It’s in times of struggle that we find our inner strength. Michael Kimelman was on top of the world before being sentenced to prison for insider trading. He was dreadfully at ground zero, but more than losing his money and freedom, losing his wife and children was what made his predicament more dishearteningly difficult to bear. Nevertheless, he never stopped relying on that glimmer of hope he had within, and he used his time in prison to enrich himself. The experience has given Michael an inner strength to become a coach, an entrepreneur, and the bestselling author of Confessions of a Wall Street Insider.


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Creating Inner Strength, Peace, And Power After A Prison Sentence with Michael Kimelman

What’s going on, Sean?

I wanted to tell everybody what you made us on the fly because your cooking is spectacular.

We did a little bit of curry, some sautéed vegetables, a little bit of curry powder, a little bit of lemon juice, a little bit of coconut milk and some organic chicken thighs.

Everything is organic and hormone-free. It’s great to have Taylor here because I call him the super chef. Everybody now wants advice from Taylor because the cooking he does, the way he connects the palate with the brain, you’re going to love food all over again and we eat healthy.

We eat healthy and we eat something that tastes good because they are not mutually exclusive.

You can cook Mexican, Indian, Japanese, Euro, American, Ethiopian and just all are delicious. I don’t like to eat chicken or a lot of beef and the way you do this, you make it pleasant or enjoyable to eat. It stays with me for a long time.

Thank you. I’m glad your stomach is happy and your microbiome. We have someone coming on who’s going to come to talk about the microbiome, so stay tuned for that episode. If you don’t know what the microbiome is, you better keep following. Speaking of following the podcast, we need your help because we can’t do this alone. We’re only two men in a world of seven billion people. We think a lot of those people should listen in and understand the information that we’re trying to bring, the stories we’re trying to tell. Part of that is having you guys help us out by going over to iTunes and leaving a five-star review.

In the spirit of leaving five-star reviews, I’m going to read one from one of our dear friends and listeners. Her name is Tina Tries, which I’m going to assume is Tina Hollins, who did an episode with us. Tina comes on, “It’s Survivors Turned Thrivers. Sean shares his story and the rawness of being a stroke survivor. Hearing him encourage new survivors and their families that they are not alone during this emotional time in recovery. Sean and Taylor are great hosts and do a fantastic job during their interviews. I love that Sean has taken what could be considered a devastating disability and has risen above it and is giving back to the community. The community is a better place because of survivors like Sean. Way to give back and explore what’s next in this lifetime.” Thank you, Tina.

Thank you, Tina Hollins, a lot and her husband, Shane and her kids because with their family, they supported her and she’s now back to being almost 100%. More than often, Taylor, you played baseball, right?

Yes, catcher, first base outfield.

I did the same. I played at the hot corner at third. I played some first. I played some outfield. As a kid in Los Angeles, in this community, I played ball. A lot of people went to the pros and went to play in college. There was always this one friend of mine. His name is Michael Kimelman. He always tried his best and he’s awesome at what he does and what he did. I think Michael never played ball after even high school. He was an athlete of athletes because he dedicated his life to it.

Michael Kimelman, he’s our guest on the show.

Mikey, as I call him. We grew up together and his traumatic experience is comparable to mine because here’s a guy who went to law school at USC and fights on the Trojans. He ended up going out to New York and built a huge company in the VC world and made millions and more. Then all of a sudden, he gets busted by the FBI and he gets sent to prison. We’re talking minimal security, but still he has to go away for eighteen months. This is going to be his story. His triumph and victory of how he got through it, what he did and what he does now. He inspires me and Mikey is awesome.

I think what he did was he took a tough situation and turned it around. He turned lemons into lemonade. Let’s go jump in with Mr. Michael Kimelman.

Elsa Ramon here with Sean Entin. We have someone on the show that you know very well. You guys have known each other for years and you both have traumatic experiences and life-changing experiences in different ways. Everyone knows you’ve had a stroke. You’ve had an eight-year comeback and are continuing to come back. Michael Kimelman, our guest on the show, had his own setbacks. They may not have been physical, but they certainly were some serious setbacks. Michael, welcome.

Thanks. It’s great to be here.

I’m so glad you agreed to come. I’m sure being a lifelong friend with Sean had something to do with it, so thanks.

He twisted the arm but it’s ready to be twisted.

