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Colossus (Invest Like the Best / Business Breakdowns)Podcast5 Nov 2021Source: joincolossus.comHost: Patrick O'Shaughnessy

Roelof Botha - Sequoia’s Crucible Moment - [Invest Like the Best, EP. 250]

In plain words

Sequoia partner Roelof Botha announces a radical change: replacing the traditional 10-year fund with a permanent fund, because great companies create most of their value after going public. Example: Square returned 9x before IPO but 90x when Sequoia held on longer. Botha is bullish on long-term holding. Key picks: Square (IPO at $9, exited at $80-90), YouTube (invested when only 9,000 users, later sold to Google), MongoDB (cloud database now 50% of revenue, bets on developer tools).

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At a Glance Sequoia Capital partner Roelof Botha announced the firm's boldest innovation since its founding in the 1970s: abandoning the traditional venture capital fund cycle model and restructuring into a single, open-ended, perpetual "The Sequoia Fund." The core argument is that this structural c

~12 min full read · 8 sections
Deep Analysis

At a Glance

Roelof Botha (Sequoia Capital partner) announced on the program the boldest innovation since Sequoia's founding in the 1970s: abandoning the traditional venture capital fund cycle model and restructuring into a single, open-ended, perpetual "The Sequoia Fund." The core thesis is that the traditional 10-year closed-end fund is fundamentally at odds with the long-term goal of "building legendary companies," and that an IPO should not be the endpoint for venture capital—in the Square case, continuing to hold post-IPO boosted returns from 9x to 90x.


1. Structural Transformation: From 10-Year Funds to Perpetual Capital

Roelof Botha argues that the traditional VC model (invented in the 1970s) has a fundamental mismatch with investment reality: the 10-year lock-up period forces venture capitalists to exit shortly after an IPO, yet value creation for "legendary companies" accelerates precisely after going public.

  • Square case: The investment was made at approximately $0.95/share in 2011, with an IPO price of $9 (roughly 9x return); but Sequoia patiently held until $80-90 before exiting in tranches, ultimately achieving about 90x returns. The market cap at IPO was $2.95 billion, reaching $86 billion five years later, and today stands at approximately $115-120 billion — "the company went from 0 to $3 billion in the first five years, and from $3 billion to $86 billion in the next five."
  • Core contradiction: "We tell founders that an IPO is a milestone, but why should it be an endpoint for investors? We have all the context, relationships with founders, and the ability to help companies continue growing — yet the traditional model defaults to 'step down from the board, distribute shares shortly after IPO.'"
  • LP interests: Sequoia's LPs are primarily endowments, foundations, and non-profits. "Most returns occur after a company goes public, so why are we selling the stock so quickly?"

New fund mechanism:

  • In the allocation decisions of existing sub-funds (seed/venture/growth funds), LPs can annually choose to roll 0%-100% of their shares into Sequoia Fund (a collective investment vehicle where LPs hold a proportional stake in the overall portfolio rather than specific stocks).
  • Future new funds will have Sequoia Fund as their sole LP, with LP capital commitments deducted directly from their balance in Sequoia Fund, simplifying the capital call process.
  • LPs can redeem a portion of their balance annually to meet liquidity needs.

Readers should note: Botha uses Square's extreme success case to justify the new structure, which reflects a holder's perspective — not all portfolio companies will achieve similar post-IPO growth.


II. Additional Capabilities and Fee Design Unlocked by the New Structure

Roelof Botha points out that traditional VC exemption rules restrict funds from allocating more than 20% of assets to non-primary issuances (secondary transactions, crypto assets, public securities, fund-of-fund investments). The new structure will break this constraint.

  • Secondary Transactions: Over the past decade, many companies have created employee liquidity opportunities before going public (e.g., PayPal's secondary transaction in the summer of 2001), but Sequoia was unable to participate due to structural limitations. "That secondary transaction helped the team be more patient during the eBay acquisition negotiations — because some capital had already been locked in."
  • Crypto Assets: Sequoia has been active in the crypto space for five years with strong returns, but has been constrained by the 20% cap.
  • Scouts Program: Sequoia's pioneering Scouts program is also subject to this constraint.

