Analyzing 13 Years of My Investing History: Part Two
Yesterday I shared the first batch of findings from my holiday “audit” of my last decade-plus of deal logs.
In the comments, Ram Reddy asked a simple but important question: “What were the percentage of successes?”
Here’s the answer plus two other financial realities that jumped out of the data.
The “batting average” is messy.
To answer Ram’s question directly: out of 75 investments, I have 19 write-offs.
That’s roughly a 25% failure rate. In almost any other profession, that would get you fired. In early-stage venture, we’re in the business of taking risk and missing regularly. I’m okay with that;)
The data reinforces the power law reality. Those 19 zeros hurt my ego, but they don’t hurt the fund’s returns nearly as much as missing a single outlier would. Still, I feel deeply for those founders. Each one represented a long, hard-fought effort, and none of those outcomes were easy.
Today’s seed round is essentially 2015’s Series A.
This isn’t just price inflation, it’s stage inflation.
By the time a founder reaches me for a Seed round today, they’ve often already raised a pre-seed or friends-and-family round of $1–2M. They usually have a shipping product, real usage metrics, and sometimes meaningful revenue.
In 2015, Seed really meant first money in. In 2026, I’m underwriting early product–market fit.
The price has roughly doubled, but the maturity of companies has increased as well though not proportionally. Valuations are up ~2.5x on average since I first started investing, which is more than the stage progression alone would suggest.
I seem to pay a “Certainty Premium.”
This one surprised me.
We bucket our investments into two categories:
- “Big Checks” (Core / Lead investments)
- “Small Checks” (Angel pool)
The data shows that my small checks consistently get in at meaningfully lower valuations than my larger ones.
Why? With Core checks, I’m often paying for certainty. By the time I have enough conviction to lead a round, the company is usually more mature and the metrics are clearer. The diligence process is often longer. I’m writing a bigger check when there’s more visibility and apparently, I’m paying for it.
With small checks, I’m investing earlier, before consensus forms. I’m getting a discount in exchange for taking on more risk.
The resolution?
At our offsite, we wrote our priorities on tennis balls. I wrote one simple line: “Take more calculated risk.”
