The Twenty Minute VCAkshay Kothari: How Notion Has More Money Than Ever & Why Startup Fundraising is Broken | E1203
CHAPTERS
- 0:36 – 2:16
Scaling Notion as COO: many hats, one job
Akshay explains that while his titles at Notion varied wildly, his core role as COO was consistent: scale everything around the product so Ivan and Simon could stay focused. He shares how he approached unfamiliar functions by jumping in wherever the company needed him.
- •Reframing “multiple roles” as one scaling mandate (COO)
- •Operating principle: founders stay product-focused; COO absorbs the rest
- •Learning new functions quickly by doing them firsthand
- •Using product background to transfer skills across disciplines
- 2:16 – 4:35
Systems design applied to operations: building a support→product feedback loop
Akshay gives a concrete example of applying product thinking to customer support. Instead of simply hiring more support agents, Notion designed a system to turn every ticket into structured product signal visible to engineers in near real time.
- •Avoiding linear headcount growth by improving systems and tooling
- •Creating a canonical taxonomy (~200 request types) mapped to features
- •Training support to tag every ticket; automating daily sync into Notion
- •Giving engineers direct access to customer pain without extra layers
- •Reducing need for early product ops and formal research hires
- 4:35 – 6:01
“Founder mode” and rethinking traditional org structures
The conversation shifts to whether modern companies should redesign org structures around founder-style operating models. Akshay argues leaders should actively question inherited management norms and choose structures that fit their company’s reality.
- •Questioning default org designs and management rituals
- •Examples of unconventional leadership structures (many direct reports, fewer 1:1s)
- •Org design as a choice, not a rulebook
- •Founder-led operating models pushing experimentation in structure
- 6:01 – 7:17
Preventing “creep” after big rounds: veto power and enduring pain
Akshay describes how Notion avoided sprawling teams and premature initiatives despite rising brand and cash. The key mechanisms were founder veto power, high hiring standards, and patience even when roles felt urgently needed.
- •Founder veto as a core discipline mechanism
- •“Meet everyone” hiring rigor up to ~500 employees
- •Waiting for great instead of settling for good
- •Being willing to endure short-term pain to protect long-term quality
- 7:17 – 9:17
Speed through leanness: why small teams can move faster
Akshay reconciles patience in hiring with the need for execution speed. Notion optimized for long-term velocity by staying lean, limiting parallel projects, and forcing prioritization rather than scaling headcount to say yes to everything.
- •Small team as a long-term speed advantage
- •Under 20 PMs and ~12 designers across the product surface
- •Avoiding committee-driven product and design decisions
- •Saying no to more projects to execute the right few better
- •Fundraising-fueled hiring can create the illusion of speed while slowing outcomes
- 9:17 – 12:39
Hiring principles and values: optimizing for builders and clear debate
Akshay explains how Notion learned to codify values and what “kind and direct” really signals culturally. He also shares hiring lessons: shape the function first, sometimes hire ICs before leaders, and prioritize builders who thrive without heavy corporate machinery.
- •Codifying four values at ~50 people (owners, pacesetters, truth seekers, kind & direct)
- •“Kind and direct” as permission for candid internal debate
- •Often defining the function by doing it internally before hiring a leader
- •Hiring ICs first in some functions to establish the work
- •Mistake pattern: leaders from big-tech orgs struggling in lean, builder-centric environments
- 12:39 – 16:12
Sales as the hardest function: lessons from trying to reinvent the wheel
Akshay names sales as the function he’d redo. Notion initially tried a quota-less, consultative model, but learned that great sales talent often wants quotas and clear attribution—and that enterprise growth ultimately requires outbound capability.
- •Attempting consultative, quota-less sales and why it failed
- •Top salespeople often join to win against a quota and outperform
- •Early impact: sales-assisted contribution didn’t grow as expected
- •PLG as both blessing and curse (over-reliance on inbound leads)
- •Realization: enterprise requires outbound and a true sales leader; bringing in Pravesh
- 16:12 – 18:21
The “unmade decision” weighing on Notion: consumer + enterprise in one horizontal product
Akshay addresses the strategic tension of building a horizontal product that serves both consumers and large enterprises. Rather than choosing one, Notion frames itself as a “compound company,” where connected products share building blocks and a data layer, with consumer use powering distribution and B2B driving revenue.