You guys both have interesting stories. Michael, you and I have talked before how you had this great life. You and Sean had parallel lives growing up. Tell me a little bit about your childhood and growing up.

We grew up in one of the more ideal situations. I’ve known people from all walks of life my entire life and certainly have met a lot more in the past four or five years. I grew up in the San Fernando Valley with Sean and you couldn’t have asked in many ways for a better place to grow up. It was the 1980s. The economy was just starting to do better. You had sunshine. I was born in Philadelphia but moved out at an early age. It was pretty much sports and making good friendships and everybody was excited about this re-awakening of America. There was definitely a spirit of optimism in the air. I had a pretty ideal childhood. I had two parents, nuclear family, younger brother, did well in school, played sports and grew up with privilege. I did have the privilege of having both parents and all my faculties and anything else that was needed was there for the taking.

You and Sean both had parallel lives. You both had very similar upbringings. You both had dads who are OB-GYN surgeons and you both end up going to USC. What is it that you study when you go to school?

People sometimes end up despairing and falling into a very dark hole. Click To Tweet

I studied law at the time I got to USC. I went to undergrad on the East Coast and came back for law school. I figured I wanted to practice where I grew up. My opinion is you should probably go to a school where you end up wanting to work in because that’s where you make your networking and your contacts. That didn’t go as smoothly as I planned. I ended up doing well in law school and taking a job with a New York firm and moving back to New York right after graduation. I worked for one of the big law firms called Sullivan & Cromwell. Even though my intent was to stay in LA for the rest of my life, I got sucked into that New York charm and magnetism. I ended up in the late ‘90s heading out there to work for that firm.

I don’t blame you. New York’s fantastic and you already had an experience going to school undergrad in New York. You are familiar. It wasn’t like this was going to be a brand new place where you didn’t know anyone. There is familiarity there.

One of my best friends was the bullpen catcher for the Yankees at the time. Yankees were just starting their ran under Joe Torre. Being single and young in New York and having your friend worked for the Yankees was probably not great for my work performance. When you’re young, you’re semi-bulletproof and superhuman to pull out of 2:00 or 3:00 and back at work by 6:00 or none the worse for wear, which Sean can attest to and Elsa as well. As you get older, that becomes increasingly difficult, to put it mildly.

The last thing I can think of wanting to do is be out now at 2:00 in the morning. I’m like, “I want to go to bed.” I like going out and all but those days of coming in to work with a few hours’ sleep, forget it.

Michael, you end up back East in law but then you transition over to finance.

It was the late ‘90s and you get pitched the story in law school about how noble it is and how interesting depending on where you end up. I ended up in a big law firm. You’re a little bit of a cog in a wheel. It’s not the most interesting work. It is a bit of a grind. This was in the late ‘90s. There was a lot of excitement in technology in New York, which is the finance capital of the world. Everybody seemed to be doing much more interesting things than what I was doing. I got tired of sleeping under my desk a couple of times a week and I lateraled into finance. I went to work for a trading firm. I did well there. Over the next five or six years, I was the top trader at a couple of different firms and I ended up eventually starting my own hedge fund.

How old were you then, Mike?

I was in my mid-30s. This was around the end of 2007, 2008. I started the fund. At that time, I was probably 35, 36. It coincided with the financial collapse, which is anybody who was on Wall Street or in finance remembers it was a pretty rough time. It wasn’t just funds and businesses going out of business, it felt like the entire system was teetering on the brink. That was the crucible time for when we were in business and opened up. We actually did quite well navigating that crisis. I think as the S&P was down 38%, we were up to something like 18%. From a fund perspective, we did quite well.

Let’s back this down. You in your 30s opened this hedge fund. I’m going to ask you a straight question. What’s a guy like that making? How much are you taking home a year? Is it in the millions? Is it in the thousands?

It all depends on the situation. Working for a big firm when I was in law, you were probably making around $120,000. Again, this is twenty years ago. It sounds like a big number. It was a big number but then if you look across the street and you find a friend who was working for JP Morgan or Goldman Sachs, they could be making ten times that amount and probably working fewer hours, to be honest. Finance, it’s all over the map. It depends what your role is whether you’re an analyst, a money manager, a director. I’d say in finance, people at that time period at least were probably making between $250,000. Then on the upside, it was uncapped. If you ran your own fund or had a hedge fund and managed money, the top performers in that industry made billions like Steven Cohen and James Simons and all these other guys. If you work for a bank, you’d probably still made a few million dollars but it all depends on what your role was and how senior you were.

