How Ego and Denial Led Me from Merrill Lynch to Federal Prison

When I Refused to Join the Team, I Thought I Was Standing for Integrity

In 1997, I graduated from USC and started working at Merrill Lynch. Within a year, I passed the Series 7 and 63 exams and raised around $10 to $15 million. I thought I was on my way. I was 23, making good money, wearing nice suits, living in Brentwood, and eating at sushi spots that made me feel important.

Then the memo came down: if you want to stay at Merrill, you need to join a team.

I said no.

Not because I had some noble objection. I said no because I thought I didn’t need them. I thought I was better than the guys being told to merge their book with a senior broker. In my mind, they were suckers.

Over the next two months, I watched the junior brokers—the ones with $5 or $10 million under management—give in. They were promised mentorship. They were promised growth. But all I saw was the same pattern:

They’d hand over their book, manage a senior broker’s clients, handle every customer service issue, and stop prospecting altogether. Their days were full of busywork. No time to build. No time to bring in new clients. They didn’t just slow down—they stopped.

Eventually, they’d burn out. Quietly leave. And the senior brokers would absorb their accounts like vultures.

I remember watching that and telling myself, “That will never be me.”

And that’s when things started to go wrong.

Ego Dressed as Principle

I didn’t understand the difference between protecting your values and protecting your pride.

Back then, I told myself I was walking away from a corrupt structure. That I was standing up for something. But in truth, I was using the system’s flaws to rationalize my refusal to adapt.

I didn’t want to learn from people. I didn’t want to follow anyone’s lead. I didn’t want to be part of a team. I wanted the credit. I wanted to move fast. I didn’t care who I stepped over.

So I left Merrill. I joined Bear Stearns. And I started cutting corners.

Not all at once. Not in some big dramatic way. But gradually. It started with commissions. Then came the rationalizations. Then the outright fraud. And eventually, I ended up in federal prison.

But it started here—with the belief that I was better than everyone else.

Why This Story Matters If You’re Under Investigation

I’ve worked with thousands of defendants over the last 15 years. This pattern shows up over and over again:

They rationalize early decisions as “standing their ground,” when in reality, they were just avoiding accountability.

They take pride in not being like “those other guys”—and that pride prevents them from preparing.

It shows up in pre-sentencing interviews when they try to explain why their conduct wasn’t as bad as it looks.

It shows up in sentencing memos where they talk about unfair treatment or flawed systems but say nothing about what they could have done differently.

And it shows up in the way they waste time waiting—thinking they’ll be judged on their intentions instead of their outcomes.

What Judges and Probation Officers Actually See

They don’t care that you didn’t like your company culture.
They don’t care that you once refused to go along with the crowd.
They don’t care how it started.

They want to know what you did once you realized it was wrong.

They want to see whether you learned to recognize your role in the problem—and whether you’re doing anything to prove that the same thinking won’t lead to the same behavior again.

If your entire mitigation strategy is still about comparing yourself to someone worse, you’re going to get crushed.

What I Wish I Did Instead

I wish I documented what I saw at Merrill with specificity—how those systems made me feel, what I believed at the time, and where I got it wrong.
I wish I owned that I wasn’t principled—I was arrogant.
I wish I had written letters, kept a journal, done something to show the probation officer that I was learning from it before the FBI knocked.
I wish I had spent less time defending my decisions and more time examining them.

If You’re in This Phase Right Now

You might be telling yourself, “I didn’t do what those guys did.”
Or “I didn’t set out to break the law.”
Or “I was just trying to make a living in a broken industry.”

That’s not enough.

What matters is whether you’re willing to do the hard work of owning it, documenting it, and building a record that shows growth. Quietly. Consistently. Not for show—but because the people judging you are trained to see through the show.

You’ve Read This Far—Now Ask Yourself:

What story are you telling yourself that’s actually just protecting your ego?

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