Skip to content
20VCSep 18, 2024

Notion's Founder on "Founder Mode": When it Works & When it Doesn't

Why The Way Startups Fundraise & Construct Boards is Broken · Raising at a $10BN Valuation in Peak Bubble Times and How Notion Has More Money Than Ever Before with Akshay Kothari

With Akshay Kothari · Harry Stebbings

Full transcript · 49 min · 9,634 words · 2 speakers

Cold open

Founder mode is really good if you have a founder who’s right a lot. If they’re not, God bless that company. There’s more cash in Notion’s bank today than the history of its race. So it’s like in some ways like we’ve produced cash, haven’t spent any of it. I think the thing I would say about Sequoia, I think it is probably the best brand similar to how we demand excellence from our from our employees. I think they demand excellence from their companies.

Akshay Kothari0:00

Intro

Unknown

Welcome back to 20 VC with me, Harry Stebbings. And today, we have the man who makes the show at Notion run smoothly in the hot seat, Akshay Kothari. Akshay is the cofounder at Notion, and he has run almost every function in the company. From sales to marketing to finance, he’s even led their fundraising efforts, raising over $340,000,000 from Sequoia, Index, and Coatue with the latest round pricing them at $10,000,000,000. Before Notion, Akshay was VP of product at LinkedIn for five years, and he joined LinkedIn when his previous company, Pulse, was acquired by them in 2013.

But before we dive in today,

· Sponsor read0 min · 485 words
Unknown1:04

all of you listening use tons of software every day. Sometimes it fills us with rage. You can’t figure something out. The chatbot in the bottom right is useless. You keep getting bombarded with these useless pop ups. And for those of you who build products, no one wants their product to feel like this. Thankfully, a company exists to help users without annoying them. Command bar. It does a couple of very helpful things. First, it’s a chatbot that uses AI to give users extremely personalized responses and deflect tickets.

But it can be beyond just text. It can also co browse with the user and show them how to do things inside the UI. Magic. But it can also detect when users would benefit from a proactive nudge, like a helpful hint or an invitation to start a free trial. Command bar is already used by world class companies like Gusto, Hashicorp, Yotpo, and Angelist. If you’re a product CX or marketing leader, check them out at commandbar.com/harry. And talking about incredible companies with Command Bar, I want to talk to you about a new venture fund making waves by taking a very different approach.

It’s a public venture fund anyone can invest in, not just institutions and accredited investors. The Fundrise Innovation Fund is democratizing venture capital, which could have big consequences for the industry. The fund is already off to a good start with $100,000,000 into some of the largest, most in demand AI and data infrastructure companies. Companies like OpenAI, Anthropic, and Databricks. Check out the innovation fund’s impressive list of investments for yourself by visiting fundrise.com/20vc. Carefully consider the investment material before investing, including objectives, risk charges, and expenses. This and other information can be found in the innovation fund’s prospectus at fundrise.com/innovation.

This is a paid sponsorship. And finally, let’s talk about Squarespace. Squarespace is the all in one website platform for entrepreneurs to stand out and succeed online. Whether you’re just starting out or managing a growing brand, Squarespace makes it easy to create a beautiful website, engage with your audience, and sell anything from products to content all in one place, all on your terms. What’s blown me away is the Squarespace Blueprint AI and SEO tools. It’s like crafting your site with a guided system, ensuring it not only reflects your unique style, but also ranks well on search engines.

Plus, their flexible payment options cater to every customer’s needs, making transactions smooth and hassle free. And the Squarespace AI, it’s a content wizard helping you whip up text that truly resonates with your brand voice. So if you’re ready to get started, head to squarespace.com for a free trial. And when you’re ready to launch, go to squarespace.com/20vc and use the code 20 v c to save 10% off your first purchase of a website or domain. You have now arrived at your destination.

Conversation

Harry Stebbings3:49

Akshay, I am so excited for this dude. We did this four years ago in COVID when no one was getting out, and now you’re in London, man. This is so special. Thank you for being here. Thank you for hosting, and so great to see you in person. Now I spoke to Ivan before the show. I spoke to many people before the show. Basically, he’s taught the shit out of you. And what I heard was actually that you have had so many different hats across the Notion journey from CMO to CFO to head of inside sales, CHRO, head of IR, CPO.

I mean, Christ, I hope you’re accumulating different salaries for this. But how did you learn new disciplines so quickly on the job?

Akshay Kothari4:28

I didn’t really think of my job as those titles. Like, my job was COO. My primary job was to like help scale the business and the company and let my co founders Ivan and Simon stay focused on the product. And so that meant whatever the company needed, I would jump in and try to figure it out. How did I do it? This is actually kind of interesting. So my background is product, right? And Ivan told me to join and take care of everything except product. And so I essentially put myself on all these new functions and just try to learn on the job.

So one thing I realized was even though I had never really done any of these things before, actually like first principles thinking and like systems design that you learn in product development actually like applies a lot to these functions too.

Harry Stebbings5:14

Can we take one, apply systems design in a way that you did, just so we can understand that in a more contextual manner?

Akshay Kothari

Yeah. So let’s the first job I had at Notion was actually like the three people reported to me were support, customer support, right? Now, as the number of tickets or as the number of requests go up, the first thing that people typically do is they just add more people. They sort of like divide the tickets by productivity and then they come up with some number of people. The product manager in me was like, well, we could build a better system, right? And so we could build better tools so that each support person can do more every day.

