Notion’s Ivan Zhao: The Refounder

21 May 2026 · 1 h 3 min · 34 chapters

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In short

Ivan Zhao (Notion co-founder/CEO) explains how Notion “refounded” twice—first in Kyoto (2015) to rebuild after missing product-market fit, and again in Cancun (2023) to become AI-native—then details how AI changes org design, hiring, compensation, marketing, and planning. He frames organizational change as “jazz mode” (adaptive, technology-first experimentation) rather than “marching band” (top-down execution).

Guest backgrounds

Ivan Zhao is co-founder and CEO of Notion. He previously worked in venture-backed SaaS (Sequoia is referenced; he also mentions HubSpot as a comparison point). Notion’s co-founder Simon is repeatedly cited as a key partner in both refoundings.

Key claims

AI makes role boundaries blur; language models can “write the pipes” and handle micro-decisions, enabling flatter-but-still-hierarchical structures. Hiring should optimize for agency, optimism, curiosity, and taste/value system (not just experience). Product strategy has no fixed plan; financial planning is a running-track.

Notable examples

“manager mode/founder mode/jazz mode”; Notion’s AI product launched two weeks before ChatGPT; Kyoto refounding involved laying off to just two founders; Mexico refounding followed early GPT-4 access; marketing split into storytelling/community vs demand generation/sales go-to-market.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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The Jazz Band Philosophy

0:45 to 4:40

Discussion on company culture and the importance of a jazz band mindset.

“I like to think of him as the re-founder.”

The Evolution of Notion

4:40 to 7:00

Ivan Zhao shares the journey of Notion's growth and pivots over the years.

“Relative to other companies, still resistant to grow a lot in terms of headcount.”

Navigating AI Integration

7:00 to 11:00

Exploring how AI has influenced Notion's organizational structure and product development.

“Designer who can co-engineer have strong product sense.”

Redefining Talent and Team Structure

11:00 to 14:00

Ivan discusses the hiring strategy and the changing role of engineers and designers.

“How have you changed your company, how you compensate people, how you build your org, how you hire people?”

The Evolution of Design Criteria

14:01 to 15:10

Discover how the criteria for hiring PM designers has evolved over time.

“Well, how are PM designers, by the way, we interview them, we evaluate them.”

Shifting Marketing Structures

15:10 to 16:18

Learn about the changes in marketing departments and their impact on product alignment.

“Because taste is not in language models.”

Hiring in a Decentralized Environment

16:18 to 18:02

Explore how hiring practices are adapting to a more decentralized organizational structure.

“And just like really, really focus on that.”

Meritocracy in SaaS Companies

18:02 to 18:57

Understand the importance of meritocracy in changing work environments.

“I think the SaaS era is kind of like playbook peanut butter.”

Transitioning to a Jazz Band Organization

18:57 to 20:56

Learn about the shift from a traditional to a more flexible, 'jazz band' organizational model.

“Are you more top-down versus bottoms-up?”

Navigating Financial and Product Strategy

20:56 to 22:55

Explore the balance between financial planning and the necessity for agile product strategies.

“But product strategy is all, there's no freaking plan.”
Show all 34 chapters

The Changing Landscape of Gross Margins

22:55 to 24:28

Discuss the impact of market dynamics on gross margins and operating costs for startups.

“I'm assuming your gross margins have gotten worse, but maybe you didn't hire as much headcount, so maybe operating margins are better.”

The Art of Refounding

24:28 to 25:59

Delve into the concept of refounding and its importance for startups and established companies.

“You're kind of, in my mind, the king of refoundings.”

Cultural Inspiration from Kyoto

25:59 to 28:01

Examine how the culture and aesthetics of Kyoto influenced the refounding of Notion.

“Like, you know you're dead if you don't do it.”

The Craft of Kyoto and Its Inspiration

28:01 to 29:06

Discover how the cultural richness of Kyoto influences creative work and storytelling.

“The story we tell ourselves is like, Kyoto is a special place.”

Refounding: A Journey of Persistence

29:06 to 30:10

Learn about the challenges and motivations behind the act of refounding a company.

Craft Ethos vs. Commercial Culture

30:10 to 32:01

Explore the decline of craft culture in Silicon Valley compared to its historic roots.

“You study very important computer scientists from the 60s.”

Navigating Setbacks as a Founder

32:01 to 33:39

Understand the importance of intuition and drastic decisions for founders facing challenges.

“what's in front of you, what your competitor is doing versus if you bring humanity, you have all other disciplines around you.”

Evolving with AI: The New Frontier

33:39 to 36:58

Examine how AI technology has reshaped product development and company direction.

“I think there's no better time than now to do that.”

Pathfinding in the Market Landscape

36:58 to 38:47

Discover how companies must adapt to new technologies and market conditions.

“treated like brewing beer, not building bridges.”

Decalcifying Organizations Through Acquisition

38:47 to 39:21

Learn how acquisitions can help rejuvenate and energize stagnant companies.

“i think you're right you use a word that i cringe at but i think is good called a lot of companies calcify as they get older.”

Challenges for Startup Founders Today

39:21 to 40:56

Discuss the difficulties and competitive landscape faced by new startups in today's market.

“So founders found for a reason, and now all of a sudden they're in a thousand-person company.”

Future of Organizations and Knowledge Work

40:56 to 42:00

Speculate on how organizations will evolve in the face of technological advancements.

“But there's a birdie inside of me listening to Ivan and maybe I should refound advice.”

Organizational Changes and Human Nature

42:00 to 43:40

Explores the future of organizations and the static nature of human behavior.

“industry is supporting different flavor knowledge work, we're at the beginning of how this can do due to this industry.”

AI's Role in Decision-Making

43:40 to 45:30

Discusses how AI will increasingly influence decisions in organizations.

“Group of humans all have different biases, preferences, different values.”

The Evolution of Knowledge Work

45:30 to 47:10

Reviews the historical context of knowledge work and its importance today.

“You're soft-spoken, and I thought you were an introvert.”

Introversion in Leadership

47:10 to 49:40

Ivan shares his experiences with introversion as a leader and advice for other founders.

“I literally like, okay, the night before, or then I just like talk to myself and got what I roughly want to say.”

