Pilecki's rule of thumb—seeking stocks that can double in three years (26% IRR)—acts as a strict filter. This high hurdle prevents him from tying up capital in ideas with only marginal upside, forcing a focus on truly substantial opportunities.
Contrary to the 'get in early' mantra, the certainty of a 3-5x return on a category-defining company like Databricks can be a more attractive investment than a high-risk seed deal. The time and risk-adjusted returns for late-stage winners are often superior.
Pilecki argues that classic value investing fails by ignoring momentum. He waits for a stock's chart to form a base before buying and lets winners run past initial price targets if momentum is strong. This avoids buying "falling knives" and cutting winners short.
An analysis of 547 Series B deals reveals two-thirds return less than 2x. This data demonstrates that a "spray and pray" strategy fails at this stage. The cost of misses is too high, and being even slightly worse than average in your picks will result in a failed fund. Discipline and picking are paramount.
Effective due diligence isn't a checklist, but the collection of many small data points—revenue, team retention, customer love, CVC interest. A strong investment is a "beam" where all points align positively. Any misalignment creates doubt and likely signals a "no," adhering to the "if it's not a hell yes, it's a no" rule.
Top growth investors deliberately allocate more of their diligence effort to understanding and underwriting massive upside scenarios (10x+ returns) rather than concentrating on mitigating potential downside. The power-law nature of venture returns makes this a rational focus for generating exceptional performance.
Don't chase every deal. Like a spearfisherman, anchor in a strategic area and wait patiently for the 'big fish'—a once-in-a-decade opportunity—then act decisively. This requires years of preparation and the discipline to let smaller opportunities pass by, focusing only on transformative deals.
Acknowledging venture capital's power-law returns makes winner-picking nearly impossible. Vested's quantitative model doesn't try. Instead, it identifies the top quintile of all startups to create a high-potential "pond." The strategy is then to achieve broad diversification within this pre-qualified group, ensuring they capture the eventual outliers.
The standard VC heuristic—that each investment must potentially return the entire fund—is strained by hyper-valuations. For a company raising at ~$200M, a typical fund needs a 60x return, meaning a $12 billion exit is the minimum for the investment to be a success, not a grand slam.
The effort to consistently make small, correct short-term trades is immense and error-prone. A better strategy is focusing on finding a few exceptional businesses that compound value at high rates for years, effectively doing the hard work on your behalf.
Internal Rate of Return (IRR) is a misleading metric because it implicitly assumes that returned capital can be redeployed at the same high rate, which is unrealistic. The true goal is compounding money over time. Investors should focus more on the multiple of capital returned and the average capital deployed over the fund's life.