AIH 23 | Creating Inner Strength

Creating Inner Strength: Sometimes, the court trial is just the ability to parade some rich Wall Street guys in front of the public and make a show.


You’re here in the financial crisis, 2008, 2009, 2010. That bubble, that burst and for what it is, you guys are doing well but something happens.

In a single second, my entire existence in the world gets erased. In late November of 2009, this is a little bit after the financial crisis started to settle down, it looked like we had successfully navigated it. We probably had $250 million or so under management and about 40 or 50 people working for us. One morning at about 5:00 AM, an FBI SWAT team complete with K9 dogs raided my house and arrested me for insider trading.

In an instant, this all happens. What was going through your mind when you wake up? Your house is being raided. There are K9s everywhere. This has got to seem like a bad dream or a nightmare scene out of a movie.

It was surreal. I didn’t feel as it was going on. I’m a trained lawyer and even with the FBI there, it’s like you’ve seen enough movies and what not. You want to have something to say to them when they shoved the warrant in your face and tell you you’re under arrest. I describe it in the book that I wrote about it as it’s like a car that won’t start your brain. You keep pumping the gas pedal, trying to get some type of information to it. The shock is so great and it’s so overwhelming that there’s nothing that comes out of your mouth. It took me probably 30 or 45 seconds to even utter for what and to try to get some information about what I was being arrested for. It was one of those situations where they wouldn’t even tell me other than securities fraud and then try to get me to cooperate. They told me I’d be doing ten years in prison. I wouldn’t see my kids until they were in high school unless I cooperated. I wasn’t even sure why they were there and what it was about or anything else.

They wouldn’t provide that information other than saying it was securities fraud. I had some idea of what was going on. Raj Rajaratnam, who was a big shot on Wall Street, had been arrested about two weeks before. My partner that I hired at my firm had formerly worked for Raj during the same time period that Raj got in trouble for what he did. It wasn’t a complete shock, but I didn’t think at any point that I had done anything even remotely illegal. Hearing it’s securities fraud, “Talk now or you’ll do ten years in prison,” was beyond the shock to me, especially without having had any questions or anybody approached me or asked for my side of the story. I was in handcuffs in front of my crying children and wife.

How old were they?

At that point, I think my daughter was seven. My son, my middle guy was four or five and we had a newborn who was about four or five months old at the time.

Lights are blaring. It’s an ambush. They’re designed to be that way. It’s no surprise that you couldn’t get the words out. Everything’s happening at lightning speed and through all of this, you’re finding out that they’re trying to tell you you’ve got ten years in federal prison. You start connecting the dots though and then you start finding out more of the story.

This raid was designed solely to terrorize. That’s what they do in order to catch you at a point and get you to talk. We’ve seen that happen to many other people. Having been trained as a lawyer, I didn’t speak to them. We went downtown, they try it again and then literally it’s like an all-day affair. At the end of the day, maybe twelve hours later after sitting in a holding tank, they showed me the criminal complaint. It said I was being charged with insider trading in one stock called 3Com. They were charging me with making $16,000. I had no idea that’s what the stock they were looking at. I thought it was a different stock that had been mentioned in the Raj arrest and the numbers were baffling to me.

We ran a firm that’s about $250 million in assets. The numbers were minute and even the quotes that they mentioned in the arrest complaint didn’t make any sense to me. I wasn’t involved in it. We made a very concerted push over the next few weeks to get the government to drop the case but unfortunately, they had made such a big public splash and had paraded us on CNBC and frog-marched us handcuffed in front of the press. It’s very difficult to drop a case like that once it’s out there. It would be a career killer for the people involved. Instead, they came to me and said, “We realized you’re a guy that’s very different than any of the other people that were arrested in the case.” There were about fourteen people arrested and they offered me a plea if I plead guilty, not cooperating, just plead guilty to one count of conspiracy.

It’s not even actual insider trading, but conspiracy to commit insider trading, that I would get no jail time and have to pay no fine. That’s a very big difference from an FBI SWAT team arrest in the morning, predawn raid, “You’ll do ten years on some prison unless you talk,” to a couple of weeks later, no jail, no fine, just plead guilty to one count. It was a very big reversal but it didn’t change my faith. I had been in the newspapers, on TV, I’d been arrested and I had a very serious decision to make whether to take that plea or whether to risk my liberty and go to trial to try to clear my name.

