Square

“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.”

“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.”

“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.”

“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…”

“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.”

“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.”

“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…”

“I'm going to roll out, even at a small company in a square, somewhere between six and 10 people who are going to be involved in a deal process, and they're all going to be asking the CEO founder for stuff.”

“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…”

“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…”

“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…”

“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…”

“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…”

“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.”

“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.”

“Take something like Square. What it is today wasn't part of the plan when we originally invested. It was a hardware dongle.”

“Today, Square Capital is probably a multi-billion dollar business within Square itself.”

“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.”

“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.”

“Oh, that would probably be square because it's something like a thousand X return or something.”

“It turns out that fund had Uber and Square and Roblox in it.”

“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…”

“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.”

“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,…”

“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…”

“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.”

“And so, you know, and we built a bank at Square. We were the only tech company to ever have built a bank, right?”

“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.”

“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.”

“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,…”

“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…”

“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.”

“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.”

“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.”

“The company never basically had to spend on marketing for the first year, sort of five plus years of its life.”

“You know, you may be better served by a Clover or a Square or a Shopify.”

“They started to come out and even though they were very simple, they had hundreds of millions of dollars being funneled into them.”

“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 …”

“I got pitched early in stripe and square, and I Didn't do the investments because I knew how hard payments was from PayPal.”

“When I left, we had, I think, 11 products each doing more than fifty million in revenue”

“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.”