Elon Musk on the most important lesson he learned at PayPal “The initial thought with PayPal was to create an agglomeration of financial services. So you’d have one place where all of your financial services needs would be seamlessly integrated and work smoothly. And then we had a little feature for email payments. And whenever we’d show the system off to someone, we’d show the hard part — the agglomeration of financial services, which was quite difficult to put together. Nobody was interested. Then we’d show people email payments, which was actually quite easy, and everybody was interested.” Elon continues: “I think it’s important to take feedback from your environment. You want to be as closed-loop as possible. And so we focused on email payments and really tried to make that work. And that’s what really got things to take off. But if we hadn’t responded to what people said, then we probably would not have been successful. So it’s important to look for things like that and focus on them when you see them and correct your prior assumptions.”

Jack Dorsey on the power of great storytelling “One of the biggest things that has helped me [as CEO] is learning how to become a better storyteller.” The co-founder of Twitter and Square explains: “If you want to build a product that is relevant to folks, you need to put yourself in their shoes, and you need to write a story from their side.” At Square, Jack explains, they spent a lot of time writing what they call “user narratives.” He gives an example: “This person is in the middle of Chicago, and they go to a coffee store… Then this is the experience that they’re going to have. It reads like a play — it’s really beautiful.” He continues: “If you do that story well, then all the prioritization, product, design, and coordination that you need to do with these products just falls out naturally because everyone can relate to the story from all levels of the organization… And we want one epic, cohesive story that we tell the world.” Video source: @Stanford (2011)

Shopify CEO Tobi Lutke explains Goodhart’s law and why he doesn’t like KPIs or OKRs “Goodhart’s law is real. The moment a metric becomes a goal, it’s no longer a useful metric… No metric by itself is a complete heuristic for a complex business. There’s a million different tensions in a company, and you can’t keep all of them in harmony by optimizing for one thing.” For this reason, Shopify doesn’t use KPIs or OKRs. But as Tobi explains, this doesn’t mean they don’t value data and metrics. “We are extremely data informed. We have invested enormous amounts of money and time into systems that give us basically everything at our fingertips… But what Shopify attempts to do is just not over-fit for what’s quantifiable.” People love optimizing for highly-quantifiable things because there’s immediate gratification that comes from seeing a number go up. But Tobi thinks that the most important aspects of a product are rarely quantifiable: “The overlap of the most valuable things you can do with a product and the things that happen to be fully quantifiable are like maybe 20%. Which leaves 80% of a value space unaddressable by the people who only look at quantifiable things.” He continues: “Shopify is comfortable with unquantifiable things like taste, quality, passion, love, hate… The sort of deep satisfaction that a craftsperson feels when they’ve done a job well is actually a better proxy if you allow it to be.” They then have robust analytics systems that tell the company if something’s wrong or a new rollout breaks something. “We think about it as a cockpit for a pilot. The decisions are still made by pilots, and we think this leads to better results… I think there needs to be more acceptance in business of unquantifiable things… And then metrics take a support function.” Video source: @lennysan (2025)

Jack Dorsey: I think of the CEO role as “Chief Editor” of the company “I think of my role as CEO of Square as an editorial function,” Jack Dorsey explains. “By editorial, I mean there are a thousand things we could be doing, but there’s only one or two that are important.” He continues: “All of these ideas and stories from users, engineers, support people, designers, are going to constantly flood what we should be doing. We need to choose the one or two that are really going to drive and sustain the product. As an editor, I’m constantly taking all these inputs and deciding on that one — or the intersection of a few — that makes sense for what we’re doing.” There are three “access points” that Jack pays attention to in particular: 1. The team. “We have to bring the best people in and edit away any negative elements… At the end of the day, we’re just a group of people working on one single goal, and if we can’t step in a cohesive, coordinated fashion, we’re going to trip all over the place. Recruiting is no. 1.” 2. Internal & External Communication. “Internal communication is just the coordination of what we’re doing and why we’re doing it… If you have the vision, the next 30 days, 3 months, 6 months, and year maybe, it makes it very easy to set priorities and for all the edges of the company to do the right thing. The external communication is the product, and the product is the story we’re telling the world… We don’t want it to be about a person. We want it to be about how people are using it, fitting it into their lives, and what they’re doing with it. That’s the strongest story we have.” 3. Editing the “money in the bank” story. “This comes in two ways: 1) through investment… or 2) through revenue.” Jack concludes: “My three priorities and focus areas are in that order. That’s what I’m constantly editing as CEO, and I think it makes managing a growing company in a fast-paced environment very easy because there’s basically one thing you have to do: You have to make every single detail perfect and you have to limit the number of details. That’s it. If you can do that well… you’re going to succeed because you’re paying attention to the smallest things. And if you pay attention to the smallest things while knowing what’s important, then everything else takes care of itself.” Video source: @Stanford (2011)

