Wisdom from the trenches and what to avoid if you’re a startup looking for funding
Published in the San Diego Union-Tribune, June 29, 2026
by Neil Senturia
While Pauline waits for the train, I will share with you some cogent thinking from a famous angel investor, who came to visit me and who has requested anonymity, fearing that certain founders may come looking for him in a dark alley.
We will call him Fred.
Fred was a member of several angel venture funds and for 20-plus years was a major force in supporting founders, startups and entrepreneurial programs. As he would say, he has the scars and the tax losses to prove it.
He came to visit Pauline recently, and while he was unable to release the ties that bind her to the track, he did bring a pastrami sandwich and some advice. After all, he had a captive audience.
“Thus Spoke Fred,” with a polite nod to his twin, Fred Nietzsche.
“Venture funding is not a team sport,” Fred says, “I advise entrepreneurs to avoid organized angel groups. I believe they are a waste of time, energy and hope.” He gives some reasons.
Many members are not serious investors. They join to enhance their own business networking.
The process is time consuming, endless rounds of presentations, due diligence, proof of concept, etc.
Angel groups have a long queue of eager entrepreneurs waiting at the door, so there is no sense of urgency.
Another guy, in a black duster, comes toward me, backlit out of the setting sun. (You know that scene, “High Plains Drifter.”) He wants to offer me some cogent thinking on my current dilemma. Another man with no name, but for now we will call him Clint.
“I believe that capital does not flow to the best opportunities, I think capital flows to the opportunities that are easiest to explain.” Clint says that the easy ones have growth stories — with annual recurring revenue, strong consensus, social proof — while the best opportunities often have uncertainty, complexity, disagreement, temporary problems and incomplete information.
“When the opportunity becomes easy to explain, much of the asymmetry, which is where the massive value lies, has usually disappeared,” he says.
Clint points out that most of the valuable opportunities initially feel uncomfortable because they don’t fit neatly into a simple story. After all, if the deal is obvious and gold-plated, why the heck are they coming to you? Money is fungible, but real opportunities are not.
A woman stops by, and you can tell by her demeanor that she is clearly not someone to trifle with. She joins the discussion.
“Look, let me make it easy. If you want a sure thing, buy a T-bill. Otherwise, man up.” I found this pretty compelling. She knows all about glass ceilings and founders and startups and investing. (If I get out of this mess, I’m going to ask her to join the board.)
The conversation wanders to the calendar. Fred says that you need to be ready to raise money starting in January and closing in June. No chance to make a deal in the summer. The venture capitalists are in Jackson or Marbella, and you can’t get more than two angels in a room at the same time until September. So, it seems that my timing was a bit off with my latest company.
The three strangers wander off. Me, I’m thinking the sun is out, nice breeze. Just waiting for the phone call. After all, it could be worse.
June 26, 5 p.m: The train showed up right on schedule. The company closed.
Rule No. 831: “I think I’m gonna be sad,” Ticket to Ride by the Beatles