- •Horizontal product identity: “consumer or enterprise?” → historically ‘yes’
- •Adopting “compound company” framing (connected products via shared layer)
- •Internal clarity: being more forthright about what kind of company Notion is
- •Data point: ~46% of business traced to personal-life usage origin
- •Consumer use as natural distribution; B2B as the bill-paying growth engine
- 18:21 – 19:38
Cashflow positivity as leverage: control, optionality, and fewer fundraising distractions
Akshay explains how becoming cashflow positive early changed Notion’s trajectory. It removed existential runway pressure, reduced fundraising time, and gave the team the freedom to raise capital only when strategically useful.
- •Cashflow positive early (~5 years ago) reduced external pressure
- •Feeling “in control of destiny” without a forced fundraising clock
- •Optionality: raise only with a clear purpose, not necessity
- •Time saved redirected to product building and selling
- 19:38 – 22:27
Are startups built the wrong way? Long-term valuation realism and capital purpose
Akshay weighs the modern fundraising playbook against long-run market realities. He emphasizes understanding terminal valuation drivers—revenue multiples and cashflows—and warns against assuming the return of extreme ARR multiples without fundamentals to support them.
- •Funding abundance as a gift, but can distort strategy
- •Long-run valuations revert to revenue/cashflow multiples (often ~5–10x revenue)
- •Three drivers of premium multiples: growth rate, cashflow margins, terminal growth potential
- •Raise money with a clear plan for use, not “hope multiples”
- •Historical examples: constrained early fundraising can force customer closeness and stronger execution
- 22:27 – 27:25
Raising $50M at $2B (COVID): using capital as a recruiting signal without losing discipline
Akshay recounts raising $50M at a $2B valuation early in COVID, emphasizing it wasn’t driven by cash need. The round functioned as a stability “stamp” to attract talent during a flight-to-safety moment—while Notion tried to maintain focus despite new resources.
- •Context: early COVID 2020 raise, $50M at $2B with minimal dilution
- •Raising from strength: ability to “break the rules” when not capital constrained
- •Primary goal: signaling stability to recruit during uncertainty
- •Maintaining discipline despite cash influx; Notion’s cultural wiring toward restraint
- •Finance insights: benchmarking, strategic FP&A/BizOps, and test budgets to validate channels
- 27:25 – 32:12
Raising $270M at $10B (2021): competing in a heated go-to-market era, then pulling back
Akshay explains the 2021 raise as a response to competitors becoming aggressive in marketing and sales. Notion chose to “play the game on the field,” pushed go-to-market for about a year, and then adjusted quickly as markets turned in 2022—while reflecting on how hard it is to find scalable, efficient spend channels.
- •October 2021: ~$270M at $10B amid frothy markets
- •Motivation: match competitors’ aggressive go-to-market moves
- •Decision: go aggressive temporarily; pull back when conditions changed in 2022
- •Nuanced competition: don’t burn down the company, but do test capture opportunities
- •“99 ways to burn money, one good way to make money” and scaling unit economics challenges
- •Valuation perspective: matters internally for employee equity and hiring narratives
- 32:12 – 36:05
Fundraising reflections, Sequoia’s path in, and why Notion minimized board seats
Akshay says he wouldn’t change their fundraising approach and describes how Sequoia initially passed in 2020, then joined later alongside Coatue. He also explains how low dilution enabled Notion to avoid automatic investor board seats and instead consider a board built for long-term capability fit.
- •Sequoia story: wanted the stamp in 2020, got a ‘no’; relationship deepened
- •2021: returned first to Sequoia and Coatue; Sequoia joined as coinvestor
- •What Sequoia adds: excellence pressure, pattern recognition, high-quality questions
- •Low dilution (~2–3%) enabled Notion to avoid giving board seats by default
- •Board as a future “recruiting” exercise, not a transactional right
- 36:05 – 48:53
Designing the board like an executive support system + quick-fire closing
Akshay outlines a first-principles approach to board composition: CEO coach, audit chair, go-to-market expert, people/compensation governance, and an investor with macro context. The episode closes with quick-fire answers spanning AI jobs, favorite classics, contrarian advice, parenting, and concerns about short-form social media incentives.
- •Board blueprint: distinct seats aligned to core executive needs
- •Idea: 1:1 pairing between board members and execs as coaches
- •Rethinking the standard ‘lead round = board seat’ model
- •Governance vs CEO coaching tension (fiduciary duty)
- •Quick-fire: AI creates more jobs than it kills; Bhagavad Gita; desire for Charlie Munger; advice skepticism; boredom for kids; concern about TikTokification and ad incentives; delaying children’s social media
