Published in the San Diego Union-Tribune, January 19, 2026
by Neil Senturia
Financing your company at this time is more challenging than ever. Measuring risk in your company is more important than ever. In fact, both of these puzzle pieces are existential.
Together they are Scylla and Charybdis, the Greek sea monsters that guard a narrow strait. They snatched sailors from passing ships and are often invoked when you are caught between two equally dangerous choices.
One of the reasons that financing is difficult today is because of what happened three years ago when the rivers overflowed with money and the people writing checks couldn’t launch boats fast enough.
The assumption then was that there will be liquidity for their investments, and they can go back to the well and get some fresh water again. But if the river gets too low, your raft cannot get over the rocks. Right now, the venture capital fund racket is praying for rain.
They need to keep whatever dry powder they have, just in case. Just in case is code for they need to keep the best deals alive with follow-on financing, and they need to take the fees that keep themselves alive.
So, for your young company, this is the butterfly that flaps its wings in Poughkeepsie and two years later a tornado devastates a village in Botswana. In other words, it’s not your fault.
Let’s think about how to measure risk in a world where unintended consequences are hard to calculate and occur with increasing frequency. My current entrepreneurial risk assessment whiteboard is filled with X’s and O’s, courtesy of the football playoffs.
For a full analysis, you can turn to one of 50 sports blogs for analysis of what just happened. The pundits will explain the game to you, the very one you just finished watching, as if you were unable to understand what you just saw.
The bottom line is mostly something like, “Wow, who woulda thunk, can you believe what just happened.” Because what happened was a confluence of at least a dozen disparate factors that came together in order to win in the last 60 seconds.
In my little AI company, we are no different than 100 other startups that are looking for their next financing. What is nice about risk assessment is that as the clock winds down, the optionality decreases, which means your choices become limited but very clear. Just like the infamous “two-minute warning.”
Our little AI company is not unique. Every startup has seen this movie. We have two or three “long bombs,” which, if they are completed, will let us win the game. We also know the clock is winding down. We can play conservatively, husband cash and wait for the rain that the weather forecast says is coming, maybe not a tsunami but enough to get farther downriver, where there is the prospect of even more water.
At this point, I recommend that the executive team of your company rewatch the movie “The African Queen.” As for relying on weathermen, please reference Mr. Dylan: “You don’t need a weatherman to know which way the wind blows.”
So, do you decide to launch the boat and start the run to the rapids, assuming that something good will happen? Or sit it out on the bank and wait?
Oh, and did I mention, on that bank there are snakes and bears, but if you fall out of the boat on the way down, the river has alligators in it.
It is easy to give advice, to break it down, to tell the viewer/reader what they should or would or could do. I hate the pundits. So do the roughly 15 Division I college head football coaches who were fired by this December. Walk the sideline or talk show host, pick your poison.
Now let’s go back to the investors, VCs, et al. If they could actually spot the winners with any real accuracy, they wouldn’t all be trying to pile into the same boat, or deciding whether to stay on the bank, get eaten by the bears or write another check and lay a bet that the creek is going to rise.
And you and your little company, well, maybe it’s like Indiana football. Either way, it will make a really good movie.
Rule No. 813: Play for overtime.