It's in times of struggle that you will find your true strength and will have the gratitude and perspective for everything you have. Click To Tweet

What was it like being paraded in front of the media while you’re handcuffed? This was a big display. This was something that law enforcement routinely does in high profile cases so that the public and the media gets a chance to get videos or trying to talk to some of the people who are accused. What was it like for you seeing all those cameras?

You nailed it on the head. It’s a very big show or parade and it goes against the core grain of due process and presumed innocent as we’ve seen before. If you look at some of the Innocence Project and some of these other types of wrongful convictions, once you’re arrested or convicted, especially in the age of Google, it almost doesn’t matter if your name gets clear later or if you get freed or whatnot. Like any other correction that you see now, especially how journalism has gotten now with the Gotcha, if it bleeds, it leads and the clickbait. It’s front page, the actual occurrence. If they change that story or there’s a retraction or anything, it’s B31 tiny little paragraph. This was again done to aid to terrorize, to create a distraction for the public who is still quite angry over the financial collapse and the financial crisis.

You had hundreds of billions of dollars in mortgage fraud. You had people losing their houses. You had the banks, the big North American banks paid $200 billion in fines and virtually nobody went to prison. They needed some type of, I don’t want to use the word scapegoat because there were plenty of people who did break the law and deserve to be prosecuted, but they did need some big show of force to say, “We’re on this and we’re going after the people who caused this.” Even though that’s a very cynical and a ridiculous statement because insider trading had nothing to do with the financial crisis. The amounts involved were tiny compared to the hundreds of billions that the bank stole or the fraud committed.

That’s what confused me. You said when you saw the complaint, this was over $16,000?

They tried to up that number later on, but it was a very small number compared to what was going on in the broader economy and the financial crisis. What it was, was the ability to parade some rich or semi-rich Wall Street guys in front of the public and say, “We’re on the case and we’re making sure this won’t happen again and we’re going after the bad guys.” It was a PR display, for lack of a better term.

It’s a dog and pony show sometimes. They have this offer in front of you to plead guilty to conspiracy and in turn, you would get no jail time, no fines. What did you do?

It was an incredibly difficult choice. I didn’t believe I did anything wrong or illegal and I wanted the opportunity to clear my name. I was prepared to go to trial despite my lawyer at least giving me some advice. At least one of them told me that he thought with the climate that we were in, with Occupy Wall Street was happening just down the street from the federal courthouse, that it was not a good time to be a so-called Wall Street fat cat as Barack Obama had labeled us and to try to go to trial to clear our names, especially with the amounts of money that were involved. Even though they were small from a broader point of view, for people on a jury who weren’t making a lot of money to hear some of these trades. My partner ended up going to trial as well, which was a mistake, but he sat right next to me and there were trades he made where he made $100,000 or $500,000 a day.

You could see the jury’s faces dropped when they heard some of those numbers. I did decide to go to trial. I was prepared to pay the consequences if I was wrong. I may have handicapped the criminal justice system incorrectly in that I thought growing up as a lawyer, being trained as a lawyer, working in a law firm, I believed in that no bull, it’s an objective system. You’ve got a jury of your peers, the way the evidence in a neutral objective fashion and make a decision. Anybody who’s been through the system understands that that’s a complete farce. It rarely happens and that there’s also endemic prejudice in the system in favor of the government or the state and the defendants especially. As a white defendant with the means to defend myself, I was probably in the best position I could be and still had no chance. It’s something that minorities and other people who have gone through the system for the last few decades have understood that there are incredible prejudices involved in and it’s not a great system, to put it mildly.

This was your first time being prosecuted.

I had a speeding ticket when I was seventeen.

AIH 23 | Creating Inner Strength

Creating Inner Strength: It’s sad how people are punished for exercising their constitutional right to go to trial.


How much did it cost you for your legal team, just in this case?

The other point besides all these endemic institutional biases like the inability to afford bail or to afford legal counsel or to find decent legal counsel. I didn’t suffer from that last part, but to go to trial, you’re talking seven figures and up depending on how complicated the trial is and how long it goes. It could be $5 million to $10 million depending on the complexity of the case and whatnot. When you think about that, there were very few people who are even in the situation and have the ability to get a fair trial and defend themselves. It’s a very tough system. I don’t think it was a trial that was fair and we would find out later that the judge in our trial had a predisposition to the government that was incredibly unfair. He ended up giving incorrect jury instructions that favor the government and it would be too late for me, but every case he heard after mine on the insider trading, he ended up getting overruled because he did give those incorrect jury instructions, but justice grinds very slowly. By the time my appeal was heard, I had already been convicted and I had already served a sentence.

