Notion’s Ivan Zhao: The Refounder

Intro

Ivan Zhao: We started a mantra in the company. We want to be a jazz band, not a marching band.

Brian Halligan: I love that.

Ivan Zhao: It’s like a self-reflecting value thing. It’s auto-equilibrium with me. So it’s like, okay, I’m a jazz band person. So we’ve been hiring more and more jazz band people. Also, AI happened in the past two and a half years, so more jazz band people can really shine during this moment.

Brian Halligan: Okay, so we had manager mode, we have founder mode. There’s this new mode. What should we call it?

Ivan Zhao: Jazz mode, maybe.

Brian Halligan: That’s not bad, actually.

Ivan Zhao: Yeah.

Brian Halligan: Hey everybody. Today we have Ivan Jawan, the co-founder and CEO of Notion. I like to think of him as the refounder. He started the company a long time ago, and in 2015 he didn’t have product-market fit. He and his co-founder moved to Kyoto, of all places, and kind of restarted the company and rebuilt it. After that, they got product-market fit and it really took off.

He did the same thing in 2023 around generative AI in an offsite down in Cancun and literally restarted the company. In my mind, he’s the canonical example of how a SaaS company can move and become an AI company. So that’s super interesting.

The second thing that’s interesting is just hearing how he builds the company. He’s very AI-native in the way he organizes the company, the way he compensates people, and the way he builds today. And it rhymes a lot with some other CEOs that I’ve interviewed, like Jack Dorsey a couple weeks ago. I hope you like it.

Main conversation

Brian Halligan: What do you think of my outfit, by the way?

Ivan Zhao: I think your outfit—it’s, uh… your pants could be looser.

Brian Halligan: Looser. Okay. On the bottom or just in general?

Ivan Zhao: In general. Uh, I like your sneakers. I don’t know what they are.

Brian Halligan: Okay. They’re Italian. Premiata.

Ivan Zhao: That’s cool.

Brian Halligan: You’re known as a very fashionable fellow. Where do you shop these days here in New York?

Ivan Zhao: New York has a good store near here in SoHo-Tribeca called La Garçonne. Not like a designer designer, but more like a European, easy-to-wear.

Brian Halligan: I like the vibe.

Ivan Zhao: Thank you.

Brian Halligan: I got to up my game, Ivan.

Ivan Zhao: You’re just channeling some Nike.

Brian Halligan: Let’s go shopping. You want to go shopping?

Ivan Zhao: It’s right around here.

Brian Halligan: Let’s go shopping.

Ivan Zhao: Afterwards we can go.

Brian Halligan: I want to talk about CEO stuff, not just fashion. I’ve been doing this Sequoia thing for a couple of years, and a lot has changed in CEOdom. Like, the whole manager mode/founder mode thing happened and now founder mode and some new mode seems to be happening. Let’s just reflect back when Paul Graham’s founder mode memo came out.

Ivan Zhao: You know what? That’s a 2020 issue, right?

Brian Halligan: No, no, no. It’s later than that. Like ‘24. My reaction, by the way, was relief, because I was a quirky kind of founder mode type of person, always being—everyone started trying to talk me out of doing that. What was your reaction?

Ivan Zhao: I didn’t have too much of a reaction, to be honest. Yeah.

Brian Halligan: Nowadays Jack Dorsey is kind of redesigning his company to put AI in the middle, and Brian Armstrong is doing the same thing. My sense is you’re kind of heading this way as well. Can you talk about your journey there, your company’s journey? What’s new? How are you thinking about the organization? How is it changing?

Ivan Zhao: Yeah, my journey actually has a small detour off the founder mode, which is trying to delegate, trying to grow. Notion has been very small as a company in the early days. We had product-market fit in 2019, early 2020—we were sub-10-ish people in 2019, and the company became profitable because we were small.

Brian Halligan: Did you raise venture in the early days or did you bootstrap it?

Ivan Zhao: We raised venture.

Brian Halligan: You did? Okay, that must have been tough.

Ivan Zhao: It was tough. First five years just seed-stage money dragged us for five years.

Brian Halligan: Yeah, HubSpot was like that. Took us a long time to get to product-market fit.

Ivan Zhao: It’s very tough. Yeah, it’s a different type of tough compared to now. Back then, with no product-market fit, it’s despair. It’s just black, you don’t know where to go. So we had been very small from the get-go, and we sort of tasted the sweetness of it, because if you’re small, you’re profitable, easier to raise money, you’re default alive. And we had been resisting growing team size. And during COVID a lot of companies really blew up. Remember that?

Brian Halligan: I’m sure you did.

Ivan Zhao: Relatively, yeah, blew up.

Brian Halligan: You got to product-market fit at the right time.

Ivan Zhao: We got to product-market fit around the same time. There was a lot of advice that you’ve got to grow. So we did grow relative to other companies, still resistant to grow a lot in terms of headcount. But that’s the moment that I sort of learned, oh, you need to delegate, you need to introduce professional management.

Brian Halligan: Why? Who was telling you that?

Ivan Zhao: That’s a good question. Some investors. You didn’t tell me that, I don’t think so.

Brian Halligan: It was conventional wisdom amongst the investor class.

Ivan Zhao: I would say there’s a pro and con for that. I resisted that for a long time. So we did not build a sales team. In retrospect, I should have started a sales team earlier, because I thought I could first-principle the whole way, like create some new kind of PLG, some brand new motion. That was a mistake. The other parts—product marketing, engineering—those functions, I wouldn’t call it a mistake, but we were opting for the traditional way of building them.

Brian Halligan: Did you hire been-there, done-that people in that phase?

Ivan Zhao: We did.

Brian Halligan: And do you have any of them still?

Ivan Zhao: Many of them are still with us, yeah. Our CTO, it’s been the last three years. Before that, there was another CTO during that phase. But I would say some parts of Notion’s DNA are defined by the classic SaaS executive. Now things have changed in the past three years since we’ve been building with AI. We’re one of the earlier adopters of language models in product. And you start thinking about how things are breaking when building with this new technology—the classic boundary between roles doesn’t quite work. The analogy I like to use, back then—and still is—is that building classic software is like engineering a bridge. If you can design it, you can usually build it fairly predictably. Like, the product manager talks to customers, passes to designer, passes to engineers. Building with language models back then, and somewhat still now, is like brewing beer. You can’t truly predict the underlying thing.

Brian Halligan: Good analogy.

Ivan Zhao: You cannot tell the yeast, “Hey guys, go towards that flavor profile more.” You can’t do that. You sort of have to throw your best people in there, see what the technology gives you. So it’s not customer-first, it’s more like experiment with this technology first. Although in the last year or so, the models have gotten so much better. But still the spirit is technology-first-driven development rather than customer-driven-first development. That really forced us to change at least how we build product. Designer is the most productive thing. Our designers and engineers and product people all just sit in the same bucket and work with evals, work with experiences and figuring things out.

Brian Halligan: Inside your company, has one of those personas kind of dominated and the other ones fallen aside, or do they all kind of do the same thing now?

