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John Collison: We only had 50 users two years after founding Stripe “We started working on Stripe in the Fall of 2009, and we launched Stripe in September 2011,” John Collison reflects. “I remember right at the beginning when we were starting it I said to Patrick [Collison], ‘Yeah...

190,896 views • 7 months ago •via X (Twitter)

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Stripe CEO Patrick Collison shares the tactics he used for finding product/market fit “We tried very hard to understand in granular detail what exactly it was that people were doing, where they were tripping up and so on.” Patrick gives some examples of specific tactics: • A public chat room to provide support to people integrating Stripe • For the first 10 users of Stripe, every API request sent an email to the founders so they could better understand how users were using their product and see if users were doing anything weird • All errors generated a high-priority email to the founders. This created a pleasant user experience where 15 minutes after hitting an error, Patrick could reach out to them and let them know the issue was fixed “These are all kind of examples of a general pattern of trying to be hyper-attentive to all the micro details of what people were doing in the product and iterating rapidly in response to it. Generally speaking, I think pre-product/market fit metrics are actually relatively unhelpful because probably not that many people are using your product. If it’s 20 users, you can in some sense afford to just look at everything they’re doing to understand what’s working and what isn’t.” Another example of this Patrick gives is embedding a text input on each of their web pages with placeholder text prompting users to give them useful feedback(e.g. “The worst thing about Stripe is…”, “The worst thing about this page is…”, or “I really hate the way Stripe does…”). As Patrick explains: “At that stage, you have to be kind of masochistic. We’d always be waking up to all these emails telling us all the terrible things about Stripe. But that was a helpful to-do list for the day ahead. Video source: Y Combinator (2018)

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45,642 views • 5 months ago

Jason Citron on the growth hack that got Discord its first few thousand users “We started working on [Discord] in January 2015, and within I’d say two months, some of our friends were very excited about it but we didn’t really have any users. It was pretty clear they wanted to use it, it just wasn’t exactly correct. We rebuilt the voice chat engine three times, for example. But I’d say within 3-4 months, we had 20 DAU that weren’t us.” However, as Jason explains, growth stalled after those first 20 users: “We were like, ‘How do we get the word out?’ Because everyone was actually very skeptical about a group chat app for gaming. People would say, ‘This is the dumbest idea ever, no one is going to use this.’ And even people who played games, many of them thought, ‘Why would I want this? I already have whatever app I’m using.’ And so we were having a hard time getting other people to try it.” Jason recalls a period of 3-4 weeks sitting around thinking, “We like this, but maybe no one else does.” Then they figured out their growth unlock: “The unlock for us was inviting people to give feedback on the app, as opposed to saying, ‘Try this thing out we’re selling to you.’ What we actually did was we went to the Final Fantasy 14 subreddit, and we got one of our friends to make a post on the subreddit basically saying, ‘Hey, I’m trying out this new voice over IP app. What do y’all think about it?’” Jason continues: “People found it on Reddit, clicked on that link, went into the server, and then they were talking to us and trying it out. And they went back to the subreddit and were like, ‘Hey, this is pretty cool. I met the devs. They seem pretty cool.’ We got 50 users that day from that post and then that 50 turned into 100 the next day and it sort of started to snowball. And then we did this playbook for six months and that was basically the beginning of how it started growing.” Video source: The Twenty Minute VC Harry Stebbings (2024)

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20,407 views • 6 months ago

Patrick Collison recounts Stripe’s darkest moment Patrick recounts his first meeting with a bank where he was told “in no uncertain terms” that there was “no possibility” they would work with Stripe. Stripe faced roadblocks like this for two years, and Patrick tells the audience of entrepreneurs: “I really feel this imperative to emphasize the long period—two years is long time when you’re in it—of working away with so many of these roadblocks and headwinds and people telling us that it couldn’t work or shouldn’t work or was a bad idea… It could mean that you can’t actually do it or the idea is bad. Or it might not.” When asked what the darkest moment for Stripe was, he tells a story six months into the company’s existence when an upstream switch at their data center failed and took down Stripe’s API. Patrick’s pager alerted him at 4am, and he immediately went into the office. “This is not like a social media app or something. This is the conduit for our customer’s revenue. So it was a big deal.” It ultimately took 8 hours for the data center to fix the switch—the whole time Patrick was worrying this might damage customer trust and be the end of Stripe. “The darkest moment of course was because I was bracing myself for the deluge in complaints and dissatisfied customers and anger and vitriol and everything else. And 1pm rolled around and as far as I could tell, nobody had cared or notice. On some level, that was good news. But as I reflected on it, I realized that it was actually kind of existentially bad news.” Video source: This Week in Startups @jason (2017)