Sam Altman: “The good founders are people who have ideas all the time” “You can give a founder an idea and they can start a company. The problem is they need to come up with new ideas for the company basically every week. You have to come up with crazy new ideas and big changes all the time.” When Sam was at Y Combinator, they tried an experiment where they funded 20 teams of strong founders that didn’t have ideas but were otherwise really good. They all failed. “What we learned is that the good founders are people who have ideas all the time. There’s an intelligence component to this. There’s a creativity component to this. There’s an ability to think independent thoughts component to this. But whatever you want to call this - this particular kind of intelligence that leads to seeing problems in different ways and thinking of ideas that don’t yet exist but should - you’ve got to have that in a founder.” Video source: @ycombinator (2018)

Larry Ellison: You won't be successful doing the same thing everyone else is doing “My standard advice to entrepreneurs is you can’t be successful as a small company doing the same thing everyone else is doing… If you’re an entrepreneur, you have to find errors in conventional wisdom.” When you tell people your startup idea, most of them should say, “None’s doing that. You’re crazy!” Ellison continues: “When you hear that, there are two possibilities: One is you’re first with a really good idea. Unfortunately, the other is that you’re crazy.”

Paul Graham explains his rule of thumb for when to launch your product “The risk of launching early is not as great as the risk of launching late… So you’ve got to have a good rule of thumb about when to launch. And my rule of thumb is launch as soon as you have a quantum of utility, which means as soon as there’s one person in the world who is glad you launched because now they can do something that they couldn’t do.” He continues: “If you have something that if you launched it, no one would be happy, then you’re not ready to launch… [But] if there’s 10 people who are super excited and nobody else cares, totally launch. That’s perfectly fine. That’s great.” Video source: @ycombinator (2018)

Jensen Huang: “My will to survive exceeds everybody else’s will to kill me” Jensen is asked how Nvidia survived the intense competition in the 3D graphics industry. To which he replies: “I would say that our company wanted it more than everybody else. I do believe that, as a company and an entrepreneur, you have to want to succeed more than your competitors want you not to.” He continues: “That’s hard to teach. Someone said recently that I’m the most tenacious CEO they’ve ever seen. I’m not exactly sure whether that’s a compliment or not, but my will to survive exceeds almost everybody else’s will to kill me.” Video source: @ECorner (2003)

Mark Zuckerberg: “You can’t 80/20 everything” When Facebook first launched, a user’s profile included things like the dorm they lived in and the courses they were taking. Paul Graham asks Mark if he thinks Facebook would’ve worked without these features, to which Mark replies: “I remember this early debate that Dustin [Moskovitz] and I had where we had to do some manual work for every school that we released Facebook at. To do that, we went through and parsed the course catalogs at the schools to make sure that the data was clean.” Dustin argued that it would be easier to launch new schools if they didn’t parse these catalogs, while Mark thought this would be an unacceptable drop in quality. “We just had this really long debate about what quality meant for us and the community that we wanted to establish and the culture. In retrospect, maybe it wouldn’t have made a huge difference in how things played out. But it definitely set this tone where there’s a lot of clean data on Facebook, you can rely on it, it feels like a college-specific thing—which was valuable early on for setting the culture.” Mark then offers the following advice to the YC Startup School audience: “In the projects you work on, you will have a lot of similar questions. There’s the famous 80/20 rule where you get 80% of the benefit by doing 20% of the work, but you can’t just 80/20 everything. There have to be certain things that you are just the best at and that you go way further than anyone else on to establish this quality bar and have your product be the best thing that’s out there.” Video source: @ycombinator (2012)

Jensen Huang: I don’t need to change the world overnight “Having a simple idea that you can execute perfectly is sometimes better than having a grandiose idea that your company can’t execute on.” Jensen reflects on how he’s constantly bombarded with ideas and feature requests from customers and engineers at Nvidia. But he believes it’s prudent to keep things simple. As he puts it: “I don’t need to change the world overnight; I’m going to change the world over the next 50 years. I don’t need to build a killer product overnight; I just need to build a winning product. And the goal of winning is so that you can play again. It’s just like pinball… Most companies need to realize that it is a long road and you can’t build that perfect product [overnight].” He continues: “Once you do that and keep the project’s scope confined — you have a long-term vision but your product definition is rather simple — your people can now execute flawlessly on a simple plan. Then you come back and do it again.” Video source: @ECorner (2003)