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Assertion Contradicted
Pishevar: Benchmark Hired Private Investigators Against Naval Ravikant
“There's a history of VCs who have done this type of thing and in Benchmark's case, they did it against Naval. They hired private investigators and Naval Ravikant. He had a company called eGroups, and he got thrown out of it.”
Shervin Pishevar Jan 13, 2025 ▶ 57:39 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Partly supported
Asparouhov: Benchmark cornered Travis Kalanick in a hotel room after mother's death
“Travis committed no crime and they, you know, sort of ousted him despite the fact that, you know, they actually didn't necessarily, you know, have the legal control to do so. They just cornered him in a hotel room, you know, two days after his mother had passe…”
Delian Asparouhov Jul 29, 2024 ▶ 45:21 Delian Asparouhov: Inside the Walls of Founders Fund: What the World Does Not See | E1183 · 20VC with Harry Stebbings
Assertion Supported
Siroker: Top VC funds will break ownership minimums for hot startups
“Yeah, the best investors benchmark and recent, they will invest less than their supposed minimums for the right company.”
Dan Siroker May 15, 2024 ▶ 29:43 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Assertion Supported
Rajaram: Benchmark made money on WeWork by investing early
“Even in V work benchmark made money. Genchmark made money at WeWork because they invested early enough.”
Gokul Rajaram Mar 16, 2026 ▶ 49:24 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Assertion Supported
Randle: Benchmark's top fund investments outperform all post-ChatGPT OpenAI rounds
“Out of our last fund, our five best investments in that last fund today held at LRP last round price are about a 60 X. We have two 30 X's and we have two 20 X's. Since ChatGPT was released, there isn't an open AI round that touches That return multiple and tha…”
Everett Randle Nov 10, 2025 ▶ 34:15 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Assertion Supported
Jason Lemkin: Benchmark is no longer in top VC conversations on X
“If you look on social media, benchmark isn't listed the way Andreessen and Sequoia was like it was a generation ago. It's just not, does it matter? Harry, Harry's built a big brand. He's concerned. It matters. You could argue both sides, but when the industry …”
Jason Lemkin Aug 7, 2025 ▶ 1:23:44 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Benchmark led $75M round for Chinese AI startup Manus
“Manus raised seventy five million for its last valuation led by Benchmark. It's a Chinese company.”
Harry Stebbings May 1, 2025 ▶ 1:05:25 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
Assertion Supported
Benchmark sued Travis Kalanick in Delaware court over Uber board seats
“About in early August They then sued in Delaware courts after they had already gotten rid of Travis. They then sued to get rid of him and his two board seats that he had gotten that he hadn't appointed yet. So three board seats. So they wanted, you know, effec…”
Shervin Pishevar Jan 13, 2025 ▶ 42:02 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Partly supported
Delaware judge rejected Benchmark's effort to remove Uber board seats
“We make our arguments and the judge finds with us and rejects Benchmark's attempt to get rid of the three board seats.”
Shervin Pishevar Jan 13, 2025 ▶ 43:08 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Supported
Gurley: Benchmark practices stage discipline, not price discipline
“I think he's misinterpreting price discipline for stage discipline. So we have notably stayed focused on early stage investing, whereas most people have moved to multi-stage. I think that makes the impression look like that your price discipline because you're…”
Bill Gurley Feb 9, 2024 ▶ 9:45 20VC: Doug Leone, Bill Ackman, Bill Gurley and Orlando Bravo on "Does Price Matter"; When to Pay Up vs When to Stay Disciplined, The Biggest Lessons on Price Discipline from 8 of the World's Best Investors
Assertion Supported
Lemkin: Data shows operator VCs do not outperform professional venture investors
“I remember a few years ago, I forget whose analysis was, there was no advantage, like, to being an operators were no better than professional. That may not include pre-seed, right, or other things. But it wasn't, when I wrote this up a few years ago, that what…”
Jason Lemkin Nov 3, 2023 ▶ 13:20 Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077 · 20VC with Harry Stebbings
Assertion Supported
Tavel: Benchmark does not delegate operational work to platform teams
“At Benchmark, our model is that we don't delegate any part of our job. We've tried not to scale our business and just be focused on scaling the founders with whom we work. And so that means that there isn't a talent partner that is doing recruiting calls for m…”
Sarah Tavel Nov 23, 2020 ▶ 30:50 20VC: Benchmark's Sarah Tavel on Why Chasing GMV Will Lead To The Wrong Direction, The 2 Crucial Tipping Points For Marketplace Adoption, Why UGC Plays Are Like Marketplaces & How To Determine Between Existential and Non-Existential Risk
Prediction Held up
Gurley: Benchmark will not invest in a startup without a board seat
“We won't invest without a board seat. It's a tenant that we have that a lot of other firms don't.”
