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- [00:00]
A
We start a mantra in the company. We want to be a jazz band, not a marching band.
- [00:04]
B
I love that.
- [00:05]
A
It's like a self reflecting value thing. It's out of 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.
- [00:20]
B
Okay, so we had manager mode. We have founder mode. There's this new mode. What should we call it?
- [00:24]
A
Jazmo maybe.
- [00:26]
B
That's not bad actually. 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. 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 off site down in Cancun and literally restarted the company. And in my mind, he's the canonical example of 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, the way he builds today. And it rhymes a lot with some other CEOs that have interviewed, like Jack Dorsey a couple of weeks ago. I hope you like it. What do you think of my outfit, by the way?
- [01:44]
A
I think your outfit, it's your pants could be looser.
- [01:48]
B
Looser. Okay. On the bottom or just in general?
- [01:50]
A
In general.
- [01:51]
B
Okay.
- [01:52]
A
I like your sneakers. I don't know what they are.
- [01:54]
B
Okay. They're Italian premiata.
- [01:56]
A
That's cool.
- [01:57]
B
You're known as a very fashionable fellow. Where. Where you shop these days? Here in New York.
- [02:01]
A
New York has a good store near here in like Soho Tribeca, called La Casson. Not like a designer designer, but more like a European easy to where I like the vibe. Thank you.
- [02:15]
B
I got up my game, Ivan.
- [02:17]
A
Just channel some.
- [02:18]
B
Let's go shopping. You want to go shopping?
- [02:20]
A
It's right around here. Let's go shopping afterwards. We can go.
- [02:22]
B
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 and CEOed him. 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.
- [02:43]
A
What's that? Since 2022, right? 2021.
- [02:46]
B
No, 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 founder mode type of person. Always being. Everyone's trying to talk me out of doing that. What was your reaction?
- [02:59]
A
I didn't have too much of reaction, to be honest. Yeah.
- [03:02]
B
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's it changing?
- [03:23]
A
Yeah, my journey actually I have a small detour of the founder mo which is like try to delegate, trying to grow. Your notion has very being small as a company in the early days, like we had product market for 2019, early 2020 or sub 10ish people. 2019 and company become profitable because we're small. Right.
- [03:48]
B
Did you raise venture in the early days or you bootstrapped it?
- [03:51]
A
We raised venture.
- [03:52]
B
You did okay. That must have been tough.
- [03:55]
A
It was tough. Like first five years just C stage money dragged us for five years.
- [04:00]
B
Yeah. HubSpot was like that took us a long time to get the product market fit.
- [04:03]
A
It's very tough. But yeah, it's a different type of tough compared to now. Back then there's no product market fit. It's despair. You 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 it's your small, you're profitable, easier to raise money, you're default alive. And we've been resisting growing team size. And during COVID a lot of companies really blew up. Remember that, Right?
- [04:29]
B
I'm sure you did.
- [04:31]
A
We relatively. Yeah, blew up.
- [04:32]
B
You got to product market fit at the right time.
- [04:34]
A
We got to product market fit around the same time. There's a lot of vibes that you got to grow. So we did grow. I see relative to other company 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, need to have introducing professional management.
- [04:52]
B
Why? Who is telling you that?
- [04:53]
A
That's a good question. Who Tell us some Investors. You didn't tell me that. I don't think so.
- [05:00]
B
It was conventional wisdom amongst the investor class.
- [05:03]
A
I would say there's a pro and con for that. Like we sort of. I resist 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 Prada marketing engineer. Those functions sort of I wouldn't call mistake. But we're up in the traditional way of building it.
- [05:32]
B
Did you hire been there, done that people in that phase?
- [05:35]
A
We did.
- [05:36]
B
And do you have any of them still?
- [05:38]
A
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 earlier adopter of language modeling our product. You start think 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 that you usually can build it fairly predictable. Like product manager. Talk to customers, pass to designer, pass to engineers. Building with language model back then and somewhat still is it's like brewing beer. You can't truly predict the things the
- [06:40]
B
underlying thing good analogy.
- [06:42]
A
You cannot tell the east. Hey, 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 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. That really forced us to change the at least how we build product designer is the most productive thing. Are designer and engineer and product people all just sit in the same bucket then work with evals, work with experiences
- [07:22]
B
and figure out inside your company has one of those Personas kind of dominated and the other one's fallen aside. Or is this error they all kind of do the same thing now?
