Skipping the Line
Capital Thinking · Issue #790 · View online
“You can’t skip the line, James.”
I wanted to be a hedge fund manager but I was broke. I lost $15 million of my money because I’d invested poorly. So of course I became obsessed and wanted to do it for a career.
Only problem was, I was a computer programmer and writer.
And our world loves labels.
YOU CAN’T DO THAT!
“You lost all your money investing and now you want to be a professional investor?”
He worked for JP Morgan. He was a professional investor.
I was feeling shy asking him. I wanted JP Morgan to give me money so I could start a hedge fund.
I had already stopped paying my mortgage. I had two children. I was suicidally depressed. I had no friends. My friends were with me on the way up but I had no friends on the way down. It’s a cliché but true.
“Yes, I know I went broke. But then I wrote software to model the markets. I look for trades that have historically have had a high probability of success. It works.”
“Can’t your parents give you some money?”
“They don’t have money. And they don’t talk to me anymore.”
Steve had that look. Not a frown like he was trying to figure out how to get me money. More like a look that he was sorry for me.
“You can’t do that. Listen, I have to tell you. You probably need an MBA. Then you need to work at a big bank for a few years. Like Goldman Sachs. Then maybe you work for a big fund or two. Get experience. And THEN maybe you can break out and start your own hedge fund.”
How was I going to support my kids?
I had taken on too much in expenses. I had worked so hard building a company and then selling it and now it was all for nothing and nobody respected me.
And nobody cared.”“Good luck,” he said.
“You can’t do that,” Cindy told me.
It was 1995. I was on the way to the CEO’s office. Companies didn’t have websites back then. HBO didn’t even own HBO.com.
I wanted to tell Jeff Bewkes, the CEO of HBO at the time (and later of all Time Warner), that he needed to create a website for HBO and that he should do original web shows on the website just like they did original TV shows.
My title at the time was junior analyst programmer in the IT department. I can’t even remember what I was working on all day. Nothing probably.
Cindy wanted to stop me from going directly to the CEO.
“He’s your boss’s boss's boss’s boss’s boss’s boss. You can’t skip the line over all of those people."
The only people who ever tell you “you can’t” do something you want to do, something you love to do, are people who can’t do it themselves.
They don’t want you to change. They like the version of you that “doesn’t.”
I started my hedge fund in a year (see chapter on the 10,000-experiment rule in Skip the Line) and did it for the next 10 years.
It led to books, writing for the Financial Times, starting new businesses, and every adventure I’ve had since. (See, the “Spoke and Wheel” chapter.)
Creating HBO’s website led to me starting my own business creating websites for Fortune 500 companies.
Richard Branson was a 27-year-old music magazine publisher when he wanted to start an entire airline to be the only competitor to British Airways.
“You can’t do that!” everyone told him. “It’s not only impossible, but you know nothing about how to run an airline.”(See the chapter on frame control).
Sara Blakely was selling fax machines door to door when she came up with the idea of Spanx. “You can’t skip the line like that!” everyone told her.
“You don’t know how to design clothes, manufacture them, make a clothing line. You’re just a fax machine saleswoman.”
In my 40s I became obsessed with doing standup comedy. I had changed careers so many times everyone thought I was ridiculous. The other comedians kind of hated me.
“You can’t skip the line, James,” Dante (an excellent comedian) said.“We’ve all been doing it 20 years. You have to do open mics, then hang out at clubs, then do the check spot, then MC, then maybe you get a Tuesday night. You can’t just skip the line.”
He said this to me five seconds before I was to go up to do my first hour-long show. I don’t know why he chose that moment to tell me that I was going to fail if I tried to skip the line.
Since then I’ve toured all over the country and the world.
I skipped the line.
Photo credit: Kelli McClintock on Unsplash