Spot on about the 2021 vintage underperforming. I was just looking at the latest Carta data showing median IRRs for 2021 funds finally creeping up to a tiny 0.5 percent recently. Those peak entry prices completely cursed any chances of realistic exits for a lot of folks. Also, massive agree on fixing workflows before adding AI. Slapping an LLM onto a broken process just scales the chaos exponentially. Brilliant analysis! Subscribed!
The most dangerous kind of smart content is the kind that only helps you sound informed.
The more valuable kind changes where you place your next bet.
That's what I appreciate here. The strongest thread running through these examples isn't really “AI is big” or “venture is hard.” It's that a lot of winners are being misread because people are still staring at the model, the market, or the headline instead of the workflow, the distribution layer, or the price paid at entry.
That's the practical edge.
Better technology matters.
But better timing, better structure, and better positioning still decide who actually captures the value.
The sharper version: a 2021 entry price wasn't a valuation, it was a wager that 2021 conditions would last. Those funds didn't misjudge companies, they misjudged the durability of the environment, and the loss was priced in on day one regardless of how the portfolio performed. The tell is the 2022 vintage already looking better in a harder market. Same GPs, same skill, opposite outcome, decided entirely by which side of the repricing they deployed into. So the vintage gap isn't a quality story, it's a timing one, which is exactly the variable VC's "we're long-term, we don't time markets" pitch insists is irrelevant. Turns out entry timing may be the most important call a fund makes and the one it's least able to claim credit or blame for. Does the data let you isolate that, or does entry price swamp everything else this early?
Spot on about the 2021 vintage underperforming. I was just looking at the latest Carta data showing median IRRs for 2021 funds finally creeping up to a tiny 0.5 percent recently. Those peak entry prices completely cursed any chances of realistic exits for a lot of folks. Also, massive agree on fixing workflows before adding AI. Slapping an LLM onto a broken process just scales the chaos exponentially. Brilliant analysis! Subscribed!
The most dangerous kind of smart content is the kind that only helps you sound informed.
The more valuable kind changes where you place your next bet.
That's what I appreciate here. The strongest thread running through these examples isn't really “AI is big” or “venture is hard.” It's that a lot of winners are being misread because people are still staring at the model, the market, or the headline instead of the workflow, the distribution layer, or the price paid at entry.
That's the practical edge.
Better technology matters.
But better timing, better structure, and better positioning still decide who actually captures the value.
The sharper version: a 2021 entry price wasn't a valuation, it was a wager that 2021 conditions would last. Those funds didn't misjudge companies, they misjudged the durability of the environment, and the loss was priced in on day one regardless of how the portfolio performed. The tell is the 2022 vintage already looking better in a harder market. Same GPs, same skill, opposite outcome, decided entirely by which side of the repricing they deployed into. So the vintage gap isn't a quality story, it's a timing one, which is exactly the variable VC's "we're long-term, we don't time markets" pitch insists is irrelevant. Turns out entry timing may be the most important call a fund makes and the one it's least able to claim credit or blame for. Does the data let you isolate that, or does entry price swamp everything else this early?