Founders must have conviction, as even their most sophisticated investors can fundamentally misjudge a bold strategic shift. A Sequoia Capital partner admits their own investors strongly opposed a pivotal move into logistics, demonstrating that founder vision must sometimes override expert consensus.
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For a controversial strategic shift, a co-founder's "moral authority" is invaluable. They can absorb the risk of looking foolish and give up their responsibilities ("Legos") to spearhead a new initiative. This allows them to champion a new direction with a level of credibility that can overcome internal skepticism.
Breakthrough companies often succeed not by iterating endlessly, but by 'planting a flag'—making a strong, often contrarian bet on a core thesis (e.g., email-first media) and relentlessly executing against that vision, even when it's unpopular or lacks momentum.
Managerial companies derive legitimacy from "the plan," creating enormous inertia against change. In founder-led companies, legitimacy is vested in the founder as an individual. This is their key structural advantage, allowing the entire organization to pivot on a dime based on conviction.
A founder must simultaneously project unwavering confidence to rally teams and investors, while privately remaining open to any evidence that they are completely wrong. This conflicting mindset is essential for navigating the uncertainty of building a startup.
Deciding to pivot isn't about perseverance; it's a cold, rational decision made when you've exhausted all non-ridiculous ideas for success. The main barrier is emotional—it's "fucking humiliating" to admit you were wrong. The key is to separate the intellectual decision from the emotional cost.
Founders with deep market fit must trust their unique intuition over persuasive, but generic, VC advice. Following the standard playbook leads to cookie-cutter companies, while leaning into the 'weird' things that make your business different is what creates a unique, defensible moat.
Large, contrarian investments feel like career risk to partners in a traditional VC firm, leading to bureaucracy and diluted conviction. Founder-led firms with small, centralized decision-making teams can operate with more decisiveness, enabling them to make the bold, potentially firm-defining bets that consensus-driven partnerships would avoid.
A truly exceptional founder is a talent magnet who will relentlessly iterate until they find a winning model. Rejecting a partnership based on a weak initial idea is a mistake; the founder's talent is the real asset. They will likely pivot to a much bigger opportunity.
Sequoia's internal data shows consensus is irrelevant to investment success. A deal with strong advocates (voting '9') and strong detractors (voting '1') is preferable to one where everyone is mildly positive (a '6'). The presence of passionate conviction, even amid dissent, is the critical signal for pursuing outlier returns.
While it's crucial to listen to markets and clients, founders must also be prepared to stick to their convictions when investors, who may not be specialists in their niche, offer conflicting advice. Knowing when to listen and when to hold firm is a key startup skill.