Balancing Strengths and Weaknesses

49:40 to 52:40

Discusses strategies for founders to balance their strengths and weaknesses.

“I usually, like, five minutes between meetings and 25, 25, 25.”

Building an Enterprise Sales Organization

52:40 to 55:40

Ivan shares lessons learned in building a successful enterprise sales team.

“There's a necessary thing you have to do.”

Navigating Sales Culture

55:40 to 56:00

Discusses the dynamics between engineering and sales teams within organizations.

“Enterprise sales has changed very little since I did it in the 1990s.”

Understanding PLG and Sales Dynamics

56:00 to 56:44

Learn about the challenges and successes in aligning sales strategies with product-led growth.

“And it's not like the PLG give you the luxury that your customer want to buy your product.”

Company Culture and Leadership Styles

56:44 to 58:31

Explore the connection between company culture, leadership, and the concept of being a 'cult leader'.

“This is when things start to work in the past year and a half.”

Key Takeaways from Ivan Zhao’s Leadership

58:31 to 59:16

Discover valuable insights from Ivan Zhao's approach to leadership and company philosophy.

“We used to have a thing with our all hands that Darmesh and I wanted it to be so inspirational that people would well up or cry during the all hands.”

Refounding Moments and New Company Structures

59:16 to 1:01:12

Learn how companies can undergo refounding moments to revitalize their growth and adapt to new challenges.

“And I think at the end of the day, companies really reflect those CEOs.”

The Future of Company Organization

1:01:12 to 1:02:58

Understand the evolving organizational structures and the potential role of AI in decision-making.

“But just roughly the way I kind of think about the way they're organized is historically there is a triangle shape org chart.”
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Transcript

Automatic transcript. May contain errors.

0:00We start a mantra in the company.

0:01Brian Halligan:We want to be a jazz band, not a marching band. I love that. 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 person. Also AI happened in the past two and a half years. So more jazz band people can really shine during this moment. Okay. So we had manager mode. We have founder mode. There's this new mode. What should we call it? Jazz mode, maybe. That's not bad, actually.

0:44Brian Halligan:Hey everybody, today we have Ivan Jawan, the co-founder and CEO of Notion. I like to think of him as the re-founder. He started the company a long time ago. In 2015, he didn't have part of MarketFit. 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 off-site down in Cancun and literally restarted the company. And 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.

1:24Brian Halligan: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, the way he builds today. And it rhymes a lot with some other CEOs that have interviewed like Jack Dorsey a couple weeks ago. I hope you like it. What do you think of my outfit, by the way? I think your outfit, your pants could be looser. Looser. Okay. On the bottom or just in general? In general. Okay. I like your sneakers. I don't know what they are. Okay. They're Italian, Primiata. That's cool. you're known as a very fashionable fellow where you shop these days here in New York New York has a good store near here in like Soho Tribeca called La Gassonne not like a designer designer but more like a European easy to wear I like the vibe I got up my game Ivan just channel some let's go shopping it's right around here afterwards we can go okay I want to talk about CEO stuff not just fashion i've been doing this sequoia thing for a couple years and a lot has changed in ceo-dom like the whole manager mode founder mode thing happened and now it's founder mode and some new mode seems to be happening let's just reflect back when paul graham's founder mode memo came out my my personal what's that it's 2020 right no no it's like it was later than that it's like 2024 my reaction by the way was relief because i was a quirky kind of uh founder mode type of person and always being, everyone's trying to talk me out of doing that.

2:58Brian Halligan:What was your reaction? I didn't have too much of a reaction, to be honest. Yeah. Nowadays, you know, Jack Dorsey kind of redesigning his company to put AI in the middle, and Brian Armstrong 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? Yeah. My journey, actually, I have a small detour of the founder mode, which is like try to delegate, trying to grow your notion has very been small as a company in the early days. Like we had product market for 2019, early 2020 or sub 10-ish people, 2019.

3:43And the company would become profitable because we're small.

3:47Brian Halligan:Did you raise venture in the early days or you bootstrapped it? We raised venture. You did? Okay, that must have been tough. It was tough. Like first five years, just C-stage money dragged us for five years. HubSpot was like that. It took us a long time to get to the product market. It was very tough. Yeah, it's a different type of tough compared to now. Back then, there's no product market fit. It's despair. It's just black. You don't know where to go, right? So we have been very small from the get-go, and we sort of taste the sweet of it because you're small, you're profitable, easier to raise money, you're default alive.

4:20and we've been resisting growing team size. And during COVID, a lot of companies really blew up. Remember that, right?

4:29Brian Halligan:I'm sure you did. We relatively, yeah, blew up. You got to product market fit at the right time. We got to product market fit around the same time. There's a lot of advice that you got to grow. So we did grow. I see. 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 have introduced in professional management, Why? Who is telling you that? That's a good question. Who tell us? Some investors. You didn't tell me that. I don't think so. It was conventional wisdom amongst the investor class.

5:02I would say there's a pro and con for that. Like, we sort of, I resisted that for a long time, so we did not build a sales team. In retrospect, I should have started sales team earlier because I thought I kept first principle the whole way, like create new kind of PLG, some kind of brand new motion. That's a mistake. The other part is product, marketing, engineer, those functions sort of, I wouldn't call a mistake, but we're upping the traditional way of building it.

5:31Brian Halligan:Did you hire, been there, done that, people in that phase? We did. And do you have any of them still? Many of them are still with us, yeah. Our CTO, it's last three years. Before that, there's another CTO during that phase. but I would say some part of Notion DNA are defined by the classic SaaS executive. Now, the thing changed in the past three years since we're building with AI. Like we're one of the earlier adopters of language modeling or product and you start thinking things are breaking building with this new technology. The classic boundary between roles doesn't quite work. the analogy i like to use back then it still is it's like building classic software is like engineering bridge if you can design it you usually can build it fairly predictable um like product manager talk to customers pass to designer pass to engineers and building with language model back then as somewhat still is it's like brewing beer you can't truly predict the things right the underlying thing good analogy you cannot tell the east hey hey guys go go go towards that flavor profile more you can't do that right you sort of have to throw your best people in there see what the model see what technology gives you so it's not customer first it's more like experiment with this technology first although the last year or so model gets so much better now but still the spirit is technology first driven development rather than customer driven first development um that really forced us to change the at least how we build product um designer is the most productive thing our designer and engineer and product people just sit in the same bucket then work with evals work with experiences and figure out new things your company has one of those personas kind of dominated and the other ones falling aside or is there they all kind of do the same thing now we always started by like our dna in the early days always blurry like we are one of the first hired designer who can call i'm a designer who can call right so we build a company based on my image and my co-founder's image.

