How to be legitimate

Here’s a concise executive summary of “How to Be Legitimate” by Steven Sinofsky (via a16z), written specifically for you as a startup founder, CEO, and CTO 👇

🧭 Core Idea

Being technically good is not enough — your startup must look legitimate to the market you’re selling into. Legitimacy signals make people trust your product, your technology, and your vision of the future.

🕰️ Evolution of Legitimacy in Tech

Era	Legitimacy Source	What It Meant
1960s–70s	Special Interest Groups (SIGs) & User Groups	The original "GitHub" — technical communities where credibility was earned by showing up, sharing knowledge, and contributing.
1980s–90s	Tech Magazines (e.g. PC Magazine, Byte)	Editorial reviews and awards became kingmakers. A “PC Magazine Editor’s Choice” could make or break a product.
1990s–2000s	Influential End Users	Grassroots adoption by curious, creative employees who quietly tested new tools (like early PC or ChatGPT users). Legitimacy spread through real usage.
2000s–2010s	Media & Analysts (e.g. Walt Mossberg, Gartner)	A single influential review could define perception of your company. Public narrative = credibility.
2010s–Now	VCs, GitHub, Product Hunt, Enterprise Briefings	Venture capital, visible open-source contributions, and network introductions serve as “legitimacy loans.” Being in the right rooms still matters.

💼 Lessons for Founders, CEOs & CTOs

Legitimacy Precedes Sales
- Customers buy belief before they buy software.
- Especially in enterprise or regulated industries, legitimacy is a prerequisite to even get the meeting.
Credibility Comes From Showing Up
- Microsoft gained legitimacy by engaging with technical communities — teaching, listening, publishing.
- Today’s equivalent: being active on GitHub, Substack, podcasts, and developer communities.
Vision > Features
- Once you’re in the room with enterprise buyers, they care less about your product demo and more about your 10-year plan.
- You must sound credible forecasting the future, not just describing what you’ve built.
Influential Users Drive Early Adoption
- Like the early PC power users or today’s prompt engineers, early adopters within organizations legitimize new tools internally.
- Empower and publicize their stories — they are your “grassroots PR.”
VCs as Legitimacy Banks
- Venture capitalists don’t just provide money — they lend you credibility.
- A16z, Sequoia, or similar firms help you “cross the legitimacy bridge” into enterprise boardrooms.
Legitimacy Is Contextual
- What makes you credible in open source (stars, commits) might mean nothing in enterprise.
- Adapt your legitimacy signals to the audience — hospitals, banks, or Fortune 500s each have their own filters.

⚙️ Practical Takeaways

Invest in reputation early. Write, teach, and share technical insight — like Bill Gates did in user group newsletters.
Design legitimacy loops. Engage with both developers and executives; both must trust you for scale.
Treat PR and partnerships as part of engineering. You’re building not just tech, but trust.