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

Akshay Kothari is Co-Founder at Notion, one of the fastest-growing companies of the last decade. Akshay has run every function in the company from sales, to marketing to finance and even led their fundraising efforts raising $340M+ from Sequoia, Index and Coatue with the latest round pricing them at $10BN. Before Notion, Akshay was VP Product at Linkedin for 5+ years, leading all of their content efforts. He joined LinkedIn when his previous company, Pulse, was acquired by LinkedIn in 2013. ----------------------------------------------- Timestamps: (00:00) Intro (00:47) Adapting to Multiple Roles & Learning Fast (04:34) Founder Mode & the Transformation of Traditional Org Structures (06:00) Managing Growth Without Losing Focus Amid Increased Funding (07:16) The Importance of Speed (10:58) Lessons on Hiring (16:12) Unmade Decisions Weighing on Notion's Future (19:37) Are We Building Companies the Wrong Way Today? (22:26) Raising $50M at $2BN Valuation (27:25) Raising $270M at $10BN Valuation (32:12) What Would You Change About Fundraising? How Did Sequoia Join? (36:15) What Was Unique About How Akshay Structured His Board (39:50) Quick-Fire Round ----------------------------------------------- In Today’s Episode with Akshay Kothari We Discuss: 1. Founder Mode, Veto Powers and Focus: Does Akshay agree with “founder mode”? What are the biggest downsides to founder mode that not enough people are discussing? Why does Akshay believe that the single greatest power of a founder is their “veto power”? What is the biggest opportunity that Notion jumped on that they should not have done? What is the biggest opportunity that Notion did not jump on that they should have jumped on? 2. Raising $50M at $2BN Valuation: Why did Ivan and Akshay decide to do this raise when they did not even need the money? How did the fundraising process for this round go? Why did they choose Coatue and Index? Why did Sequoia say no to this round? With the benefit of hindsight, what does Akshay wish that they had done differently? 3. Raising $270M at $10BN Valuation: How did Sequoia come back into the frame with this round? Why did they say yes here when they did not before? Why does Akshay believe that of all the investor brands, Sequoia is the most powerful? In what way does having Sequoia as an investor change the trajectory of the company? Is Akshay concerned about how he will be able to scale into the $10BN valuation? How does Akshay address the challenge of bringing new team members in with stock options priced at $10BN? How much of a blocker is that? 4. Boards and Social Media are F*******: How is the way in which boards are constructed broken? How does Akshay believe that boards should be constructed? What roles should founders hire for in their board members? Why is Akshay most concerned about the “Tiktokification of everything”? Why does Akshay believe that social media has never been more concerning? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Akshay Kothari on Twitter: https://twitter.com/akothari Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #akshaykothari #venturecapital #founder #notion #linkedin #sequoia #coatue

Akshay KothariguestHarry Stebbingshost
Sep 17, 202448mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

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

  1. 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.
  2. 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.
  3. 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.
  4. 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.

IDEAS WORTH REMEMBERING

5 ideas

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.

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.

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.

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.

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.

WORDS WORTH SAVING

5 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

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

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