I had the same question reading this. Ron, which was the idea you had highest conviction in?

Smart Charter. I think that might still be a viable business even today, though I have not really kept up with the industry so I don't know.

Ironically, today I have a part-time consulting gig at a company designing network switches, and I see them wrestling with the exact same problems we were tackling 30 years ago. So FlowNet would be a very close second.

I personally know of one ongoing effort whose founders think it's very much still viable. Well done uncovering and acting on it back in the day, Ron. Too bad about the outcome. I'm grateful you spent the time to write these stories. Thank you as well for being a public champion of lisp, for which I owe a great deal of my own undeserved success.

> I personally know of one ongoing effort whose founders think it's very much still viable.

Link?

>> Smart Charter. I think that might still be a viable business even today,

I'm less convinced. Although to be fair, I'm really not the target market.

I think the root fail of this kind of business is that it's a Venn diagram of two circles, with very tiny overlap.

Firstly, flying commercial is "simple". You want to go from A to B at some point in the future. You want to buy a ticket, show up, and fly.

Sure, I get the TSA crap and so on, but it's fundamentally reliable. Not to mention cheap.

Private travel bypasses TSA, and sure there's glamor, and a bigger seat. But unreliable is built in also.

Or put another way, the jet owner goes wherever and whenever they like. The pay a lot for perfect convenience. But it makes that "empty return leg" unreliable. And of course, the further ahead you plan, the less reliable it is.

So there's one circle of people who can afford their own (whole or partial) jet. There's one circle who just want reliable A to B.

What you're left with is people who have enough to make it a business, but not enough to charter a plane themselves.

So your market are price insensitive enough to be preparedto pay more, but also don't really plan their travel, or don't need to travel reliably. Which just seems like a vanishingly small group.

In other words, what you are selling is worse than commercial (planing and reliability) coupled with worse than private (no control over where or when).

Which leaves such a tiny sliver of a market, where brokers practically outnumber customers.

> the jet owner goes wherever and whenever they like

You'd think that, but it turns out not to be true. There are a lot of constraints even on the owner: weather, mechanical failure, crew members getting sick. And it's even worse for them because when something goes wrong it can be a lot harder to recover. When you're flying commercial, or even chartering, the worst-case scenario is a delay.

The only real benefit to owning a plane is that you can keep some of your stuff on board.

> a tiny sliver of a market, where brokers practically outnumber customers.

It depends. If you measure the market size in terms of customers that's probably true. If you measure it in terms of dollars, it's not. It's a question of: all else being equal, would you rather pay less than more? Most people say yes no matter how fundamentally price-insensitive they are.

solve problem people care about, and charge from day 1

> there seems to be a common theme around not believing in the idea/product/people too deeply, thus leading to faulty or mis-step execution. would it be right to say that?

Not sure whether you're asking whether that sentiment exists or if it's correct. But either way, there's no easy answer to that. If you don't believe that's not helpful, but on the other hand, if your beliefs don't align with reality that's not helpful either. It's possible to succeed without strong convictions, and it's possible to succeed with convictions that don't align with reality, but if you have to choose one or the other, believing in yourself is a better than believing in reality if your goal is material success. (Look at Donald Trump.)