- [07:31]
A
We always started by like our DNA in the early days always blurry. Like we are one of the first hired designer who can code. I'm a designer who can code right so we build a company based on my image and my co founder's image. So those profile really shines. Designer who can co engineer have strong product sense. PM's not afraid to roll up sleeve and try things like one of our heaviest token consumption person in the company is a P for example. Those people really shines and we have quite a few of in the notion.
- [08:04]
B
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
- [08:35]
A
the same thing in some sense we're creating product for other company to do that but yourself. The high premise is similar at least my interpretation of it. It's so much knowledge work is paper pushing. In the past it's really hard required software to push information from one person another but so much of a knowledge works fuzzy. So human need to be in the middle to pushing information from one to the other. And 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 pushing 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. So a lot of used to companies, a lot of people just in the middle too pushing information decision around to sustain a business at scale that could be rethink.
- [09:28]
B
Okay.
- [09:29]
A
The analogy I like to use we'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 you information or weight structure can go much higher Since Samsung language model plus software is that it's the steel for organizations.
- [09:56]
B
What does the organization look like now that we have the steel? I think I know buildings got taller. What happens to organizations?
- [10:03]
A
I think everybody's trying to figure out right Like Dorsey's structure is like three layers or something or three type of people, right?
- [10:10]
B
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.
- [10:20]
A
I think all the spirits are right.
- [10:22]
B
Yeah.
- [10:22]
A
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.
- [10:36]
B
And do you think that's changed now we have AI that it can be flatter or you're like that's bs oh
- [10:40]
A
definitely can be flatter. Like we are getting flatter and flatter.
- [10:43]
B
Okay. How many direct reports do you have? I have 7A in generally, what is
- [10:49]
A
it the company wise? Probably around 7, 8, 9 people per person.
- [10:54]
B
A lot of people are going to 15, 20, 25.
- [10:56]
A
Yeah. Many of our best people. 15, 20, 20 something got it.
- [11:00]
B
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.
- [11:11]
A
Yeah. Two years ago we started to hire different shape of engineers. 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. 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. 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 optimize for the latter to today.
- [12:09]
B
Okay.
- [12:10]
A
That means in engineering science we're hired for much younger people. Internally we're like IC early out of school ic.
- [12:18]
B
This is the opposite of the way Most of the CEOs I'm interviewing are going. It's interesting.
- [12:22]
A
No, I think more people are thrilled.
- [12:23]
B
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 100.
- [12:31]
A
Yes. So hire for super junior, super senior.
- [12:35]
B
Oh, interesting.
- [12:36]
A
So the shape it's not. It's more like the barbell. Barbell shape. Right. Because the senior provide taste. There's still a lot of auto distribution information out in language model architecturing and language models known very bad with that. So they need to provide a direction. It's Almost like this. A good engineer managing 4 to 6 coding agent at once. Right. But a good really senior architectural engineer can managing two to three junior interns or engineers. 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 more optimal shape than bunch of senior people manage coding agents.
- [13:18]
B
Okay. And I assume you're still hiring designers and still hiring PMs. Is the ratio changing or are you just hiring people do the whole thing?
- [13:26]
A
The definition of designer PM are different. Like we're intentionally hired designer who work as pm. 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 genetic thing. It's more like a visual craft takes years to train. Right.
- [13:46]
B
But designers want to talk to customers and get feedback.
- [13:48]
A
Yeah, that rare. But don't stereotype designer though they do exist.
- [13:53]
B
So if I look at your website, you're hiring engineer, junior, senior. Are you hiring PMs in designers or do you have some. I don't know how to combine those two words together.
- [14:03]
A
Well, hire PM designer. By the way, we interview them. We value 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 good ideas. How much are you interfacing with customers? Besides you're good with craft design craft.
- [14:25]
B
Some of this stuff is like the fashion's change. Like for the longest time was experience. Then the word everyone used was slope. We hire for slope and now it's kind of taste and curiosity and agency.
- [14:37]
A
That's kind of slope though. That's like the slope.
- [14:39]
B
Ish.
- [14:40]
A
How is it different?
- [14:41]
B
Slope to me is just horsepower smart.
- [14:44]
A
Well, intelligence is first intelligence.
- [14:47]
B
Multiple dimensions like GPU speed, like how'd you do on your friggin SAP.
- [14:52]
A
But there's a plenty smart people are
- [14:53]
B
lazy, that's for sure.
