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.
why aren't all 41 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
Dasilva: Simpler merchants are better served by Clover, Square, or Shopify
“You know, you may be better served by a Clover or a Square or a Shopify.”
Reses: Raw Intelligence and Grit Beat Domain Knowledge for Novel Products
“I would rather focus on things like raw intelligence, judgment, curiosity, grit, ability to manage ambiguity, rather than looking for things like domain knowledge or operators with prior scale experience, you know, that's another big mistake where you assume b…”
Gurley: Benchmark passed on Jack Dorsey's Series A pitch for Square
“Another one that's very similar, and it wasn't me, it was a different partner, but I don't think I was helpful, was Jack That brought Square to us on the A.”
Square Wallet failed because Square backed it too long without 10x value
“We tried Square Wallet. It was unsuccessful. We backed it for too long. We kept it going for too long. I think there wasn't enough focus on creating the same kind of 10 X value proposition in that product that Square's core product originally had.”
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.”
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.”
Kaul: Khosla's biggest wins came from regulated sectors like healthcare and food
“Square is in the banking industry. Gardent and Oscar have been in the healthcare industry. Impossible Foods is in the food industry. These are, you know, very, very regulated markets, and they've been some of our biggest wins.”
Lanman invested in Square without understanding the payments industry
“I mean, my first one was square and I had looked into payments a bit for Microsoft because, you know, we had so much cash in the balance sheet that one of the things we could have done was become a bank. And we could have gone after digital currencies and stuf…”
Hoover doubts a single person can run Twitter and Square simultaneously
“I don't know how he can do it. I don't know. I just don't know how anyone can run two companies, especially two massive prominent companies as a single person.”
Rajaram: Square had 11 products generating over $50M each upon his departure
“When I left, we had, I think, 11 products each doing more than fifty million in revenue”
Hoffman passed on early investments in Stripe and Square
“I got pitched early in stripe and square, and I Didn't do the investments because I knew how hard payments was from PayPal.”
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.”
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.”
Rabois: Khosla and Botha warned me 11 direct reports was excessive
“I used to get yelled at. I went pretty flat at square when I was running hot at like 11 and like Vinod and Roloff gave me feedback that that was too much.”
Rabois: Taking eight years off operating caused severe executive skill atrophy
“Like I took eight years between square and taking over, you know, CEO of open store. It's like muscle atrophy, you know, kind of going with the same metaphor. And it took me the first year at least to get back to be decent as a CEO.”
Franceschetti: Everything at Eight Sleep is public internally except compensation
“Everything is, everything, this is another rule from Keith, I think, from the, his time at Square, where, so essentially everything is public in our company except comp. Usually comp, you don't want to share it, but everything else is shared.”
Reses: Square Built Products Directly Inspired by Alipay's Capabilities
“We drew a lot of inspiration from that in what we built at Square, Because we had seen what was being built at Alipay with firsthand insight, and were able to look at that and draw inspiration from it.”
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.”
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,…”
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?”
Tung: GGV Invested in Square at an $800 Million Valuation
“We invested in Square at about an eight hundred million dollar valuation, and then when a company went public, the valuation for the first two years was not great, but thereafter, they really found the right market fit and found the right engine for the scale,…”
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.”
Morris: Bank executives no longer believe they can outcompete fintech giants
“Five years ago, the people were saying, this is a flash in the pan, this is not going to work, we are better at technology, we have these customer relationships, look, we've got all these branches. This whole fintech thing is tulips in Amsterdam. I think there…”
First Round Capital's Second Fund Included Uber, Square, and Roblox
“It turns out that fund had Uber and Square and Roblox in it.”
Leaders must sometimes act as islands and demand disagree-and-commit
“There will be many moments in a company where you're, as a leader, you will be an island, and you will need to make a decision that you think is best, and you will expect your team to disagree and commit.”
Khosla Ventures invested in Square's Series A at a $30M valuation
“You know, I think when we invested in the Series A of Square, I think it was around a thirty million dollar valuation. It was Jack and Jim in a PowerPoint.”
First Round flexed on valuation to back Square at $40M pre-money
“So when Jack was starting square and we met with him, he said, well, you know, if you thought Twitter was expensive, this is going to be even more expensive. And his first round was at a 40 pre and we learned our lesson and we were fortunate enough to be the S…”
Loftus: Pre-term sheet Silicon Valley M&A deals have under 50% close rate
“By and large, and this isn't necessarily true for Square, but across Silicon Valley, once that term sheet is signed, that's a pretty high outcome rate. I wouldn't want to guess a percentage, but those deals usually close, but before you have a term sheet, befo…”
Loftus: Tech M&A Valuations Cannot Rely on Standard Profit Models
“Pricing tech companies in particular is incredibly difficult, especially I've spent most of my career in consumer internet. You're buying a lot of companies where you're looking at talent and technology are the main drivers, and so you can't sort of build a mo…”
Loftus: Active acquirers should review M&A outcomes two to four times yearly
“I think the important thing is to have a systematic check back, especially if you're doing a significant amount of M&A to say, you know, somewhere between two and four times a year, we're all sitting down and we're going over the metrics on outcome for each de…”
Mark Pincus missed investing in Square because he thought he was too busy
“I don't know that it was offered to me, but Square, when Jack Dorsey was walking out in the hallways at a conference with a dongle, and I thought I was too busy.”
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.”
Finkelstein: Bundling point solutions for retail creates an inefficient 'Frankenstein' system
“If you don't use Shopify and you don't want to use our platform to sell in all these different places, you can bundle up a bunch of different single point solutions. You can do just e-commerce plus just point of sale plus, you know, maybe a card reader from li…”
Twitter and Square have no operational or business conflicts
“The good news is the companies are not conflicting in any way, so there's no chance of him having some kind of awkward situation where he feels he's on the fence because he sort of has two different companies to deliver value to.”
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.”
Dasilva: Lightspeed should have launched its cloud product earlier
“We could have done it a couple of years earlier and it could have benefited us to have done it a few years earlier. Our cloud product was out by, you know, 2000 13. You know, Square some other folks like Shopkeep had which we acquired later maybe had a couple …”
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…”
Hefetz: Square Capital Is a Multi-Billion Dollar Business Within Square
“Today, Square Capital is probably a multi-billion dollar business within Square itself.”
Khosla: Square was just a hardware dongle when Khosla Ventures invested
“Take something like Square. What it is today wasn't part of the plan when we originally invested. It was a hardware dongle.”
Loftus: Major tech corp dev teams are perpetually overwhelmed by deal flow
“Corporate development teams across the Silicon Valley, including at Facebook and Google, are small compared to the opportunity set that they're evaluating. There's just so many companies out there all the time to evaluate, and if you're even at Square, you kno…”