Ivan Zhao: We always started—like, our DNA in the early days was always blurry. We were one of the first to hire designers who can code. I’m a designer who can code, so we built a company based on my image and my co-founder’s image. So those profiles really shine—designer who can code, engineer with strong product sense, PMs not afraid to roll up their sleeves and try things. One of our heaviest token consumption people in the company is a PM, for example. Those people really shine, and we have quite a few of them at Notion.

Brian Halligan: Okay, so you read the Dorsey stuff, you read the Armstrong stuff. My summary of it is they think of a big triangle org chart—very inefficient flow of information up and down and across it—it’s been around for thousands of years and it’s time to rethink it. Basically stick AI in the middle and start delegating more and more over time, and letting the system make decisions and feeding it context in good ways. That’s kind of my high-level summary of it. What’s your take on what those two are doing? And are you doing basically the same thing?

Ivan Zhao: In some sense, we’re creating a product for other companies to do that.

Brian Halligan: But yourself?

Ivan Zhao: The high-level premise is similar, at least my interpretation of it. So much knowledge work is paper-pushing. In the past, it was really hard—it required software to push information from one person to another, but so much of the knowledge work is fuzzy, so humans needed to be in the middle to push information from one to the other. And it turns out language models are really good at two things. One thing is to write the software to design the perfect pipes for your company to push information and decisions. The second is actually doing this kind of mini decision-making in the stops between one decision point and another decision point. So a lot of people used to just be in the middle pushing information and decisions around to sustain a business at scale. That can be rethought.

Brian Halligan: Okay.

Ivan Zhao: The analogy I like to use and we’ve been using somewhat is like, before steel, buildings couldn’t be higher than five or six floors. And New York City is largely six floors tall—iron and stone and bricks. After steel, the information or structure can go much higher. Language model plus software is that. It’s the steel for organizations.

Brian Halligan: What does the organization look like now that we have the steel? I know buildings got taller. What happens to organizations?

Ivan Zhao: I think everybody’s trying to figure that out. Dorsey’s structure is like three layers or something or three types of people.

Brian Halligan: Yeah, three types of people that sit around the AI system that mostly train it. Extremely flat. And I think Brian Armstrong said it’s five layers, and everyone’s a player-coach, which I think is pretty interesting.

Ivan Zhao: I think all the spirits are right. And I believe it should be hierarchical. I think people tried flat organizational structures in the past, I don’t think that’s part of human nature. Human nature is hierarchical.

Brian Halligan: And do you think that’s changed now that we have AI, that it can be flatter? Or do you think that’s BS?

Ivan Zhao: Oh, it can definitely be flatter. We are getting flatter and flatter.

Brian Halligan: Okay. How many direct reports do you have?

Ivan Zhao: I have seven or eight.

Brian Halligan: And generally what is it?

Ivan Zhao: Company-wide, probably around seven, eight, nine people per person.

Brian Halligan: Okay. A lot of people are going to 15, 20, 25.

Ivan Zhao: Yeah. Many of our best people have 15, 20, 20-something.

Brian Halligan: Got it. How have you changed your company—how you compensate people, how you build your org, how you hire people—just in the last year as all this stuff has developed?

Ivan Zhao: Yeah, two years ago we started to hire a different shape of engineers.

Brian Halligan: Okay.

Ivan Zhao: No longer optimizing for people’s experience, but optimizing for people’s agency, energy, optimism, curiosity. A rough framework we’re using is like, okay, what is a talent in the company? A talent equals this person’s capability/experience times this person’s taste or value system times this person’s agency and will. What language models change is, just like Google allowed everybody to access information, language models allow everybody to be a pretty good writer and programmer. So capability got normalized, democratized. Taste becomes so important—what’s your value system, what do you want to bring to the world, which direction do you want to go? That you cannot change as easily. And your will—how hard do you work—you cannot change that either. So we optimize for the latter two today.

Brian Halligan: Okay.

Ivan Zhao: That means in the engineering sense, we hire much younger people internally—IC, early out of school.

Brian Halligan: This is the opposite of the way most of the CEOs I’m interviewing are going. It’s interesting.

Ivan Zhao: No, I think more people are …

Brian Halligan: They say that a junior engineer powered by this stuff is more productive. But if you get a senior engineer who understands the whole system, been there a while and they’re pilled, they’re like 100x.

Ivan Zhao: Yes. So hire for super junior, super senior.

Brian Halligan: Oh, interesting.

Ivan Zhao: So the shape is more like a barbell. Because the senior people provide taste. There’s still a lot of auto-distributed information out there in the language models, architecture in the language models is very bad for that. So they need to provide a direction. It’s almost like this: a good engineer managing four to six coding agents at once, but a really senior architectural engineer can manage two or three junior interns or engineers, they each manage two or three agents, and then that number is higher. And they can train the next generation. I think that might be a more optimal shape than a bunch of senior people managing coding agents.

Brian Halligan: Okay. And I assume you’re still hiring designers and still hiring PMs? Is the ratio changing, or are you just hiring people to do the whole thing?

Ivan Zhao: The definition of designer and PM are different. We intentionally hire designers who work as PMs. Usually it’s designers who can work as PMs. It’s harder for PMs to work as designers because the visual craft …

Brian Halligan: It’s a genetic thing.

Ivan Zhao: It’s more like a visual craft takes years to train.

Brian Halligan: But designers want to talk to customers and get feedback?

Ivan Zhao: Yeah. It’s rare, but don’t stereotype designers—they do exist.

Brian Halligan: Okay. So if I look at your website, you’re hiring engineers, junior and senior. Are you hiring PMs and designers, or do you have some—I don’t know how to combine those two words together.

Ivan Zhao: We hire PMs and designers, but the way we interview and evaluate them—like, we’re in talks with two or three design leaders. We value them essentially as PMs—how can you drive things yourself? It’s not just coming up with good ideas. How much are you interfacing with customers besides are you good with design craft?

Brian Halligan: Some of this stuff is like the fashions change. For the longest time it was experience. Then the word everyone used was “slope”—we hire for slope. And now it’s kind of taste and curiosity and agency.

Ivan Zhao: That’s kind of slope, though.

Brian Halligan: That’s slope-ish.

Ivan Zhao: How is it different?

Brian Halligan: Slope to me is just horsepower smart.

Ivan Zhao: Well, intelligence—first, intelligence is multiple dimensions.

Brian Halligan: Like GPU speed. Like how’d you do on your friggin’ SATs?

Ivan Zhao: But there are plenty of smart people who are lazy.

Brian Halligan: That’s for sure.

Ivan Zhao: Do you call that high slope or low slope?

Brian Halligan: I don’t know. I just always bucketed it into hire the people who learn fast and are very smart. And I think it’s changed to—the word taste comes up a lot, and you’ve been talking about taste for a long time. Now the whole industry talks about it. Why is that all of a sudden a thing? Why is that word everywhere now?

Ivan Zhao: Because taste is not in language models. If you zoom out a long, long time, maybe yes, but right now it’s not.

Brian Halligan: Yeah.

