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The 5 Biggest Assumptions I've Made About Business

After starting about 20 businesses and being invested in about 30 more at this moment, I’ve probably seen most of what you can see. I’ve been on the boards of billion revenue…

After starting about 20 businesses and being invested in about 30 more at this moment, I’ve probably seen most of what you can see. I’ve been on the boards of billion revenue companies and tiny startups. I’ve written about hundreds of companies. And you know what: I’m sick of it. I am sick and tired […]

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Give Yourself Permission To do THIS (and "things" I miss)…

When I threw out all of my belongings and started living in AirBnBs (I don’t own or rent), people say, “Ohh! That must be so freeing!”. I don’t know. I know when…

When I threw out all of my belongings and started living in AirBnBs (I don’t own or rent), people say, “Ohh! That must be so freeing!”. I don’t know. I know when I see something I want to buy, I feel relief. I have an easy answer: I can’t buy it. It won’t fit into […]

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Regrets of the Living. More Important Than Regrets Of The Dying…

In six months I’ll be 50 but I already know what I’ll regret. This is the cliche answer. “If anything had been different I wouldn’t be who I am today.” If I…

In six months I’ll be 50 but I already know what I’ll regret. This is the cliche answer. “If anything had been different I wouldn’t be who I am today.” If I wanted to, I could put an “!” at the end of that sentence. Like what I am today is so great I’d never […]

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10 Things I Do To Guarantee Failure For Myself and Others

A) DATE SOMEONE WHO IS DATING SOMEONE ELSE They are not trustworthy, which means I become untrustworthy. They won’t be able to end it with the other person as easily as they…

A) DATE SOMEONE WHO IS DATING SOMEONE ELSE They are not trustworthy, which means I become untrustworthy. They won’t be able to end it with the other person as easily as they say they will. What goes around comes around. B) SPEND TIME WITH TOXIC PEOPLE Toxic people are contagious. Their thoughts get inside one […]

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Everything You Need To Know About Cyber-Hacking And the Russian Election Hacks

I’ve spent 30 years hacking computers. I’ve done just about every trick in the book. Many people I’ve known over the years have spent time in jail or in some other capacity…

I’ve spent 30 years hacking computers. I’ve done just about every trick in the book. Many people I’ve known over the years have spent time in jail or in some other capacity that is specifically unclear after their hacking was uncovered. And many people I know have never been discovered. A) THE ABCs OF HACKING […]

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The Power of Stupidity: How I Dumbed My Way Out of Failure

The worst moment in my life was when I thought I was at the peak of my intelligence. I honestly thought I was the smartest person on the planet. I had built…

The worst moment in my life was when I thought I was at the peak of my intelligence. I honestly thought I was the smartest person on the planet. I had built and sold a company that year, something I had never done before. I had started another one that was going to eventually raise […]

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10 Reasons Why Procrastination is a Superpower

First, I need to address the elephant in the room. After I post this here’s what many comments and tweets will immediately say: “I want to read this but I will put…

First, I need to address the elephant in the room. After I post this here’s what many comments and tweets will immediately say: “I want to read this but I will put it off until later.” Or some variation on that. It’s a joke. They are procrastinating! It’s kind of funny. But if everyone is […]

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