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29,387 views • 1 year ago

Evan Spiegel explains why he didn’t sell Snapchat to Mark Zuckerberg for $3 billion “A lot of people in the early days told us we should sell it,” Snapchat founder Evan Spiegel recalls of the time. He tells story from the early days of the company: “I remember joining a conference call with some of our lawyers and they were saying, ‘This thing is basically going to zero,’ ‘It’s just a fad.’… And I’m like, ‘Oh hey guys.’… They didn’t know I was there because I joined a minute or two early.” But it wasn’t just their lawyers. Everyone at the time thought that the big players in social media were going to put Snapchat out of business. Yet Evan and his co-founder Bobby Murphy ignored them. They even had so much faith in his vision for the company that they turned down a reported $3 billion dollar acquisition offer from Mark Zuckerberg and Facebook. The founders were only 23 years old when Facebook reached out over email. Facebook told the young founders that they were working on a competitor called Poke and asked if they’d want to join Facebook’s growing social media portfolio after their acquisition of Instagram. But Evan and Bobby said no: “I wish I could say it was wisdom but I think Bobby and I just loved what we were doing. We loved what we were working on, and we believed in the future of it. Ultimately we were able to convince our investors too that our opportunity was much bigger over time.” Evan explains that him and his founder each taking $10 million of secondaries also played a big role: “[Our investors] did something very smart early on in a prior financing round. Bobby and I were each able to sell $10 million of stock… And that allowed us to just swing for the fences… There wasn’t that feeling of, ‘Oh no, I’m not going to be able to buy a house or have a family.’ We were like, ‘We each got $10 million bucks. Let’s go for it.’” Today Snap is valued at $13 billion. Video source: Steven Bartlett (2025)

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38,309 views • 1 year ago

If you take strong action and it is very different action from what your country has known before...you can only be confident that your action is right if it is founded on strong principles. Mine was founded on the belief that governments are there to serve the liberties of the people under a rule of law, a free enterprise economy, and strong defence. After we lost the election in 1974, and the Labour Government came in, we had departed from our fundamental principles. And I set up a great study with many people—not only politicians but businessmen, academics, journalists—and we redrafted our whole principles. From the principles, we decided the policies and we sorted out what needed to be done and how it was to be done when we got into power. That took four years. I had confidence we were in the right and our policies would achieve the right. Although, as you know, great change means great dislocation. We had to cut expenditure; we had to privatise; we had to get down taxation; we had to cut the bureaucracy. All of the people objected, and for two and a half years my name was marred. It's always difficult to do the right thing. But my father had taught me to persevere: It's easy to be a starter, but are you a sticker-to? It's easy enough to begin a job, it's harder to see it through. And I saw it through. After three years, all of a sudden, the good things in the economy began to show through. At the same time, we had the Falklands, and against all odds we won. Although, the world thought it was really rather astonishing that Britain sent a fleet 8,000 miles away into the bitter cold Antarctic against a foe that had air cover from land when we only had it from aircraft carriers. So the two reinforced one another. But I couldn't have done it unless I had been confident that we had the right principles and that if we persisted, it would show through to the benefit of our people. I was never defeated in an election by the people of my country. That is my proudest boast.

Margaret Thatcher

11,205 views • 1 year ago

This is maddening. Speaking of the 2004 election in Ohio, John Kerry told Brian Lehrer in 2018 that “The problem for us was we were doubting whether the [voting] machines themselves had been appropriately measured & whether the algorithms were correct, etc. We challenged that ahead of time by the way. People don’t know that. And we were told by the court that we were not able to get that algorithm, to check it, bc it was proprietary information. And I believe that it was absolutely incorrect that in the United States of America, the election for the presidency of the United States should somehow be the purview of privately owned machines where the public doesn’t have the right to know whether the algorithms can be checked or whether they are hackable or not. And we now know they are hackable. But we knew as we sat there to decide where to go in terms of the challenge, that we were a nation at war, we had just been through a Supreme Court test of an election four years earlier. I thought once I measured it that whatever constitutional challenge we brought or whatever appropriate challenge we brought to the ballots that were counted, it was going to wind up ultimately in the Supreme Court, and the Supreme Court would do the same thing that it did before. We would take the country through a three month exercise with a 5/4 decision that would award the presidency back to George Bush. Now some people may think that’s the right thing to have done. I thought it would have been horrendous for our country one year into a war, at that moment when there were serious doubts about terrorism and other things, to be going through a long period of questioning of the presidency, and I didn’t think it was the right thing to do for the nation.” 1/ Vice President JD Vance Marc E. Elias