- [14:55]
A
Do you call that high slope or low slope?
- [14:57]
B
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 in your. 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?
- [15:15]
A
Because taste is not in language models. Yeah, taste is in if you zoom a long long time maybe. Yes. But right now it's not and it tastes more rooted based on your value system. Are you drinking sparkling water or still water? Are you drinking diet coke or iced tea?
- [15:31]
B
Yeah.
- [15:31]
A
It's to each of their own. There's no right answers.
- [15:35]
B
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. Is the criteria change there too?
- [15:46]
A
We actually change our marketing department. We no longer have a CMO organization. This is this year. Last year. This year. Yeah. 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. Right. So let's just have that sit next to product directly connect to social where people are discussion are happening. And then the other part is like serving the sales go to market function like demand gen lead gen lead gen. Just like we really really focus on that. So rather than information round trip to a CMO then figure out how to serve both the product set and the go market. No more just like let both side figure out themselves.
- [16:33]
B
Okay.
- [16:33]
A
Themselves but more decentralized.
- [16:35]
B
And are there any other of the classic marketing functions in there? It's sort of. Those are the two.
- [16:41]
A
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 community as part of the community ecosystem or organization which is startup with where is one of the most important communities notion fans around the world. And figure out how does to move our market through those people. Right. That's a bucket of people.
- [17:10]
B
And has the criteria changed? Sales, marketing, all the different other functions. Have you changed the way you think about the hire? Like most companies have a form. When you interview someone has that form change.
- [17:21]
A
We're actually in the middle of. I just described engineer Juan. Right. Engineer designer. We changed two years ago.
- [17:27]
B
Yes.
- [17:28]
A
Go to markets. Marketing would change. No. 6 months ish ago sales were changing.
- [17:34]
B
Right now when you hire a sales rep do they have to be AI pilled?
- [17:37]
A
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.
- [17:49]
B
How about compensation? Is that changing? My sense is we had an environment where at least in HubSpot we people are much more productive than the average person. Now it's even more so.
- [17:59]
A
Yeah. Have you rethought we are changing that as well?
- [18:02]
B
Okay.
- [18:02]
A
So they need to be extremely 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 wartime totally actually makes us ask feels like what are we doing back then?
- [18:26]
B
Well, nothing changed for the longest time. Like nothing. It's kind of boring, right?
- [18:31]
A
Like notion we had.
- [18:32]
B
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.
- [18:42]
A
Well, you can welcome back to become operator if you like.
- [18:45]
B
That's why I joined scoia. I'm like, well there's so much exciting things going on.
- [18:48]
A
When we hit product market when Covid happened. It's more like world changing but not like as people building things and technology changing.
- [18:55]
B
Do you prefer wartime or peacetime?
- [18:56]
A
Wartime's way more fun.
- [18:58]
B
It's like what's the difference? What do you do differently?
- [19:00]
A
You feel more alive.
- [19:01]
B
Okay, but what methods do you use that are different?
- [19:04]
A
I need to take care of my body. I need to exercise every day.
- [19:07]
B
I didn't think you were going to say that, but okay.
- [19:09]
A
Yeah, it's like it's more fluid.
- [19:13]
B
Are you more top down versus bottoms up?
- [19:15]
A
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 either direction. There's enough people I trust really well they can bottom up and it's constantly surprised me like we're a company, a thousand people. We have about 50, 60 founders in a company. Ex founders. It's like they really can lead things right and they welcome me to top down into jump into any part that I can work on. I'm interested in where I can provide you new value and they don't feel territorial. This is in a good place that people who didn't feel that way either no longer at notion or let them go. So the company I meet in a pretty interesting equilibrium at the moment.
- [19:59]
B
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.
- [20:23]
A
That's my real remember I said right after Covid with 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.
- [20:39]
B
I love that I. I do the orchestra versus jazz band. I like the marching band.
- [20:42]
A
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 I. I can't do that. So it's like a self reflecting value thing. It's out of equilibrium with me. So. 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.
- [21:10]
B
Okay, so we had manager mode. We have founder mode. There's this new mode. What should we call it?
- [21:15]
A
Jasmo maybe. That's not bad actually because Jasmo has some structure. Right. You don't want to be like you want other people to contribute. You want people to have fun. Not just you having fun or dictating everything.
- [21:28]
B
Okay, let's give that a go. Let's push that out on X and see if it sticks.