Let’s talk about that. You don’t take the deal, you go to trial, you’re found guilty of what?

It’s called securities fraud but colloquially, it’s just insider trading. What that means is that the jury found that somebody had passed me information that should have been secret. I don’t want to get too into the weeds but that’s what I was convicted of. I ended up getting a 30-month sentence for that conviction and paid a $30,000 fine to disgorge my gains. I made about $30,000, received a 30-month sentence, which is quite different from the $400 billion in fines that the big banks and the other bad actors paid during the crisis when not a single person virtually went to prison for that malfeasance.

It seems so disproportionate for what you were being accused of $16,000. It seems like such a waste of federal tax dollars for this trial. A waste for you and your attorneys all around, but here you are and you’re convicted 30 months in federal prison.

I can’t disagree with that, but at the same time, that’s the system. If you take that risk, which I took to go to trial, I don’t believe that people should be punished for exercising their constitutional right to go to trial but that’s what happens. It’s hard to go from a zero-month probationary sentence if I took the deal and now you’re giving me 30 months because what’s changed other than the fact that I went to trial. Nevertheless, that’s 30 months. That was the sentence. I said goodbye to my family and was off to Lewisburg prison in Pennsylvania.

How did you say goodbye? What prepared you for going in and what did you have to do before you went in?

I don’t think anything prepares you. I was fortunate enough in that I had a bunch of friends and still do and was able to talk to people who had been through something similar. One of the funny things about going through what I went through is in many ways, it’s a blessing. It’s cleaned out the hangers on the pretending friends that are out there and you find out quickly who your real friends are. You also learn that those real friends all have family members, friends, other people they know that went through a similar situation. It’s a secret that they didn’t feel comfortable sharing before. When they know you’re going through it, they’re willing to introduce you to somebody or tell you, “I never told you this but my dad went to prison when I was in college,” and so on and so forth.

I probably met with a half dozen to a dozen people who had been through the system and go into prison just to get the lay of the land and find out what it was like. Those people helped me quite a bit to understand what I would be facing and where I was going. I’ve done my best to return that favor. Once I got out, I do some of the same now. I don’t charge people anything. I know there are prison consultants that do. I wanted to pay it forward and return the favor to some of what those people did for me by talking to people who are facing what can be an incredibly frightening and uncertain future as they march off to a place that most people have only seen in movies.

Because of that, I would imagine that after this entire process, the trial, the attorneys, the government, everything, and you’re in federal prison, this has got to be taking a toll on your health at this point.

It did in some ways. This is a little bit counter-intuitive, but the three best days of my life were the day my three children were born. The fourth best day of my life was the day that I walked into federal prison because once I walked in, I actually knew at that point that if I played my cards right and did my time right, I could be home in an exact amount of time. I knew it was set and I knew that I would see my children again. I prayed that I would see them again and that they’d be healthy and everything will be fine. At least I had a calendar where I can x off and know that I was getting home before that. What most people don’t understand is that it’s not like Law and Order where you get arrested, you go to trial and get sentenced and it all happens in 42 minutes without commercials. Our system is glacial and that glacial illness is some of the most damaging parts of the entire experience.

Insider trading has nothing do with financial crisis. Click To Tweet

It was two years on pretrial before I could even get to go to trial to try to clear my name. Then it was another couple of years under BOP supervision, the Bureau of Prisons. Then even once I got done with that, and I don’t want to skip ahead, but you have three-year probation after that. It was like an eight-year ordeal for something that you’ve figured that part I didn’t entirely understand when I turned down the deal, the smart money or a smarter person would have said, “I’ll take whatever is offered now just to try to move on with my life quicker,” but I didn’t take that path and it took forever.

How were you managing all the stress? What were you doing? Were you drinking?

That returns to the point it was a great day because I not only knew what my time would be when I would get home, but it forced me to be sober. It forced me to recalibrate and understand what I wanted to do with my life. During that stress of, “Am I facing ten years? Am I facing five years? What’s my sentence going to be? Will I be convicted?” I did drink. It’s not like I wasn’t drinking previously. I drank probably from the age of fifteen in high school and then turned it up when I got to college. I was blessed with enough not to be immodest but with enough raw intelligence that I didn’t have to work that hard in college and drank if not every night, six days a week in college.

