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Will this startup get funds or die? Follow this columnist’s journey

April 20, 2026 by Neil Senturia

Over the next 45 days we will find out if our company continues or comes to an abrupt ending

Published in the San Diego Union-Tribune, April 20, 2026

by Neil Senturia

To get financing or not to get financing, that is the question.

When I started my third and final career as a newbie in the technology racket, I religiously attended all the panels where big shots got up and essentially said, “Well, I raised the money and then we scaled, and then we sold for a billion dollars.”

OK, I just paid $20 to attend this panel of experts. Would it kill you to give me a bit more detail? As in, just exactly how did you do this? I get that you did it, but unless you are a magician, it would be nice if you would explain the steps.

Was it straight up, no bumps, or did you almost die like a dog in the desert, when, at the last moment, a man from Fiji Water showed up and gave you a drink in exchange for 62% of your company? Tell me the truth.

I hated these panels. But as time passed, eventually I went from the audience to being asked to be on the panels. I was fierce in my desire to give full disclosure. I remember all the times when I was the supplicant, seeking the key to the man in the iron mask.

So, here is the deal I am going to make with my readers. My little AI company is trying to raise some money. It is existential. The deal is simple. If we find the money, we go on to greatness. If we don’t, we will close and sell what remains for banjo picks.

As best I can, the next series of my columns will share the truth of the Perils of Pauline as reimagined by Alan Turing. Essentially, we are tied to the railroad tracks, and over the next 45 days we will find out if the movie ends or we can come back next Saturday to see a new episode.

March 17: The Askturing.ai team frantically applies to two angel groups in New York. The questions are extensive. We can’t find a dime locally so we are heading East.

March 20: Both groups accept our applications. Now we wait to see if we make the cut. They get 150 applications, and they accept eight for actual pitching.

March 30: We made the cut. We get to pitch. We get 20 minutes in front of the New York Angels, and we get 12 minutes in front of the Harvard Business School Angels of New York. The good news is that both pitches will happen on the same day.

April 2: I asked Turing how many angels could stand on the head of a pin, and it told me to put a lid on it.

April 3: Now the game is afoot. We need a data room. A data room is where you stuff all the documents from the beginning of the company, including your baby pictures and the locks from the first haircut.

The prospective investor wants to see the contracts, the consulting agreements, the capitalization table, the employee PIIA agreements (a document that says an employee is not going to abscond with your technology, even though if they do, you will have a tough time proving it in a court of law). Why do they need to see everything? It seems they should be willing to take our word for it.

Next, what really counts are the cards you claim to have — the infamous “pitch deck” itself — where you demonstrate in less than 13 slides the brilliance of the platform, the unassailable moat you have created, unbreachable even by Attila the Hun, as well as clear and positive proof that you can get to millions in revenue and billions in valuation in the blink of an eye — or at least quickly.

April 4: The CEO called and said his wife has insisted he get a haircut before traveling. He has a bit of the Travolta-from-Pulp-Fiction look, and I did mention the Samson story to him, but his wife has prevailed. What to wear: blazer, white collared shirt, jeans, no hoodie, my job is done.

April 5: Easter. The CEO is a handsome, 53-year-old, seasoned technology veteran. He is also a religious fellow, so the only way he can both get to church and get to New York is the red-eye. And of course, the first pitch is at 10 a.m. Monday, April 6.

Stay tuned.

Rule No. 825: Why didn’t you tell me that the first time?

Filed Under: Entrepreneurship

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