But also once you have enough of these customer tickets, then the next role you want to hire would be something called a Product Ops. Product Ops would take all this feedback and synthesize it and share it with the engineers. So one thing Ivan and I did in the early years, we created this like canonical database of about 200 types of requests that would come, which would map to like features, right? And we trained our support team to tag every request that come in with one of those 200 tags.

You have to do that, right? That was part of the job. Every morning at 6AM, we wrote a script which would take all these tags from Intercom and write it against these database tags in Notion. And so essentially what every engineer at Notion had was a real time view of what people were talking about yesterday or the last week or the last month. And so if you could see like, oh wow, people are talking about the Android app over the last month and it’s really gone up.

They can go in and start solving that problem. And we use this tag across the tools we had, right? So for example, if you were working on Android, you could essentially put that tag in Intercom and you can basically see all the customer support tickets that have come. So you could essentially, in many ways, you don’t even have to hire a researcher. If you put all these things together, we didn’t have to hire as many support people. We did not have to hire a product ops person and we also did not have research early days.

In fact, all of these were given to the engineer directly to be able to tap into that feedback and actually solve that problem, right?

Harry Stebbings7:27

This is a strange question, but, you know, everyone is going mad over founder mode and the difference between manager mode and founder mode. When you listen to the way that you’re talking, it really is quite a change from traditional org structures and org designs. And it’s really driven by a very product driven founder mindset. Do you think in the future and with founder mode, we will see completely redesigned orgs and the traditional functions be very changed?

Akshay Kothari

Everybody is starting to question things that we’ve been taught about this specific org structure and the fact that, you know, has like 40 direct reports and doesn’t do one on one. So I think it’s actually kind of good that we’re reopening what does this lead to? And I think every leader has to sort of question what is sort of the best way to run their company.

Harry Stebbings8:15

What things do you think we should question that we aren’t questioning today?

Akshay Kothari

If you go back to Notion and sort of why we did some of these things, I think a lot of it came from Ivan really prioritizing keeping a very small team. And that part was not done just because we thought we would be profitable because of that. But I think we did it because it really meant that we can stay a lot more nimble by doing that.

Harry Stebbings

How did you prevent the creep? There’s quite a few people that start very nimble and they’re really aligned to how you built the company. And then with a 100,000,000 round or with that big mouth, you know what, we can hire that extra, we can hire that, we can start that new division, we can go into enterprise early. We can do X. How did you prevent the creep with the increased branding cash?

Akshay Kothari9:01

The best power founder has is like the veto power. And Ivan used that a lot when I was in the early days. Like, you know, I remember, I don’t know how many salespeople we’d interviewed for the first six months and Ivan was like, Well, this person is quite good, but not great. So let’s keep looking. And I think for up to about 500 people, we’re about 700 people today, but up to 500 people, the last interview was always with Ivan or myself. So we met literally everyone before.

And because we did that, I think it already sort of forced a certain rigor inside the company. But also in general, we were okay with enduring the pain. Like a lot of times you feel like this person needed to be hired yesterday and we would be okay waiting a few weeks, few months until we found the best person for that job.

Harry Stebbings

You said that back enduring the pain. That kind of goes in stark contrast to what we’re told, which is the speed of execution is the most important thing in relatively early stage companies. The willingness to wait goes against that. How do you think about that and the importance of speed?

Akshay Kothari10:01

I think we took a slightly different approach where we did try to keep the team lean and we felt like it might feel like short term it’s slowing us down, but in the long term, keeping the team small allowed us to move a lot faster. Today, all of Notion with all the different surfaces we have, under 20 product managers and we have about 12 designers. 12 designers sort of design the entire surface of Notion including Calendar and it really allows us to move faster. Like it’s not a committee of design or committee of product managers where someone’s only responsible for a very small part of the problem.

And so because we have a, we are a lean team, we can actually take a little bit longer because we’re not trying to hire a lot more people. We’re trying to hire maybe a couple of people every year. And it also forces a certain prioritization that makes you a lot more effective, right? Instead of just taking the fundraising money that you took, hiring a lot of people, saying yes to all the projects, I think that is actually comes at a cost. The cost is that your bandwidth is now split among so many different projects.

And so I think you may feel like you’re going faster by hiring more people and saying yes to more projects, but in effect it is actually going slower. So we’ve actually chosen the path where we’re doing fewer things and doing them better.

Harry Stebbings11:18

I love the statement you said, which is the power of the veto. What did you and Ivan veto that with the benefit of hindsight maybe would have been better to do in the moment?

Akshay Kothari

Initially, we didn’t have our values codified. And so a lot of the initial final round interviews was a little bit around our intuition, where we felt like whether this person is going to be actually a good fit for the company. After about, I think when we were 50 people, we actually did the exercise of codifying the values. And we have four values. We are owners of a mission. We are pacesetters. We are truth seekers, and we are kind and direct.

Harry Stebbings

My team would be watching this going, oh, that’s a red rag. I think values are are very, very challenged when you can’t take the other side. So kind and direct. I want someone nasty and indirect. No one would ask for that. Is it a good value because you could not take the alternative side? So like, as an example, we look for obsessed people. Not like passionate, like, that’s that’s not enough. You need to be completely obsessed. How do you think about that and what makes a really good value in that case?

Akshay Kothari12:25

To answer your question, we wouldn’t take someone who’s nasty and direct. But no one would. There’s a few nuances to this. If you take that example of kind and direct, the and direct part has an extra signal there. It’s not like be nice to each other. We want people to be direct, which means that we are inviting people to be able to debate internally.