Ivan Zhao: And taste is more rooted in your value system. Are you drinking sparkling water or still water? Are you drinking Diet Coke or iced tea? It’s to each their own. There’s no right answers.

Brian Halligan: The rest of you, you’ve got more than just engineering. You’ve got a bunch of HubSpot people here, which is great. But let’s just take marketing. Has the criteria changed there, too?

Ivan Zhao: We actually changed our marketing department. We no longer have a CMO organization. This is this year—last year/this year. We broke up our CMO organization into storytelling.

Brian Halligan: Yep.

Ivan Zhao: Which is closer to product, because the product is changing so fast. Classic marketing can’t keep up. We haven’t shipped this fast before. So let’s just have that sit next to product, directly connected to social where multipart discussions are happening. And then the other part is serving the sales go-to-market function—demand gen.

Brian Halligan: Lead gen.

Ivan Zhao: Lead gen. We really, really focus on that. So rather than information making a round trip to a CMO who then figures out how to serve both the product side and the go-to-market side—no more. Just let both sides figure it out themselves.

Brian Halligan: Okay.

Ivan Zhao: Not themselves, but more decentralized.

Brian Halligan: And are there any other of the classic marketing functions in there, or are those the two?

Ivan Zhao: Those are the two. There are also designers and creative people on the storytelling side.

Brian Halligan: Like community?

Ivan Zhao: Yeah. Community is in there. Community as part of the community ecosystem organization, which for a startup is one of the most important communities—Notion fans around the world—and figuring out how to move markets through those people.

Brian Halligan: And has the criteria changed? Sales, marketing, all the different functions, have you changed the way you think about the hire? Like, most companies have a form when you interview someone. Has that form changed?

Ivan Zhao: Yes, we’re actually in the middle of—I just described the engineering one, right? Engineers and designers, we changed two years ago. Go-to-market and marketing changed about six months-ish ago. Sales, we’re changing right now.

Brian Halligan: And when you hire a sales rep, do they have to be AI-pilled?

Ivan Zhao: Yes. We actually changed our first interview. No longer look at your resume. Build something for us, send a Notion link, send something that you built. We look at what you built.

Brian Halligan: How about compensation? Is that changing? My sense is we had an environment where certain people were much more productive than average person. Now it’s even more so.

Ivan Zhao: Yeah.

Brian Halligan: Have you rethought comp?

Ivan Zhao: We are changing that as well. It needs to be extremely a lot more meritocracy. You can’t peanut butter things. I think the SaaS era was kind of like a playbook peanut butter—everybody is like a pretty peaceful era. And right now it’s wartime.

Brian Halligan: Totally.

Ivan Zhao: It actually makes you ask, what were we doing back then?

Brian Halligan: Well, nothing changed for the longest time.

Ivan Zhao: Nothing changed. It’s kind of boring, right?

Brian Halligan: The reason I left HubSpot, it was like, okay, we’re building this platform, we need to build more apps, we need to keep opening the platform, we need to hire more reps and just keep going. Until a couple years ago. Now it’s completely changed.

Ivan Zhao: Well, you can come back to become an operator if you like.

Brian Halligan: That’s why I joined Sequoia. I’m like, well, there are so many exciting things going on.

Ivan Zhao: When we hit product-market fit and COVID happened, it was more like the world changing, but not like people building things and technology changing.

Brian Halligan: Do you prefer wartime or peacetime?

Ivan Zhao: Wartime is way more fun.

Brian Halligan: What’s the difference? What do you do differently?

Ivan Zhao: You feel more alive.

Brian Halligan: Okay, but what methods do you use that are different?

Ivan Zhao: I need to take care of my body. I need to exercise every day.

Brian Halligan: I didn’t think you were going to say that, but okay.

Ivan Zhao: Yeah, it’s more fluid.

Brian Halligan: Are you more top-down versus bottom-up?

Ivan Zhao: I think Notion is in a good spot right now with me in the sense that I can dance around really smoothly in either direction. There are enough people I trust really well abd they can bottom-up. And it constantly surprises me. Like, we’re a company of 1,000 people and we have about 50 or 60 ex-founders in the company. They really can lead things. And they welcome me to jump top-down into any part that I’m interested in, where I can provide new value, and they don’t feel territorial. This is in a good place. The people who didn’t feel that way either are no longer at Notion—we let them go. So the company and me are in a pretty interesting equilibrium at the moment.

Brian Halligan: I interviewed Parker Conrad from Rippling, and he’s similar to a lot of founders. And the way it kind of strikes me is the bigger HubSpot got, almost all the important things cut across all those organizations, and it was just very hard to find someone who could really drive something across the org as opposed to within their org. We did not do that. I regret not doing more of that.

Ivan Zhao: That’s my real—remember I said right after COVID, we tried to scale more traditionally, and I realized that’s not us. At that point, this was three years ago, we started a mantra in the company: we want to be a jazz band, not a marching band.

Brian Halligan: I love that. I do the orchestra versus jazz band. I like the marching band.

Ivan Zhao: I realized I cannot be a marching band person. That’s just not me. I’d feel like if I delegate everything and everybody does things, what do I do? I can’t do that. So it’s like a self-reflecting value thing. It’s auto-equilibrium with me. So it’s like okay, I’m a jazz band person. So we’ve been hiring more and more jazz band people. Also, AI happened in the past two and a half years, so more jazz band people can really shine during this moment.

Brian Halligan: Okay, so we had manager mode, we have founder mode. There’s this new mode. What should we call it?

Ivan Zhao: Jazz mode, maybe.

Brian Halligan: That’s not bad, actually.

Ivan Zhao: Because jazz mode has some structure. You don’t want to be—you want other people to contribute, you want people to have fun. It’s not just you having fun or dictating everything.

Brian Halligan: Okay, let’s give that a go. Let’s push that out on X and see if it sticks.

Ivan Zhao: Jazz mode?

Brian Halligan: Yeah. Because I put a survey out the other day like, what mode is this? Is it Dorsey mode? Is it native mode? And I said is it other mode? And somebody put in there, “It’s Depeche Mode.” [laughs]

Ivan Zhao: The band.

Brian Halligan: Yeah. They were making a joke. But I like jazz mode. I think that’s a good idea. One other question on this new world. I work with all these startup founders, and the planning is tricky. I sat through your pitch at Sequoia, and you had a plan and a P&L. What is it actually like internally planning-wise?

Ivan Zhao: We grew past our plan, which most companies at this point if it works you grew past your plan, right? So I would say the financial planning is still—at least I find it useful. It gives you a sense of how fast you’re running. That’s like a financial plan in my mind. It’s like, oh, am I running seven, eight, nine? What number is it? But product strategy, there’s no freaking plan. [laughs] No plan. Because what changes the market, the technology, is so fast. It’s not even six months, it’s not three months, it’s week by week. So you have to jazz those things. Financial things, march band. We try to be conservative to mid-conservative with financial things, and take risks on the product side. And cost becomes another dimension. Like, if you’re just building software, you don’t think about cost.

Brian Halligan: No?

Ivan Zhao: Now you have to. At least I have to really think about cost.

