Everyone Deserves a Second Chance

yitz grossman

I felt bad about how I mentioned the other day about Yitz Grossman going “away”.

Someone wrote me afterwards and said I got the facts all wrong and that Yitz was one of the most generous, charitable people he knew.

Yitz helped me sell my first company back in 1998.

He was always very fair to me and I not only mentioned that in the article, I mentioned how I was sad he had to go “away” in the way where “away” involves the government, the authorities, and all the bosses in cahoots together, figuring out futures we didn’t know were possible when we were tiny boys playing kickball in the street.

[Related: Not every “second chance” is about “camp”. Here’s a time when I very much was in need of a second chance. Everyone has these experiences in one form or other.]

So yesterday, I called up Yitz and said “lets meet for lunch.” I wanted to get all the facts right. It’s the first time I had spoken to him in about ten years.

He was very surprised to hear from me.  He agreed to come in from Long Island and meet me for lunch. His hair was a little more gray than the last time I saw him but he looked in good shape, “prison must’ve been good for me,” he said and laughed.

“The hardest day for me,” he said after we sat down, “was the day I had to actually go in and I knew I would be away from my family for 19 months. I woke up really early and packed away all my suits, put plastic over them to keep them good…my wife drove me to the prison camp…I walk in with normal clothes on…they make me strip down naked…search me all over…and then I get my sweat pants and a t-shirt. That’s basically what I wore for the next 19 months.”

But Yitz, what did you actually do? When I read about it in the news they had all this stuff about currency brokerages, etc.

“All of that was lies,” he said, “the same FBI agent brought in two cases that day, me, and the currency broker thing, and it all got mixed together in the news. The FBI even gave me this jacket to wear so that the newspaper photographers wouldn’t photograph me since he knew it was a different case. Read the indictments. There was nothing about the currency thing.”

Yitz explained to me the crime he was indicted for in 2003. It’s a little bit detailed. “Why didn’t you fight that?” I said, “I used to see hedge funds do those deals every day. I don’t understand, I read your indictment. Why didn’t you even fight this?”

“Listen,” he said, “a guy I had known forever was being convicted of something much worse. They said to him, ‘we’ll take some time off your record if you turn in some of your friends’. So they had a guy in with a wire on and they worded it just right so there was no way to fight. I didn’t want to fight it and risk losing to a jury and get triple the time away from my family.

“Even more important…I was indicted in 2003 but they didn’t put me away until 2006. You know why? They asked me over 50 times to turn other people in. They said to me, ‘don’t you have any resentment against this guy or that guy? Now’s your chance to wear a wire, we’ll get him for something and you’ll do no time at all in prison.’ They call this ‘doing business with the government’. I didn’t want to do business with the government. I didn’t want to turn in any of my friends.”

“So I plead guilty and in 2006 I began serving my 19 months.

“And let me tell you something. There’s a difference between prison and jail. I was in what’s called a ‘camp’. I was a “camper”. There were no guards. There were no bars. There was no barbed wire. I had to report in to a ‘counselor’. There was one correctional officer on the whole facility.

yitz grossman

(Yitz in the prison camp)

“Our cafeteria looked better and had better food than this restaurant we’re sitting in. You just have to be there the few times a day that they counted everyone.  I had visitors up to five hours a day. I hear now they can even have visitors via video and they have wi-fi on the campus.”

The waiter served our food. I was having spicy tuna. Yitz was having some fried sushi thing that looked too good for me to try.

“I became the rabbi of the camp. I would give sermons once a week. I had books shipped into me so I could study and do reading. I walked five miles a day. I studied. I returned letters.

“Over 3000 letters were sent to me from my friends. I wrote replies to every single letter. When I got out we inscribed a new Torah and each letter was dedicated to another friend who visited me in prison.”

“And again, there’s no bars. Sometimes the people in there with me would even get jobs off campus. They’d lend us the cars, we’d drive off campus to our jobs, we’d drive back when the jobs were over. It was totally open.”

I felt bad then. I didn’t visit him. I hadn’t written him any letters. I didn’t know anything about it.

“Yitz,” Beth, Yitz’s assistant, said to him, “you make it sound like it was all sugar. There were some dark times. And what about the people who were there who can’t always come out and start making deals again like you were able to. Talk about all the people you helped while you were in there.”

“Its true,” he said, “I missed my son’s Bar Mitzvah. I was only glad that when I woke up that day it was already over. And I am lucky. I was in there with at least five or six mayors. One congressman. Other politicians. Their careers are ruined. What they have to do is get to know the big executives who are in there. Once they’re out they can maybe get a job as an executive working for that guy’s firm.

