I’m the Worst Judge of Character

I wanted to raise some money. My neighbor said, “Meet my boss. He runs a hedge fund.”

I met the boss. He gave me the tour of the office. Everyone was buying and selling stocks.

Then we sat in the boss’s glass office. We could see all the employees and they could see us.

He sat down. “So, tell me, James. What can I do for you?”

I was impressed with him. He’d spent 30 years building this great business.

I described my hedge fund. “It’s a strategy you don’t pursue,” I said. “so If you put money with me, it’s diversification for you.”

He said, “Look. You seem great. I’ve enjoyed talking with you and we can use someone like you. You can have a job here anytime you want.”

He said, “But if you take my money, I have no idea where you put it. If you put it somewhere illegal, I could get into trouble. The last thing we need,” he said, and he pointed at himself, “is to see the name Bernard Madoff Securities, LLC on the front page of the Wall Street Journal.”


14 years later I was thinking of investing in an exciting company. It had several divisions.

One division grew its own marijuana and was profitable. Another division sold marijuana to retail in states where it was legal.

But then I did my research.

I did background checks on everyone involved. They had all been sued several times after prior bankruptcies where it was thought they had embezzled the money.

I called other hedge funds. One friend of mine said, “Stay away from those guys. No good.”

So after doing about 10 hours of work and research and reference checking, etc., I decided this was a DEFINITE NO.

Jeff, my partner on this, said, “Well, it’s a no but they flew into town so let’s meet them. Bring up all these issues and see what they say.”

“Ok,” I said, “but you have to promise me one thing.”


“When I leave the meeting with them, I’m going to want to invest. I will bring up all the questions but I am SURE they will have answers for everything.”

I said, “I know they are going to win me over. They will convince me. But look at all you uncovered. You know it’s a no.”

“I can’t help it,” I said, “I know they are going to convince me.”

Face to face, guys like this have zero trouble convincing me.

“Not only will he convince me but I’m going to try and argue you into investing.”

We met the CEO and CFO of the company. I asked all my questions. They responded with smart, intelligent answers that explained everything.

Problems with bad distributors in the past. Bad brokers. Bad bankers. Bad partners. The industry wasn’t ready yet. Etc.

I was convinced!

“OK,” I said to Jeff afterwards, “I know I said a definite no before, but they are doing the right things and the potential is huge. And they are probably right about all the prior issues. And I really liked them.”

I said, “Let’s invest.”


I was having breakfast at E.A.T. with a 95-year-old billionaire.

I had cut myself shaving and he held a napkin to my chin while we waited for our food. I was embarrassed.

He said to me, “James, eat blueberries.” The waiter delivered me a stack of pancakes.

He said, “James, I’m working today from 6 a.m. until 10 p.m. Look at my schedule.”

A wrinkled notebook was in his hand. Notes all over it.

He had built up his venture capital business in the recession of the ’70s.

“I made a huge mistake starting then. You know who tried to talk me out of it? Warren Buffett. But I did it anyway. But then four years into it I invested $200,000 in a deal and within 18 months it was worth $60 million.”

“I stayed optimistic,” he said, “Even though everything was going bad all around me. And, you know what, James? Optimism is what helped me survive. Kept me going.”

He was my friend.

He always let me into deals he was investing in. “This one is the future!”

I lost money on every single one of them.

Afterwards, I found out that he had pulled his money out of all of them and never told me. I felt cheated. I never had breakfast with him again.

“Are you kidding?” a friend of mine said to me years later. “He’s been screwing people over for 40 years. You’re the latest in a long line.”

Jeff said, “No! You did the work. You did the due diligence. They charmed you. And you TOLD ME this would happen. We have to say no.”

“But,” I said, “this could be huge.”

“So what?” Jeff said. “NO!”


We reached out to the prison where Bernie Madoff is a prisoner.

We asked the warden if Madoff could come on our podcast.

We’d go there or we could do it on the phone.

After a few days we got a message back. No.

“What else is Madoff doing all day?” I asked Steve Cohen, podcast producer extraordinaire.

“He’s making license plates all day and he’s still saying no to us?” I said.

I felt rejected. Bernie Madoff was rejecting me.


I keep chasing him, hoping for love, and he keeps rejecting me like I’m the class IT guy and he’s the cheerleader.

Bernie just has my number over and over again.


I like people. And I want then to like me.

One person once pitched me on a time machine business. I believed him.

So many times I’m fooled. So many times people take advantage. You mean, they didn’t like me?

Research shows that 90% of people who are actually bad judges of character think they are great judges of character.

I don’t.

My name is James A. and I am addicted to giving people every benefit of the doubt. I have a very low JQ (“judgement quotient”).

I’ve had my heart and bank broken because of this. Hundreds of times.


I no longer have breakfast with that billionaire.

Here’s the thing about that diner:

Every morning would be a bunch of old guys in sweatpants, reading the paper, eating their blueberries or whatever.

All of them were billionaires or close to it. All of them knew each other. It’s like this secret club.

They’d stare at each person walking in. Measuring them with their laser eyes.

Slicing them up. Trusting nobody.

I don’t think I will ever be in that club. I trust everyone.

I eat breakfast by myself mostly.

When I’m by myself, the only one I am judging is me.

I like me. But, based on experience… I’m probably wrong.

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