Square

“I think I learned a lot there from my days at Square, where that's kind of how Sarah and Jack talked about the IPL. It wasn't the finish line. It was just another milestone amongst many milestones.”

“Square Capital. It was actually a Hack Week project. That a bunch of folks had started, and so I took over for this amazing Hack Week project, and I ended up going to run literally this thing that had started. It had 10 colleagues that were pulled together fro…”

“He took three engineers and he sat at the corner of the sixth floor at 14 55 market and didn't leave the office for three days. And so everyone sat there, he included, and they coded up the crypto trading platform.”

“And so we almost got held up that first quarterly earnings period because we couldn't get accountants in the SEC to agree that we were accounting it correctly and then actually get it in the numbers in order to launch the product.”

“Like, honestly, the worst job I ever had was being the head of HR at Square. So I ran these financial services products, and I ran HR. And the HR job at Square Could have been okay, but for the fact that Jack is running Twitter, and any time that there was dra…”

“After seeing all the success that Square had, Amazon, big baby Amazon, they launched a competitive product called like Amazon Local Register. It's a mobile credit card reader for small businesses, and it had lower fees. So it was way cheaper. It's backed by a …”

“The team you build is the company you build. And that adage is the most important thing when you're creating a startup. People get distracted with the market, with customers, with the product, with technology, ultimately it's a team. If you have the right peop…”

“Jack came out and just said, no, I'm pivoting the entire infrastructure of this company for an AI era. We think you're going to need to be remote. Because you're going to move faster if you're remote, and so he's kind of laid out a whole vision about how he wa…”

“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.”

“Airbnb, DoorDash, Unity, Snowflake I'm sure I'm missing a few others. Mongo, Square.”

“Square is cutting from 10,000 to 6000 employees, a 40% reduction.”

“Basically, if you didn't have a 100,000 dollars of business, You would not take credit cards. That was sort of the cutoff. Because it was too expensive. You had to have a sponsoring bank. You had to have a certain level of accounting. You had to have a physica…”

“And at the time, it was this big port at the bottom, and you had to pay Apple for access to that port. You had to pay Apple for a special chip that allowed you to build your hardware, and then you had to Convince them to let you do it, and at the time the iPho…”

“And each reader cost you how much? 97 cents.”

“Originally the company was called Squirrel, because we thought squirrels, you know, were cute and saved nuts and thought that was a good payment name. Turns out it was a good payment name, and another company had a payment system called Squirrel, so we pivoted…”

“Everything worked, but it was breaking many, many laws and rules.”

“I remember one guy telling me, oh, Amazon's gonna attack you? Don't worry, I'm on the board of Amazon, and I developed Amazon Prime, and we can get them to leave you alone. Like, if you take our money, we'll guarantee that Amazon doesn't attack you.”

“We had several dozen term sheets. I mean, I don't think we had More than three pitches that didn't result in offers.”

“If you want to know the real story, just get the first issue of Make Magazine. It's publicly available. It describes exactly what we were building, and I knew that when I went to Bob.”

“And it failed so badly that Amazon gave us all their soon-to-be former customers and mailed them a Square reader and said, we're out, go to Square.”

“If you invent something truly new, you're not inventing one thing. You're inventing a stack of things, and that invention becomes its own protection. And as long as you behave properly, I mean, it turns out there are a bunch of rules that if you follow these r…”

“So pure self-serve product would never have any reviews of any kind. You're going to be immediately activated Go on, and we'll do checks in real time based on what you're doing versus banning you or stopping you.”

“After I invested in Figma, I joined Square one and a half years later. I tried to basically push Figma down top-down into the design team, because I didn't design. I said, you've got to use Figma. The designers refused to use it. They were using a tool called …”

“My predecessors had the great foresight to invest in Stripe and Square and Klarna and Marquetta and a lot of these companies as they were getting going.”

“We had a lot of momentum in each of these silos, be it cash app, be it after pay. Be it square or even title or music streaming service. And no one was really talking to each other. No one was really aligned on technical strategy on what we even wanted to be f…”

“You know, I remember even in the early days, people used it to pay each other as a peer to peer money transfer system. And that's why we built Cash App and that was really successful on the back of that.”

“I remember I was an investor in Square and the Stripe founders pinged me and asked if I wanted to invest. And so I pinged one of the key executives at Square and said, Hey, do you think this is a conflict? And he said, absolutely. This is a conflict. You shoul…”

“At PayPal, we had of the 254 employees we had in Mountain View when we went public to maybe three had any expertise in financial services at Square. If you included me, which is I'm certainly not a prototypical financial services guy of the first 300 employees…”

“A company like Square, half the revenue today comes from a product called Cash App that hadn't launched for the first five years in the company's life.”