JennyCohn ✍🏻 📢

125,175 views • 1 year ago

Peter Thiel tells the founding story of PayPal “When you start one of these companies, it’s typically not the case that you get the whole idea fully formed instantaneously,” Thiel begins. “There was this incredible internet boom going on in Silicon Valley in the late 1990s. It felt like there was this open frontier or gold rush, and one of the natural things to look at was finance.” At the time, Thiel was very interested in the idea of creating new forms of money. “There’s always something super mysterious, powerful, and important about money,” He explains. “And we had this general idea to do something with security, money, and payments very early on in the founding of the company. Then you iterate a lot on how to get the idea out.” Thiel continues: “The critical question for any consumer internet product is not what the idea is, but ‘how do you get distribution?’ There had been a lot of internet payments companies that had already started and failed by 1998… They would’ve worked if everybody used them, but you could never get the first person to start. So the challenge was how to make it go viral and how to get something to work where it’s good for the first person, the 10th person, and the 100th person. Once you have millions of people, you have a network and network effects. That was sort of the chicken and egg problem we wanted to solve.” Eventually the team stumbled on the idea of linking money with email: “There were already 300 million people in 1999 that had email accounts. So if you could send money to an email address… you didn’t need both counterparts to a transaction to be part of the PayPal network. Only the sender could be part of it, and then the recipient would sign up as they took money out. We started with the 24 people in our office, and they sent money to friends and other people. Then we gave these referral bonuses of $10 if you got someone to sign up, and it just grew exponentially. It grew about 7-10% compounding daily… We had 1,000 people in mid-November of 1999. By the end of December it was 12,000. By February 3, 2000, it was 100,000. By mid-April 2000, it was up to a million.” The other critical component of PayPal’s success was starting with customers who had an intense need and minimal downside risk: “One of the natural places that it started was on the eBay auction site where you had small dollar transactions of maybe $40 as the typical amount. If you send a check across the country, that’s a 10 day delay. It’s slow, and most people aren’t set up to process credit cards.” Thiel reflects on what it felt like to go from 1,000 users to 1 million in just a few months: “[It felt like] you were at the forefront of some sort of revolutionary thing. It’s incredibly exciting and incredibly scary. It was like ‘we’re going to take over the world’ or ‘we’re all going to die’ and you move between those two several times a day.” Fraud was a major challenge the company had to solve — especially because making a product hard to defraud is usually at odds with making it easy to use. Thiel had an interesting perspective of operating in strange regulatory zone with this new form of moving money: “I often thought of it at the time that we were in a race between technology and politics. The politicians didn’t like us, but if we got the PayPal network to be big enough, it would sort of overwhelm the regulators and they’d have to accept it as a fait accompli… One of the execs at PayPal said we needed to hire a whole bunch of lawyers to tell us what we can or can’t do, and we said no we’re not going to hire them. They’ll just tell us what we can’t do. We have to just go ahead and not hire the lawyers and just do it.” Video source: Dave Rubin Dave RubinShow (2018)

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17,214 views • 3 months ago

Patrick Collison on what he wishes he did differently when scaling Stripe “I think one of the most pernicious mental models you can have is that you are on some growth curve… I think a much better mental model to have is that you’re serving some market, and then there’s the percentage of the market that you’re serving. And whatever percentage you are not serving, you just haven’t built the go-to-market functions and organization that’s brought the product to those market segments.” In the early days of Stripe, they assumed they were on some growth curve, but Patrick believes they could’ve accelerated their growth by viewing growth as a function of their go-to-market apparatus: “What we did not do, but what I wish we did, is six months after launch, we should’ve mapped out the concentric circles of our market.” As he suggests, Stripe should’ve started with very early stage startups then mapped out the larger set of all technical startups - not necessarily very early stage. Then continue this process in successive increments until they got to all companies handling online payments. Each step along the way, figuring out the size of each market, the fraction Stripe was currently serving, what it would take to serve more, and so on. And then work backwards from there: “What would the organization look like that was serving the entire market? Let’s just start building that organization, because the growth curve is under my control. Of course, it’s not 100% under your control, but I think it’s much more under your control than people tend to think.” Video source: Y Combinator (2018)