Brian Halligan: Can I ask you about that? A lot of these startups’ gross margins are awful. Companies like HubSpot were like 86 percent gross margins—that’s sort of SaaS normal. What is happening to your costs and your gross margins, and where do you think it settles out for companies like yours?

Ivan Zhao: I don’t have an answer for you.

Brian Halligan: I’m assuming your gross margins have gotten worse, but maybe you didn’t hire as much headcount, so maybe operating margins are better. And how willing are you to let gross margins get radically worse?

Ivan Zhao: Oh, you have to.

Brian Halligan: You’re down for that?

Ivan Zhao: What are you doing? Then you’re not in a war mode. I think Notion is for knowledge work, which might have a different curve than coding products. Coding products, you run frontier models—usually the smarter the better. And knowledge work, you can—we’re already starting to see this—you sort of can settle with second-tier Chinese models, the open-weight ones. They’re not super smart, but a lot of this kind of paper-pushing information in your company doesn’t require Opus to file tickets. So that’s a lot of the problems we’re best at solving at Notion. It will have a different gross margin profile than, of course, the biggest product-market fit today, which is a coding agent.

Brian Halligan: Yes. Okay. You’re kind of in my mind the king of refoundings.

Ivan Zhao: Yeah.

Brian Halligan: You’ve done it I think twice. Your first one—you and your co-founder moved to Kyoto, locked yourself in a very small room and rebuilt.

Ivan Zhao: It’s not that small, but yeah.

Brian Halligan: Okay. And more recently, obviously—you went to Mexico and you had early access to the models and you turned into an AI company. Talk about the different refoundings and what was your mindset at the time? There are lots of early-stage founders who need to refound, and there are a lot of bigger SaaS companies that definitely need to refound.

Ivan Zhao: I like this idea—the best artists reinvent themselves. Miles Davis has at least three phases, right? Picasso, two to three phases. Michael Jordan—the second one probably not as good. But the best one truly is Steve Jobs, the king of refounding. The first version of Notion took us four or five years to find product-market fit. In the middle of that, we sort of found the shape of the product we wanted to build, but we were running out of money building it. So my co-founder Simon and I said, let’s just lay off everybody and go by ourselves. That’s the Japan story. We rebuilt Notion from Japan.

Brian Halligan: How hard was that, the laying off everyone?

Ivan Zhao: It’s not easy, but sometimes your body just tells you you have to do it. You know you’re dead if you don’t do it. And, you know, there’s a pent-up energy that’s just like …

Brian Halligan: Why the hell did you go to Kyoto of all places?

Ivan Zhao: We had never been to Japan. When you say goodbye to your friends, all those people you work with—it wasn’t a big group, five people-ish—the morale is so low. So Simon and I said, let’s go somewhere where we just change the mood a little bit. And we’d never been to Japan. Initially I picked Tokyo. On Airbnb I realized the houses are so small. I love Simon, but I don’t want to cram into a small apartment with him. And Kyoto, the apartments are much bigger because they didn’t get burned in World War II.

Brian Halligan: They weren’t bombed.

Ivan Zhao: They weren’t bombed. They spared that city—too much treasure. And the housing is much bigger and cheaper. So that’s why we picked Kyoto. And we rented out our place in SF, our office in SF, and we actually became cash flow positive doing that. That’s the first time. But once you land, you start coding—just that rapid coding, eating, coding, eating rhythm. It’s actually really liberating.

Brian Halligan: I lived in Japan for a couple of years. Was there something about Japan that was inspirational in your refounding, or the way you built the product? There’s a certain aesthetic there that sort of rhymes with Notion. Or could you have been anywhere? Could you have been in Thailand?

Ivan Zhao: Well, usually we like somewhere warm. Simon likes warm climate, ideally where he can swim. Japan just happened to be something we were both curious about. But once you go to Kyoto—I don’t know, you’ve probably been to Kyoto—it’s a very special city.

Brian Halligan: Very special. Very inspirational.

Ivan Zhao: Very inspirational. Everything there is hundreds of years old. Oh, this shop—150 years old. Open that door.

Brian Halligan: There’s a beautiful place in Thailand—Phuket, whatever. Do you think you still would have pulled it off, or was there something magical about the location that really worked?

Ivan Zhao: Most things are stories we tell ourselves.

Brian Halligan: Of course. What story is the true story?

Ivan Zhao: The story we tell ourselves is that Kyoto is a special place. If you can pull it off anywhere, you can pull it off being reborn in Kyoto. And it’s also inspiring. Just look at the surroundings. The craft is probably the craft capital of Asia. It makes you think: if Notion is fundamentally a tool—the tool for humans—and those people are building knives, ceramic cups, tatami seats, those are tools too, other tools for craftspeople.

Brian Halligan: Craft central.

Ivan Zhao: It’s a craft central. And how can you not be inspired to build better software?

Brian Halligan: Okay, you still haven’t answered my question.

Ivan Zhao: Which is?

Brian Halligan: If you had gone to—wherever, let’s pick someplace in the Philippines. And it was pretty. Would you have pulled this off, or was there something exceptionally important about being immersed in such a craft-centric place?

Ivan Zhao: I think I would have pulled it off.

Brian Halligan: You would have. Okay.

Ivan Zhao: But the story is the better story.

Brian Halligan: [laughs] Okay, fine. So big refounding, not easy. Didn’t immediately hit product-market fit after—still not easy.

Ivan Zhao: No, it took a while after that. It took a year and a half to rebuild from scratch.

Brian Halligan: Why didn’t you just quit and start a new company at that point?

Ivan Zhao: We never start a company for the sake of starting a company. You want to build something. I got obsessed about this Notion-shaped tool problem since the last year of college. And Simon and I were both in this tools-for-thought community, which you can trace the lineage back to the Grateful Dead era—the first generation of computing pioneers around the Bay Area. Like, the lineage traces way back directly to there. I wanted to continue that lineage. So to me it wasn’t …

Brian Halligan: It wasn’t like you had another idea kicking around—this is your life’s work.

Ivan Zhao: And this is bigger than I can ever chew on, this idea. So I wouldn’t do anything else. Simon was in that community and obsessed with this idea, too. So if we didn’t work on this, we’d work on another company doing the same thing.

Brian Halligan: Okay, I’m going to get back to the refounding, but just on the Grateful Dead, you study very important computer scientists from the ‘60s. You’re a student of Steve Jobs, I’m sure. There was sort of a craft ethos about the Grateful Dead and the music back then, but certainly about the company, certainly about Jobs. Is it still here? It seems like it’s a lot more commercial than craft today in Silicon Valley. Have we lost that?

Ivan Zhao: I think most people don’t have it. Most companies don’t have it.

Brian Halligan: I agree.

Ivan Zhao: Like, Steve Jobs, I look up to him or people like him as the intersection of humanity with technology. Silicon Valley is largely a technology and tinker culture. And tinker culture doesn’t even know the history of—it’s not even science, it’s tinkering. It’s people who like to build things in their garage, and something works and maybe has product-market fit and grows a business out of it.