Fee Structure:

  • Fees at the sub-fund level remain unchanged.
  • The newly added liquidity pool (public securities portion) charges extremely low management fees, only covering actual operating costs.
  • Incentive Fee: Charged only when performance exceeds the benchmark index — using a three-year rolling perspective to avoid short-term incentive distortions. "This is not a 'roach motel' — we don't want to just pile up assets."
  • Strong Alignment of Interests: Sequoia partners will commit at least 5% (likely 10%) of the total fund, and Botha himself has pledged to invest more than one-third of his net worth.

Comparison with Other Models: Botha believes that true "crossover investors" should be able to "see the company from inception through its full lifecycle," rather than entering from public markets back into private markets. Competition drives Sequoia to innovate, and the ultimate beneficiaries are founders.


III. Investment Philosophy: Value Creation First, Curiosity-Driven

Roelof Botha emphasizes that in early-stage investing, "value creation is far more important than value capture" — "It is rare for a company to create enormous value and still fail to build a good business."

  • Evaluation framework: First, understand the "Eureka moment" — why a founder is so deeply troubled by a problem that they are willing to dedicate their life to it (e.g., the founder of Natera, whose sister lost a baby due to an undetected genetic disease).
  • Unique value proposition: It must not only be compelling but also unique — "If it is not unique enough, there will be a flood of competitors, making it difficult to build a differentiated business."
  • Exclusion criteria: If a founder appears more like a "mercenary" than a "missionary" — "Mercenaries wither in adversity."
  • Business model: Almost no focus in the early stages. "Sometimes business model innovation is needed (e.g., Google's second-price auction) to turn a good business into a great one, but typically, value is created first, and a way to monetize can always be found."

The common DNA of great investors: Curiosity — "If you lose curiosity and become cynical, you should stop being an investor." Other essential qualities include analytical ability, judgment of people, intuition about market direction, and imagination (YouTube had only 9,000 registered users at the time of investment).

Standards for investment memos: Clarity and conviction — "Being able to explain a complex business or technology so that anyone can understand it shows you have truly mastered it." At the same time, one must "make a judgment amid uncertainty — whether it is a 60-40 or 55-45 decision."


4. Key Lessons Learned from Portfolio Companies

Roelof Botha distills core insights from cases including Square, Unity, YouTube, and MongoDB:

  • Square: Successfully incubated the consumer-facing Cash App from its DNA of serving small businesses—this was a "second founding moment." "Most organizations are their own worst enemy; they often kill these nascent ideas."
  • Unity and the Open Ecosystem: Unity believes in an open metaverse (real-time 3D interactive technology), contrasting with closed ecosystems. "In the late '90s, we nearly compressed the open internet into Microsoft's internet—if the DOJ hadn't sued Microsoft, Web 2.0 might never have happened." Open ecosystems unleash everyone's creativity, while monopolists have no need to innovate.
  • YouTube: A platform for creators—"25 years ago, if you wanted to be heard, you had to write a letter to a newspaper and hope they'd publish it." YouTube enables creators to connect with brands, engage in e-commerce, and make a living.
  • MongoDB and the "Rise of the Developer": Only about 25 million people worldwide make a living writing software—"Any technology that boosts the productivity of these developers has a massive multiplier effect." MongoDB's "second act," Atlas (cloud database as a service), now accounts for roughly 50% of revenue, and its success stems from an extreme focus on developer experience.

"Crucible Moment": A company faces one or two decisive moments each year; the challenge lies in identifying them and making the right decisions. When MongoDB pivoted to cloud services, Sequoia brought in a former AWS executive to join the board, helping the company "retrain its muscles"—shifting from selling on-premise products to cloud services, including adjusting sales compensation, product features, and resource allocation.


5. Leadership and Long-Termism

Roelof Botha argues that as the role shifts from investor to leader, the core challenge becomes "people problems rather than product problems" — ensuring team composition, collaboration, and organizational capability building.