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64,296 views • 2 months ago

The founders of Stripe and Pinterest on how to convince people to join your startup Stripe CEO Patrick Collison argues that part of the reason startups resonate so much is because the outcome is not guaranteed: "If it were guaranteed, it would be boring... Whether or not you're the best person in the world at what you do, you're probably not going to alter Google's trajectory. But if you really want to benchmark yourself and see how much of a contribution and impact you can make--which is a really compelling prospect for a lot of the best people--a startup is a much better place to test that." Pinterest founder Ben Silbermann emphasized this as well: "No smart person that you're hiring is under the illusion that you have a crystal ball into the future and that joining is a guaranteed thing. In fact, if you're telling them that and they select in, you shouldn't hire them because they didn't pass a basic intelligence test. I think it's important to tell them what's exciting and where you think the company can go. But also tell them where it will be hard and chart your best plan. And then tell them why their role can be instrumental--because it will be... What I would discourage doing is whitewashing all of that. If people are joining your company because they want all of the certainty and safety of working at Google but also the perks of working at a small startup with lots of responsibility and transparency, that's a really negative sign." Apparently in the early days of PayPal, Peter Thiel and Max Levchin would tell people after they interviewed all the reasons that the company would fail: "Visa and MasterCard want to kill us. We also might be doing something that's illegal. But if we succeed, we'll redefine payments." Don't whitewash the risks. Instead tell them how your startup will change the world if you succeed and how their role will be instrumental in affecting that change. Video source: Y Combinator (2014)

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11,811 views • 7 months ago

Aman Sanger on scaling Cursor to $100M in revenue in 12 months The four co-founders started working on Cursor in January 2023. “It was about 2-4 months of experimenting, trying different things and finding something that fit,” Aman recalls. “Then we shipped it and it had an okay launch.” The initial version of Cursor got some initial buzz because they shipped it with GPT-4 at a time where very few products were using Open AI’s latest model. But then usage tanked. The team began to doubt their approach after the failed launch. Aman explains: “The entirety of that summer was just incredibly slow growth, and that was somewhat demoralizing. The big question in our minds was, ‘Are we being too ambitious?’ We were trying to build this general purpose thing for all engineers, but with this really small team, maybe we should focus more narrowly on some particular use case like tests or bug detection.” But the fact that they were users of the product gave the team the confidence to keep going down their initial path: “The really magical thing about this product was that we were users of it. So we could iterate incredibly quickly, and we tried all these different things that summer. Then we found this core set of features that worked incredibly well.” The two key features were Command K for instructed edit ability and code-based indexing that let you ask questions about your whole code base. “After we integrated those two features and launched them, growth kind of just took off.” Aman continues: “A lot of the work of Cursor has been just experimenting with what is possible. For everything you see in the product, there’s like 10 failed experiments that didn’t work… All of our work for the first 6 months to a year was trying to find new ways to harness these models and make these models better for programming.” Another factor that contributed to Cursor’s success was their willingness to ship half-finished features: “We released these half-finished things, which a lot of our competitors refused to do. The first version of Copilot++ and Cursor Tab sucked. But once you release it to the world and see how people react to it, you can improve on it a ton… We biased toward releasing as soon as something shows signs of usefulness to the team.” Video source: Peak XV Partners (2025)