Bill Gurley Jun 24, 2019 ▶ 14:27 20VC: Benchmark's Bill Gurley on 5 Traits Benchmark Look For When Adding To The Partnership, Why The Abundance of Capital Is Today's Biggest Challenge in VC & The Right Way To Think About Market Size When Assessing Opportunities
Assertion Supported
2018 crypto startups secured nine-figure valuations based solely on white papers
“And then what's different though, from ad tech is that, and it makes it even harder is that you're often investing in a white paper or a deck. There's no code or traction that you get to invest behind. The company often has, you know, over a hundred million do…”
Sarah Tavel Sep 24, 2018 ▶ 26:58 20VC: Benchmark's Sarah Tavel on Why Investing Success Lies In Small Markets Adjacent To Very Large Ones, Why You Have To Be Judicious On When To Pay Up vs Be More Price Sensitive & Why Crypto Investing Is Like The Early Days of AdTech Investing
Prediction Held up
Top VC firms will be forced to adapt to new funding models
“Sequoia, Benchmark, Andreessen Horowitz, they're not going away anytime soon. This isn't like, we're out to beat them and kill them. Not in the same way Airbnb is not going to delete hotels overnight. It's going to change how hotels work. I think that's a bett…”
Dustin Dolginow Feb 10, 2016 ▶ 18:55 20VC: The First Online Venture Fund Built On AngelList with Dustin Dolginow @ Maiden Lane
Assertion Partly supported
O'Driscoll: Benchmark, Foundation, and Eclipse each hold 8–9% of Cerebras
“Ah, you just, because you see, Harry, you just listen to Twitter, but if you go and you actually look up the S-one, they have eight or nine percent ownership, right? Because I do these things, because every VC reads an S-one the same way, you read the front pa…”
Rory O'Driscoll May 14, 2026 ▶ 53:33 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
Assertion Supported
Benchmark offers backdated carry pools to newly joined General Partners
“I also know Benchmark are extremely generous in terms of like backdated carry and being brought into this carry pool for this fund with fireworks and with McCore and with Legora and with Manus and with many others.”
Harry Stebbings Oct 23, 2025 ▶ 3:04 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Assertion Contradicted
Junestrand: 99% of Benchmark portfolio companies reach Series B
“I think there's some stats that, like, 99% of benchmark companies end up raising a Series B. That's the only stat you need to hear.”
Max Junestrand Aug 15, 2025 ▶ 32:23 20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand
Assertion Supported
Asparouhov: Tier-one VC firms Benchmark, a16z, and Sequoia ousted founders recently
“There are firms, tier ones that I mentioned, Benchmark, A-sixteen Z, Sequoia, et cetera, all have examples of sort of founder oustings in the past sort of decade.”
Delian Asparouhov Jul 29, 2024 ▶ 43:27 Delian Asparouhov: Inside the Walls of Founders Fund: What the World Does Not See | E1183 · 20VC with Harry Stebbings
Assertion Partly supported
Grimshaw: Benchmark is first institutional capital in 50-60% of deals
“I think it's something like 50 to 60% of all the investments we make, we're the first partner. I might want to use the word real, right? But like first sort of institutional investor, so to speak.”
