Sometimes Living On The Edge Is Where Magic Happens

Published in the San Diego Union-Tribune, April 18, 2016

They lower you into a large glass-and-steel cabinet – filled with water – upside down in a straight jacket, handcuffed. All you have to do is hold your breath and get out of the manacles, before you drown.

This seemed perfectly reasonable to Harry Houdini. All in a day’s work, he did it more than a hundred times. I think this magic trick best approximates what it is to be an entrepreneur today. The trick is to “get out of the box.” And what you need to know is that every deal starts in a box.

When I was younger, I imagined viscerally this image of holding your breath. When I started out in real estate development, I didn’t have much money, so the only deals I could do were the ones that “had a lot of hair on them.” That is code for deals that were so screwed up that no one really wanted to mess with them. But they were perfect for a guy with no dough and an outsized dollop of chutzpah. They were always like “The Perils of Pauline,” a last-minute escape from the tracks before the train ran me over.

One time I literally flew down to the city of San Diego’s redevelopment agency with a check for $500,000 that I had to present before their 9 a.m. Friday meeting on that day or I would lose all my development rights to a high-rise that I had spent more than two years securing. I was hanging out for more money than I really had. I got the dough 36 hours earlier on Wednesday evening. I got out of that box – barely.

This image of having your head held under water – and you simply having to hold your breath until you can figure a way to get out and breathe – is classic for the entrepreneur. I tell this story because in the past few weeks, I have witnessed five entrepreneurs get out of their handcuffs. I know every one of these chief executives personally, and I admire their skills and their lung capacity. None of them had a lot of air left to spare.

So what is it that allows some of us to get out of the box, while some of us drown?

One thing that stands out is the willingness to throw every idea against the wall – to tap on every inch of that wall looking for the loose board and the secret passage out – to be willing to be stupid, to be willing to repeat the same set of puzzle sentences until somehow you see something different.

You need the willingness to go to the stupid-waste-of-time meeting across the country, to be willing to quit, to be done with it, to admit defeat and failure and humiliation – and then somehow when you can acknowledge that you may in fact die, that you may have to really close, that there is no more money and there is truly no way out, then sometimes, resurrection shows up.

I can’t explain this phenomenon to non-entrepreneurs. There are a hundred stories of meeting payroll with two hours to spare, of getting an order when it is the last day and without the order, it is over. I cannot explain how or why this happens, but I don’t think it is random. I think the “entrepreneur personality” must hold a special place in heaven.

Don’t misunderstand me. I have drowned more than once. It doesn’t always work out. The damn handcuffs do not come off.

But when I see success snatched from the darkest corners, I applaud. It is magic. And I adore magicians (have seen Penn & Teller five times, as well as all the Las Vegas magic shows and have been to the Magic Castle in Los Angeles). I love the illusion. I don’t believe my eyes. It can’t be. He can’t catch a bullet in his teeth.

This is the startup game. Hold your breath long enough to escape drowning, then pop to the surface and with a flourish create the illusion that brings them to their feet.

Rule No. 463

How did he do it?

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