Regret as an Asset Class
There is something oddly fitting about a venture panel on the future of AI where one of the speakers is wearing gym shorts. It captures the mood perfectly: casual, slightly chaotic, intensely competitive - and very aware that something big is happening.
On the surface, the discussion was about collapsing build cycles, accelerating adoption, and the speed at which entire categories are being reshaped. But beneath the AI headlines, what stood out was behavioural pressure. Not panic. Not euphoria. Something more subtle - the quiet force of anticipated regret.
Three things were particularly revealing.
First, regret is becoming the dominant risk factor. When an investor says, “that deal keeps me up at night,” they are not describing a mispriced revenue multiple. They are describing identity risk. In venture, missing the next breakout winner hurts more - reputationally and psychologically - than backing something that fails. Being wrong is better than being left behind and it is this asymmetry alters behaviour. Speed becomes virtue. Price discipline weakens at the margin. Being “in” feels safer than being right. As dispersion widens, the fear of missing begins to outweigh the fear of losing.
Second, social contagion accelerates everything. Panels like this are not neutral exchanges; they are behavioural amplifiers. When respected investors signal urgency or excitement, it spreads. What felt stretched six months ago begins to feel reasonable. Growth at any price becomes growth at necessary price. Nobody feels irrational, because everyone else is moving too. Norms shift quietly, collectively, and far faster than anyone admits.
Third, uncertainty produces overconfidence theatre. One of the more honest lines of the evening was an admission of feeling more insecure than ever as an investor. That tension - private doubt paired with public conviction - is classic inflection-point psychology. The louder the narrative, the more fragile the footing often is beneath it.
None of this diminishes the opportunity. AI is genuinely lowering the cost of experimentation and expanding the asymmetry of upside. But when regret becomes an implicit asset class, it shapes capital flows as much as fundamentals do.
The world is not ending. It is simply moving quickly. And in a room where someone is debating billion-dollar infrastructure shifts in gym shorts, the real edge may not be speed at all - it may be self-awareness.
Rebecca Lewis is Partner & Co-CEO at Arisaig Partners. The views expressed are personal.