- [21:31]
A
I mean, Jasmo.
- [21:32]
B
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,
- [21:44]
A
the patch mode. Yeah.
- [21:46]
B
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. The planning's tricky. And I sat through your pitch at Sequoia and you had a plan and you had a P and L. Like what is it actually like internally planning
- [22:03]
A
wise, more group has our plan, which most company at this point, if it works, if group has your plan.
- [22:08]
B
Right.
- [22:09]
A
So I would say the financial planning is still at least I find useful to give you a. But you know, you're on treadmill, you know how fast you're running. Right. That's like a financial plan in my mind. It's like, oh, am I running 7, 8, 1 9, what number that is? But 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 for financial things. March that right. Then at least we try to be conservative, mid to conservative with financial things and take risk and there's a buffer. Like cost becomes another dimension. Like if you're just building software, don't think about cost.
- [22:59]
B
No.
- [23:00]
A
Now you have to like at least I have to really think about cost.
- [23:03]
B
Can I ask you about that? Like a lot of these startups gross martins are awful. And like I companies like HubSpot were like 86% gross margins. That's sort of SaaS normal. What are happening to your costs and your gross margins? And where do you think it settles out for companies like yours?
- [23:20]
A
I don't have an answer for you.
- [23:22]
B
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?
- [23:34]
A
Oh, you have to.
- [23:35]
B
You're. You're down for that?
- [23:37]
A
Like what are you doing then? You're now in the war mode, Right. I think notion is for knowledge work which might have a different curve than coding products. Coding product. You run frontier models. Usually the more the smarter the better. And knowledge work you can. 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.
- [24:26]
B
Yes. Okay. You're kind of in my mind the king of refoundings.
- [24:32]
A
Yeah.
- [24:33]
B
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.
- [24:47]
A
It's not that small, but yeah.
- [24:48]
B
Okay. You know, more recently, obviously everybody knows the story. You went to Mexico and you had early access to the models and you turned into an AI company. Talk about the different re foundings. 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 refound.
- [25:07]
A
Yeah. I like as an idea, as 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 refunding. The first version of Notion is like it 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 Sam and I said, let's just lay off everybody. Just go buy the two of us. Then that's the Japan story. We rebuilt Notion from Japan.
- [25:52]
B
How hard was that? The laying off everyone?
- [25:55]
A
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.
- [26:05]
B
Just like, why the hell did you go to Kyoto of all places?
- [26:08]
A
We actually, we never been to Japan. Because when you just say goodbye to your friends, all those people you work with, Notion, by all means. Not big five people. Ish. It's morale so low. Right. So Simon and I was saying, let's go somewhere that we 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. I love Simon, but I don't want to cram into a small apartment with him. And Kyoto, the apartment much bigger because they didn't get burned on the World War II.
- [26:44]
B
They weren't bombed.
- [26:45]
A
They weren't bombed. They spared that city too much treasures. And the house is much bigger and cheaper. So that's why we 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 those kind of coding, Eating, coding, eating. It's actually really liberating.
- [27:11]
B
I lived in Japan for a couple 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 in anywhere? Could you have been in Thailand?
- [27:28]
A
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.
- [27:42]
B
Very special, yeah. Very inspirational.
- [27:45]
A
Very inspirational. Those things are hundreds, everything. Oh, this shop, 150 years old. Right. I'll open that door. The shrine.
- [27:52]
B
Beautiful, beautiful place in Thailand. Phuket. Whatever. Do you think you still would have pulled it off. Or is there something magical about the location that really worked?
- [28:01]
A
Most of things are a story we tell ourselves, of course.
- [28:04]
B
What story is the true story?
- [28:05]
A
The story we tell ourselves. Like Kyoto is a special place. If you can pull off anywhere you can pull off from reborn in Kyoto, then it's also inspiring. Just look at the surrounding. The craft is probably craft capital of Asia. Right. So just make you okay. If notion fundamentally is tool the tool for humans and those people are building knives, ceramic cups, tatami seats. Like they're the tools other tools for craft central. It's a craft central and how can you not be inspired by building a better software?
- [28:43]
B
Okay, you still have an answer to my question, which is 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?
- [29:01]
A
I think I pulled it off. Yeah. But the story is the better story.
- [29:06]
B
Okay, fine. Okay. So you big refounding not easy. Didn't immediately hit product market fit after still not.