Then on Wall Street, it’s a cultural thing to do happy hour and entertain clients and everything else. I was probably out three, four nights a week doing the happy hour thing and drinking. By the time of the financial crisis and the stress of all of that, the stress of the conviction or the arrest and all that, I was drinking every day. On weekends, I was taking a break by only drinking a bottle of wine. I was doing significant damage I think to my health and I didn’t realize the amount of that damage until I walked into prison and had to get sober. You realized sobriety is not the day after of not drinking. It takes a month or more to try to clear that fog. It was a 25-year fog where I had drank without a significant break for decades.

In the world of silver linings or possibly this being a blessing in disguise, it got me sober and I don’t know what would have happened if I didn’t. I probably would’ve cut my life short in some manner or even worse, do some damage to somebody else because of my drinking habits or substance abuse. Walking in and getting sober after all that time and finally realizing, “This is what it’s like to actually be able to think and to be clean and clear and then to try to start.” There are tons of time away. There’s a lot of time. There’s no privacy or decency or anything else, but you have an endless amount of time. I was able to do some exercise and to get in shape or better shape, at least. The important thing was the ability to stop drinking or to be forced to stop drinking.

In prison, what did you do? Did you have AA? Do you have a sponsor? Was there anything to help you to get clean or just all by yourself?

Those programs did exist. There was also a more formal institutionalized program called the RDAP, Residential Drug and Alcohol Program, which I was enrolled in. I was able to get some time off from my sentence by being in that program and that’s a six to nine-month intensive recovery type of program. The real way to get sober, and the way I got sober in the beginning at least, is fear. There’s very little tolerance for anything in prison if you get caught. People do everything and there’s an abundance of contraband that you can get access to everything from drugs to alcohol to steroids to women or whatnot. You can do all those things, but if you get caught, the consequences are fairly severe.

At least for somebody like me who had what’s called a skid bit, a relatively short sentence. I was able to cut my sentence to about 21 months through halfway house time and through this drug program and through good behavior, getting time credit. If I got caught drinking or doing something like that, I would have served the full 30 months and could have gotten additional time as well. Even worse, I could have gone up in security. I was in a minimum security facility, which is known as a camp. If they put me up higher, which is a lower medium, that’s the type of place where you start to get raped and where violence starts to become prevalent. Fear alone was enough to keep me sober.

It wasn’t exactly easy being in the level you were in either. You may not have been in the higher security and more of the maximum security and the higher-level offenders but it wasn’t all roses and easy and you just having time to yourself to think. You got into some fights and had some issues.

I had a particular issue that was only specific to me and that the Bureau of Prisons in their infinite wisdom put my partner and his brother in the same prison with me. In his mind, he was the one who went to trial with me. He got convicted. He got a ten-year sentence. He was incredibly angry about that sentence and I was the only person nearby to take it out on. He came after me a few times and we had to mix it up. In general, a camp for a minimum, there’s zero tolerance for violence policy. It’s a very stressful situation in that I had somebody who had his worst intentions directed at me and was trying to both physically and emotionally come at me. Life is very cheap away so you can pay people small amounts of money to hurt other people as well.

AIH 23 | Creating Inner Strength

Creating Inner Strength: When you’re sober, you face a lot of the lies that you’ve told yourself.


I’ve been told he had done that as well. The hard part is had he gotten to me and even sucker punched me if I had been marked up and cold in, there’s no like, “He hit me or he started it.” They ship you both first to solitary which is more or less torture under any type of Amnesty International or ACLU type of analysis. Then up in security to a lower medium, you had to do your best. There were several times that other inmates had said, “You got into it with someone,” or I think these guys mixed it up when a guard wasn’t there. We would get some and then they’d strip search us and pull us down and look for any marks on our body to see if we had gotten into it. It was tough. He did everything he could, including telling people I was a rat and I cooperated, which is not a label that you want to have in prison. It was nonsense. No rats go to trial. It’s functionally impossible, but it didn’t stop him from lying about that and just about everything else. I was on my toes or on my heels for the first few months quite a bit before I met enough people that were decent people. After that, I was more or less okay.

What was the scariest thing that happened while you were in prison?

