Akshay Kothari: How Notion Has More Money Than Ever & Why Startup Fundraising is Broken | E1203

Akshay Kothari: How Notion Has More Money Than Ever & Why Startup Fundraising is Broken | E1203

The Twenty Minute VCSep 18, 202448m

Narrator, Akshay Kothari (guest), Harry Stebbings (host)

Using product and systems thinking to build non-product functions (support, ops, finance, sales)Staying lean: hiring philosophy, veto power, and enduring resource constraintsSales in a product-led growth company and the pain of trying to reinvent itFundraising strategy, cash-flow positivity, and realistic valuation mechanicsDesigning org structures and boards from first principles rather than conventionBalancing Notion’s horizontal product across consumer and enterprise use casesBroader views on AI, social media incentives, education, and parenting

In this episode of The Twenty Minute VC, featuring Narrator and Akshay Kothari, Akshay Kothari: How Notion Has More Money Than Ever & Why Startup Fundraising is Broken | E1203 explores notion COO Akshay Kothari Redefines Hiring, Sales, Fundraising and Boards Akshay Kothari, COO of Notion, explains how first-principles, product-minded thinking let him span multiple executive functions while keeping the company extremely lean and fast-moving.

Notion COO Akshay Kothari Redefines Hiring, Sales, Fundraising and Boards

Akshay Kothari, COO of Notion, explains how first-principles, product-minded thinking let him span multiple executive functions while keeping the company extremely lean and fast-moving.

He details Notion’s deliberate choices around small teams, disciplined hiring, and eventually embracing a traditional enterprise sales motion after initially trying to reinvent it—and losing years in the process.

Kothari also outlines Notion’s unusual fundraising path: becoming cash-flow positive early, raising low‑dilution rounds primarily for signaling and go‑to‑market firepower, and deliberately avoiding investor board seats.

The conversation widens into how startups are built and funded today, the importance of understanding real valuation mechanics, how to design boards and orgs from first principles, and his concerns about social media incentives versus education and creation.

Key Takeaways

Apply product-style systems design to every function, not just product.

Kothari turned customer support into a structured data system—tagging tickets into a canonical database and piping insights directly to engineers—eliminating early needs for product ops, research, and large support headcount while improving responsiveness.

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Stay lean longer and endure short-term pain to move faster long-term.

Notion deliberately kept teams small, personally vetted nearly every hire up to ~500 employees, and accepted operating ‘understaffed’ so that focus, prioritization, and autonomy remained high instead of diluting velocity across too many people and projects.

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Don’t over-innovate on proven motions like enterprise sales.

They initially tried a quota-less, ultra-consultative sales model in a product-led context, which hurt sales contribution and hiring; Kothari now believes they should have adopted a standard quota-driven sales machine much earlier instead of reinventing the wheel.

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Use cash-flow positivity to change your relationship with fundraising.

Becoming cash-flow positive gave Notion control over timing and terms: they could raise when it helped with signaling or go-to-market, secure low-dilution deals, and avoid board-seat obligations, instead of fundraising simply to survive.

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Anchor decisions in long-term valuation realities, not hype multiples.

Kothari stresses that in the long run, SaaS companies are valued on revenue and cash-flow multiples (historically ~5–10x), which can be improved only through faster growth, better margins, or structurally large markets—founders should raise and spend with that in mind.

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Design boards as a support system for your executive team, not a byproduct of rounds.

He argues boards should be intentionally assembled around complementary expertise (CEO coach, audit chair/CFO partner, GTM operator, people/governance, one strong investor) so each exec has a true ‘coach,’ rather than defaulting to whoever led the last round.

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Horizontal products can leverage consumer usage to drive B2B growth.

Nearly half of Notion’s business traces back to personal use cases; Kothari sees Notion as a ‘compound company’ where consumer love is a distribution engine, while monetization and ‘paying the bills’ still come primarily from business and enterprise customers.

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Notable Quotes

There are 99 ways you can burn money and only one good way to effectively make money.

Akshay Kothari

We may feel like we’re going faster by hiring more people and saying yes to more projects, but in effect it is actually going slower.

Akshay Kothari

We tried to reinvent the wheel on sales and it probably cost us three years.

Akshay Kothari

Once you’re cash-flow positive, you suddenly feel in control of your destiny—you don’t have an end date.

Akshay Kothari

Almost all advice is genius for a subset of people and completely rubbish for the rest.

Akshay Kothari

Questions Answered in This Episode

How can an early-stage founder practically apply Notion’s systems-design approach to support, sales, or finance with a team of fewer than 10 people?

Akshay Kothari, COO of Notion, explains how first-principles, product-minded thinking let him span multiple executive functions while keeping the company extremely lean and fast-moving.

Get the full analysis with uListen AI

What concrete signals should a product-led startup watch for to know it’s time to invest seriously in outbound and traditional enterprise sales?

He details Notion’s deliberate choices around small teams, disciplined hiring, and eventually embracing a traditional enterprise sales motion after initially trying to reinvent it—and losing years in the process.

Get the full analysis with uListen AI

If you’re not yet cash-flow positive, how can you still negotiate for more founder-friendly fundraising terms—such as avoiding automatic board seats?

Kothari also outlines Notion’s unusual fundraising path: becoming cash-flow positive early, raising low‑dilution rounds primarily for signaling and go‑to‑market firepower, and deliberately avoiding investor board seats.

Get the full analysis with uListen AI

How should a horizontal product company prioritize between consumer delight and enterprise-specific features without losing focus or brand clarity?

The conversation widens into how startups are built and funded today, the importance of understanding real valuation mechanics, how to design boards and orgs from first principles, and his concerns about social media incentives versus education and creation.

Get the full analysis with uListen AI

Given today’s AI and social-media landscape, what responsibility do product builders have to shift incentives toward learning and high-quality creation?

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Transcript Preview

Narrator

(instrumental music plays) Akshay, I am so excited for this, dude. We did this four years ago in COVID (laughs) uh, when no one was getting out, and now you're in London, man. This is so special. Thank you for being here.

Akshay Kothari

Thank you for hosting, and so good to see you in person.

Harry Stebbings

Yeah.

Akshay Kothari

Yeah.

Harry Stebbings

I spoke to Ivan before the show. I spoke to many people before the show. Basically, just talked the shit out of you.

Akshay Kothari

(sniffs)

Harry Stebbings

Uh, 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. How did you learn new disciplines so quickly on the job?

Akshay Kothari

Uh, I didn't really think of my job as those titles. Like, I think I, I, I... My job was COO, uh, and, and in many ways, I... My, 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, and so that meant whatever the company needed, I would jump in and try to figure it out. Um, how did I do it? This is actually kinda interesting. So, so my background is product, right? And, and, and, and Ivan told me to join and take care of everything except product. And so I was... I s- essentially put myself on all these new functions and, um, and, and just tried 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 Stebbings

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 there were three people who reported to me were support, customer support, right? Now, typically, as the number of tickets or as the number of requests go up, um, 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. Uh, the product, um, manager in me was like, "Well, we could build a better system, so we could build better tools so that each support person can do more every day." But also, you know, once you have enough of these, uh, customer tickets, then the next role you want to hire would be something called a product ops, right? Product ops would take all this feedback and synthesize it and pro- pr- and share it with the engineers. So one thing Ivan and I did in the (laughs) in the early years was, um, 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. And every morning at 6:00 AM, (smacks lips) 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 last, 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, and we use this tag across the tools we had, right? So for example, if, if you're working on Android, you could essentially put that tag in Intercom, and you can lis- 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, 'cause now... So now, if you put all these things together, we, we, 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.

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