Going to Federal Prison Doesn't Qualify Anyone to Give You Advice

A journalist reached out about writing a piece on white collar crime. Before our call she asked if she could send over some questions. I said sure, it would probably be good training for me.

She sent 50.

I said let's cut it to 25 I can answer on my own and build into whatever you choose to create. Then I sat down to record the answers. I got through three before I had to leave to go work with the Navy.

Here are those three.

Who are you and what do you do?

I grew up in Encino, California, a Jewish enclave outside of Los Angeles. I was a baseball player through USC. I graduated, became a stockbroker at Bear Stearns and then UBS, and eventually I made some horrific, terrible decisions. Lying. Covering up. Cheating. That led to a government investigation, and I responded terribly to that investigation. I was sentenced to 18 months in federal prison.

While there, I began recalibrating with help from Michael Santos. Building White Collar Advice was his idea, not mine. We help people dealing with federal investigations, pleading guilty, sentencing, prison, and the collateral consequences that follow a conviction.

In prison I was number 44499112. That is where I began to get it together and strive to use the experience as an asset that could help other people and help me.

Why should anyone listen to you?

I think that is the more important half of her question, and I filmed a Short about it a few days ago.

Just because I went to prison does not qualify me to give advice.

Do you recognize how many people go to prison for sentences measurably longer than mine? That doesn't make them qualified to give advice either. I know too many good men who wasted the experience on the inside, blaming and excusing. They are not in a position to teach anyone.

The same goes for failure. You hear people talk about mindset and overcoming adversity. There's value there. I never wanted to embrace the overcoming adversity message, because I don't think I overcame adversity through one year in a camp. I did want to accept responsibility for my life and begin to rebuild. I failed miserably. Failing does not give you the credibility to suddenly offer advice, just like going to prison does not position you to suddenly offer advice.

It can. I think it depends on what you did with it.

Did you learn from it? Are you in a position to use the experience to help someone else get what they actually want, a shorter sentence, an earlier release, a better life? To do that, you have to introspect, which is what I ask of the people we work with.

What were the choices behind your decisions?

What were the consequences of your actions?

In retrospect, what would you have done differently?

What will you do differently now?

We have had the privilege of watching a lot of people rebuild and others waste the second chance. I share both so you can make an informed decision.

I was fortunate to have a mentor in Michael Santos who did not just talk about his values. I watched him live faithfully to them every single day. That is what made me think, if he could do this through a quarter century in prison, I can do it through 388 days.

So be clear. Do not listen to me, or to anyone else, because they went to prison. Ask whether they have a record that suggests they can help you. Hear the idea, then challenge it. Look at what they built. Are they authentic? Are they asking you to do something they have actually done and documented? If you deduce that someone can help, whether that's me or somebody else, act on it and use it.

How did you go from USC and Wall Street to federal prison?

It didn't happen all at once.

I didn't wake up, graduate from USC, and say someday I'm going to fail miserably and go to federal prison. Some people presume that's how white collar crime happens, that you wake up one morning, make one terrible decision, and just like that you're standing for count. It rarely works that way.

I would argue most people who become immersed in this system had good intentions. They wanted to build a business. They faced some pressure, they rationalized it, and just like that they're in trouble. Then they learn they're in trouble and they respond terribly.

In my case I was building a business and having success. At 26 I thought I was entitled to more money, even though I was already making a lot of money. I didn't get the recognition or the raise I wanted. So I took a shortcut. I stole commissions I was not entitled to.

I did not get caught. That emboldened me to keep going.

After USC I stopped following my mentors' advice. I stopped reading good literature. I gave no thought to how a decision today shapes the rest of my life. I let the environment around me set the standard, and when I watched men take shortcuts and get promoted for it, I figured that was the way to go. Nobody was holding me accountable for the decisions I was making.

I never thought, slowly and surely I am becoming a criminal. It doesn't work that way. You convince yourself you do more good than bad. I convinced myself I was the good guy in a difficult situation, the one trying to reconcile things with our hedge fund client while UBS knew about the commissions and supported them. Clearly they know, I told myself.

Then the FBI showed up.

Of the three parts of the fraud triangle, pressure, rationalization, and opportunity, the rationalization is the one that still fascinates me most. You look at yourself in the mirror, you know what you're doing is wrong, and you convince yourself you're the good guy anyway. You convince yourself you are fixing a situation. You convince yourself there is more good than bad.

It took until I was in prison before I could ask myself the questions I now ask audiences. What pressure did you face? What opportunity did you seize? How did you rationalize it?

Do you think you deserved to go to prison?

I have said in a lot of videos that we send too many people to prison, for too long, at great taxpayer expense. There are no fences and no barbed wire at a camp. Many of those people should be in the community working.

Deserved is a different question than whether prison is the right response to every nonviolent crime.

I know I deserved consequences. I broke the law. I hurt people. I betrayed trust. Even though the victims in my case got their money back, that does not replace the shame and pain they went through. My family suffered. I suffered because of my own choices.

Standing for count, being separated from my family, the showers and the toilets and the toilet paper that felt like sandpaper, that had an effect on me. It hit me when I got there.

People ask what would have happened if I hadn't been caught. I don't know. I'd have probably been a 35-year-old chubby stockbroker in Los Angeles who felt entitled and believed he could get away with just about anything. I'd have probably been a real a-hole. There would have been no introspection, no thought about doing anything differently.

Some people find meaning in prison and will tell you they needed it. Plenty of others did not need to go at all, and they learned the same lessons through the collateral consequences that follow a conviction anyway.