At Dellecod, we spend a lot of time thinking about decisions. What to build, which ideas to pursue, where to allocate our energy and attention. That’s not so different, really, from how a good venture capitalist thinks about capital. After all, time and money behave in similar ways when it comes to risk and return. Both are finite, both must be deployed with intent, and both can generate asymmetric outcomes.
Venture investing is a peculiar game in that regard. The risk is capped — at most, a venture investor loses what they put in, so 1x on the downside. But the upside? Theoretically limitless, with returns of 10x, 100x, even 1000x not being unusual when the stars align.
That kind of asymmetry requires a very different mindset. Traditional investing disciplines like private equity or real estate often use leverage, optimize for stability, and avoid big swings. But venture capital succeeds by embracing uncertainty and recognizing that a small number of outliers drive nearly all the returns.
There are two big ways to get it wrong in this game.
The first is what most people think of: making a bad bet. Backing a team or idea that flames out. That’s called an error of commission — investing in something that fails. It’s painful, it’s visible, and it tends to attract most of the postmortems.
But the second kind, the error of omission, is usually more costly. That’s the one where you passed on an investment in a company that went on to become massive. You didn’t write the check — maybe it felt too early, too weird, too uncertain — and the next time you hear about them, they’ve just raised at a billion-dollar valuation and you’re not on the cap table.
The commission error stings the ego. The omission error quietly haunts the spreadsheets.
And here’s the thing: mathematically, the error of omission is far more significant. In an asymmetric model, avoiding losses gives you a 1x win — you preserved your capital. But missing out on a 100x return can blow a hole in the entire portfolio strategy. The risk isn’t evenly distributed. The power-law curve doesn’t care about your batting average. It rewards the few home runs that pay for the strikeouts.
This is something we remind ourselves of often, even though we’re not venture investors. We build software, not portfolios. But the logic crosses over.
In our world too, it’s easy to avoid errors of commission. Don’t launch something unless you’re sure. Don’t bet on a new platform before it’s stable. Don’t change that thing everyone uses. Over time, though, that kind of caution starts to calcify. You end up playing defense when the game calls for boldness.
The real cost — the opportunity we never took — becomes clearest in hindsight.
Avoiding errors of omission in our work means we have to get more comfortable with uncertainty. It means carving out space for ideas that might never work but just might. It means accepting that sometimes, to catch something exceptional, you have to swing and miss more often.
No one loves getting it wrong. But missing the next big thing, because it felt a little uncomfortable? That’s harder to live with.
In asymmetric environments, the right mistake to make is often trying and failing — not failing to try.