Miles Grimshaw Sep 18, 2023 ▶ 41:06 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Assertion Partly supported
Grimshaw: Roughly one-third of Benchmark investments occur at inception
“I think it's something like 30 odd percent. We're like literally the first investment. We don't use the term incubation. I'm sure there's a bunch of things we've done. People would call incubations. We don't use that term, but like, I think probably about a th…”
Miles Grimshaw Sep 18, 2023 ▶ 41:24 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Assertion Contradicted
Benchmark turned a $33M Uber investment into $10B in four years
“Bill Gurley was on our board, lost her nerve. And the reality is there's another economic principle called loss aversion, right? If you invest thirty three million dollars in Uber and it looks like ten billion four years later, ten billion on a thirty three mi…”
Emil Michael Oct 25, 2022 ▶ 39:04 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings
Assertion Supported
Gurley: Benchmark Provides Equal Financial Economics to All Investment Partners
“Benchmark's structured in a very unique way where our investment partners all have equal economics, and I think that does an amazing job of speaking to the newer members of our team that their voice matters,”
Bill Gurley Jun 24, 2019 ▶ 20:11 20VC: Benchmark's Bill Gurley on 5 Traits Benchmark Look For When Adding To The Partnership, Why The Abundance of Capital Is Today's Biggest Challenge in VC & The Right Way To Think About Market Size When Assessing Opportunities
Prediction Partly held up
Lasky: Benchmark partners will retire within the next decade
“Well, I think we have an opportunity as the current group of partners comes to the, in the next decade or so, comes to the end of their careers to really reinvigorate the firm with youth, and I think an increasing awareness of diversity.”
Mitch Lasky Jul 10, 2017 ▶ 20:33 20VC: Benchmark's Mitch Lasky on The Snapchat Journey From Series A to IPO, Why Small Is Beautiful In Venture Partnerships & Why Venture Is Very Much Like Hollywood
Assertion Partly supported
Enterprise AI Startup Town Valued at $1B by Index and Benchmark
“Consensus status as well in the B to B world, because town, which is kind of the B to B enterprise alternative has also been funded to the tune of a billion dollar price by index. And I think it was benchmark who co led that round.”
Harry Stebbings Sep 3, 2026 ▶ 34:49 NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
Assertion Supported
Stebbings: Benchmark returned roughly 640x on Uber versus 25x on WeWork
“Uber made benchmark roughly 640 X versus around 25 X with WeWork.”
Harry Stebbings Jul 29, 2026 ▶ 52:47 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Assertion Supported
Randle: Tech offers far more $100B opportunities today than 15 years ago
“The outcomes are much, much, much larger in today's in today's technology landscape than they were 10 years ago, 15 years ago, there's more bites at, you know, potential hundred billion dollar, trillion dollar companies.”
Everett Randle Nov 10, 2025 ▶ 39:06 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: Benchmark will hire replacement partners and remain successful
“Benchmark will be fine. So let's start with that. They'll find two other people to fill those slots and they'll be fine because they've been fine for 30 years.”
Rory O'Driscoll Jul 31, 2025 ▶ 2:20 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
Assertion Supported
Tavel: Benchmark partners make only 1-2 new investments annually
“Our way of thinking of things that benchmark is that each of us makes one or two new commitments a year.”
Sarah Tavel May 6, 2024 ▶ 30:17 Sarah Tavel: Will Foundation Models Be Commoditised? | E1149 · 20VC with Harry Stebbings
Assertion Supported
Grimshaw: Benchmark backs only about three inception-stage startups per year
“The N of that in a given year, even for that percentage is like three companies, right? And so it's not like we're doing 30, ah, that way and again, you know, so, so the N is small.”
