Ep. 183: Jenny Blake – Pivot: The Difference Between Making Millions and Failure…

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I had to stop trying to get ahead.

There are 8 million people in New York City. And 7 billion in the world. That’s 875 New York Cities.

You can’t get ahead. Information is compounding. Technology is growing exponentially. Nothing is predictable—except maybe your expectations.

But not your success.

I used to complain. Now I pivot.

“There is no try,” Yoda says. Luke Skywalker didn’t believe he could use the force. Trying is just a form of doubt.

“Do or do not,” he said.

When I was 23, I tried figuring out how long it would take me to make a million dollars. I just bought computer. It was the first thing I bought with “hard-earned money.”

Fast forward 25 years and I’ve thrown all my stuff away.

And I’ve stopped trying to get ahead.

I want an F in effort. And an A in not giving a shit.

I’m writing because I’m writing. Not because I’m trying to write.

People make this mistake all the time. If you say, “James, what can I do to help you?” you’re doing two things right and one thing horribly wrong.

Right: you’re good-intentioned (maybe) and you’re not hurting anyone (again, maybe). But here’s where you’re wrong…

And I’ve done this before too.

I’ve tried to be a good boss, a good employee, a good investor, but for all the wrong reasons.

There’s only one good reason: you want to provide value.

If you don’t want to add value, you’re not helping. You’re hurting.

Growing up, when my family argued, I’d ask, “Can I say something?”

“Will it help?” my father would say.

I didn’t answer.

Offering ideas is not valuable. You have to give the “how.” Say what you’re going to do and list the steps. That’s where your idea list comes in.

I’ve started and ran more than 20 businesses. And I can tell you one thing for sure: when I did it for money, I failed 100% of the time.

Here’s the test… before you do anything, ask yourself this one question: “Do I want to add value?”


“That’s how I got Mark Cuban to come on my podcast,” I said.

Jenny Blake started a podcast. She came on my show to ask what works. And what doesn’t. It would be brilliant strategy… Except it’s not a strategy. It’s genuine.

And that’s why it works.

She asked to interview me and provide value to you. Jenny’s an ex-Googler. I wrote a blurb for her book, “Pivot: The Only Move That Matters Is Your Next One.”  So did Cal Newport, Seth Godin and a few people I owe return emails to.

I wrote, To pivot well is the difference between millions and failure. Former Googler and entrepreneur Jenny Blake (one of my favorite human beings) dissects the pivot, how to do it, and how to do it right.”

I can’t tell you the right way to pivot. I’ll leave that to Jenny. I went on her podcast as a guest host.

And she came on mine to dissect my brain. Reorganize it, and give you all the milk.

Listen now to learn how I make money, keep it and grow it [12:39], how I got Mark Cuban on the podcast [41:48] and more…

    • the exact steps I’m taking to pivot in my career right now [6:09]
    • if and when it’s the right time to pivot [8:29]
    • How I currently make money and diversify my portfolio [13:53]
    • How to do what you love everyday [16:16]
    • The 9 experiments I did before creating a stockpickr.com, which sold for $10 million [19:50]
    • The best and worst way to network [38:38]
    • What my day-to-day looks like [47:39]

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