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56,166 views • 1 year ago

AI legal startups are a thing in 2024. But as Ironclad’s Jason Boehmig puts it, “nobody was trying to buy an AI legal assistant back in 2015.” Ironclad has one of the most interesting and underexplored stories out there IMO. As we were developing First Round's PMF Method, we learned so much from their journey — super grateful Jason took the time to share his insights for other builders. 🙏 Here were a few of my takeaways: 🔬 Zoom in to find focus “It was actually fairly easy to sign up early customers — what was difficult was finding a product that could address that market. That took us several years of iteration. We had to try to figure out what pieces we could peel off into a repeatable, discrete software product. We quickly realized the really interesting part of the problem was in repeatable business transactions — sales agreements, employment agreements, NDAs licensing agreements, partnership agreements. A lot of our competitors tried to do everything that corporate legal teams do. But we were only doing the contract part.” 📣 Expand an existing category (with an existing buying cycle) But the initial AI legal assistant positioning wasn’t resonating. I’ve talked to 100s of founders about PMF and the story of how Ironclad got unstuck is one of the wildest ones I’ve heard. “100% of the time I had to explain what an AI legal assistant was. We had a [email protected] email on our site. One day I got a one-liner message that said, ‘Hello, are you a CLM?’ I was so close to hitting archive, but it was from someone at a publicly traded company. But what was a CLM? Turns out it’s a Contract Lifecycle Management platform that helps enterprise companies create and manage their legal contracts. By that definition, we were. So of course I wrote back, ‘Yes, we are definitely a CLM, we would love to come demo our CLM for you.’ But while we were really great at creating contracts with our AI legal assistant product, we hadn't put a lot of thought into how you deal with contracts afterwards, with a feature called a repository. And so we had set up this demo with the legal team from this publicly traded company, and I turned to my co-founder Cai, and said, ‘By the way, we have 3 hours to build a repository.’ We took the train from SF to San Jose and he built the first version of a repository, which we demoed live at the end of the train ride. This customer was in a CLM evaluation cycle that had 12 other solutions in it, but they loved the demo. So we went and actually built the full product, and we won. And after that, of course, we changed our messaging. We got serious about building CLM functionality and that's our flagship product to this day. There were lots of people out there trying to buy a CLM so we just got to participate in a lot of buying cycles, but with the AI legal assistant buying cycle, we had to create every one of those.” 👥 Artificially constrain the buyer and build community early “One of the things that we did which was really helpful in hindsight was we artificially constrained the buyer we were going after. Once we decided to make the shift to enterprise, instead of trying to address the whole US market or the whole global market, we decided we only cared about being the number one CLM in SoMa. We got a list of every company that could use the CLM in SoMa and got intros to them — it just provided a ton of focus for us. It's how we also stumbled into doing community. We would host these community dinners and if you were a general counsel of a company based in SoMa, you probably knew other people that were coming to them. We just started to get this buzz of ‘Are you going to the Ironclad thing tonight?’ There's a ton of value if you can discover a part of the organization that no one cares about, and connect that part of the organization to a larger business problem.” 📚 Founder-led sales is learnable I was impressed to learn that Jason still sends cold outreach himself to this day. But founder-led sales didn’t come naturally. “A misconception I had about early-stage startups was that the cartoon character salesperson who's slapping everyone on the back and is a total extrovert is the best salesperson. And it's actually the person who's almost like an engineer in their mindset — super methodical, sends great follow ups, could be very shy. It's a very learnable skill.”

Todd Jackson

50,683 views • 2 years ago

Alexandr Wang on why Paul Graham’s “Schlep Blindness” essay was seminal for Scale AI “One of the secrets to Scale AI — and I think this applies to almost every industry — was that the problem we were solving of building really high quality data sets was something that most machine learning teams knew was very important but it wasn’t necessarily the sexiest problem that every AI scientist wanted to spend their days and nights working on.” Alexandr continues: “There was one article that was pretty seminal for me early on. It was an essay by Paul Graham called ‘Schlep Blindness.’ I’d encourage everyone to read it if you get a chance. But basically the idea was that most people avoid thinking about the really difficult, hairy, ugly, and annoying problems that exist in the world but they’re really important. He actually uses Stripe as one of the examples in his essay, but these problems are everywhere. The ugly, hairy problems that everyone knows are important but aren’t sexy to work on — if you can identify what those problems are, they generally make really exciting startup ideas.” This was a lot of the original pitch for Scale: “You know this is important but you probably aren’t the most excited to work on it.” And then the early Scale team was super scrappy, which helped them earn the trust of their customers: “They saw our product velocity and how fast we were moving. They thought to themselves, ‘Even if they don’t have the perfect product today, they’re going to get to a product that we’re going to be able to rely on really quickly.’” Source: Startup Grind (Apr 2022)

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56,503 views • 27 days ago