7:43So those profiles really shines. Designer who can co-engineer have strong product sense. PMs are not afraid to roll up sleeve and try things. Like one of our heaviest token consumption person in the company is a PM, for example. Those people really shines, and we have quite a few of them in the notion.

8:04Brian Halligan:Okay, so you read the Dorsey stuff. You read the Armstrong stuff. My summary of it is they think of like a big triangle org chart. It's 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? Right. If sometimes we're creating product for other companies to do that.

8:39Brian Halligan:But yourself? The high premise is similar. At least my interpretation of it, it's so much knowledge where it's paper pushing. In the past, it's really hard to require software to push the information from one person to another, but so much of the knowledge where it's fuzzy, so a human needs to be in the middle to push information from one to the other. And it turns out language model can do 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. Second is actually doing this kind of mini decision-making in the stop between one decision point to another decision point, right?

9:15So a lot of companies, a lot of people just in the middle to pushing information, decision around to sustain a business at scale, that could be rethink.

9:28Brian Halligan:Okay. The analogy I like to use, what you've been using somewhat is like before steel, buildings cannot be higher than five, six floors. And New York City are largely six-floor tall, iron and stone and bricks. After steel, there's information where weight structure can go much higher. Since sometimes language model plus software is that. It's the steel for organizations. What does the organization look like now that we have the steel? I think - I know buildings got taller. what happens to organizations i think everybody's trying to figure out yeah like dorsey's structure is like three layers or something or three type of people right yeah three types of people that sit around the ai system that mostly train it um extremely flat and i think brian armstrong said it's five layers and everyone's a player coach which i think is pretty interesting i think a spirits are right yeah i don't think and i believe it should be a hierarchical like i think people tried in the in the past like flat organizational structure i don't think that's part of human nature human nature are hierarchical and do you think this change now we have ai that it can be flatter or you're like that's bs oh definitely can be flatter like we are getting flatter and flatter okay how many direct reports do you have i have 7a um in generally what is it the company wise probably around 789 people per person a lot of people are going to 15 20 25 yeah Many of our best people, 15, 20, 20 something.

10:59Brian 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. Yeah. Two years ago, we started to hire different shape of engineers. Okay. No longer optimized for people's experience. optimized for people's agency, energy, optimism, curiosity. A rough framework we're using, like, okay, what is the talent in the company? A talent equal to this person's capability slash experience times this person's taste or value system times this person's agency, will, right? What language model changes, like, just like Google, everybody can access information language model allow everybody to be a pretty good writer and programmer so capability got normalized democratized and taste becomes still important like what's your value system what do you want to bring to the world which direction you want to go that you cannot change as easily and you will how hard do you work this you cannot change so we're optimized for the latter to today okay that means in the engineering science we're hired for much younger people okay internally we're like i see early out of school i see this is the opposite of the way most of the ceos i'm interviewing are going it's interesting i think more people are they say that like a junior engineer powered by this stuff's more productive but if you get a senior engineer that understands the whole system been there a while and they're pilled they're like a hundred yes so higher for super junior super senior oh interesting so the shape it's more like the barbell shape, right?

12:40Because the senior provide taste. There's still a lot of auto-distribution information out in the language model. Architecturing in the language model is known very bad with that. So they need to provide a direction. It's almost like this. A good engineer managing four to six coding agents at once, right? But a good really senior architectural engineer can managing two or three junior interns or engineer, they each manage two or three, then that's the number is higher, right? And they can train the next generation. I think that might be a more optimal shape than a bunch of senior people manage coding agents.

13:18Brian 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? The definition of designer PM are different. Like we're intentionally hired designer who work as PM. and PM can, usually the other way, usually it's designer who can work as PM. It's harder for PM to work as designer because it's the visual craft. It's a genetic thing. It's more like a visual craft takes years to train, right? But designers want to talk to customers and get feedback? Yeah, it's rare, but don't stereotype designer though. They do exist.

13:52Brian Halligan:So if I look at your website, you're hiring engineer, junior, senior. Are you hiring PMs and designers or do you have some pot? I don't know how to combine those two words. Well, how are PM designers, by the way, we interview them, we evaluate them. Like we're in talk with two to three design leaders. They're kind of, we value them as PMs, basically. Are you, how can you drive things yourself? It's not just come up with good ideas. How much are you interviewing customers? Besides, you're good with craft, design craft. Some of this stuff is like the fashions change. Like for the longest time it was experience.

14:29Brian Halligan:Then the word everyone used was slope. We hire for slope. And now it's kind of taste and curiosity and agency. That's kind of slope, though. That's like the... It's slope-ish. How is it different? Slope to me is just horsepower smart. Well, intelligence is... First, intelligence is multiple dimensions. Like GPU speed, like... How'd you do on your friggin' SAT? But there's plenty smart people who are lazy. That's for sure. Do you call that high slope or low slope? I don't know. I just always bucketed in to hire the people who learn fast and are very smart. And I think it's changed to the word taste comes up a lot.

15:08Brian Halligan:And you've been talking about taste for a long time. The industry talks. Why is that all of a sudden a thing? Why is that word everywhere now? Because taste is not in language models. Yeah. Taste is, if you do a long, long time, maybe it is, but right now it's not. Yeah. And taste is more rooted based on your value system. Are you drinking sparkling water or still water? Are you drinking Diet Coke or iced tea? It's to each of their own. There's no right answers. The rest of you, you've got more than just engineering. You've got a bunch of people here, which is great. But let's just take marketing.