  • Brand and Legacy: Don Valentine deliberately chose not to name the firm "Valentine Capital," opting instead for the redwood tree, which can live for a thousand years — he wanted to build "a partnership that could outlast himself." Botha's title is "Steward," meaning to serve others. "Our job is to leave the partnership in better shape than when we took it over, and then recruit the next generation to take over."
  • Actuary Mindset vs. Accountant Mindset: An accountant looks at the past year; an actuary looks at the next 20 years — "Most of my bad decisions came from too short a time horizon, failing to imagine the power of compounding." Compounding is not intuitive (prehistoric humans had no need for it), but 1.1 raised to the Nth power becomes enormous as N grows — this is the core philosophy of the Sequoia Fund: people underestimate the ability of successful companies to compound over time.
  • Genius vs. Talent: Genius is more about inspiration (from 0 to 1), while talent is more about perspiration (from N to N+1). But success requires both to complement each other — "Like a football team, players of different sizes and speeds each have their roles; there are no individual statistics, only team victory."

The Preplay and Premortem Framework (attributed to Larry Summers): Imagine the company achieving tremendous success in 3-5 years — what conditions led to that success? Then write a "premortem" — everything that could go wrong. Sequoia uses this framework internally: "Imagine Sequoia disappears in 10 years — what did we do wrong? What did we fail to do?" This drives continuous innovation, including the creation of the Sequoia Fund.


Mentioned Positions

Position Guest Stance Key Data
Square Bullish (long-term holding case) Investment price ~$0.95/share, IPO price $9, exit price $80-90; IPO market cap $2.95B → $86B after 5 years → ~$115-120B today
YouTube Bullish (early participation, later credited to Google) Only 9,000 registered users at time of investment; founder was a former PayPal colleague
Unity Bullish (open ecosystem stance) 70% of the top 1,000 App Store games built on Unity
MongoDB Bullish (developer rise theme) Atlas cloud product accounts for ~50% of revenue
Natera Bullish (holding) Global leader in non-invasive prenatal testing technology
PayPal Reflective (sold too early) eBay acquisition price $1.5B, today's market cap over $300B
Filecoin Bullish (crypto investment) Smart contracts automatically pay for storage fees
DoorDash Not explicitly stated (citing Alfred Lin's memo) -
ServiceNow Not explicitly stated (citing Pat Grady's memo) -
Zoom Not explicitly stated (citing Pat Grady's memo) -
WhatsApp Not explicitly stated (citing Jim Getz's memo) -

Judgments Worth Remembering

1. Botha: The traditional VC 10-year fund cycle fundamentally conflicts with building legendary companies — IPO should not be the endpoint for venture capital, because "most value creation happens after going public." In the Square case, holding the position post-IPO boosted returns from 9x to 90x.

2. Botha: The new fund fee structure "only rewards us when we exceed the benchmark" — It adopts a three-year rolling perspective to avoid short-term incentive distortions. Partners commit at least 5% of the total fund, and Botha himself has pledged over one-third of his net worth.

3. Botha: In early-stage investing, "value creation is far more important than value capture" — "Rarely does a company create enormous value without building a good business." First understand why a founder is deeply troubled by a particular problem (the Eureka moment), then assess the uniqueness and persuasiveness of the solution.

4. Botha: The core DNA of a great investor is curiosity — "If you lose your curiosity and become cynical, you should stop being an investor." Other essential qualities include analytical ability, judgment of people, and imagination (YouTube had only 9,000 registered users at the time of investment).

5. Botha: Open ecosystems are superior to closed ones — Unity believes in an open metaverse, whereas "in the late 1990s, we nearly compressed the open internet into Microsoft's internet." Monopolists don't need to innovate; openness unleashes everyone's creativity.

6. Botha: Only 25 million people worldwide make a living writing software — "Any technology that boosts the productivity of these developers has a massive multiplier effect." This drove Sequoia's investments in Unity, MongoDB, GitHub, and Confluent.

7. Botha: Actuarial thinking (looking 20 years out) is better than accounting thinking (looking 1 year out) — "Most of my bad decisions came from having too short a horizon and failing to imagine the power of compounding." 1.1 raised to the Nth power becomes enormous as N grows — this is the core philosophy of the Sequoia Fund.

8. Botha: Use the "preplay and premortem" framework for strategic decisions — Imagine the conditions for success or failure 3-5 years out, then reverse-engineer what to do today. Sequoia uses it internally to ask: "10 years from now, Sequoia has disappeared — what did we do wrong?" This drives continuous innovation.