Brian Halligan: To be fair, Woz was tinkering in the garage.

Ivan Zhao: Yeah, but that requires you to meet someone to bring the human side of that. I think tinkering culture, the risk of it is that you don’t know what came before you. Science, at least, you respect the history. If you ask people who Douglas Engelbart or Alan Kay, those computing pioneers are, most people in tech have no idea.

Brian Halligan: Honestly, the only reason I know them is I worked for this guy Ray Ozzie.

Ivan Zhao: Ray Ozzie.

Brian Halligan: Who you would know, of course, because he’s the father of Notes, but he was obsessed with those two and talked about them constantly.

Ivan Zhao: I know Ray Ozzie. He was Microsoft CTO for a while, too, right? So that lineage is broken, by the way. The people who remember the ‘70s and ‘80s no longer work in tech today. So tech is an industry that doesn’t know its past. If you don’t know your past, you don’t know history, which is humanity. I think your point of view becomes just what’s in front of you, what your competitor is doing, versus if you bring humanity, you have all other disciplines around you, all the history behind you. There’s way more good stuff you can steal from. I wish more tech founders would steal from the side or from behind.

Brian Halligan: I think they’d benefit from it, too. Back to the refounding. Lots of founders are going sideways. Lots of companies that started in 2021 are going sideways. They’ve got 10 people, maybe they’re cash flow break-even. What’s your advice to somebody as a founder who’s been going sideways for a long time, got venture dollars in like you, and is working on product-market fit? Should everybody just rip the Band-Aid off, shrink it, move to Kyoto and refound?

Ivan Zhao: If their body tells them so. For me, it’s like you just feel it. You have to do something drastic. And Simon during that time was broke—he got his wisdom teeth taken out or something. So I’m by myself, and I remember I was at my ex-girlfriend’s studio. I just had this inner urge like there’s no way out, I have to do this. And then you feel liberated once you land in Japan.

Brian Halligan: I guess your advice would be that probably more people should do it, and they should listen to their inner body and be more risk-seeking on that. Because they can get stuck for a long time in a venture-backed startup. They can spend 15 years of their career on something going sideways.

Ivan Zhao: I think there’s no better time than now to do that, because the market dynamic is wide open.

Brian Halligan: Yeah, I agree. Okay, you refounded a second time when you had 1,000 employees.

Ivan Zhao: Back then it was probably 500, yeah.

Brian Halligan: Okay, 500 employees. Different animal. Without telling the same story you’ve told a thousand times, because I think everyone knows the lore, what was it like behind the scenes? What did you feel? Was it the same thing, your body felt it? Like, what’s the story?

Ivan Zhao: So the second time was in Mexico—Cancún.

Brian Halligan: Right.

Ivan Zhao: Happened to be out somewhere.

Brian Halligan: Right. You’re always in a nice place.

Ivan Zhao: We had just gotten early access to the GPT-4 model. It felt like the world was stopping. When you first interact with GPT-3, it’s fine. GPT-4 is a religious experience for me. Like, holy shit, it’s a full-body religious experience. It’s like you have to do something with this. This is what changes everything. Anything you do if you don’t do this it will be meaningless. I think the company had been fairly—there were people who doubted because remember, that around three years ago, it was the crypto era, the lending era. A lot of people asked, “Is this another crypto thing?” There were a lot of doubters. Some of them are obviously no longer at the company. But the conviction was so clear, at least for me and Sam in the early days, like, we just had to do this.

Brian Halligan: Did you take two steps back in the business to go ten steps forward? Did revenue really slow while you were rebuilding everything?

Ivan Zhao: Our first product actually had a meaningful revenue boost. We launched our first AI product two weeks before ChatGPT happened. It was an AI writing product. That had a boost, but after that, we’d been wanting to build an agent product since the end of 2022. And that was a slog. That took us a year and a half to really …

Brian Halligan: Yeah. It didn’t really work back then.

Ivan Zhao: Didn’t work at all. My problem and Simon’s problem might have been living too much into the future. It bites you with new technology. We tried everything. Anthropic built a model for us, we worked on OpenAI fine-tuning and other models—just none of them worked. That was like a year and a half of going nowhere, and morale was definitely low. It only started to work a year and a half later, and our revenue growth inflection is around the same time.

Brian Halligan: When the underlying AI got better.

Ivan Zhao: Yeah, but that was a pretty painful period.

Brian Halligan: Was that the most painful period in Notion history for you?

Ivan Zhao: Different type of pain.

Brian Halligan: What was the most painful?

Ivan Zhao: Just the early days, pre-product-market fit is despair.

Brian Halligan: “Despair,” is that the word? Okay.

Ivan Zhao: You don’t know where it’s coming from, you don’t know where to go. When your growth rate is low, like during that period of time where we were rebuilding our AI foundation multiple times, yeah, that’s not great. Right now, everything is on fire. It’s a different type of pain.

Brian Halligan: Nice. So a lot of 500-person companies, a lot of SaaS companies, are doing the AI thing but certainly haven’t refounded. Advice?

Ivan Zhao: Start with your product. We just talked about treating it like brewing beer, not building bridges, because at the end of the day most tech companies are defined by the product. So start with the product, because then the founder has to be really hands-on to experience that way of building things.

Brian Halligan: Can non-founder-led companies pull it off?

Ivan Zhao: I don’t know. It will be tough. I think founder has the moral high ground to change things. People are more tolerant and forgiving with founders, right? I think the person needs to use language models and just know how to feel it. Like you’ve got to feel the AGI, feel the AI.

Brian Halligan: Yeah, you can’t read about it, you can’t watch YouTube, you’ve got to build.

Ivan Zhao: You have to feel it. Building is one of the best ways for your product or build for your internal systems.

Brian Halligan: Build for yourself.

Ivan Zhao: Yeah, tinker on the weekend, tinker on the side. You have to do that, because at the end of the day, businesses are kind of like pathfinding entities, right? Like we’re in this thing called a market. There’s equilibrium for your company with the market, with your shareholders, with your company. Like, we’re just finding local optima, local maximums for each different niche. When this brand new ingredient got introduced into the market—in this case language models—doors or paths are opened up, and we are—each company is at a different point in the market. Each has a different angle, a different niche. You have to take this, internalize this new ingredient, figure out which path got opened for you. The truth is with the customer, with yourself, if you don’t know what this can do, you cannot find a new path. I think you have to do something. You have to feel this. You feel the AI, feel the AGI.

Brian Halligan: I think you’re right. You use a word that I cringe at, but I think is good—a lot of companies “calcify” as they get older. Let’s just say you’re a company that’s calcified. How do you get uncalcified?

Ivan Zhao: We intentionally do a lot of acquisitions. We have 50, 60 founders at Notion.

Brian Halligan: And were they acquihires?

Ivan Zhao: Acquihires, acquisitions. Founders are kind of this little decalcified meathead machinery just trying to break things, right? So keep you regenerating.

Brian Halligan: I agree with that.

Ivan Zhao: I find that really helpful.