15:42Brian Halligan:Is the criteria change there too? We actually change our marketing department. We no longer have a CMO organization. This is this year. Last year, this year. We break up our CMO organization into storytelling, which is closer to product, closer to... 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 connect to social where people are discussing that are happening. And then the other part is serving the sales go-to-market function. Like demand gen. Lead gen. Lead gen. And just like really, really focus on that.

16:24So rather than information, round trip to a CMO, then figure out how to serve both the product side and the gold market. No more. Just like let both side figure out themselves. Not with themselves, but more decentralized.

16:35Brian Halligan:And are there any other of the classic marketing functions in there? It's sort of those are the two. Those are the two. The designers, there are also designer and creative part on the storytelling side. Like community? Yeah, community is in there. It's a community as part of the community ecosystem organization, which is startup, where it's one of the most important communities, notion fans around the world, and figure out how to move our market through those people, right? That's the bucket of people. And has the criteria changed sales, marketing, all the different other functions? Have you changed the way you think about the hire?

17:17Brian Halligan:like most companies have a form when you interview someone has that form changed. Yes, we're actually in the middle of, I just described the engineer one, right? Engineer and designer, it's the, we changed two years ago. Go to markets, marketing would change, you know, six months-ish ago. Sales were changing right now. And when you hire a sales rep, do they have to be AI-pilled? Yes. We actually changed our first interview. No longer look at your resume. Build something for us. Send the Notion link. than something that you build, but look at what you build. How about compensation? Is that changing?

17:51Brian Halligan:My sense is we had an environment where at least in HubSpot, people are much more productive than the average person. Now it's even more so. Yeah. Have you rethought? We are changing that as well. So there need to be extremely a lot more meritocracy. You can peanut butter things. I think the SaaS era is kind of like playbook peanut butter. everybody it's like a pretty peaceful era right now it's a war time totally actually make the SaaS feels like what are we doing back then well nothing changed for the longest time like nothing it's kind of boring nothing changed like the notion we had the reason I left HubSpot it's 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 like keep going until a couple years ago now it's completely changed or you can welcome back to become operator that's why i joined skoy i'm like wow there's so much exciting things going on when we hit problem market when covid happened it's more like a world changing but not like as people building things and technology changing do you prefer wartime or peacetime wartime's way more fun it's like what's the difference what do you do differently you feel more alive okay but what methods do you use that are different i need to take care of my body i need to exercise every day I didn't think we were going to say that, but okay.

19:08Yeah, it's like it's more fluid.

19:12Brian Halligan:Are you more top-down versus bottoms-up? I think the company has a good spot. Notion right now is a good spot with me in the sense that I can dance around really smoothly in either direction. There's enough people I trust really well, they can bottom-up. And it's constantly surprising me. Like, we're a company of 1 ,000 people. We have about 50, 60 founders in the company, ex-founders. It's like they really can lead things. And they're welcoming me to top down and to jump into any part that I can work on, I'm interested in, where I can provide new value, and they don't feel territorial. This is in a good place.

19:50People who didn't feel that way, either no longer at Notion, let them go. So the company I meet in a pretty interesting equilibrium at the moment.

19:58Brian Halligan:I interviewed Parker Conrad from Rippling, and he's similar as a lot of founders. And the way it kind of strikes me is like 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 in their org. So we did not do that. I regret not doing more of that. That's my real, remember I said right after COVID, we scale and then we try to scale more traditionally. I realized that's not us, right? At that point, this was three years ago, we start a mantra in the company we want to be a jazz band not a marching band i love that i do the orchestra versus jazz band i like the marching band yeah i realize i cannot be a marching band person that's just not me i will feel like if everybody i delegate everything everybody do think what do i do i feel like i can't do that um 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 person also ai happened in the past two and a half years so more jazz band people can really shine during this moment okay so we had manager mode we have founder mode there's this new mode what should we call it jazz mode maybe that's not bad actually because jazz mode has some structure right you don't want to be like you want other people to contribute you don't want you want people to have fun it's not just you having fun or dictating everything okay let's give that a go let's push that out on on x and see if it sticks i mean jazz mode yeah because i put a survey out the other day like what mode is this and i was like is it dorsey mode is it native mode and i said is it other mode and somebody put in there it's depeche mode the patch the patch that's a band yeah they were making a joke but i like jazz mode that's a good idea one other question on this new world um i work with all these startup founders the planning's tricky and i sat through your pitch at sequoia and you had a plan and you had a p &l like what is it actually like internally planning wise more group has our plan which most company at this point if it works if group has our plan right so um i would say the financial planning is still at least i find useful to give you a but you know you're on track and you know how fast you're running right that's like a financial plan in my mind it's like oh am i running seven, eight, one nine, what number that is.

22:25But product strategy is all, there's no freaking plan. No plan. Because what changes the market, the technology is so fast. It's not in the six month, it's not three months, it's week by week. So this, you have to jazz this thing. Financial things, March death, right? Then at least we'll try to be conservative, mid to conservative with financial things and it's take risks and there's a buffer like cost becomes another dimension like if you're just building software don't think about cost no now you have to like at least i have to really think about cost can i ask you about that like a

23:04Brian Halligan:lot of these startups gross margins are awful and like i companies like hubspot we're like 86 gross margins that's sort of sass normal what are happening to your costs and your gross margins and Where do you think it settles out for companies like yours? I don't have an answer for you. 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 be like gross margins to get radically worse? Oh, you have to. You're down for that. It's like, what are you doing? Then you're not in the war mode, right?

23:39I think Notion is for knowledge work, which might have a different curve than coding products. Coding product, you run frontier models. Usually the smarter, the better. And knowledge work, we already start to see this. You sort of can settle with the second tier, the Chinese models, the open-weight ones. They're not super smart. Like a lot of this kind of paper-pushing information in your company, I spill coffee on the carpet. Can HR team come someone to tidy this up next week? That doesn't require Opus to file tickets, right? So that's a lot of problem we are best at solving at Notion. So that will have a different growth margin profile than the biggest product market fit today, which is a coding agent.

