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 12 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
Stone's angel investment in Square yielded a 1,000x return
“Oh, that would probably be square because it's something like a thousand X return or something.”
Biz Stone Jan 8, 2021 ▶ 31:36 20VC: Twitter Co-Founder Biz Stone on The 3 Stages of Wealth, The Return To Twitter in 2017 and the Associated Missions and Challenges & Why Silicon Valley is not an "Insiders Only" Universe?
Assertion Supported
Cash App hedged Square when over half its revenue was exposed
“Half of their entire business, actually arguably more, was directly linked to small businesses being affected, but then the way Hashapp came about and became such a great hedge on the rest of the business, it's just been fascinating to watch.”
Avlok Kohli Dec 21, 2020 ▶ 9:34 20VC: Why the Theory of Pro-Rata is Often False, How Rolling Funds Impact Both Pricing and Competition & The Biggest Lessons from Working with Jack Dorsey with Avlok Kohli, CEO @ AngelList Venture
Assertion Partly supported
Dasilva: Early POS rivals raised hundreds of millions on simple initial products
“They started to come out and even though they were very simple, they had hundreds of millions of dollars being funneled into them.”
Dax Dasilva Aug 9, 2024 ▶ 10:44 Dax Dasilva: $900M ARR at $2.6BN Market Cap?! Lightspeed, The Most Undervalued Public Company |E1188 · 20VC with Harry Stebbings
Assertion Contradicted
Asparouhov: Square Spent Nothing on Marketing in Its First Five-Plus Years
“The company never basically had to spend on marketing for the first year, sort of five plus years of its life.”
Delian Asparouhov Jul 29, 2024 ▶ 12:34 Delian Asparouhov: Inside the Walls of Founders Fund: What the World Does Not See | E1183 · 20VC with Harry Stebbings
Assertion Partly supported
Reses: Dorsey Locked Himself in Square's Office to Build Bitcoin Integration
“I remember in 2017, maybe, yeah, it was end of 20 16 when Jack wanted to put Bitcoin into Cash App. And he, ah, two engineers sat, ah, on the sixth floor of 14 55 market and wouldn't leave the office until they were able to build that product.”
Jackie Reses Mar 31, 2023 ▶ 59:13 Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996 · 20VC with Harry Stebbings
Assertion Partly supported
Reses: Square Mobilized Entire Workforce as 24/7 PPP Loan Reviewers During COVID
“We developed PPP, this is at Square, in a crisis. And we ended up with a core team of people working on it, and then we literally got the entire company of Square to volunteer for us to be, you know, loan reviewers twenty-four-seven during that period of time,…”
Jackie Reses Mar 31, 2023 ▶ 16:53 Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996 · 20VC with Harry Stebbings
Assertion Contradicted
Reses: Square was the only tech company to build a bank
“And so, you know, and we built a bank at Square. We were the only tech company to ever have built a bank, right?”
Jackie Reses Mar 13, 2023 ▶ 18:14 Jackie Reses & Kris Dickson: What Happened with SVB? Are VCs to Blame? | E988 · 20VC with Harry Stebbings
Assertion Supported
PayPal and Square surpassed Bank of America and Goldman Sachs in 2020
“Last year, you probably know this, but you know, you've heard some of these stats, like PayPal became more valuable than Bank of America and Square became more valuable than Goldman.”
Nick Shalek Jul 26, 2021 ▶ 23:38 20VC: Ribbit Capital's Nick Shalek on How To Think Through Ownership and Price Sensitivity, When More Money and Pre-Emptive Rounds are Good vs Bad & Investing Lessons from Yale's David Swensen
Assertion Partly supported
Ascher: Jack Dorsey's Square Series A pitch listed 75 company risks
“I remember seeing Jack Dorsey's pitch for squares series a, and he literally started with like, these are 75 things that could kill this company in the short term.”
Brian Ascher May 31, 2017 ▶ 12:24 20VC: How Both Founders & GPs Should Construct Their Pitch, Why VCs Are Eternal Optimists & What Makes The Best Post-Investment VC/Founder Relationship with Brian Ascher, Partner @ Venrock
Assertion Partly supported
Rajaram: PayPal raised prices five times in three years early on
“And he told us that PayPal back in the day, raised prices five times. In three years, because there's such stickiness. They knew their customers really couldn't do anything.”
Gokul Rajaram Mar 16, 2026 ▶ 40:34 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Assertion Supported
Square reduced merchant onboarding from weeks to instant approval for 93%
“Before Square, people sometimes forget, before Square in the United States to get access to the credit card infrastructure. You can apply, in quotes, for a merchant account And that would take three weeks. It would require a credit check and a manual investiga…”
Keith Rabois Sep 30, 2021 ▶ 22:01 20VC: The Opendoor Memo: Keith Rabois on The Origins of Opendoor from a Conversation with Peter Thiel, Why Cash is Not a Competitive Moat for Startups Today and What People Misunderstand About Black Swan Events in Real Estate and How it Impacts Opendoor
Assertion Supported
Hefetz: Square Capital Is a Multi-Billion Dollar Business Within Square
“Today, Square Capital is probably a multi-billion dollar business within Square itself.”
Adena Hefets Mar 13, 2020 ▶ 4:19 20VC: 3 Addictions Of Early-Stage Startup Founders, How Founders Should Strategically Think Through Unit Economics From Day 1 & Why Micromanagement Can Be Beneficial In The Early Days with Adena Hefets, Co-Founder @ Divvy Homes
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