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Funding down to one last investor

May 18, 2026 by Neil Senturia

Published in the San Diego Union-Tribune, May 18, 2026

by Neil Senturia

I have written three books in the “I’m There For You Baby” series. Volume three has a cover page — an image of an entrepreneur wrapped in chains, underwater, desperately trying to get to the surface and breathe before he drowns.

Sound familiar to any entrepreneurs?

Schmuck, did you ever think of taking a scuba tank? Underwater or tied to the railroad tracks, time is running out.

April 29

Parallel tracks. The New York Harvard Angels continue to horse us around. They ask some very technical questions, our CEO does a brilliant job of answering and here is what I get back from the lead whisperer.

“Not looking promising. Our AI genius was underwhelmed by your CEO’s responses, which he called superficial.”

I was impressed by our answers but let’s face it, I’m impressed by the Rockettes.

Nota bene to all founders: The primary role of a venture capitalist or an angel is to figure out the easiest and fastest way to say no.

OK, we are still in the game. Remember we have the rich guy who wants to buy the company. We do a big pitch; he has five folks on the call. I wait a few hours, then send a text. Nothing. I ping him again next day. Nada. It seems he is on a river trip down the Amazon, with no internet.

Then a week later, he resurfaces. He makes a low-ball offer, having studied with the piranhas. We reject it out of hand — but caution here, we may need to come back on bended knee, so rule No. 1 is always be polite when saying no. It might not be yet.

We land a big customer. It is clear we solve a problem, that our technology is relevant and desired. What is it that the angels don’t understand?

The unspoken, dirty secret is simple. The investors believe that Anthropic Claude will own the world, and no company, big or small, can ever compete with Claude Monet or Claude Rains or Claude Code.

We believe we have built a unique car, but it seems we are trying to get someone to invest in a DeLorean when there are 129 other cars on the market, all of them AI-enabled and all of them promising to take you wherever you want to go, with or without a driver, at high speed, reading your mind and knowing in advance the best way. Google Maps with AI?

I hear the whistle again. Getting closer.

All right, next up, a giant angel, someone I know well and who has invested with me in the past and made money. This should be a rollover no-brainer. The meeting is set, again, with five people in the room. Four are advisers, one is really rich.

They want a “venture return.” Of course, you want a venture return and the private jet that goes with it. But here is the dirty secret: most investors are lucky to just get their money back. Only 25 to 40% of venture-backed companies even return the original investment.

And then we get a rebound off the backboard. Remember, the VC who told us to drop dead, no moat, no chance against Anthropic. After getting the first no, I wrote back and explained politely that perhaps he had misunderstood and had not seen the greatness of our technology. Pry doors open.

April 30

That VC comes back and re-engages, asks some more questions. I know the managing partner. I have done a deal with his fund, they are great, and I want them.

But I am given to irrational optimism. It is a personality defect of entrepreneurs. But I have waged war before, and I am privately deeply afraid.

“She knows there’s no success like failure, and that failure’s no success at all,” Bob Dylan sang.

And finally, let’s put a stake in the Anthropic owns the world paradigm. Remember Blackberry. They were going to own the world. Now look up the market cap of RIM and the market cap of Apple.

May 6

The Harvard Angels pass. No castle, no moat. Time is running out. One last shot on goal, a previous investor who does biotech. Maybe we have a place to stand.

But I am peering into the darkness.

Rule No. 828: I should have gone to med school?

Filed Under: Entrepreneurship

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