24:26Brian Halligan:Yes. Okay. You're kind of, in my mind, the king of refoundings. Yeah. You've done it, I think, twice. At least, Claude thinks you've done it twice. your first one you and your co-founder moved to kyoto locked yourself in a very small room and rebuilt it's not that small but yeah okay you know more recently obviously you know this everybody knows the story you went to mexico and you had early access to the models you turned into an ai company talk about the different refoundings and what was your mindset at the time there's lots of early stage founders who need to refound and there's a lot of bigger SaaS companies that definitely need to refund?

25:07Yeah, I like it as an idea, as the best artists reinvent themselves. Miles Davis has at least three faces, right? Picasso, two to three faces. Michael Jordan, the second one, probably not as good. But the best one, truly, Steve Jobs, the king of refunding. The first version of Notion is like, We took us four, five years to find product market fit. In the middle of that, we sort of find the shape of the product we want to build, but we'll be running out of money building it. So I co-founder Simon and I said, let's just lay off everybody. Just go by the two of us. That's the Japan story. We rebuilt Notion from Japan.

25:51Brian Halligan:How hard was that, the laying off everyone? It's not easy, but sometimes your body just tells you you have to do it. Like, you know you're dead if you don't do it. You know, just there's like a panda energy, just like. Why the hell did you go to Kyoto of all places? We actually, we never been to Japan. Because when you just say goodbye to your friends, all those people you work with, by all means, it's not big. Five people-ish. It's morale so low, right? So some of us were saying, let's go somewhere that would just change the mood a little bit. And we never been to Japan. So initially I picked Tokyo on Airbnb, realized that the house are so small.

26:34I love Simon, but I don't want to cram into a small apartment with him. And Kyoto, the apartment was much bigger because they didn't get burned on the World War II.

26:44Brian Halligan:They weren't bombed. They weren't bombed. They spared that city, too much treasures. And the house is much bigger and cheaper. So that's why I picked Kyoto. and we ran our place in SF and our office in SF, we actually become cash flow positive doing that. That's the first time. But once you land, you start coding, just kind of rapid coding, eating, coding, eating. It's actually really liberating. 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.

27:23Brian Halligan:or could you have been in anywhere? Could you have been in Thailand? Well, usually we like summer warm. Simon likes warm climate. Ideally, he can swim. Japan just happened to be we're both curious about it. But once you go to Kyoto, I don't know. You've probably been to Kyoto. It's a very special city. Very special. Yeah. Very inspirational. Very inspirational. Those things are hundreds, everything. Oh, this shop, 150 years old, right? I'll open that door. The shrine being there for 800. 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?

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28:00Most of our things our story would tell ourself. Of course.

28:03Brian Halligan:What story is the true story? The story we tell ourselves is like, Kyoto is a special place. If you can pull off anywhere, you can pull off from reborn in Kyoto. And it's also inspiring. Just look at the surrounding. The craft is probably the craft capital of Asia, right? So just make you okay. If notion fundamentally is tool, it's a tool for humans. And those people are building knives, ceramic cups, tatami seats. Like they're the tools, other tools for humans. It's a craft central. It's a craft central. And it's like, how can you not be inspired by building a better software tool? Okay, you still haven't answered my question.

28:44Brian Halligan:Which is? If you had gone to, whatever, 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 i think i pulled it off but yeah but the story is the better story okay fine okay so your big refounding not easy didn't immediately hit product market fit after still not no it took a while yeah because it took a year and a half to rebuild from scratch why didn't you just quit and start a new company at that point we never start a company for starting a company you want to build something like i got assessed about this notion shape tool problem since last year college and simon and i were both in this kind of tools for thought community which is you can trace the lineage back to grateful dead areas the the first generation computing pioneers around the bay area like the linear trace way back directly back to there i want to continue that lineage um so to me it's not it wasn't like another idea kicking around this is your life's work and this is like bigger than i can ever chew on this idea so i wouldn't do anything else he's in that community he's obsessed with this idea too so if we don't work on this work work on another company doing the same thing okay i'm gonna i'm gonna get back to the refounding but just on the grateful Dead.

30:11Brian Halligan: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? I think most people don't have it. Most companies don't have it. I agree. Like Steve Jobs, I look up to him, or people like him, it's like interception of humanity with technology. Versus Silicon Valley, at least tech is largely a technology and tinker culture.

30:51And tinker culture doesn't even know the history of, it's not even science, it's tinkering, right? It's like people like to build things in their garage and something works and maybe has a product market fit and grow a business out of

31:01Brian Halligan:this to be fair was and was was tinkering in the garage yeah but you require to meet someone to to bring the human side of it right um i think tinker culture that the risk of us like you don't know what comes before you science at least you respect the history like if we ask people who um dougas angle bar or alan kate was computing pioneers are most people in tech with no idea honestly the only reason i know that was i work for this guy ray ozzy realty like you would know of course because he's the father of notes but he was obsessed with those two and talked about them constantly i know reality uh it's like microsoft cto for a while too right so um that lineage is broken by the way the people who remember this 80 70s and 80s they were sort of people don't even yeah they're no longer working in tech today um so tech is like industry doesn't know its past if you don't know its past you don't know history which is humanity i think your point of view is like what's in front of you, what your competitor is doing versus if you bring humanity, you have all other disciplines around you.

32:10You have all the history behind you. There's way more good stuff you can steal from. I wish more tech founders steal from a side or from behind.

32:23Brian 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 it's like maybe their cash flow break even what's your advice to somebody as a founder has been going sideways for a long time adventure dollars in like you and working on product market fit like should everybody just be like rip the band-aid off and shrink it and moved to Kyoto and and refound if their body tell them so like I for me it's like there's you just feel it you have to do something drastic and Simon during that time was he broke his he got his wisdom teeth taken out or something so I'm by myself I was like I remember I was at my ex-girlfriend's studio I just like inner urge like there's no way out I have to do this and And it's like, then you'd feel liberated once you land in Japan.

33:24Brian Halligan:I guess your advice would be is 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. I think there's no better time than now to do that. Because the market dynamic is wide open. Yeah, I agree. Okay, you re-founded a second time when you had 1 ,000 employees. Back then it was probably 500, yeah. Okay, 500 boys. Different animal. Without telling the same story you've told a thousand times, because I think everyone knows the lore, what was it like kind of behind the scenes?

