Investor Stories 448: Hard Lessons in Investing: Mistiming Trends, Relying on Partnership Debate, and Avoiding Good Money After Bad (Hilaly, Dash, Rizik)

What It Covers

Three venture investors share critical lessons: mistiming technology adoption cycles, leveraging partnership debate to avoid bad investments, and recognizing when conviction is lacking.

Key Questions Answered

• •Trend Timing: Technology adoption takes far longer than Silicon Valley assumes. Cloud computing seemed obvious by mid-2000s, yet on-premise software still exceeds 50% market share twenty years later.
• •Partnership Discipline: IVP uses a "sleep on it" practice where partners pause before committing, allowing investors to process feedback and assess whether conviction level justifies long-term partnership responsibility.
• •Trust Your Confusion: When an investment thesis doesn't make sense to you, it likely has fundamental problems. Avoid group think and acronym-heavy pitches—founders must make concepts clear or it signals misalignment.