Brian Halligan: So founders found for a reason, and now all of a sudden they’re in a 1,000-person company. How do you keep them motivated and not leaving and starting something new?

Ivan Zhao: Well, first, some of them work on the domain that they were working on before. Like the person leading our AI meeting notes product had a startup in AI meeting notes before. The person leading our enterprise search is the founder of an enterprise search product. So you give them a better platform and support to do this. The people feel appreciated. Like, I just had lunch with the founder who started an enterprise search product before.

Brian Halligan: You give them leverage. They give them leverage.

Ivan Zhao: The actual people care about the thing they’re building, right? Versus fighting for product-market fit in a really crowded market. You can argue that it might be more difficult to start new companies today compared to even a year ago.

Brian Halligan: Okay?

Ivan Zhao: Because the world’s getting more noisy, like the shipping cadence from existing companies is just increasing. Everybody got Twitter fatigue, right? So …

Brian Halligan: And the SaaS companies have got the memo. Most of them got the memo and are shipping fast now. You were ahead of everyone, but …

Ivan Zhao: Yeah, people—it’s still …

Brian Halligan: Like HubSpot’s cranking.

Ivan Zhao: No, but people are still kicking and they have to kick in a different gear.

Brian Halligan: My thing these days is like, it’s never been easier to start. Man, it’s never been harder to scale, because in every little micro segment, if there’s a little traction, there are 100 competitors two days later. And the thing I’ve also noticed about startup land is almost in every one of these verticals, it’s a duopoly. There’s like a one and a two, and then 50 tied for third. They’re way off. And when you look back in time, the great companies were often founded in shitty times, because people who are really grinders and people who really want to start a company and really have a vision start in, like, 2022, 2023—a terrible time to start. In times like 2026, you get a lot of tourist entrepreneurs. And so I’ve heard people say 2026 ventures are gonna be crap even though the valuations are …

Ivan Zhao: Crypto vibe energy.

Brian Halligan: Yeah, a little bit.

Ivan Zhao: A little bit. I don’t disagree. Market will do their thing. Market is kind of beautiful in that way.

Brian Halligan: Yeah. Advice to founders of reasonable-sized companies who are a little scared to refound. You know, I’m CEO of a 500-person company. It’s going pretty well. I’m doing some AI stuff. My board’s kind of happy with me. But there’s a birdie inside of me listening to Ivan, and maybe I should refound. Advice?

Ivan Zhao: Does a person need to feel the AGI first? If you feel it, you realize most of the tech industry supports different flavors of knowledge work, and we’re at the beginning of how this can transform this industry.

Brian Halligan: I agree with you. How do you think organizations look like? So they’re changing a lot now, but what do you think they look like in three or four years? Knowledge work—you’re right at the center of this.

Ivan Zhao: I think the truth is probably somewhere—there’s the Jack Dorsey thing. There is the traditional hierarchical ones. I like to think, what are the invariables? Let’s look at what’s invariable—in this case, human nature is rather static.

Brian Halligan: We don’t change that fast.

Ivan Zhao: Humans don’t change. Humans as a species don’t change. That’s where I think it should—it will be a hierarchical organization. If you’ve just observed bamboo or chimpanzees, if you watch nature programs, there’s a hierarchy. That doesn’t change. This hasn’t changed since we left Africa. Division of labor makes sense. So people have different interests. You look at all the different personality tests, right? They’re just different ways of saying people are different. They’re not 10,000 flavors of them, but there are probably a dozen flavors of humans that cluster around those different dozen things. And we know that our legal system—well, at least right now there’s no autonomous companies, right? It’s the CEO, CFO that have to sign off on something. So it will be a small team of humans to start. So those to me are the invariables. So this invariable tells me you need to figure out how those groups of humans collaborate. A group of humans all have different biases, preferences, different values, and you will be somewhat a small, some kind of hierarchical system there. Then how do we use this new technology, new ingredient, to pass information and decisions around a small to mid-sized group of humans? That’s how I think about it.

Brian Halligan: I kind of think about it as like, right now in companies, the AI system makes very few of the decisions—let’s call it one percent. But as that system gets more context—using Notion, for example—it’ll make better decisions than humans. It’ll have more context and more history, and then humans will be more training that system and giving it context and giving it taste. And I think over time the system makes more and more of the decisions instead of the humans, but the humans are still really necessary.

Ivan Zhao: Yeah. People say AI researchers in 18—in 15 months will not be able to make a decision to improve AI models. Kind of the same thing, but they’re just seeing the bleeding edge of this.

Brian Halligan: Yes. By the way, I think you’re incredibly well positioned for all this.

Ivan Zhao: Oh yeah.

Brian Halligan: I worked for a while with this guy Ray Ozzie. It was a company called Groove Networks. We were in the knowledge management industry, which is a difficult industry because chief knowledge officers have no money and it was never urgent. In theory, it sounded great. Now knowledge management is actually incredibly important and works incredibly well.

Ivan Zhao: I know. What’s that industry called in the ‘90s? People hired consultants to map out their org chart and information flow. That became what AIM for deployment and …

Brian Halligan: Totally. Totally. And your platform is ideally suited for it.

Ivan Zhao: Yeah, I think we always forget that modern knowledge work is only about 150 years old. It’s invented. It’s not as old as fire or language. It’s only 150 years old. So why can’t there be a new flavor of it?

Brian Halligan: Okay, I want to talk about you.

Ivan Zhao: Okay.

Brian Halligan: I don’t know you super well. You’re soft-spoken and I thought you were an introvert, but in getting to know you better, was I wrong about that?

Ivan Zhao: I think I’m still introverted.

Brian Halligan: Okay.

Ivan Zhao: Yeah, I like one-on-one conversations more than one-to-many. I trained myself to do company all-hands just by doing a lot.

Brian Halligan: A lot of founders are introverts. The world is sort of built for—I’m kind of extroverted extrovert. Advice for founders who just don’t like talking to other—don’t like the whole extrovert game.

Ivan Zhao: I’ve had to evolve a lot. Like I hate …

Brian Halligan: Did you force yourself? Like, how did it work?

Ivan Zhao: Yeah, I did.

Brian Halligan: Did a significant other push you?

Ivan Zhao: No, I forced myself.

Brian Halligan: Okay.

Ivan Zhao: To lead a group of humans, you need to do one-to-many communications. Otherwise people don’t trust you. They want to hear from you. Writing is one mode, which is sometimes enough, but even more so is face-to-face. Do the all-hands. So for a while I tried to delegate all-hands to my co-founders, to other execs. No way. Now every all-hands, I open the mic, I do it, I lead the whole all-hands. Now I’m pretty comfortable with that. I still don’t love it, but I don’t dread it.

Brian Halligan: Okay. Advice for people doing all-hands. Everyone seems to do it differently.

Ivan Zhao: Get a teleprompter.

Brian Halligan: [laughs] I’m the opposite. I can’t read fast enough for the teleprompter.

Ivan Zhao: Really?

Brian Halligan: Yes, I hate it.

Ivan Zhao: Well, that changes me, because English is my second language, so if I have to think and speak at the same time, it’s hard. So I just prefer to [inaudible]. And right now, all those speech-to-text local models are so good.