34:02Brian Halligan:What did you feel? Was it the same thing? Your body felt it? Like, what was the story? So the second time was in Mexico, Cancun. Right. Happened to be out somewhere. Right. You're always in a nice place. We just got early access GPT-4 model. It feels like the world is stopping. like when you first interaction with the gp3 is fine gp4 is a religious experience for me it's like holy shit it's a full body religious experience like you have to do something with this this is what change everything anything you do if you don't do this it will be meaningless um i think the company has been fairly there's be people doubt because they remember that around three years ago that's the crypto era landing right a lot of people is this another crypto thing there were a lot of doubters.

34:51Some of them, obviously, no longer at the company. But the conviction is so clear, at least for me and Sam in the early days. Like, we just have to do this.

35:01Brian Halligan:Did you take two steps back in the business to go 10 steps forward? Like, did revenue really slow while you were rebuilding everything? Our first product actually has a meaningful revenue boost. We launched our first AI product actually two weeks before ChatGPT happened. it's like AI writing product that has a boost but after that we've been pretty much want to build Asian Prada in 2022 end of 2022 and that's a slog that took us a year and a half to really didn't really work back then didn't work at all like Simon I would say my problem and Simon's problem we might be living too much into the future it bites you with new technology like we try everything Entropi built a model for us we work opening fine tuning or another model just none of them work that will like a year and a half just go with nowhere and morale is definitely low only start to work a year and a half our revenue growth inflection this around the same time right when the ai product the underlying got better yeah it's like um but that was the that was a pretty painful period was that the most painful period in notion history for you?

36:14Different type of pain.

36:15Brian Halligan:What was the most painful? Just when it was two, three, early days, pre-product market fit is despair. I was just like... Despair, is that the way it is? Okay. You don't know where it's coming from. You don't know where to go, right? When your growth rate low, like during that period of time, we were trying to rebuilding our AI foundation multiple times it's yeah that's not great um right now just everything on fire it's a different type of pay nice so a lot of people 500 person companies a lot of sas companies are doing the ai thing but certainly haven't refounded advice start with your product we just talk about treated like brewing beer, not building bridges.

37:05Because that's, end of the day, most tech companies, it's the product, right? So start with the product because then the founder has to be really hands-on to experience that way of building things.

37:18Brian Halligan:Can non-founder-led companies pull it off? I don't know. It would 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 be used language modeling and just know how to feel it. Like you got to feel the AGI, feel the AI. Yeah, you can't read about it. You can't watch YouTube. You got to build. Building is one of the best ways for your product or build for your internal systems. Build for yourself. Yeah, tinker on the side. You have to do that because like I think the business are kind of like pathfinding entities, right?

38:01Like we're in this thing called a market. There's equilibrium for your company with the market, with your shareholder, with your company. Like we're just finding local optimists, local maximums for different our niches. When this new brand new ingredient got introduced into the market in this language model, doors are pathed, are opened up. And we are each company at different point in the market. You have different angle. You have different niche. you have to take in this internalize this new ingredient figure out which path got opened for you choose this with a customer with yourself if you don't know how this 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

38:47Brian Halligan:i think you're right you use a word that i cringe at but i think is good called 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? We intentionally do a lot of acquisitions. We have 50, 60 founders at Notion. And were they aqua hires? Aqua hires. Aqua hires, acquisitions. Founders are kind of just kind of like little decalcified meathead machinery just trying to break things, right? So keep your regenerating. I agree with that. Yeah, I find that really helpful. So founders found for a reason, and now all of a sudden they're in a thousand-person company.

39:25Brian Halligan:How do you keep them motivated and not leaving and starting something new? Well, first, some of them work on the domain that they were working on before. Like the person leading our AI meeting knows has a startup of AI meeting knows before. The person leading our enterprise search is the founder of enterprise search product. So you actually give them a better platform support to do this. People feel appreciated. I just had lunch with the founder who started enterprise search product before. You give them leverage. They give them leverage. The actual people care about the thing they're building versus fighting for product market thinking of really crowded market.

40:01They don't. You can argue that it might be more difficult to start new companies today compared to even a year ago because the world is getting more noisy. like the shipping cadence from existing companies are just increasing it's like the

40:18Brian Halligan:everybody got twitter fatigue right so in the sas companies have got the memo most of them got the memo and are shipping fast now you were ahead of everyone but yeah people like it's still hubspot's cranking that's good no the people are still kicking and they're they have to kick in different gear no my thing these days is like it's it couldn't it's never been easier to start man it's never been harder to scale because like in every little micro segment if there's a little traction like there's a hundred competitors two days later and the thing i've also noticed about the 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 that the the great companies were often founded in shitty times because people were really grinders and people 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 you know 2026 ventures are gonna be crap even though the valuations are like crypto crypto vibe energy yeah a little bit a little bit um i don't disagree market will do that thing market is kind of beautiful in that way yeah advice to founders of reasonable size companies who are a little scared to refound.

41:40Brian Halligan: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. Does the person need to feel the AGI first? If you feel you realize most tech industry is supporting different flavor knowledge work, we're at the beginning of how this can do due to this industry. I agree with you. How do you think organizations look like? So they're changing a lot now. What do you think they look like in like three, four years? Is your knowledge work, you're right at the center of this?

42:20I think truth is probably somewhere. There's a Dorsey, Jack Dorsey's thing. There is the traditional hierarchical ones. I like to think what are invariables. Like, let's look, invariably in this case, human nature are rather static. Like, we all...

42:43Brian Halligan:We don't change that fast. Human don't change. Human as a species doesn't change. That's where I think it should, you will be a hierarchical organization. If just observe bamboo or chimpanzees, right? It's like very, if you watch nature program, there's hierarchy. That doesn't change. It hasn't changed, left us since we left Africa. Division of labor makes sense. Um, so, um, people have different interests. You, you look at all the different like personality tests, right? They're just different ways of saying like people are different. There are not 10 ,000 flavor of them there, but there are probably a dozen flavor of humans, a cluster around this different dozen things.

43:22And we'll know that our legal system. Well, at least right now there's no autonomous companies, right? It's the CEO CF will have to sign up for something. So it will be a small team of humans to start. So those two are invariables. So this invariable tells me you need to figure out how those group of humans collaborate. 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 ingredient to pass information decision around the small midsize group of humans? That's how I think about it.