- [29:13]
A
No. It took a while.
- [29:14]
B
Yeah.
- [29:15]
A
After that. Because it took a year and a half to rebuild from scratch.
- [29:18]
B
Why didn't you just quit and start a new company at that point?
- [29:21]
A
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 that era, the first generation computing pioneers around the Bay Area. Like the lineage trace way back directly back to there. I want to continue that lineage. So to me it's not.
- [29:50]
B
It wasn't like you had another idea kicking around.
- [29:52]
A
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, we'll work on another company doing the same thing.
- [30:06]
B
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?
- [30:33]
A
I think most people don't have it most companies don't have it.
- [30:36]
B
I agree.
- [30:37]
A
Like Steve Jobs. I look up to him or people like him. It's like interception of humanity with technology versus Silicon Valley. least tech is largely a technology and tinker culture. And tinkerculture 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 this.
- [31:02]
B
To be fair, was tinkering in the garage.
- [31:05]
A
Yeah. But you require to meet someone to. To bring the human side of that. Right. I think tinker culture. The rest of us, you don't know what comes before you. Science. At least you respect the history. Like if we ask people who Douglas Engelbar or Alan Kate those computing pioneers are. Most people in tech have no idea.
- [31:27]
B
Honestly. The only reason I know them is I work for this guy Ray Ozzy.
- [31:30]
A
Ray Ozzy.
- [31:31]
B
You would know of course because he's the father of notes. But. But he was obsessed with those two and talked about them constantly.
- [31:36]
A
I know reality. It's like Microsoft CTO for a while too. Right. So that lineage is broken. By the way, the people who remember the 70s and 80s, they were sort of people don't even. Yeah. They no longer work in tech today. 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 discipline around you. You have all the history behind you. There's way more good stuff you can steal from. I wish more tech founders steal from ASAI or from behind.
- [32:24]
B
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. Have venture 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 move to Kyoto and.
- [32:53]
A
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 him myself. I was like I remember I was at my ex girlfriend's studio. I just like an inner urge like there's no way out. I have to do this. And it's like then you feel liberated once you land in Japan.
- [33:24]
B
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.
- [33:39]
A
I think there's no better time than now to do that because the market dynamic is wide open. You.
- [33:45]
B
Yep. I agree. Okay. You refounded a second time when you had a thousand employees back then it was probably 500.
- [33:53]
A
Yeah.
- [33:54]
B
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. What did you feel? Was it the same thing? Your body felt it? Like what was the story?
- [34:07]
A
So the second time was in Mexico. Cancun.
- [34:10]
B
Right.
- [34:11]
A
Happened to be out somewhere.
- [34:12]
B
Right. You're always in a nice place.
- [34:15]
A
We just got early access GPT4 model. It feels like the world's stopping. Like when you first interaction with the GPT3 is fine. GPT4 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. I think the company has been fairly there speed people doubt because they remember that around three years ago. That's like the crypto era lending right. A lot of people. Is this another crypto thing? There were a lot of doubters, some of them obvious no longer at the company. But the conviction is so clear at least for me and Sam. Early days like we just have to do this.
- [35:02]
B
Did you take two steps back in the business to go 10 steps forward? Like did revenue really slow while you're rebuilding everything?
- [35:09]
A
Our first product is actually hazardous, meaningful revenue boost. We launched our first AI product actually two weeks before ChatGPT happened. It was like AI writing product that has a boost. But after that we've been pretty much want to build agent product in 2022. End of 2022 and that's a slog that took us a year and a
- [35:32]
B
half to really didn't really work back then.
- [35:33]
A
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 anthropic built a model for us. We work OpenAI 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 is around the same time. Right.
- [36:03]
B
When the AI product the underlying got better.
- [36:07]
A
Yeah. It's like. But that was the, that was a pretty painful period.
- [36:12]
B
Was that the most painful period in notion history for you?
- [36:14]
A
Different type of pain.
- [36:16]
B
What was the most painful?
- [36:18]
A
Just when it was 2, 3 early days pre product market fit is despair.
- [36:23]
B
I was just like despair. Is that the word? Okay.
- [36:27]
A
You don't know where it's coming from. You don't, you don't know where to go. Right. When your growth rate low like during that period of time we will try to rebuilding our AI foundation multiple times. It's yeah, that's not great right now just everything on fire. It's a different type of pain.