“You’ve all been thru something together. You all served time and know what it’s like. You all dealt with the government in the years before and know what that’s like. It’s painful and you each know the pain the other went through. There are a lot of good, decent guys in there who got trapped in the system for one reason or other.

“Important to know, 96% of all cases don’t get tried. There’s always a plea. People are turning everyone else in. Everyone’s ‘doing business’ or working out some kind of deal.

“But its never over. Its like I’m walking around with an amputated arm…I can live, breathe, work, but I always know that I have this missing arm. Banks sometimes won’t open up accounts with me. People will google me and it’s the first thing that shows up.

“People deserve second chances. Everyone has issues in life. Nobody passes through life completely unscathed. I’m even starting a company right now that deals with online reputation issues. There’s a lot of complicated algorithms to help companies and individuals reduce the effect of a bad reputation on sites like google, etc. What would a company or individual pay per month to have their reputation constantly reviewed and managed online?”

Beth said, “Yitz, why aren’t you really talking about the dark side of this?”

Yitz said, “Listen, my parents were both in Auschwitz. My father personally faced Mengele. A lot of people have been through much worse. I didn’t do anything wrong. I didn’t turn anyone in. I can face myself in the mirror every morning. I knew I was going to survive this. I exercised, I wrote letters, I read and wrote every day.”

yitz grossman

(Yitz with his 5 kids inside the prison camp)

I had to go. I had my next meeting of the day coming up. I wanted to hear more so we promised to get together again sometime soon.

The first time I met Yitz and Werner Haase, they wanted to buy my first company. This was in 1998. On and off for the next two years I always called Yitz whenever I had a business issue or needed help with anything as I was learning the business world. A world I knew nothing about and really had no mentor in at all. Yitz invested in a deal or two that I did in 2000. Deals that didn’t work out and he lost some money. Maybe $200,000.  He didn’t bring that up in the lunch but I was thinking about it.

After my next meeting, I went on the train to go home. I bought a book in the Grand Central store to read on the train but I just stared out the window.

I passed Yankee stadium. For the next hour I watched the Hudson River and the mountains. It was raining a little.

The window of the train was getting dirty from the rain. The guy sitting right in front of me passed an enormous amount of gas. Later that night I knew I was going to see Mollie, my youngest, give a music recital at her school. She was happy because she also had a “speaking part”.

I was also happy because I knew she would be playing the theme to Star Wars on the clarinet. I was proud of her. When I got off the train I knew one thing….I was free.

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Yitz wrote me later that evening. Here is what he wrote:

Why do many innocent people plead guilty to charges and go to prison rather than chancing and battling against the government. Isn’t it an oxymoron to suggest that a person pleading guilty could also be innocent. To the average person, it might be but to those who know the system, well- they understand better. Yes- I pled and yes I did time in a federal prison camp (called an FPC). Prisons are not places with bars on the windows and guards at every door- you can research that too.

I survived better than others because I have a strong family, because I’m rather planted in my community, because I didn’t become a government informer and can look myself in the mirror every day. Was it a bold move? Would it have been easier on my wife and family had I gone the other way and avoided prison? Of course! But my constitution dictated that I not do unto others…. how difficult is it to set someone up into a conspiracy? Not at all! I also survived because as I told you, because I didn’t defraud anyone out of a penny, stole nothing, hence had nothing to repay: no restitution.

Bottom line: good people can get into trouble and go away for something quite innocuous when the government wants you to help them and you won’t. many offers were made including the day of my arrest. The agent on the case pulled me aside and said “yitz- I got you. You know many people and you can help us.” He then mentioned specific names and offered that he and I go across the street, that I agree to help them, that I’d be home later that day and that no -one would even know I was arrested. I declined.

My parents both survived Hitler and I wasn’t going to ruin other lives to save mine. As an aside: most people do. Hence the government does not need a marketing division: each client brings another and more. Talk about viral marketing!!

Anyway- I’m back- doing what I know how to do.

A post from Yitz’s blog:

Is the Blackberry not kosher?

 Yitz’s religious blog



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  • Alex

    You mentioned how valuable it was to you to have someone with great business experience like Yitz for a mentor.  I guess many people don’t realize how much knowledge they are missing, especially when coming from a technical background and trying to navigate unfamiliar business landscape.  What, in your opinion, is the best way to find a business mentor?  E.g. my parents are engineers, my friends and relatives are almost all in IT.  What’s the best way to get out of the circle and start hanging out with businessmen?  Where’s their habitat?  How can I find a business mentor?