Brian Halligan: They’re so good.

Ivan Zhao: So good. I literally just, the night before, talk to myself and get down what I roughly want to say. And then during the all-hands, the teleprompter is there.

Brian Halligan: Do you do them once a week, once a month? What’s your cadence?

Ivan Zhao: We’re actually changing our cadence. Used to be once a month. Right now it’s every other week for all-hands, and every other week again for AMA. So every week now.

Brian Halligan: Do you ever step on yourself at an AMA? You ever say something and you’re like, “I’m going to get crushed for that?”

Ivan Zhao: Yeah, everybody has it, right? Or just you miss a good opportunity, you can actually rally people about something, but you give a non-answer. That’s the worst. And non-answers …

Brian Halligan: At HubSpot, in the company meetings and the AMAs, there would be a Slack channel on it, and you’d go back and look at it and be like, “Oh!”

Ivan Zhao: What?

Brian Halligan: If I said something stupid or I missed an opportunity, it would really show up in there.

Ivan Zhao: That’s good.

Brian Halligan: How do you manage your time and your schedule and your deep work? How do you manage your energy? Like, for me, my energy’s pretty good right now. It kind of goes up and down during the day more than I would like. Is that the case for you? How do you deal with that? How do you deal with your introvert versus extrovert? How do you do it? What’s your schedule like?

Ivan Zhao: It’s actually not that crazy. Wake up at 7:00 am, make coffee for my wife. I usually like to do work in the morning, do some thinking, writing at home, come to office. I come to work every day. Come to office. Sometimes I’m—a new habit I’m trying right now is doing the gym during the day.

Brian Halligan: Okay. That’s a good idea. Perk you up.

Ivan Zhao: Elevate my energy during the middle of the day, and work in office till seven-ish. Usually social dinner with my wife, back to work, sleep around midnight.

Brian Halligan: When do you have time to get down the Claude rabbit hole?

Ivan Zhao: Weekends. Weekends, my happy time.

Brian Halligan: You describe that as your happy time.

Ivan Zhao: Yeah, you can be led by your curiosity rather than by your responsibility, right? Usually Saturday, Sunday morning, I have a bit of time to read the books I want to read. Sometimes it’s work-related, sometimes purely just my guilty pleasure.

Brian Halligan: And during the day, one of my founders here in New York, my favorite is he gets his schedule in 10-minute blocks.

Ivan Zhao: Meeting-wise?

Brian Halligan: Yes. What does your day look like?

Ivan Zhao: A lot of 25-minute blocks. I usually like five minutes between meetings and 25, 25, 25. My team packs my meetings together, so I have one- or two-hour chunks to think. But most of my thinking time is in the morning or in the evening. Usually I get too tired in the evening, I can’t think really well. Morning is better. And I do a lot of Slack. My wife jokes that my Slack is my social media.

Brian Halligan: Why doesn’t Notion build a Slack killer?

Ivan Zhao: We should.

Brian Halligan: Definitely. A lot of your team said you’re humble, and I think you are, too. Why?

Ivan Zhao: I wouldn’t use the word “humble.” I use the word “true.”

Brian Halligan: Your team uses that.

Ivan Zhao: Truth-seeking, probably.

Brian Halligan: They use humble.

Ivan Zhao: I think when you seek truth, you know you’re just one perspective of the truth. Or pluralism. There are multiple flavors of truth in the world. You know the story of blind people touching an elephant?

Brian Halligan: Yes.

Ivan Zhao: We’re just different blind people touching different parts of the elephant. Sometimes it could be the tail—that elephant’s a snake. Sometimes the trunk is a tree, right? That’s my worldview.

Brian Halligan: Okay. Tonight we’re going to have dinner with a bunch of founders, and some are at, like, 10 employees and they hope to go and build a 1,000-person company in the next several years. What advice do you have for them?

Ivan Zhao: It’s a game. It’s a game that’s a social game. There’s all the good parts and bad parts of social games, like humor, status—that’s a human thing, right? Like, power. The CEO game is full of that game. Just like entertainment, just like sports, you have that. High school, college lunch sessions, right? You watch that play out in the tech scene.

Ivan Zhao: It also could be a pursuit of your personal values. This is something I realized more in the past three, four years. It’s like I need to be in equilibrium with my own values of what this company I want to build with. That gives me a more sustainable energy source. I cannot just chase something or compete for competition’s sake. Like, I’m really competitive. I need to compete to win. That’s part of me. But at the same time, I need to be true to my own values: the value of building good tools, the craft, the human side of things.

Ivan Zhao: The social part of being a CEO, the market dynamic just competing for competing’s sake, and the values you personally hold—I wouldn’t say they are—this is somewhat a zero-sum game. So you need to figure out where you want to sit in the spectrum. And your personality might be different. Some people might just compete for competing’s sake, don’t care about what they’re building. Some people just want to be popular. If you just only care about craft, then you don’t build a business. You might as well just be an artist. Took me a while to realize where my equilibrium is.

Brian Halligan: Are you someone that tries to fix your weaknesses or you just lean into your strengths? And what’s your advice on that?

Ivan Zhao: Definitely lean into your strengths. There’s a necessary thing you have to do. Like, one-to-many communication, likely you need to do that as your company scales. Maybe you can lean more on writing rather than speaking, but there’s such an invariable that works, right? Within the boundary of that, you should amplify what you’re good at, because capabilities are becoming more and more commoditized with machines. So it’s your own point of view, your strength that you can live with that’s more lasting.

Brian Halligan: Okay. Something I assume that isn’t your strong suit is building an enterprise sales org, which seems like you’re in the process of building that. And from what I hear it’s going exceptionally well. How did you get your head around it? How did you hire—sounds like you hired the right person. So many companies are PLG, and are desperate to move to the enterprise, and the founders are a similar mold to you. Talk about that.

Ivan Zhao: We made a mistake. I mentioned, like, we sort of did not buy a traditional sales motion for a good two-ish years. Because Notion sales could have started earlier, but we wanted to first-principle our way into it, which is hey, we’re going to design our own system. That doesn’t work. Again, it’s a reflection of human nature. A lot of things you want to talk to a seller. There’s a lot of reasons the modern sales playbook has been around for two-ish decades, right?

Brian Halligan: I think enterprise sales is like the last function to be disrupted.

Ivan Zhao: I agree with you. You want to see a human, you feel comfortable. You don’t want to be diagnosed by a robot.

Brian Halligan: No.

Ivan Zhao: Then why should you buy an expensive thing from a robot, right? So it’s not that hard, I would say.

Brian Halligan: Okay.

Ivan Zhao: But you need to know—like, a lot of smart people might think they can create something new. Fundamentally you should not reinvent new things unless it’s really absolutely necessary. I was trying to reinvent a new go-to-market motion. That’s stupid.

Brian Halligan: Okay. I did mine. That’s how I built HubSpot.

Ivan Zhao: Yeah, right. But that’s the thing that made HubSpot, right? The inbound thing.