- [36:46]
B
Nice. So a lot of people, 500 person companies, a lot of SaaS companies are doing the AI thing but certainly haven't refounded advice.
- [37:00]
A
Start with your product. We just talk about treated like brewing beer, not building bridges because 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.
- [37:19]
B
Can non founder led companies pull it off?
- [37:22]
A
I don't know. We'll be tough. I think founder has the moral high ground to change things. People are more tolerant and forgiven with founders. Right. I think the person need to be used language model just know how to feel it. Like you got to feel the AGI, feel the AI.
- [37:41]
B
Yeah. You can't read about it, you can't watch YouTube.
- [37:43]
A
You got to build it. Building is one of the best way for your product or built for your internal systems.
- [37:50]
B
Build for yourself.
- [37:51]
A
Yeah. Tinker on a weekend. Tinker on the side. You have to do that because like at the end of the day business 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 shareholder with your company. Like we're just finding local optimums, local maximums for different our niches. When this new brand new ingredient got introduced into the market in this case language model doors are paths that 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 taking 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 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 field AGI.
- [38:47]
B
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?
- [38:59]
A
We intentionally do a lot of acquisitions. We have 50, 60 founders at Notion
- [39:05]
B
and were they Aqua Hires, Aqua Hires,
- [39:07]
A
Aqua Hires Acquisitions founders are kind of this kind of like little decalcified meathead machinery just trying to break things. Right. So keep your regenerating.
- [39:19]
B
I agree with that.
- [39:20]
A
Yeah, I find that really helpful.
- [39:22]
B
So founders found for a reason and now all of a sudden they're in a thousand person company. How do you keep them motivated and not leaving and starting something new?
- [39:29]
A
Well, first some of them work on the domain that they were working on before. Like the person leading our AM meeting node has a startup of AI nodes 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. Like I just had lunch with the founder who started Enterprise Search Product before.
- [39:52]
B
It's like you give them leverage, they give them leverage, you give them leverage.
- [39:56]
A
The actual people care about the thing they're building. Right. Versus fighting for product market thing with really crowded market. They don't. You can argue that it might be more difficult to start new companies today compared to even a year ago.
- [40:08]
B
Okay.
- [40:09]
A
Because the world's getting more noisy. Like the shipping cadence from existing companies are just increasing. It's like the everybody got Twitter fatigued. Right?
- [40:21]
B
So and the SaaS companies have got the memo. Most of them got the memo and are shipping fast now. You were ahead of everyone.
- [40:28]
A
But yeah, people like it's still like HubSpot's cranking.
- [40:32]
B
That's good.
- [40:32]
A
No, the people are still kicking that they have to kick in different gear.
- [40:37]
B
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's 100 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 3:50 tied for third. They're way off. When you look back in time, the great companies were often founded in shitty times because people who are 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 is going to be crap. Even though the valuations are like crypto.
- [41:24]
A
Crypto vibe energy.
- [41:26]
B
Yeah, a little bit.
- [41:27]
A
A little bit. I don't disagree. Market will do their thing. Market is kind of beautiful in that way.
- [41:33]
B
Yeah. Advice to founders of reasonable sized companies who are a little scared to refound. You know I. 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.
- [41:55]
A
Does the person need to feel the AGI first? If you feel. You realize most tech industry is support different flavor knowledge work. We're at the beginning of how this can do due to this industry.
- [42:09]
B
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? Does your knowledge work? You're right at the center of this.
- [42:21]
A
I think truth is probably somewhere there's a Dorothy Jack Dorsey's thing. There is the traditional hierarchical ones. I like to think what are invariables like let's look invariable in this case. Human nature are rather static like we all.
- [42:44]
B
We don't change that fast.
- [42:45]
A
Human don't change. Humans as a species doesn't change. That's where I think you will be a hierarchical organization. You've just observed bamboo or chimpanzees, right. It's like very. If you watch nature program there's hierarchy that doesn't change. Hasn't changed left us since we left Africa. Division labor makes sense. So people have different interests. You look at all the different personality tests. They're just different ways of saying people. People are different. There are not 10,000 flavor of them but there are probably a dozen flavor of humans cluster around us different dozen things and 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 human to start. So those to me are the invariables. So this invariable tells me you need to figure out how those group of human collaborate group of human 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 technique, new ingredient to passing information decision around a small mid sized group of humans. That's how I think about it.
- [44:03]
B
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.