  • Steven L. Goff

     Thats bullshit!…only people who get second and third and forth chances…are the Elite and those with connections and money. You can sell that second chance bullshit…to someone who doesn’t know any better! That guys “prison” pic is him in a grassy meadow….are ya fucking kidding me?! Second chances…get the fuck outta here! Once a convict always a convict for anybody else in this country (the 98% of convicted felons) are extremely limited in society….even after paying it’s debt to it! I am not an athlete who can throw a football or dribble a basketball…they get to rape woman and pay them off and kill animals and go back to making multi millions of dollars a year.. whereas I can not even write a book for profit about my crimes that led me to prison at 18 years old (A maximum security prison). Because ya cant profit from your crimes laws. I am FUCKED for life because of something I did as a minor but was charged as an adult and went to prison for  5 years (10 yr sentence w/ a 5 yr mandatory minimum). I aint had a j-walking ticket since and can never do shit meaningful or substantial in this country. I am a high energy and pretty smart friggin guys. And my life is wasted. This country and that second chance bullshit can go FUCK ITSELF….as far as I am concerned. I’ve had more doors slammed in my face because of my felony conviction than ya can shake a stick at!

    This fucking article/blog pissed me off!

    • Yitz

       Unfortunately Steven happens to more right than wrong. At my lunch with James, we discussed an idea that could change all that, it’s still being developed but has real potential, especially for people like Steven. If you happen to live in NY, feel free to reach out to me; I’ve helped many others get jobs, perhaps I can help you as well.. y-

      • Sooz

         Do it Steve!!!
        This is your chance, my friend, to wear that handsome suit..:))

        Your family is beautiful a reflection of loyalty and goodness. You must be so proud of them.

        • Sooz

           Steve, I’m headed your way in five weeks and I’ll swing down your way and smack you up~side the head if you don’t take advantage of this kind invitation by said time..:))

      • Daneskold

        That is noble and generous of you.
        As one who has been is in need of a second chance, I cannot express the emotion evoked by your extending a hand.
        G-d bless you.

      • flex

        I think at the right price corporations and individuals would pay well to have their “histories” cleared or “cleaned up” to an extent. Good business idea but I’m not sure about the legal implications. Interested to see how this develops Yitz

  • Steven L. Goff


    • Well, you deserve a second chance as well. The whole system seems somehow rigged. Everyone doing their best to make a living and that sometimes means its unfair when interests conflict. I wish they would spend resources on the real crimes that destroy the country (murder, rape, theft, other forms of violence, serious white collar crimes (Madoff, Enron, embezzlement, etc). I’m not a judge or a lawyer but it does seem the system seems unfair in many cases.

  • Drippy

    I’m skeptical. I don’t know the facts of the case or what Yitz did. Anything SEC related is pretty murky. But the rules are what they are and if you’re in this business it’s your job to know the rules. Yes, some will get caught while others don’t. Life is not fair in that way and it never will be.

    What I detest is the general theme of what Yitz is saying, i.e. that those charged deserve a second chance. Or more precisely, his fellow white collar criminals do. It goes back to the notion of a “victimless crime” of which there is none. How can there be a deterrent to the crime if its known that a get out of jail card is available to them. 

  • Kevin M

    I don’t know anything about Yitz or his crimes, but I have to respect a guy looking at that much time away from family (white collar prison or not) that refuses to throw his friends/colleagues under the bus to save himself. I’m a big believer in karma, but I’m not sure I could do the same. Great post James.

  •  This post was awesome. Steven is right though, not everyone gets to go to prison camp. It’s highly sensitive to where you’re convicted, who you know etc. I’d like to know what the parameters are for “club fed” versus maximum security. 

  • Manoj P

     That story brought tears to my eyes (the last time that happened was when I thought my mother would die). Yitz is a honorable man and you are great for giving him a second chance. Better late than never.

  • Irishgirlsusie

    I believe the government has created a record for themselves that they are one of the most underhanded organizations in our country.  But, that’s a different subject and different story.

    Working at a few fortune 500 companies, I’m convinced there’s a lot of people who may not have done anything that would be considered criminal, but certainly immoral.  I don’t understand how they justify their behavior.

    It speaks volumes that Yitz can look himself in the mirror every morning.  Hope he has a grand 2nd act coming his way.

  • Seems like you gave -yourself- the second chance as well.

  • bob
  • Kevin Widdop

    James, great read. I first came across your work on the Lewis Howes podcast and saw you again on the DailyVee vlog. Love your thoughtful work!