Harry Stebbings

I I spoke to Ivan again before and he said, listen, he he’s basically hired every single leader at Notion at this point, Harry. So you have to ask him about that. When you think back over your lessons on hiring, what are your single biggest lessons on what it takes to really get the best people into Notion?

Akshay Kothari13:01

Initially, you sort of have to get a feel for the shape of what you’re trying to do in this function. And I think, so in many cases, we didn’t go to hiring the leader first. A lot of these functions, maybe I started doing the job myself, sort of shaping it to sort of what we wanted to do in Notion. A lot of these functions, we also hired the ICs first, like individual contributors who can start to like do the work. When

Harry Stebbings

you look back, what have been some of the biggest mistakes you’ve made and what are some big lessons from those?

Akshay Kothari

I think the people who do well at Notion are builders and we sort of expect even the execs and leaders to be builders. I think when we hired people who are VPs or CXOs at big tech firms, they have a machinery around how their work happens. And because Notion is so small and so lean, those people had a tough time at Notion because, A, that machinery didn’t exist. But also when we did have a crisis or moment of solution that needed to be found, I think they typically sort of went to needing another headcount or sort of blaming on the systems or so forth, right, which actually didn’t work so well.

Harry Stebbings14:12

What was the hardest team to hire and the hardest function to build out?

Akshay Kothari

The one I would change a lot if I could, or the one that I probably regret not doing the right way is probably sales. I was optimistic. I thought, you know, I think we could do sales a different way and I thought our salespeople could be more consultative, they don’t have to worry about quota, they just have to like make sure the customer is being successful and the product will grow and expand. And what I learned the hard way is that we try to reinvent the wheel on something that has been done in a specific way, does work really, really well that we shouldn’t have.

But B, like, I think the thing that I misunderstood was actually some of the best salespeople, they join because there is a quota, because they can hit a number, because they can outperform that number. And so actually not having that and not having the attribution really hurt us, I think, the first year or two.

Harry Stebbings15:10

How did you see it hurt you? Inability to hire people, the people did not having direction. What was it that was that, oh, this is hurting us?

Akshay Kothari

Well, I think, you know, the way we looked at it was just the percentage of business that is driven by sales or sales assisted wasn’t growing as much as we would have hoped. But, you know, there’s there’s actually an interesting piece here around sales at product led growth companies, right? Which is that, you know, in many ways product sells itself at these companies and you think you can do sales a slightly different way because you have all these leads, right? And that actually is also a blessing and a curse.

Yes, it’s a blessing because you have all these leads, but it’s also a curse because I think your broader team starts to depend on it. It’s like, oh, the product is not really signing up the right lead. This is why I’m not able to close sales, sales, right? Which if you didn’t have the product, if didn’t have anybody signing up on your website, you’d still be doing, going out and trying to find the lead. And so you’d be sort of complaining about that part a bit less.

Harry Stebbings16:09

And if you want to build enterprise at some point, you’ve got to build outbound and you’ve got to build an enterprise function and you cannot continuously rely on product inbound. Exactly. As nice as that would be for anyone. Exactly. When was that moment when you realized that?

Akshay Kothari

Probably like three years in. So that would have been like three years ago. We’ve obviously now moved very much into like, you know, we have an incredible new sales leader, Pravesh, who comes from like an enterprise sales background. And I think he’s brought certain amount of energy and DNA that like I didn’t have. Right? That’s the that’s the other thing is, like, you need someone who can really rally the troops and operate a slightly different way rather than, a systems builder, product thinker. Doesn’t work. I can’t stand on the stage of sales kickoff and like rally the troops as much as Pravesh can.

And I think if you’re like a sales account executive, you wanna see that. You wanna see that. You wanna see that you’re crushing your quotas and you’re, you know, you’re really building for that. And so if I had to do, I guess to back to your question, if I had to do it one function all over again, I would do sales. And the way I would do it is to not try to like overthink it, just do it the way it is run like a proper sales machine.

I think it would have saved three years in that journey. So that part that part is painful.

Harry Stebbings17:26

Slightly weird one and going off on a tangent, I heard it before this and I was like, it’s just a really thoughtful statement. And it was the hardest things in life are not iron or gold, but unmade decisions. What unmade decision does Notion have that is heavy? You can take a moment to think about it.

Akshay Kothari

I think one of the challenges for Notion has always been the fact that it’s a horizontal product, right? And so I think the question people ask is like, is it for consumers or is it for large enterprises? And the answer has always been yes. And I still very much believe in that sort of horizontalness. One of the things I’m starting to realize is like, instead of defending the answer or trying to pick, we’re much more forthright with our employees about the kind of company we are.

How so? I think the best way I’ve seen more recently is Parker at Rippling sort of calls it a compound company, which is that it is this like big mission that we’re building many different products and they all connect through the data layer. I think in many ways Notion is a compound company as well. The building blocks that we’re building really do serve consumers all the way to large enterprises. The reason the flywheel works is that we actually did the study recently and we found that, you know, something like 46% of our business, it can be attributed back to someone using Notion in their personal life.

Everybody I spoke to who was using it at a large company with, you know, wall to wall usage, they all started because their spouse is using it for their home project or they’re using it for with their kids on something or their niece told them about it. Or I saw my uncle having their portfolio on it and so on and so forth, right? So we know that this part is very important for us. Like it’s almost like a part of distribution that happens naturally because it’s a consumer y product, but it doesn’t pay the bills.