Brian Halligan: That was the thing.

Ivan Zhao: Each company should only preserve their innovation points to a few places, a couple places. You cannot spread everywhere, otherwise you’re spread too thin, you’re trying to reinvent the wheel too many times. We tried to put our innovation plan onto sales back then. So just go classic sales, it works. But you can make it a lot more efficient today with the tools we’re building internally. That’s different.

Brian Halligan: Okay, so you woke up one day, you’re like, “We’ve got to get good at enterprise sales.” What did you do? What are the mistakes everyone makes when they do it? Did you miss a hire or two before you got the right person?

Ivan Zhao: I thought this is somewhat solved today, right?

Brian Halligan: I kind of do, but people struggle with it. Enterprise sales has changed very little since I did it in the 1990s.

Ivan Zhao: Yeah. So we tried initially to only have a PLG flavor of sales, like a systems-thinking sales leader. Didn’t quite work. It’s just like then you’re just taking orders, and it’s not like the PLG gives you the luxury that your customers want to buy your product.

Brian Halligan: It’s easy to sell that, yeah. Fulfilling demand.

Ivan Zhao: You cannot get your sellers to do something difficult when there’s so much easier stuff they can do. It just doesn’t work. Then we realized okay, yes, we’re starting to respect the system. So our CRO, Erica Anderson, she was CRO of GitHub before—she’s a systems thinker, right? We paired Erica Anderson with our head of sales, Pravesh, which is a rah-rah.

Brian Halligan: Meat eater.

Ivan Zhao: Meat-eater. Perfect pairing. And so we have sellers with rah-rah Pravesh, but also respecting and working with Erica Anderson’s overall system. This is when things started to work in the past year and a half.

Brian Halligan: Got it. And so many of the organizations I deal with, the engineers look at how much money the salespeople make and look at the rah-rah, and they roll their eyes and they complain. I assume that happened here.

Ivan Zhao: No, we actually—Notion’s culture is always pretty receptive that different people are different. So we never had the organ rejection of sellers in the company. Our engineering team loves working with the sales team.

Brian Halligan: Okay, awesome. Speaking of culture, I saw online some people refer to you as a cult leader—and some people referred to me as a cult leader back in the day. I didn’t particularly like that. How does that land with you?

Ivan Zhao: I like that.

Brian Halligan: Okay.

Ivan Zhao: A company is—it’s sort of a religion. You have a point of view, you have your value system projected to the world through a business, through a product. Like, my favorite saying is the Catholic Church is one of the most successful companies of all time. Two thousand years. They have their rituals, their business models. They’re still around and kicking.

Brian Halligan: Great founder in Jesus and a great head of sales in Paul. Right?

Ivan Zhao: And there are a lot of sellers and a referral system.

Brian Halligan: Viral marketing.

Ivan Zhao: Viral marketing. OG viral marketing. And to me, a religion or belief system or value system are again one of the few dozen things that are ingrained in human nature. Like, people want to believe in something, to find meaning and purpose. That’s why wartime makes this more fun, right? Your purpose and meaning got amplified. Work and company give people that. Camaraderie gives people that. That’s why we play sports, right? It’s the same energy.

Brian Halligan: The first four words in culture are “cult.”

Ivan Zhao: Yeah, probably I need to look up the roots. But yeah, what is an all-hands? People go to church every Sunday. All-hands every week, same thing.

Brian Halligan: We had a thing with our all-hands that Dharmesh and I wanted it to be so inspirational that people would well up or cry during the all-hands. We really, really worked on our all-hands.

Ivan Zhao: Yeah, nothing—I don’t think there’s anything wrong with that.

Brian Halligan: Yeah.

Ivan Zhao: No. Okay.

Brian Halligan: Thank you for coming on the pod. Thank you for building Notion. Thank you for being an inspiration for tons and tons of founders.

Ivan Zhao: I’m glad. Hopefully it’ll be helpful for others.

Brian Halligan: Appreciate you.

Ivan Zhao: Thank you for your time.

Takeaways

Brian Halligan: Okay. I hope you liked that episode with Ivan. One of the things I like about him—there’s a famous quote by Oscar Wilde: “Be yourself; everyone else is taken.” I like to think I am myself. I’m pretty quirky, and I’ve embraced that quirkiness. And I think, at the end of the day, companies really reflect their CEOs. I don’t think CEOs should be afraid to really be themselves and kind of build the company around them. Ivan’s really done that nicely. That might be a good plan for you, too.

The second takeaway I had is, you know, I work with lots of startups, and there are so many companies—let’s say less than $500 million in revenue—growing like 30%. They’re kind of stuck, and there are an infinite number of stuck companies out there. If you’re in that boat, I’d recommend a refounding moment.

And the refounding is harder than it looks. It typically involves a big step back and two steps forward. It’s going to be hard. Your numbers will look worse in the short term. Ivan didn’t do this, but when we wanted to do a refounding at HubSpot at one point, we started a new company inside of HubSpot that was completely independent from it, and that served us well. That’s how Apple did it back in the day.

But if you’re stuck—and a lot of companies are stuck—be risky and do what Ivan did. He was a ye olde SaaS company, and now he’s a rocket ship AI company. I think he’s on to it.

The last takeaway I have on Ivan kind of starts back in a podcast interview I did with Jack Dorsey a few weeks ago. And it does seem to me that there’s a new way to build and run companies today that’s a pretty big departure from the way people have done it for the last 30 years.

Jack’s iterating on it. Ivan’s iterating on it. A lot of the, call it, vintage-2025 startups are iterating on it, and this is something I’m thinking a lot about. I think there needs to be a new playbook on how to be a CEO in an AI-native era.

I’m early in the iteration, but roughly the way I think about how they’re organized is this: historically, there is a triangle-shaped org chart. Those org charts have been around a long, long time—since the Roman Empire. They’re a very inefficient way to run a company, but they’ve been the best way to run a company because there’s been no better one.

I think the problem with them is the bigger that org chart gets, the more information gets distorted across it, up and down, and the slower it gets. So it’s pretty inefficient.

The new way that Dorsey described—and I didn’t quite get into it with Ivan, but I suspect it’s similar—is a circle. In the middle is all of the context in the AI system, and initially humans are making all the decisions. But over time, as you give that centralized AI system more context, it gets smarter. You’re feeding in context, and you turn over more and more of the decisions to it.

I don’t think it happens overnight. I think it’s gradual, but it’s an IT task to get it right. You have to be legible. I don’t love that word, but you have to have a legible set of systems. You have to kind of record everything.

But I think this is the new way. Companies who are doing this seem to be moving a lot faster than the companies that aren’t. And Ivan is moving at breakneck speed.

I think there are a lot of things that fall out of it. They don’t need as many people. They move much faster because of that. They have much shorter planning cycles. All of those kind of one-way doors that Bezos used to talk about are really two-way doors, because nothing takes that long to do anymore.

Anyway, I think there’s this new playbook. I’m interested in it. I’m going to be talking about it on the podcast and on X. If you’re interested in it too, hit me up on Ballagan.

Thanks for tuning in.