- [44:31]
A
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 adjusting a bleeding edge for this.
- [44:42]
B
By the way, I think you're incredibly well positioned for all this. Oh yeah, I, I, I, I worked for a while with this guy Razzi 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.
- [45:04]
A
I know, it's like what's that industry called? In the 90s people hired consultants to map out their org chart and information flow that become like what aim for deployment and totally.
- [45:17]
B
And your platform is ideally suited for it.
- [45:19]
A
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. Right. So why cannot be a new flavor of it?
- [45:35]
B
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?
- [45:46]
A
I think I'm still introverted.
- [45:48]
B
Okay.
- [45:48]
A
Yeah. I like one on one conversation than one too many. I train myself to do company all hands just by doing a lot.
- [45:54]
B
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, you know, don't like the whole extrovert game.
- [46:09]
A
I have to evolve a lot. Like I hate.
- [46:11]
B
Did you force yourself? How did it work? A significant other push you?
- [46:16]
A
No, I force myself.
- [46:17]
B
Okay.
- [46:18]
A
To lead a group of human, you need to do one too many communications. Otherwise people don't trust you. They want to hear from you. Writing is one mode which is like sometimes Lingnam but even more so is face to face do the all hands. So for a while I tried to delegate all hand to my co founders, to other execs. No way. I have to now at every all hand, I'm open the mic, I do it, I leave the whole all hands. Now I'm pretty comfortable with that. I still don't love it, but I don't dread it.
- [46:47]
B
Okay, advice for people doing all hands. Everyone seems to do it differently.
- [46:51]
A
Get a teleprompter.
- [46:54]
B
I'm the opposite. I can't read fast enough for the teleprompter.
- [46:58]
A
Really?
- [46:58]
B
Yes. I hate it.
- [46:59]
A
Well, that changes me because, well, 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 like speech to text model locals are so good. They're so good, so good. 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.
- [47:24]
B
Do you do them once a week? Once a month? Once. Like what's your cadence?
- [47:27]
A
We're actually changing our cadence. Used to be once a month. Right now it's every other week for all hands, every other week again for ama. So every week now. So if you got the world step
- [47:39]
B
on yourself on an ama, you ever say something, you're like, I got a crush for that.
- [47:43]
A
Yeah, everybody has it right. Or just you miss a good opportunity, you can actually rally people about something. But you, you give a non answer. That's the worst. And non answers we in.
- [47:53]
B
At least it helps about in the company meetings and the AMAs, there would be a slack channel on it. 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 in 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? Like how do you do it? What's your schedule like?
- [48:29]
A
It's actually not that crazy. Wake up seven seven A, 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 during the gym during the day.
- [48:53]
B
Okay, yeah, that's a good idea.
- [48:55]
A
Perk you up, elevate my energy during the middle of the day and work in office till 7ish. Usually social. Dinner with my wife, back to work, sleep until midnight. Around midnight.
- [49:08]
B
When do you have time to get down the cloud rabbit hole?
- [49:12]
A
Weekends weekend's my happy time.
- [49:15]
B
No, you describe that as your happy time.
- [49:18]
A
Yeah. You can be led by your curiosity rather than by your responsibility. Right. Like usually Saturday, Sunday morning I have a bit time to read the books I want to read. Sometimes it's for work related sometimes purity of my guilty pleasure.
- [49:34]
B
And during the day like half hours like I'm seeing found one of my founders here in New York. Medicare is he gets his schedule in 10 minute blocks.
- [49:43]
A
Meeting wise.
- [49:44]
B
Yes. Like what does your day look like?
- [49:47]
A
A lot of 25 minutes blocks. I usually like five minutes between meetings and 25, 25, 25. My team packed 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.
- [50:11]
B
Why doesn't ocean build a slack killer?
- [50:13]
A
We're shut.
- [50:14]
B
Definitely. A lot of your team said you're humble and I think you are too.
- [50:20]
A
Why I wouldn't use the word humble. I use the word your team uses that truth seeking.
- [50:25]
B
Probably they use humble.
- [50:28]
A
I think if 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?
- [50:38]
B
Yes.
- [50:40]
A
We're just different blind people touching different part of the elephant. Sometimes could be the tail. That elephant's a snake, sometimes the trunk is a tree. Right. That's my worldview.
- [50:49]
B
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. What advice do you have for them?