The bills are the business is growing on the B2B side.

Harry Stebbings19:21

Which person do you think has had the most profound impact? Maybe on you and your leadership, maybe on Notion as a company, when I ask? That’s a good question.

Akshay Kothari

I would say in many ways, like Notion’s kind of unique in that the company became cash flow positive pretty early on. We did not have to spend a lot of money or spend a lot of time on sort of fundraising. So there’s very little external pressure on Notion.

Harry Stebbings

What does being cashflow positive mean you have done, that you wouldn’t have done if you weren’t cashflow positive? What has it enabled you?

Akshay Kothari

It’s a huge, like once you get there, it’s actually a huge time save. So I think I’ll just talk a little bit about Notion, it’s very nuanced, but we got there pretty early. I think we got there like five years ago. What it did was it meant that suddenly you feel in control of your destiny. You don’t have to think about, you don’t have an end date. You don’t feel like you’re going to run out of money in x months or x years, y years away.

And what that means is you can choose to raise money if you have a good need for it, but you don’t have to. All the time spent there could be spent back into building a better product and and selling to customers.

Harry Stebbings20:28

Do you think the way that companies are built today is wrong? Idea, raise 5,000,000 on ’25 after leaving Stripe, hire people, get to a millionaire or you’re an angel investor too, get to a millionaire or have Excel index and everyone fired over you, get to 10 millionaire. Do you think we are building companies wrong?

Akshay Kothari

People should have a deep understanding for what long term valuation metrics look like, right? What do you mean by that? I mean, you just look at historically what is the revenue multiple or PE multiple of SaaS companies. So like you can raise on hope today, but in the very long run, unless you’re trying to just like get acquired, you will be valued at a multiple of your revenue or a multiple of your cash flows that you’re generating. And they tend to be an average of like, what, five to 10x on the revenue multiple side.

And the way that you can increase a multiple is by three things, right? I think in my view, one is you can increase it by having faster growth rate, but you can increase it by having a better cash flow margin and you can increase it by operating in an industry or in a space where there’s the terminal growth rate can still be pretty high. So I think as as long as you have a deep understanding of those things, and I think as long as you have a good understanding of what you going to use the money for, you can build towards that, great.

I think if you’re hoping that we’re going to be back to a 100 times revenue or a 100 times ARR valuation, I think I think that’s a bit challenging.

Harry Stebbings21:58

It’s funny. I had the founders of UiPath, Klaviyo, ServiceTitan, and none of them could raise. And it meant that they all were forced to stay very close to customers for the first few years. They didn’t hire customer service teams. They didn’t even hire product people because they had to do it all themselves. All three said the company would not be the success it is if they’d raised the money.

Akshay Kothari22:17

I think it’s some of it like, also have to credit Ivan here because in the early days, I think, you know, a lot of investors did knock on our doors. A lot. A lot. A lot. I think- Did some crazy things to

Harry Stebbings

get attention from you guys.

Akshay Kothari

Correct, correct. And so literally every quarter Ivan and I would discuss, is like, should we do it?

Harry Stebbings

Just out of interest. What was that internal discussion? I’m fascinated.

Akshay Kothari

I think primarily Ivan was very focused on is money the constraining factor right now? Is like, if we had more money in the bank, would we spend it on hiring faster?

Harry Stebbings

Take me to the time where money was a really constraining factor and you decided to raise it.

Akshay Kothari

We raised 50,000,000 at 2,000,000,000 at the start of COVID, like pretty much like a couple of weeks into COVID in 2020, early twenty twenty.

Harry Stebbings23:00

50,000,000 at 2,000,000,000. I mean, that’s a weird raise in the way I mean, it’s brilliant raise, but in the raise that it’s minimal dilution actually, but a lot of money, 50,000,000 buys a lot. The traditional notion is, well, VCs wouldn’t like that because they can’t get the ownership that they need. How do you think about that raise, the structure of it? I’m just fascinated.

Akshay Kothari

Well, actually came about really fast and actually goes back to being cash flow positive and not needing it. I think you sort of are able to do You’re able to break the rules. You’re able to break the rules because there’s more demand than supply. But, you know, the reason we raised that round was also, I think was an interesting one where we didn’t have a need for $50,000,000 but we raised it because we saw that the talent was flocking to safety, where all the people we wanted to hire needed some signal to say like, oh, this company is stable and I’m willing to work there.

And so in March or April 2020, again, we didn’t have the cash needs, but we needed an index and co2 stamp that I’m putting $50,000,000 in this company that is growing and and that actually really helped us recruit and like break that.

Harry Stebbings24:09

How

Akshay Kothari

do you

Harry Stebbings

not let that alter your mindset towards focus? You got 50,000,000 now, Akshay. You can build that new team. You can build that new product. You can do that at a lack or higher. How do you retain that discipline when 50,000,000 drops?

Akshay Kothari

Frankly, I don’t know. I think this might sound weird, but I think we’re just like not wired that way. Like in some ways like Which may seem

Harry Stebbings

very rare.

Akshay Kothari

Yeah. In some ways like there’s more cash in Notion’s bank today than the history of its race. So it’s like, in some ways, like we’ve produced cash. We haven’t spent any of it. And some people might look at it and be like, Hey, you’re not really utilizing the cash that is in hand. Are you being aggressive enough? Yeah. So that’s a question people ask. One of the things I learned, this was actually one of my favorite tools of duty inside Notion was when I was running finance for a year.

