The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

clear all ✕

why aren't all 32 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

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 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 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 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 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
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 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 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 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 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 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
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.