored and Sequoia was not willing to invest until Tencent kind of make a decision and are basically running out of money.”
Jack Zhang May 26, 2025 ▶ 44:46 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
Stripe CFO Will Gaybrick initiated acquisition talks with Airwallex in 2018
“Will Gabrick, the CFO at the time I think now he's CPO, he reached out through Sequoia and he said, just want another, have a conversation to see what you guys are up to.”
Jack Zhang May 26, 2025 ▶ 56:09 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
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