Five non obvious learnings from my decade in startup investing.
Long-term success in early-stage venture capital is complex, shaped by market cycles, behavioral dynamics, and systemic inefficiencies. Here are my top 5 learnings from a decade of investing in startups. Let’s see how these age over the coming decade!
1. The Best Deals Often Look Mediocre at First
Most breakout companies don’t look obvious at seed stage. The best founders are often contrarian and misunderstood. Many investors over-index on early traction, but true long-term winners usually show strong founder insight, adaptability, and a unique way of thinking—even if they lack polished decks or conventional signals of success.
2. Luck is a Skill (If You Know How to Create It)
“Being lucky†in venture isn’t random - it’s an outcome of positioning, information asymmetry, and behavioral adaptability. The best investors actively manufacture luck by:
- Expanding surface area (helping founders before investing, building deep networks, staying top-of-mind).
- Recognizing second-order patterns (e.g., market shifts before they reflect in metrics).
- Embracing serendipity (following curiosity, taking unexpected meetings).
3. Portfolio Math Lies – It’s About Anti-Portfolio Thinking
Traditional portfolio theory suggests you need a few outliers to drive returns. But the key is actually avoiding the wrong misses. Many VCs focus on what they invest in, but what you don’t invest in matters just as much.
- Missing a Flipkart, Swiggy, or PayTM due to pattern-matching bias is far more damaging than picking a mediocre deal.
- The best investors revisit why they said ‘no’ to past unicorns and refine their filters constantly.
4. The Biggest Risk is “Too Much Convictionâ€
The more experienced an investor becomes, the greater the risk of false confidence. Early-stage VC is probabilistic, but many long-term investors fall into the trap of overestimating their ability to predict outcomes.
- Markets change. What worked in 2015 may not work in 2025.
- The best investors build mechanisms for self-doubt—forcing themselves to challenge their assumptions regularly.
5. Reputation Compounds Like Capital – But in Unexpected Ways
Most people assume VC reputation comes from returns or social status. In reality, the most enduring reputations come from trust, founder-first behavior, and non-obvious signals:
- The way you handle bad outcomes matters more than your wins.
- Long-term reputation isn’t just built with founders - it’s shaped by other investors, LPs, ex-employees, and even competitors.
- The best VCs give more than they take, often in ways that don’t yield an immediate return but create long-term leverage.
