#24 — Cold Take: You're going to fail your first pilot, and that's okay

Why it matters: Your first pilot failing feels catastrophic, but it's actually a normal part of the startup journey that can provide critical insights for your next move.§

The big picture: Founders often panic when early pilots fail, but successful startups regularly experience early failures before finding their path.§

What's happening

When pilots fail, founders typically experience:§

• Immediate panic about product-market fit
• Self-doubt about their entire business concept
• Fear of disappointing co-founders and supporters
• Isolation, believing they're uniquely failing

Learning from failure

Three common pilot failure scenarios and what they actually reveal:§

1. Differentiation problem§

• Signs: Prospects say things like "Isn't this just like [competitor]?" or struggle to see your unique value
• Reality: You haven't crafted a compelling narrative that distinguishes you in a crowded market
• Next step: Refine your positioning and storytelling, not necessarily your product

2. Product readiness issues§

• Signs: Design partners encounter bugs, missing features, or incomplete functionality
• Reality: You likely went to market too early with an incomplete solution
• Next step: Focus on product development before pursuing more pilots

3. Wrong design partner§

• Signs: Initial excitement followed by fading interest and engagement
• Reality: Your pilot partner wasn't truly invested in solving the problem
• Next step: Be more selective with partners and consider charging for pilots to ensure commitment

Between the lines

The most valuable currency in early pilots isn't revenue—it's feedback. Failed pilots provide specific, actionable lessons that help refine your approach.§

Many successful founders now view pilot rejection calls as opportunities rather than setbacks because they deliver crucial insights for improvement.§