First of all, I thought finance, at least before I actually worked on it directly, thought this is just like bookkeeping, stay out of trouble, like stay compliant. But only if I worked for a year and I sort of got introduced to the whole world of FP and A, BizOps, and I was like, wow, this is so strategic. And once you get to a certain scale, the Notion got to about 100,000,000 in ARR a couple of years ago and you realize like, oh, there’s all these interesting comps you can look at, public comps that you can measure your performance against as well, right?

So it’s very if you think about your job as like, well, there’s all different projects you need to fund and you need to resource allocate, finance becomes such a strategic partner in that. So I remember talking to, as part of like me going to hire our CFO, I talked to a lot of CFOs in the valley as a way to learn. And I remember one of the conversations was actually quite interesting where I asked like, what’s the ideal rule of 40? Should it be this? Should it be that?

Like, you know, this person said like, basically you should have test budgets for everything you want to try out. And you should just look at each part of your business through that unit economic lens. If you want to do performance marketing, give people $50,000 $100,000 it doesn’t matter. Tell them to test whatever they want to test and if they can prove the unit economics for that channel and that the channel is working, then you should load up the truck. You shouldn’t worry about rule of 40 at that period of that quarter or that month because you’ve seen an opportunity that pays you back.

You can do the same with sales. And so one of the years we did actually spend a lot of money on billboards. It was a way for us to learn that, okay, well this does improve your brand awareness, but doesn’t actually do a lot to sign ups or deal closing sort of completion rates, right? And so that’s the theory we have right now with sort of being aggressive versus being too defensive is that this

Harry Stebbings26:43

What test percent of budget should be allocated to tests across those different disciplines? Is it like 10% or is it like 50%?

Akshay Kothari

Well, the budget could be pretty small. You just need enough of a budget to be able to get signals back. That channel is working. And in many cases you don’t need it to be very large, right? I think maybe like sales might have a longer period for you sort of see what the paybacks are. But I think anything you’re doing with performance marketing or some partnership deals or other things like, I think those things, you know, you can you can do it. So we do

Harry Stebbings27:15

the 50 at 2,000,000,000. And then how much did we raise at 10,000,000,000? We raised around $270,000,000 at 10,000,000,000. Around $270,000,000 to not be precise. Talk to me about the thinking there. What were we unlocking with that fundraise?

Akshay Kothari

So this was second half of twenty twenty one, pretty crazy time. And the reason we did this raise was because our peers, our competitors were getting very aggressive in going to market, both from the marketing lens as well as from the sales lens. And we saw an opportunity to not only raise money, but also to sort of play the game on the field. And so so we did this in October 2021, and I think the plan was to sort of go more aggressive on go to market.

Did you decide to play the game on the field

Harry Stebbings28:01

and go aggressive?

Akshay Kothari

Yes, we did. For about a year or so before the markets turned, we Was it the right decision? You have to. I mean, there is no other choice. Right? I think at the end of the day, you do have to play the game that is being played on the field. And in this particular case, there were Do

Harry Stebbings

you or can you just watch others burn money in go go times and stay disciplined?

Akshay Kothari

Probably nuanced. I think you don’t wanna like bone your company down, but I think you you do wanna like compete and see if you can capture more of the customers that you’re you and your competitors are both trying to get.

Harry Stebbings

And so we go aggressive for this year and then harder times come when we pull back?

Akshay Kothari

That’s what happened in 2022. In fact, the harder times came much faster than most had imagined. And so and and maybe as the pullback happened quite a bit early in our journey.

Harry Stebbings

Just thought thought exercise here. Is that not when you get more aggressive? Your competitors, they don’t have actually the cash supplies that you do in a lot of respects. You could have gone aggressive then when they pulled back. Did you think about that?

Akshay Kothari29:01

We did do some of that. And I think the reason we were able to do some of that was because we were already cash flow positive. So we saw all the companies around us all trying to get fit, all trying to get back to cash flow positive and we were like, we’re already there. So what do we do? Through all of these things, one of things I realized, it’s actually there’s like 99 ways you can burn money. There’s only one good way to like effectively like make money, right?

There’s just like so many bad ideas out there. You can throw money in the billboards, you can throw money on YouTube, you can But I think it’s actually very few ideas that actually can continue to scale well. And even when it starts to do well, you put more money in and it starts to be a bad channel, right? So it’s actually kind of an interesting exercise of like, if something works for x, like how do you get to 10x and still have the same unit economics is pretty hard.

I have a question for

Harry Stebbings

you. On the 10,000,000,000, it’s a big, big valuation. How did you think about that and how do you think about growing into that over time?

Akshay Kothari

Well, I think the I think going back to what we discussed, right? I think in the very long term, it will be a function of the company’s sort of multiple, the function of, you know, multiple of revenue and the premium we’ll get is based on us being able to grow fast or continue to grow fast and do it at in an efficient way. The great thing about Notion is that we just operate in a very large market. The different categories that we play in has, like, think we’ve barely scratched the surface on it.

And so there’s, you know, we’re pretty excited to sort of like keep building towards that vision.