Miles Grimshaw Sep 18, 2023 ▶ 42:24 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Assertion Partly supported
eBay's original business plan and Benchmark investment focused solely on collectibles
“Jeff Skoll wrote the business plan for eBay with Pierre. And I got a copy of it when I joined the business and they were focused entirely on the collectibles market. Now their argument was collectibles market in in the U S I think was a hundred, you know, it w…”
Jeff Jordan Jan 16, 2023 ▶ 24:20 a16z GP Jeff Jordan: The Ultimate Guide to Two-Sided Marketplaces | 20VC #966 · 20VC with Harry Stebbings
Assertion Supported
Gurley: Benchmark Approves New Investments by Majority Partner Vote
“In that way, I thought that was interesting way she had phrased that, and so we simply have a discussion, and if a majority of the partnership wants to move forward, we move forward.”
Bill Gurley Jun 24, 2019 ▶ 21:02 20VC: Benchmark's Bill Gurley on 5 Traits Benchmark Look For When Adding To The Partnership, Why The Abundance of Capital Is Today's Biggest Challenge in VC & The Right Way To Think About Market Size When Assessing Opportunities
Assertion Supported
USV and Benchmark are rare exceptions to VC fund bloat
“Union Square Ventures, Benchmark, or some other exceptions to what I said.”
Ryan Caldbeck Nov 2, 2018 ▶ 14:05 20VC: Ryan Caldbeck on Why The Business Model of VC is Broken, Who is To Blame, How The Best Funds Will Use Data Intelligently Moving Forward & Whether We Are In A Consumer Bubble Or Not?
Assertion Supported
Vishria: Benchmark always takes a board seat in its investments
“We take the board seat, we aim and aspire to be the entrepreneur's first call. That's a standard we hold ourselves to.”
Eric Vishria Sep 25, 2017 ▶ 11:32 20VC: Benchmark's Eric Vishria on Why Career VCs Have Advantages Most Under Appreciate, Why We Are In An Infrastructure Renaissance & What Makes The Best VC Partnership
Assertion Supported
Vishria: Benchmark relies on a partner advocacy and voting system for investments
“Our investment process is one of advocacy of voting. So basically, there is an advocate. So one of the five of us falls in love with something, is probably the best way to describe it gets really excited about the entrepreneur and the opportunity All five of u…”
Eric Vishria Sep 25, 2017 ▶ 20:35 20VC: Benchmark's Eric Vishria on Why Career VCs Have Advantages Most Under Appreciate, Why We Are In An Infrastructure Renaissance & What Makes The Best VC Partnership
Assertion Partly supported
Benchmark: Snapchat was 12 people in a dining room at Series A
“When we invested in the Series A, the company was essentially a dozen people camping out in the dining room of Evan's dad's house in Los Angeles.”
Mitch Lasky Jul 10, 2017 ▶ 15:45 20VC: Benchmark's Mitch Lasky on The Snapchat Journey From Series A to IPO, Why Small Is Beautiful In Venture Partnerships & Why Venture Is Very Much Like Hollywood
Assertion Supported
Kimball: Benchmark operates with equal partner ownership and no support staff
“There's no more opposite approach in the industry than the one that Benchmark takes, for example. And this is a very small VC fund, you know, not necessarily in dollars, although it's not, it's by far not the largest. But, you know, it's a small number of part…”
Spencer Kimball Apr 14, 2017 ▶ 12:15 20VC: How Investors Can Get Into The Best Deals & Why Founders First Point Of Contact Should Be With The Investment Decision-Maker with Spencer Kimball, Founder & CEO @ Cockroach Labs
Assertion Partly supported
Soltero: Hyperic bootstrapped two years before Accel/Benchmark funding and $420M exit
“We ended up bootstrapping Hyperic actually for two years before we raised money ultimately from Excel and Benchmark who were great investors. And helped us take this thing to you know, ultimately a four hundred and twenty million dollar acquisition by VMware, …”
Javier Soltero Sep 6, 2015 ▶ 5:33 FF 012: Acquired by Microsoft for $200m with Javier Soltero @ Microsoft
Assertion Supported
Randle: Each Benchmark GP holds a 25% equal stake in the firm
“Like each of us is 25% of benchmark, and we work really well together, and we're a super tight-knit team, but each of us has our own styles.”