44:02Brian 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 1%. 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. Yeah. People say AI researchers in 15 months will not be able to make a decision to improve AI models.

44:37Kind of the same thing, but they're just seeing a bleeding edge for this.

44:40Brian Halligan:Yes. By the way, I think you're incredibly well positioned for all this. Oh, yeah. I worked for a while with this guy, Reazi. It was a company called Groove Networks. We were in the knowledge management industry, which is a shit 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. I know. It's like, what's that industry called in the 90s? People hire consultants to map out their org chart and information flow. That becomes like what AI and forward deployment.

45:16Brian Halligan:Totally. And your platform is ideally suited for it. 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. Yeah, yeah, yeah. Right? So why cannot be a new flavor of it? Okay, I want to talk about you. Okay. 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? I think I'm still introverted. Okay. Yeah. I like one-on-one conversations than one too many. I train myself to do company all hands just by doing a lot.

45:54Brian Halligan:A lot of founders are introverts. The world is sort of built for, I'm kind of extroverted extroverts. Advice for founders who just don't like talking to other, don't like the whole extrovert game. I have to evolve a lot. Like, I hate doing company. Did you force yourself? Yeah, I did. Like, how did it work? A significant other put you? No, I forced myself. Okay. To lead a group of human, 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 like sometimes link-naught, but even more so is face-to-face to the all-hands.

46:30So 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.

46:47Brian Halligan:Okay. Advice for people doing all-hands. Everyone seems to do it differently. I'll get a teleprompter. I'm the opposite. I can't read fast enough for the teleprompter. Really? Yes, I hate a teleprompter. Well, that changes me. Because English is my second language. So it's like if I have to think and speak, it's hard. So I just prefer to spoken before. And right now, all those speech-to-text model logos are so good. They're so good. So good. I literally like, okay, the night before, or then I just like talk to myself and got what I roughly want to say. and the time doing all hands, teleprompter is there.

47:24Brian Halligan:Do you do them once a week, once a month, once a month? Like, what's your cadence? We're actually changing our cadence. It 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. Did you ever step on yourself on an AMA? You ever say something and you're like, are you going to crush for that? Yeah. Everybody has it. Or just you miss a good opportunity that you can actually rally people about something but you give a non-answer. That's the worst. And non-assers? We, at least at HubSpot and the company meetings and the AMAs, there would be a Slack channel on it.

47:57Brian Halligan:And you go back and look at it and be like, oh. What? Just like if I said something stupid or I missed an opportunity, like it would really show up in there. That's good. How do you manage your time and your schedule and your deep work? Like how do you manage your energy? Like for me, my energy is 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? It's actually not that crazy. Wake up 7, 7, 8, make coffee for my wife.

48:38I 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 a new habit I'm trying right now is doing the gym during the day. Okay. Yeah.

48:53Brian Halligan:That's a good idea. Perk you up. Elevate my energy during the middle of the day. And work in office till seven-ish. Usually it's social dinner with my wife. Back to work. Sleep out till midnight, around midnight. When do you have time to get down the cloud rabbit hole? Weekend. Weekend's my happy time. you describe that as your happy time yeah you can be led by your curiosity rather than by your responsibility usually Saturday, Sunday morning I have a bit time to read the books I want to read sometimes it's for work sometimes it's for my guilty pleasure during the day half hours one of my founders here in New York he gets his schedule in 10 minute blocks Meeting-wise?

49:43Brian Halligan:Yes. Like, what does your day look like? A lot of 25-minute blocks. I usually, like, five minutes between meetings and 25, 25, 25. My team pack my meetings together so I have one or two-hour chunk 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's better. And I do a lot of Slack. My wife joked my Slack is my social media. Yeah. Why doesn't Ocean build a slack killer? We should. Definitely. Yeah. A lot of your team said you're humble. And I think you are too. Why? I wouldn't use the word humble.

50:22I use the word truth.

50:23Brian Halligan:Your team uses that. Truth seeking, probably. They use humble. I think you seek truth, you know you're just one perspective of the truth. Or pluralism. There are multiple flavor of truth in the world. You know the story of blind people touching an elephant? Yes. where just different blind people touching different parts of the elephant. Sometimes it could be the tail. The elephant's a snake. Sometimes the trunk is a tree, right? That's my worldview. Okay. Tonight we're going to have dinner with a bunch of founders and some are like 10 employees and they hope to go and build a thousand person company in the next several years.

51:00Brian Halligan:What advice do you have for them? It's a game. It's a game that's a social game. it's like there's all the good part and bad part of social game like humor status is human thing right like um powers is that's the ceo game is full of that game just like entertainment just like sports you have that like high school college lunch sessions right you you watch that in real in in the tech scene 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 value of what this company I want to build with.

51:44That gave me more sustainable energy source. I cannot just chase something or competition for competition's sake. Like I'm really competitive. I need to compete to win as 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. The social part of being a CEO, the market dynamic just compete for competing sake. And the value, I wouldn't say they are, this is somewhat a zero-sum game. So you need to figure out where do you want to sit in the spectrum. And your personality might be different. Some people might just compete for competing sake, doesn't care about what they're building.

52:29Some people just want to be popular. If you just only care about craft, then you don't build a business. It might as well just be an artist. Took me a while to realize where's my equilibrium.

52:39Brian Halligan:Are you someone that tries to fix your weaknesses or you just lean into your strengths? And what's your advice on that? Definitely leaning on your strength. There's a necessary thing you have to do. Like one-to-many communication likely you need to do with your company's scale. 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.

53:17Brian 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 want to hear it's going exceptionally well. How did you get your head around it? How did you hire? It sounds like you hired the right person. So many companies are PLG and are desperate to move to the enterprise and the founders are similar mold to you. You talk about that. We had a mistake. As I mentioned, we sort of did not buy traditional sales motion for a good two-ish years. Because Nelshan sales can start earlier, but we want to first principle our way into it, which is, yeah, we're going to design our own system.

53:59That 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 the reason the modern sales playbook has been around for two-ish decades.