Harry Stebbings30:31

One of the things- Does the valuation even matter if you’re cash flow positive? If you’re being blunt, valuation matters a lot if you’re not cash flow positive because there’s crunch time in eighteen months when you’re going back to the VC and your judgment day comes on your valuation. If you need to go back to the VC

Akshay Kothari

Well, valuation matters internally, I think to employees. I think it matters that the stock that they did get is able to be valued that much and continue to grow in value over the years.

Harry Stebbings31:00

Is that a challenge with leaders today? You bring them in at a 10,000,000,000 price, it’s high. Like seeing like, you know, 10x on that is hard.

Akshay Kothari

I think it is a challenge for a lot of companies when you can’t show them a path. And I think it was a bigger challenge in 2022. I think some companies have been able to sort of like show a path or or have gotten there, but I think they’re probably more rare than the number of unicorns that were sort of made during that time. When you look

Harry Stebbings

back at your fundraising, what would you have done differently? I wouldn’t do anything different. How did Sequoia come together?

Akshay Kothari

When we did the COVID round in 2020, we really, really wanted Sequoia. Again, like if you think about the goal for that round was to get a stamp of approval so that we could recruit and people feel like this is a safe company and there isn’t a better stamp than Sequoia’s. And so we pitched them and actually we got a no that time in March 2020. Is this from Pat Grady? I think partnership. I think the person we had talked to there was Mike Vernal then, who’s a early personal investor.

And I think they actually wrote a very thoughtful note for why. In many ways, like it worked out in terms of us like getting to know even each other even more over the next eighteen months. And then the next one, you came back and said, hey, we still want you. Next one, came back, we asked them first and them and Coatue, because I think Coatue had put a smaller check-in the $50,000,000 round. And so they came back and did a larger one and Sequoia was the co investor in that.

Harry Stebbings32:33

Do you find having Sequoia as an investor is a needle mover for a company?

Akshay Kothari

I think, yeah, I think it is probably the best brand. Their record speaks for itself, I think.

Harry Stebbings

What does it help most? Talent, customer acquisition, pure brand and market and ego? What is the thing that is the needle mover for?

Akshay Kothari

I think the thing I would say about Sequoia, having gotten to work with them more in the last few years, is that similar to how we demand excellence from employees, I think they demand excellence from their companies. And so if you like that pressure, if you like wanting to build a generational company, I think you get the best set of questions from them. You get a lot of really nuanced feedback and data points from them. Right now we work with Pat Grady. Mean, Pat has seen literally every like generational SaaS company closely, like really closely and everything is memory.

So he can essentially tell you, you are where, you know, ServiceNow was like twelve years and two quarters ago. Right. And I think that’s, I think it’s like he’s seen the movie so many different times.

Harry Stebbings33:41

So His mind is so structured. That’s what I, for me with him, like whatever problem you have, he’ll break down it to like core component parts and then play it back in an incredible clarity structure.

Akshay Kothari

And actually one of the things that I’ve also realized is like, it’s not just like business performance. I remember one quarter where we missed our, this was maybe like a year and a half ago or something where we missed a quarter where we sort of like missed our number. I remember saying like, oh, here are like seven things we’re doing to like close the number gap. And I remember both Mike Vernal and Pat said, I think you guys are thinking about this wrong. The question is not whether you can hit this quarter or not.

The question is whether you can actually really scale this product to 100,000,000 users and beyond, because that’s the future we see with Notion. It was a good reminder where it’s like, wow, they sort of believe in this long term mission and their sort of the long termism has sort of like helped us recalibrate in terms of what we should do.

Harry Stebbings34:39

We mentioned Pat, we mentioned Index, we mentioned Coatue. Investors invest and lead and write big checks, they generally get board seats. You did boards a little bit differently. How did you do a board differently, Akshay?

Akshay Kothari

These rounds were low dilution. I think there’s essentially 2% to 3% ownership that we that we we gave out. You know, we were able to essentially not give out board seats. We were able to do it in a way that that sort of like felt like we could almost recruit a board in the future, which we wanted to do not just because someone is investing money, but someone who could be a long term sort of board board member for us.

Harry Stebbings35:18

What do you want in the recruits that you have to your board?

Akshay Kothari

So actually, like, this is something we’ve been thinking a lot about and actually, it’s actually not that different from thinking about recruiting an executive team. There’s like five seats that we would want to fill. I think I would want one person to be like a CEO whisperer, almost like a CEO coach, ideally like a former CEO who’s done that job. I think CFOs always would like a partner in having an amazing audit chair. Then there is probably a person who’s in go-to-market and this could be like either someone who’s deep in sales or deep in marketing and you can pick whichever one you need, you’re going to need help with in the long run.

Then there’s the other, like the governance and the compensation committee is typically a person who you could match with your head of people. And what you could do if you design it this way, you could also, let’s say, Fifth One is an investor who actually gives you like a macro perspective or how things are going on. But if you design this well, you could almost have a like a one to one coach for your executive team to your board that you sort of put together, where they, as they’re growing in their careers and they’re sort of like figuring out the next phase and the next phase after that, they have an incredible board member who’s investing in them.

And so I don’t actually this is probably pretty rare. Like, I don’t know another company that has done that, but I think a lot of this sort of came from first principles thinking, what Do you

Harry Stebbings36:41

think would we we build boards the wrong way? I lead your A, board seat. Someone else leads your B, board seat. Someone else leads your C, board seat.