It was more a long slog of before this guy got straightened out of knowing that around every corner at any point, he could be waiting for me and he made threats and whatnot and having to deal with that. It was, “I’m going home in fifteen months, but if this guy got me, that sentence would be doubled.” It was more the mental fear that I wouldn’t be able to get back to my children and see my family in a reasonable amount of time through something that was completely outside of my control. That’s the lack of control and not that I’m a control freak or anybody else’s.

One thing you have to adjust to when you go to something like prison is there are people all around you whether it’s guards, inmates, or whatnot, who could care less about your life and don’t have your best interests at heart. In some ways, they could control your fate or your outcome and you have to be nimble and smart about it. It’s not easy. There are no appeals or, “That was unfair.” It’s an absolute dictatorship that’s barbaric in a lot of ways. I don’t think most Americans would allow it to exist if they understood what takes place behind the wall and what it’s like. That’s the reason they don’t like cameras in there. If they do let them in there, they’re very tightly controlled on what they’re allowed to see or broadcast.

I can remember my dad telling me something about the story. How did you see your kids? Tell me the process with that.

There are visitors that are allowed every other week. My parents would fly in from LA to New York, picked my kids up, drive three or four hours, and they’d visit me on some weekends. It was amazing, but it was also torture because they see you wearing a uniform. They see you behind barbed fences and where you are. At least my kids are kids, they don’t understand when you’re six years old what’s going on. They’re just glad to see their dad, but they didn’t know there’s something that’s not right. It doesn’t feel right and they don’t understand why I couldn’t go home with them at the end of the visit. It’s an incredibly difficult thing.

Made doubly difficult by the fact that group punishment is very big in prison. There were times where my parents would fly in, get a hotel, drive the kids for hours and be there waiting to come in to visit. Some inmate would get caught smoking a cigarette or smuggling something in or doing something stupid and they would punish the whole group and send the visitors home and say, “No visitation this weekend.” I remember being in the field, watching them walk away one time when that happened. When you see your kids crying after driving that amount of time and everything else and thinking they’re going to see their dad, it hits home and it was certainly one of the most difficult things I’ve ever seen.

That’s a punch in the gut. They don’t understand all of this is going on. It’s stressful. Did you ever battle with depression or anxiety while you were in?

I did, absolutely. I was able to deal with it better once I was in prison again because I knew I would be getting out one day or I hoped I would be getting out one day. I hung onto that hope and I was sober. When you’re sober, you face a lot of the lies that you’ve either told yourself or a lot of the behavior and feelings that you’ve masked either through excessive alcohol or excessive exercise or whatever people do. In our society, especially now with phones as prevalent as they are, people will do almost anything to avoid having to sit with themselves in silence for any amount of time, 30 seconds or 30 minutes.

We’re always trying to fill our time and distract ourselves from the difficulty and sometimes the pain of having to sit down and think and take stock of where we are in our lives and who we are and whether we’re living up to the vision or the potential we think we might have. That’s a very difficult thing but at that point, I was incredibly motivated to get back to my children, to be a father again, to start my life over and get a second lease on life. The anxiety and the depression were a lot more when I was drinking and then facing what could be five years, ten years in prison, not knowing the outcome, not understanding the system and how it works. Other than the stress of having to battle a complete sociopath, the rest of it I felt I could handle pretty competently.

While you’re inside, what were you doing to get by with the time? What were you working on? What were you looking at? What were you reading? What were you watching?

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I try to have a little bit of a system and you could see in prison, people broke down into two different camps. There were people who would sleep late and spend their whole day watching TV or screwing around. I didn’t want that to happen. I wanted to use my time productively. In this way, it was almost a blessing. I was able to do an incredible amount of reading and studying. Think about how many books you read in a typical year. We’re so busy with life, it’s hard enough to get through a couple of blog posts versus a full book. In fifteen months, I probably read 250 books or more. I studied a lot of different angles that I was interested in learning or possibly doing when I got out. I did some exercise for a couple of hours a day.

AIH 23 | Creating Inner Strength

Confessions of a Wall Street Insider: A Cautionary Tale of Rats, Feds, and Banksters

That included walking the track they had. They did have a gym for one of the few institutions. It’s like the gym you would see in Seinfeld where they’re throwing medicine balls at each other and whatnot, but they did have some weights and they had a couple of other things. I was able to stay healthy and do some of that, then it was writing as well. I wrote probably 800 pages of a free hand which turned into the book, Confessions of a Wall Street Insider that I published when I got out. Between reading, writing, studying and working out, the time passed.