54:12Brian Halligan:I think enterprise sales is like the last function. I agree with you. It's like you want to see a human, you feel comfortable. You don't want to be a doctor from a robot. No. Then why should you buy an expensive thing from a robot, right? So it's not that hard, I would say. But you need to know, like a lot of smart people might think they can create something new. Like 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. Okay. I didn't mind how we built HubSpot. Yeah, right. But that's the thing, HubSpot, right?

54:52like this inbound that was the thing you should only have each company should only preserve your innovation point to few places go a couple places you cannot spread everywhere like otherwise you're spread to thing you're like you're trying to like reinventing the wheel too many times we try to put our innovation point on to sales back then so just just go classic sales It works. But you can make a lot more efficient today with a lot of tools we're building internally. That's different.

55:26Brian Halligan:Okay, so you woke up one day, you're like, we 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? I thought that some was solved today, right? I kind of do, but people struggle with it. Enterprise sales has changed very little since I did it in the 1990s. Yeah, so we tried initially only half PLG flavor of sales, like system thinker, sales system, sales leader. Didn't quite work. It's just like then you're just taking orders. And it's not like the PLG give you the luxury that your customer want to buy your product.

56:05Brian Halligan:Easy to sell it. Yes. It's like fulfilling demand. You cannot get your sellers to do something difficult when there's so much easier thing they can do. It just doesn't work. Then we realize, okay, yes, we're starting to respect the system. So our CRO, Erica, she was CRO of GitHub before. It's a system thinker, right? We pair Erica with our head of sale, Pravesh, which is rah-rah, like the meat eater. The veins in the teeth. Perfect pairing. And so we have sellers, we rah-rah, pravesh, but also respect working with Erica's overall system. This is when things start to work in the past year and a half.

56:47Brian Halligan:Got it. In so many of the organization 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? No. We actually, notion culture is always pretty receptive for different, people are different. So we never have the organ rejection of sellers. in the company. Our engineering team love work with sales team. 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.

57:22Brian Halligan:How does that land with you? I like that. Okay. A company is, it's sort of a religion. It's you have a point of view. You have your value system project to the world through a business, through a product. Like, My favorite saying is Catholic Church is one of the most successful companies of all time. 2 ,000 years, they have their ritual, their business models. They're still around, kicking. Great founder in Jesus and a great head of sales in Paul. Right? And there are a lot of sellers and referral system. Viral marketing. Viral marketing, OG viral marketing. Yeah, and to me, religion or belief system or value system are, again, one of the few dozen things that's ingrained in human nature.

58:08Like, people want to believe in something to find meaning and purpose. That's why wartime make this more fun, right? Your purpose and meaning got amplified. Work and company give people that. Camaraderie give people that. That's why we play sports. It's the same energy.

58:26Brian Halligan:The first four words in culture are cult. Yeah, probably I need to look up the roots, but yeah. It's like, what is all hands? People go to church every Sunday. All hands every week, same thing. We used to have a thing with our all hands that Darmesh and I wanted it to be so inspirational that people would well up or cry during the all hands. It's like we really, really worked on our all hands. Nothing, I don't think anything wrong with that. No. Okay. Thank you for coming on the pod. Thank you for building Notion. Thank you for being an inspiration for tons and tons of founders. I'm glad. Hopefully, it'll be helpful for others.

59:01Appreciate you. Thank you for your time.

59:04Brian 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, like I'm pretty quirky and I've embraced that quirkiness. And I think at the end of the day, companies really reflect those CEOs. And 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 kind of takeaway I had is I work with lots of startups and there are so many companies, let's say less than 500 million in revenue growing like 30 percent.

59:48Brian Halligan:They're kind of stuck and there's infinite numbers of stuck companies out there. If you're in that boat, I'd recommend a refounding moment. The refounding is harder than it looks. It typically involves like 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 risk on and do what Ivan did.

1:00:28Brian Halligan:Like 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 there's a new way to build and run companies today. That's a pretty big departure from the way people have done it 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 the iNative, in the kind of era we're in.

1:01:11Brian Halligan:And I'm early in the iteration. But just roughly the way I kind of think about the way they're organized is historically there is a triangle shape 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 that information gets distorted across and up and down in the slower it gets. And 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 it's a circle.

1:01:49Brian Halligan:And in the middle is all of the context in the AI system. And initially, humans are making all decisions. But over time, as you give that kind of centralized AI system more context, it gets smarter. And you're feeding a context, and you turn over more and more of the decisions to them. I don't think it happens overnight. I think it's quite 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 just moving a lot faster than the companies that aren't.

1:02:25Brian Halligan:And Ivan is moving at breakneck speed. And I think there's 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. Anyway, I think there's this new playbook I'm interested in and 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 at B. Halligan. Thanks for tuning in.

From the publisher

Ivan Zhao, founder and CEO of Notion, joins me to introduce a new contender in the founder mode debate: jazz mode. Ivan has a different take than Jack Dorsey's circular org chart or Brian Armstrong's player-coach approach. He thinks hierarchy is human nature, and that you can't flatten it away but you can build a company that improvises like a jazz band instead of marching in formation. Notion has roughly 60 ex-founders on staff and a deliberately decentralized structure to make that work.

We get into why Ivan rebuilt his engineering org around a barbell — super junior ICs paired with very senior architects — which is the opposite of what most AI-pilled CEOs are doing right now. He explains why building with language models is "more like brewing beer than engineering a bridge," and how Notion's first candidate interview no longer involves a resume.

Ivan is the king of refoundings. He's done it twice, once from a small apartment in Kyoto with five employees left, once from Cancun the day he got early access to GPT-4. When I was running HubSpot, I described our scale-up years as boring compared to what's happening now. Ivan's advice for any CEO who's calcified and wondering if it's time to blow it up: feel the AGI first, then trust your body when it tells you to move.

00:00 Introduction
02:22 From Founder Mode to AI Org
11:00 Hiring for Taste and Agency
24:28 Refounding Notion in Kyoto
30:27 Craft Versus Commerce
32:26 When to Refound
34:07 GPT-4 Refounding Shock
45:35 Leadership and Founder Energy
53:17 Sales Culture and Closing Thoughts

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