Akshay Kothari

People are rethinking what org structures should be and, like, how many people should report to you. I think people should rethink what boards should be. There is an element of, if you had to like recreate what a board meant, I think just writing it down. But people don’t get to do that, right? Because I think we got lucky in that the ownership and some of the cash flow positive really helped not dilute as much and not need as much capital. I also think, like, you know, some of the investors I know, someone I really respect is Jeff Weiner, who is my old boss at LinkedIn.

Ivan and I actually tried very hard to get him to be a board member, our first board member at Notion, and he said no, because in deep down he wanted to be, you know, the CEO’s coach. And he said some of the board stuff around, I think, requires him to think about the company before he can think about the CEO.

Harry Stebbings37:46

Sure, have a fiduciary duty to shareholders. Correct. Which can be in direct conflict with your CEO coaching.

Akshay Kothari

Exactly.

Harry Stebbings

So it’s tricky. I wanna do a quick fire round. So I say a short statement, you give me your immediate thoughts. Does that sound okay? Let’s do it. Okay. So what do you believe that most around you disbelieve? I think AI will create more jobs than it will kill. I stalked your Twitter, so I know that you thought this was quite a good question. What’s your favorite book written before 1956?

Akshay Kothari38:13

You know, with kids sort of reread some of the Indian epics, and so there’s a part in Mahabharata called the Bhagavad Gita, And some of those principles in Bhagavad Gita are so timeless that I think are worth reading again.

Harry Stebbings

What’s your favorite essay, blog post or memo written post 2000?

Akshay Kothari

By the way, these two questions are really awesome questions that I think I found them in Lulu’s application, I think job application is Exactly. So there’s an essay, I think one of the inspirations for Notion has been Alan Kay and his work. He’s like one of the computing pioneers. He actually wrote an essay in 2008 where he said why the computer revolution still has not happened. And he sort of talks in detail about why a lot of the computing devices are mostly used for consumption. It’s not used for creating things that the pioneers have thought about.

Harry Stebbings39:05

It’s worth a read. Best board member that you would most like to have if you were to choose one other than Jeff Weiner?

Akshay Kothari

I personally would have loved Charlie Munger. Talk about like long term thinking, long term business building. Sad that he passed away, but him and Warden are sort of like my heroes.

Harry Stebbings

Did you ever go to the Berkshay Hathaway event? I’ve

Akshay Kothari

been many times.

Harry Stebbings

Was it amazing? It’s amazing. I’ve always wanted to go. Most memorable first investor meeting?

Akshay Kothari

So for me, I think I graduated 2010. I won’t go into too much detail, but I built this like small little app in my class project at Stanford that became a company called Pulse. And I remember meeting an investor, Emily Melton, who was at Mayfield then and she joined DFG and now she runs her own fund. And one of the things I realized as a student, the superpower of meeting investors is that what I saw in Pulse was like just another RSS reader and what she saw in Pulse was this next generation browser for the iPad.

And it really sort of made my idea like 100x stronger, just like having that meeting and having her talk about like someone seeing the vision even before you do it. I think that was incredible.

Harry Stebbings40:17

What’s the most contrarian or unorthodox advice that you’d have for founders listening?

Akshay Kothari

I think in general, would say like almost all advice is genius for a subset of people and completely rubbish for the rest of them. I think you can take literally everything, like, I mean, even founder mode. Founder mode is really good if you have a founder who’s right a lot. If they’re not, God bless that company. So I think, I don’t know, I think I’ve moved away from giving advice to more share my experience with what happened at Notion or Pulse, because I found that to be like, I think hopefully you can take the right learnings from them and apply it to what your situation is.

What have you changed your mind on in the last

Harry Stebbings

twelve months?

Akshay Kothari

One of the things, I think my wife was right on this one. One of the things I used to do about a year or two ago was try to like pack up every hour of my kids’ weekend with like activities and I was like, Oh, they can’t be bored. They got to do this, they got to do that. And then, you know, we just spent like a month in India this summer and they had no programming and they were just like sitting around with family and in many cases, my daughter complained she was bored, but I think both of them grew so much with all these interactions.

And I’ve realized that, I don’t know, boredom is good. Like, I think it’s okay for them to like, not be like occupied every hour of the day. What concerns you most in the world today? I think this like general TikTokification of every social app, I’m really worried about that. Every social app has become like one or two clicks away from infinite stream of viral videos, which I think is like just really sad. Has it not helped Notion?

Harry Stebbings41:55

Yeah. Like you have amazing community on TikTok and on a lot of short form platforms. I agree with you, but has it not helped?

Akshay Kothari42:02

Similar to this podcast, I think there’s definitely better content out there. I’m not saying necessarily like Notion content is better, but how many people have controlled over this information that they’re consuming? They didn’t have that even when they’re watching TV or something. But I, the thing that I worry about is like, is just the consumption to creation ratio has gone out of whack a little bit, like Do think

Harry Stebbings

so? So you think there’s now more consumption than ever, like the because there’s also more creation. Everyone’s a creator. You can’t walk down the street in London without seeing everyone creating.

Akshay Kothari

Yeah, but creating what though? Think Crap,

Harry Stebbings

I agree. Yeah. But the ratio is not the problem.

Akshay Kothari

You are right that I think more people are creating than ever before. A 100%. I think the question, I guess, I don’t know, maybe I’m being cynical here, but I wonder what people are creating and what people are consuming and whether it’s actually

Harry Stebbings

So I actually tweeted this this morning. The top eight enterprise valuations of ed tech companies amounts to about 19,000,000,000. OnlyFans enterprise valuation, 18,500,000,000.