“Hired two, at least two people off my soccer team that worked at Square. They started a company that's a very good company called Fair.”

“A lot of these vendors would promise you some sort of silver bullet saying like, this is the, you know, one silver bullet to solve all your identity problems, fraud would disappear, you know, very, very extreme claims. But the reality for us as a business and …”

“If there were one thing I credit to, the best thing that made personas, like, increase the persona success, it was how long I was at Square. And I'd like to say, you know, I was dedicated and like did a fairly decent job, but I think like above all else that a…”

“Ultimately, I think there's, like, a lot of reason, a lot of, like, micro reasons why, why I left, but the, but sort of, like, now as I reflect on it, I just burnt out. Like, I had, we had basically, we started this company, Sean and I started a company in, li…”

“And then a city planner is a PM that's really good at mature products, really good at driving efficiencies at scale. They have the city. They, everything that they do touches hundreds, thousands, millions of customers immediately. And so the type of PM that yo…”

“Companies like Shopify, Square, Intuit have proven that you can build, like, hundred billion dollar plus companies if the numbers are working right, if you're medicine, not vitamin for a small business customer”

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

“So I started to carry a square in my pocket, and I'd show people, and they'd give me the reaction. I'd plug the square in, and I'd say, it's live. Swipe your card. And I'd hand, hand the phone to them, and their faces would change. They'd be like, well, so the…”

“We were given a pretty strict deadline that we needed to launch by and I pushed it out three times. And that's not because of this one animation, but it's because of a series of decisions where we said, this is what we believe we need to ship. And this matters…”

“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 …”

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

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

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

“So I invested in Square when they first started, like the black small square of credit card processing, but I didn't invest in Instagram.”

“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 first institutional fund that first round ended up raising was a 50 X on a hundred and twenty five million dollar fund. It had Roblox, Uber, and Square.”

“The majority of Square businesses are solopreneurs. They're individuals, individual sellers. And, you know, the last decade or so, I think the company's really made a successful march up market. So we've got a lot of larger businesses now, but, you know, back …”

“At Square, what we did and what the company's still doing is, is came up with a vertical strategy where we had, okay, we've got our base square point of sale out of the box, you know, works for most industries with simple needs. And as you start to get more ad…”

“This can't just be like a one size fits all thing anymore. Like the differences of jobs to be done across these industries are just too stark.”

“The catch on that, and like one of the tricks is just, it's very, very difficult to be able to build awareness and be able to acquire, at least at the bottom of the market, be able to acquire at an affordable CAC if you don't have really great brand awareness,…”

“If we're going to expand off the wedge, how does the wedge product, whatever the first one is, really help unlock the door to the second? What are the sort of unique insight, unique advantage or right to win? Does the first product open up for the second?”

“That started off the unique insight that like, hey, we kind of have a pretty good view into the revenue of a business. We don't have a full view on the business. We have a unique view on the revenue coming into a business. And so that really puts us into a pos…”

“We didn't do much of that at Square, a lot of it was kind of focused on what does the next year look like?”

“Square Invoices grew to be our second biggest, I'm not sure where it is, Now, or if they disclose all this, but it grew to be at the point of the IPO, I think it was our second biggest payment product.”

“So to give you an example, when Alyssa came into Square, I think we had 13 or 14 different instances of a shopping cart, of ways that people put items into some sort of cart object, and then ultimately checked out.”

“The way that he ran the two businesses was radically different, right? I think it's everything from the org structure where square was always more. Sort of GM slash business unit, almost driven. Versus Twitter, which was always sort of functionally oriented or…”

“Even kind of prior to this kind of latest big shift in the AI landscape, you know, we were using GPT two as part of us, the square messages product being you know, a virtual assistant to help customers, you know, answer responses to customer inquiries and vari…”

“Squared launched a product a couple years ago called Photo Studio because we heard from businesses that they wanted to sail the line, but they didn't have product photos, right? And so the first iteration of it is we actually had a photo, like a physical photo…”

“Vinod Khosla was on our board for years and he had a portfolio company that was being courted by another company to acquire them. And Vinod called me up and said, Alyssa, you should go talk to these guys. And see if maybe, like, Square might be, ah, an interes…”

“And we thought like, ah, you know, I don't know if this is going to be a big product or not. And they didn't even think at the time it was going to be a big product. And then obviously that completely blew away all of our predictions in regards to how Cash App…”