Everett Randle Nov 10, 2025 ▶ 46:25 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Assertion Supported
Everett Randle joins Benchmark as GP from Founders Fund
“Topic number one, Everett Randall joins Benchmark. Benchmark don't add partners very often. It's a big news announcement that he's joining. Joins Benchmark as their latest GP. He was with Kleiner and he was with Founders Fund before.”
Harry Stebbings Oct 23, 2025 ▶ 0:53 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Assertion Contradicted
Lazarte: Benchmark's current venture fund size is $600 million
“It's actually a six hundred million dollar fund.”
Victor Lazarte Apr 14, 2025 ▶ 1:05:16 Benchmark GP, Victor Lazarte: The 3 Traits All the Best Founders Have · 20VC with Harry Stebbings
Assertion Supported
Hiremath: Mercor's board consists only of its co-founders and Benchmark
“It's, you know, Brendan, Suri, and I, and Benchmark on the board.”
Adarsh Hiremath Feb 20, 2025 ▶ 38:18 Adarsh Hiremath @ Mercor: The Fastest Growing Startup in Silicon Valley | E1261 · 20VC with Harry Stebbings
Assertion Partly supported
Benchmark invested $10M in Uber at $50M valuation in 2011
“Benchmark invested in March, 2011 at a, I believe it was a fifty million dollar pre-money valuation. They put ten million in.”
Shervin Pishevar Jan 13, 2025 ▶ 51:42 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Supported
Jordan: Benchmark Originally Invested in eBay as a Collectibles Marketplace
“When Benchmark wrote the joint, Bob Cagle and Benchmark wrote the check, he was investing in a collectibles marketplace.”
Jeff Jordan Jan 24, 2023 ▶ 18:44 The Ultimate Guide for Building a Two-Sided Marketplace | a16z's Jeff Jordan · 20VC with Harry Stebbings
Assertion Supported
Stitch Fix Reached Cash Flow Positivity in 3 Years on $42M Raised
“Prior to their IPO in 2017, Katrina raised just forty two million dollars in venture funding, from some of the very best in venture, including Bill Gurley at Benchmark and Steve Anderson at Baseline, and in just six years, Katrina took the company from foundin…”
Harry Stebbings Dec 3, 2020 ▶ 0:28 20VC: Stitch Fix Founder Katrina Lake on Growth vs Profitability, Her Biggest Lessons From Working with Bill Gurley at Benchmark and The Importance of Mental Flexibility as a Leader
Assertion Supported
Digits Raised Over $32M From Benchmark, GV, and Angel Founders
“To date, Wayne and Jeff have raised over thirty-two million dollars for Digits, from some of the best in the business, including Peter Fenton at Benchmark, and Jess Verrilli at GV, and then also the most incredible base of angels, with the founders from Box, G…”
Harry Stebbings May 1, 2020 ▶ 0:28 20VC: Framework For Hiring The Best Talent 100% Remotely, Raising $32M From Benchmark and GV Pre-Launch and How To Think Through Capital Efficiency and Runway Today with Jeff Seibert and Wayne Chang, Co-Founders @ Digits
Assertion Supported
Matt Mochary's coaching client list includes partners at Benchmark, Sequoia, and Kleiner
“On the VC side, Matt has worked with the likes of Peter Fenton at Benchmark, Several Sequoia partners, Hemond at GC, and Mamoon at Kleiner, to name a few. As for founders, Matt's worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport, and many mor…”
Harry Stebbings Mar 9, 2020 ▶ 0:24 20VC: Matt Mochary, Coach To Silicon Valley's Leading VCs & Founders on How To Deal with Imposter Syndrome and Self-Doubt, How To Manage Fear and Anger & Why Board Seats Are The Death of Investors
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