Akshay Kothari43:08

Yeah, I would love to see in some ways, how do we make learning and education more what people wanna do? And I actually think like, I don’t know, people watching this podcast hopefully learn a few things and

Harry Stebbings

Well, I actually view it as like our job and our role to package that more efficiently for today’s This gets taken and put into a 100 different clips for four different platforms. And like, I have to move with the times to deliver my content in a better package.

Akshay Kothari

Mhmm. Yeah. You have me convinced that

Harry Stebbings

it’s not all bad, but Your feed is what you make it. It’s like life. If you go on my feed, actually, my feed is protein recipes, Jim, Tony Robbins and inspirational speeches, mine’s quite uplifting. The trouble is that most people are perpetually magnetic to crap, violence and sadness.

Akshay Kothari

Yeah. That clearly sort of resonates, but also like if you’re just maximizing attention time, which these social apps are doing, it does sort of just sort of like spiral down to that. You have to change the incentive mechanism of the app. Exactly. So you have to

Harry Stebbings44:11

change the monetization mechanism.

Akshay Kothari

Yeah, exactly. And so Which would go to

Harry Stebbings

an Elon view of the world though, which is actually moving to a subscription based social network model and saying fuck you to advertisers.

Akshay Kothari

Yeah. I I just sort of worried that I think the the incentives right now, at least for these companies that are primarily ad based are just, like, it’s gonna be a hard one to like move to subscriptions. Would you let your

Harry Stebbings

children have social media?

Akshay Kothari

No, at least not till when they’re a lot older. Actually, of the best things that happened this year in the last couple, last month, my daughter’s school sort of banned devices in school. I’m just really glad because once a month I would have a conversation with her about some of her friend wearing an Apple Watch or, and I should explain like, sorry, but we’re not getting it at this age. But now I don’t have to explain that, which is nice.

Harry Stebbings

A final one for you. What question are you not asked by hires, by team members, by investors, by people that you feel you should be asked more?

Akshay Kothari45:07

One of the things that I’ve been reflecting on is a little bit sort of like that, you know, the Steve Jobs speech around how you connect the dots looking back. I didn’t appreciate it when I was growing up in this small city in Gujarat in India, how sort of growing up there and surrounded by friends and family there, how it would have shaped the things that I do today. And so I think some of those, some of that exploration is super fun too, especially as I get closer to 40.

It’s like, wow, like all my creative genes probably comes from my mom and all my business genes probably comes from my dad and like all these different things that I did when I was young in some ways has made what I do today possible.

Harry Stebbings

Actually, listen, I so appreciate you putting up with my meandering. You’ve been fantastic to have on the show. So thank you so much for joining me. Thank you

Akshay Kothari

for having me.

Unknown

So I would love your feedback. I would love to hear. Do you think shows are significantly better when recorded in person in the studio? Let me know on Twitter at Harry Stebbings, and you can watch them on YouTube at 20 VC. That’s two zero VC. But before we leave you today,

· Sponsor read0 min · 511 words
Unknown46:10

all of you listening use tons of software every day. Sometimes it fills us with rage. You can’t figure something out. The chatbot in the bottom right is useless. You keep getting bombarded with these useless pop ups. And for those of you who build products, no one wants their product to feel like this. Thankfully, a company exists to help users without annoying them. Command bar. It does a couple of very helpful things. First, it’s a chatbot that uses AI to give users extremely personalized responses and deflect tickets.

But it can be beyond just text. It can also co browse with the user and show them how to do things inside the UI. Magic. But it can also detect when users would benefit from a proactive nudge, like a helpful hint or an invitation to start a free trial. Command Bar is already used by world class companies like Gusto, Hashicorp, Yotpo, and Angelist. If you’re a product CX or marketing leader, check them out at commandbar.com/harry. And talking about incredible companies with Command Bar, I want talk to you about a new venture fund making waves by taking a very different approach.

It’s a public venture fund anyone can invest in, not just institutions and accredited investors. The Fundrise Innovation Fund is democratizing venture capital, which could have big consequences for the industry. The fund is already off to a good start with $100,000,000 into some of the largest, most in demand AI and data infrastructure companies. Companies like OpenAI, Anthropic, and Databricks. Check out the innovation fund’s impressive list of investments for yourself by visiting fundrise.com/20vc. Carefully consider the investment material before investing, including objectives, risk charges, and expenses. This and other information can be found in the innovation funds prospectus at fundraise.com/innovation.

This is a paid sponsorship. And finally, let’s talk about Squarespace. Squarespace is the all in one website platform for entrepreneurs to stand out and succeed online. Whether you’re just starting out or managing a growing brand, Squarespace makes it easy to create a beautiful website, engage with your audience, and sell anything from products to content all in one place, all on your terms. What’s blown me away is the Squarespace Blueprint AI and SEO tools. It’s like crafting your site with a guided system, ensuring it not only reflects your unique style, but also ranks well on search engines.

Plus, their flexible payment options cater to every customer’s needs, making transactions smooth and hassle free. And the Squarespace AI, it’s a content wizard helping you whip up text that truly resonates with your brand voice. So if you’re ready to get started, head to squarespace.com for a free trial. And when you’re ready to launch, go to squarespace.com/20vc and use the code 20 v c to save 10% off your first purchase of a website or domain. As always, I so appreciate all your support and stay tuned for an incredible episode coming this Monday.

It is one of the best investing shows we’ve done with David Frankel at Founder Collective.

↑ Top