- [51:03]
A
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 human or status is human thing, right? Like power. 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 watch that in real in a texting. 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 that gave me more sustainable energy source. I cannot just chase something where competition for competition's sake, like I'm really competitive. I. 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, the social part of being a CEO, the market dynamic just compete for competing sake and the value you personally I wouldn't say they are. This is some slightly. 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 compete sake. Doesn't care about what they're building. Some people just want to be popular. If you just only care about craft that you don't build a business, you might as well just be an artist. Took me a while to realize where's my equilibrium.
- [52:40]
B
Are you someone that like tries to fix your weaknesses or you just lean into your strengths and what's your advice on that?
- [52:46]
A
Definitely leaning on your strength. There's a necessary thing you have to do like one to many communication likely you need to do as your company scale. Maybe you can lean more on writing rather than speaking but there's certain 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 that's more lasting.
- [53:17]
B
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 when 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 similar mold to you. You talk about that.
- [53:44]
A
We had a mistake. As I mentioned. We sort of did not buy traditional sales motion for a good 2 ish years notion. Sales can start earlier, but we want 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 the reason the modern sales playbook has been around for 2ish decades. Right.
- [54:12]
B
So I think enterprise sales is like the last function.
- [54:15]
A
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.
- [54:23]
B
No.
- [54:24]
A
Then why should you buy expensive thing from a robot? Right. So it's not that hard, I would say.
- [54:31]
B
Okay.
- [54:31]
A
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 the new go to market motion. That's stupid.
- [54:46]
B
Okay, I did mine. How do we build HubSpot?
- [54:49]
A
Yeah, right. But that's the thing made HubSpot. Right. Like this inbound.
- [54:54]
B
That was the thing.
- [54:54]
A
You should only have. Each company should only preserve your innovation point to few places, go a couple places. You cannot spread everywhere. Otherwise you're spread too thin. You're trying to reinvent in the world too many times. We try to put our innovation point onto sales back then 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.
- [55:26]
B
Okay, so you woke up one day, you're like, we got to get good at enterprise sales. What'd 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?
- [55:37]
A
I thought that somewhat solved today. Right.
- [55:39]
B
I kind of do. But people struggle with it. Enterprise sales has changed very little since I did it in the 1990s.
- [55:46]
A
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 now like the PRG give you the luxury that your customer want to buy your product.
- [56:06]
B
It's easy to sell. Yes. It's like fulfilling demands.
- [56:09]
A
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 CROs 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. Meat eater. Right. Perfect pairing. And so we have sellers with rah Roy provesh. But also respect working with Erica's overall system. This is when things start to work. In the past year and a half.
- [56:47]
B
Got it. And so many of the organization I deal with, the engineers look at how much material money the sales people make and look at the rah rah and they roll their eyes and they complain. I assume that happened here.
- [56:58]
A
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.
- [57:11]
B
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?
- [57:24]
A
I like that.
- [57:25]
B
Okay.
- [57:26]
A
A company is. It's sort of a religion is. 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. 2000 years. They have their ritual, their business models.
- [57:46]
B
They're still around kicking great founder in Jesus and a great head of sales in Paul.
- [57:53]
A
And there are a lot of sellers and referral system.
- [57:56]
B
Viral marketing.
- [57:57]
A
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. Like 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. And it's the same energy.
- [58:26]
B
The first four words in culture are cult.
- [58:29]
A
Yeah, probably I need to look up the roots. But yeah, it's like what is aohen? He will go to church every Sunday. All hands, every week, same thing.
- [58:38]
B
We used to have 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. It's like we really, really worked on our all hands.
- [58:50]
A
Nothing. I don't think anything wrong with that. No.
- [58:53]
B
Okay. Thank you for coming on the pod. Thank you for building notion. Thank you for being inspiration for tons and tons of founders.
- [59:00]
A
I'm glad. Hopefully it'll be helpful for others.
- [59:02]
B
Appreciate you.
- [59:02]
A
Thank you for your time.
- [59:04]
B
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 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%. 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 in 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. Like he was a ye olde SaaS company and now he's a rocket ship AI company. I think he's onto 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 AI native in the kind of era we're in. 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 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 that information gets distorted across and up and down and 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 and, 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 it context and you turn over more and more of the decisions to them. 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 just moving a lot faster than the companies that aren't. 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 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. I'm going to be talking about in the podcast and on X if you're interested in it too, hit me up on B. Halligan. Thanks for tuning in.