At the beginning of my career I quit college to join a small engineering consultancy. We mostly built the nascent automation of Wall Street, but at one point became engaged by Ron Burr. He created and lost People Express in the eighties. It was the first low budget airline and earned what we now call “unicorn” status within a year. Then imploded when the bankers blew it in ’89, as they inevitably do.

What I remember, though, is a crusty exec from the time telling me that “once you go into Airlines you can’t escape.” The idea was essentially priceline, but it was 1992. A little too soon.

I learned that once you go into startups, you can’t escape. It’s exhilarating, exhausting, and almost always painful.

I could have become a rich investment banker, but I knew I’d never be able to sell other people’s ideas. Bad choice, perhaps. It takes years of commitment to get one shot at success. If you are a banker, you amass a pool of fifty shots. The odds are pretty good unless you’re a dolt.

So thirty years later I’ve launched or participated in a dozen startups. All moonshots, but I am proud of my work even as I stare down insolvency again, which is why startups are not what you think.

A startup is a risky wager. You pull in a team who, unlike the bankers, each trade years of their lives for a single shot on goal with a 1% chance of rewarding riches. Failure is omnipresent, “smart” people tell us not to try. Take a steady job and a pension.

Where’s the fun in that? Why are we here? The magic of startups is they attract the smartest, most ambitious and often most interesting people. The myth is the money. The truth is the experience. My friends and collaborators over the years relish that we built paypal before Paypal, youtube before Youtube, signal before Signal.

One of the things you learn along the way, is that youth often wins by being oblivious to the law. Paypal, at its inception, was an unregulated bank, but Musk didn’t know that. Youtube eventually paid Viacom a billion dollars for stealing The Simpsons. Give the people what they want, then discuss with the lawyers.

My most recent venture, Samizdat Online, is particularly interesting because I believe it captures a modern sentiment that is drifting in favor of startups. Talented tech workers get paid lavishly to work for a machine. The best people want to work for a cause and a team they are proud of.

Kids are smart. They truly don’t care for the, “you’ll be the next millionaire secretary” bullshit.

While I wish I could’ve made many people rich, I relish that my startup colleagues are all still friends. Most took the exhilarating and life-affirming experience to achieve more than I ever have.

I do have hope that the investment community (a bit cock-eyed by 1933 laws) will learn to participate in the engagement and joy of invention, not just the proceeds. A modern startup can and should be able to straddle charity and investment. Either way, a loss is a write-off. The laws are very fucked up in this regard. Poor people can donate, but only rich people can donate with the prospect of gain. The Samizdat venture delivers open media behind autocratic firewalls: we don’t know if it really is a business, but we do know that a few billion people are blocked from content they want and we can help fix that.

Maybe we make money and change the tech landscape. Or maybe we just provide alternate media and opinions where it’s most needed for the next year. Either way, we’ve done good work.

Song For Thought:

The Only Song – Peter Blegvad & John Greaves