Published in the San Diego Union-Tribune, April 27, 2026
by Neil Senturia
The saga continues.
It’s April 6 and 7 a.m. on the West Coast. Our CEO is back East pitching to the New York Angels. He was supposed to get 10 minutes, but it felt shorter. I think the referees should have huddled at the scorer’s table and put some time back on the clock.
Oh, and you all know this character from your high school. One genius in the room works for OpenAI, a company currently valued at $852 billion.
In some alternative universe, we might be considered a competitor to ChatGPT, so when this guy spoke up, explaining in no uncertain terms that our chance of success hovered at best a nanometer above zero, it was clear there was not going to be a buzzer beater. There were 35 votes to pass and only 11 votes to press on so the deal failed to go forward.
This moment of being rejected has been experienced by every entrepreneur from the dawn of time. There is no way to soften the blow. Sure, they didn’t understand our product, sure we needed more time to explain the brilliance of the technology, but also sure, no soup for you. Time to take our spoon to the next bodega.
Another pitch at 4 p.m. No panic yet, we’re only down 17 at the half, and we get the ball at the start of the second half. Still, there is a quiet in the locker room, knowing it is a very real concern that we may not be around much longer. But you need to keep things in perspective, it’s not like the doc called and said you had cancer and four weeks to live — except that is sort of what the doc said.Earlier in the day, my phone rings. A call back from a week ago, a real venture capitalist. Says they are still considering the investment. I’m thinking it might be a wrong number.
But just in case, I head back to the office.
Frankly, this is no way to make a living.
That night, our CEO gets another shot on goal with a new gaggle of angels in New York. With so many angels hanging around, the head of a pin problem is small potatoes given the current state of the world.
Now the issue of pitching is no different than adjusting the game plan at half time. The first pitch was all RAG (retrieval augmented generation) and vector databases, really good nerd stuff). The second pitch was revenue, market, governance and security. He shoots; he scores.
It’s 8 p.m. The CEO calls me while standing at the corner of Sixth Avenue and 48th Street. He asks, why is there is a line of 45 people standing to eat at a halal food truck. Because it is the most famous one in all of Manhattan. Eat there or Katz’s Delicatessen. Trust the locals, do the truck.
The next morning, the New York Angels agree to start due diligence. We have a chance, a touch of momentum. Me, I am going into full double straddle. I am going from dead man walking to playing folks off against each. Angels in America and VCs in Los Angeles, the world keeps spinning.
Nota bene: We are teetering on the “chasm of too cute.” That’s where the founder thinks he can play one off against the other to get the best deal. Maybe in the movies, but not in real life, and particularly when your cards are modest at best. You are not the Cincinnati Kid. Take any money and run.
The original investors from Florida are guys who love to play golf. They want to come out for a few rounds and meet the team. This was a close call. If we were going broke, it would be hard to have them come, like putting into a casket, propped up on the 18th hole.
Next up are due diligence calls with the angels and the venture capitalist. Yada yada — promises, promises. No term sheet waving in the wind yet.
But there is still hope, so bring your clubs.
Rule No. 826: Fore