You use this time to enrich yourself and also inadvertently became sober and clear-minded while you were in prison. What was it like that first day you were out?

It’s incredible. You don’t go from prison to out on the street and having fun. I went to a Bronx halfway house, so I got picked up by my family, by my wife and kids. They give you about three and a half hours to get to that Bronx halfway house and check in. It’s a different type of freedom. You’re not in Lewisburg or not behind a wall or anything else, but you’re still under the supervision of the BOP. At least I was in the Bronx. I could see my family more often. Then when you’re in a halfway house, you get the ability to work. If you get a job, they’ll let you go out during the day to work that job. It’s a slow passage towards normalcy or towards re-entry into society. It’s a wonderful thing, but also when you see it and how it’s practiced, it’s an absurd thing because the halfway houses are designed to help people re-enter society and you see how they’re operated and anybody with any bit of logic or compassion or anything else, sees that it’s a fundamentally flawed system that’s incredibly corrupt as well.

Your wife filed for divorce while you’re going through all these?

She did.

Did you expect that?

I didn’t and it’s one of those things that’s not easy to talk about. I think she, at least at the time, regretted it but people sometimes end up despairing and falling into a very dark hole. She felt like that’s what she needed to do. I asked her not to and she said she had to. I said, “That’s fine but if you do go forward with it though, I want to make sure that you understand that it’s done and that there’s not going to be a, ‘I made a mistake. Let’s get back together,’ or anything like that.” I was in the worst place in the world, at my lowest almost and I needed someone who would in sickness or in health be by my side and for her to walk away at that time I thought made no sense.

I said, “Wait until I get out if you want a divorce. Then after giving it a try then I’m happy to give that to you and uncontested, but there’s no reason to do it now.” She said she had to. That was a couple of days left, I was supposed to get picked up by friends and she called and said she wanted to pick me up. On the ride home, she said she wanted to reconcile. We did give it a chance but it had been very tough and I had mentally moved on and wasn’t willing to go back into a relationship that had a lot of problems to begin with. It wasn’t a storybook marriage at that point either. The resentment was too much for both of us at that point.

This was a big test and understandably some people can’t make it through the test. I understand but as it stands now, how are the kids?

Kids are good. It’s funny, it’s a comment on girls versus boys. My daughter who is the oldest, she’s fourteen now, understood at the time what was going on a little bit and made some very astute observations. I had told her and if it wasn’t me, maybe my parents told her when I went away that I went to more of a camp. They try to downplay the severity of it because they didn’t think as a seven-year-old that she would understand. She read and she showed up, she would say, “Why do I think prison camp not camp? It doesn’t look like the camp I went to last summer.”

They’re trying to protect the children.

She was always aware of it. We have a very good relationship. I’ve always been open about it if she ever wants to discuss it, if she ever wants to talk about it. She asked if she could read my book several years ago. I asked her to wait until she was a little bit older. I think she was twelve at the time. The content in the book is very raw and real and it certainly will be personal for her. I thought, “Wait until you’re fourteen, fifteen, sixteen to read that if you want to read it.” My boys are boys and not to make fun of them, but there will be times where I’ll do an interview on TV or write an article and it will be like, “Dad, it says you went to jail. When did you go to jail?” I’m like, “We talked about that probably 38 times. Here’s what happened.” They don’t remember nor do they care. To them, I’m their father and that’s it. A humorous comment on age, but also on boys versus girls to some degree.

After everything you’ve been through, what keeps you going? What is your why? Do you look back at all of this craziness? What is your why for continuing forward and how do you keep yourself sober and clear and work on your mental health?

You’re very successful right now, which you turned it around.

It’s a combination of things. Everybody has to have a why. My why was my children while I was going through that time. All I prayed for when I was away was not my own health or anybody else’s, but for theirs and that they would be there in one piece when I got out and I was granted that wish. I’ve tried to live a life since then of service and a purpose. I’ve done, from an entrepreneurial perspective, quite a few things. I’ve done a lot of writing. I’ve done a lot of coaching and speaking. I’m passionate about trying to help people who have been through something, not necessarily exactly what I went through but I think everybody has their own demons in their own struggles. Mine happened to be a little bit more public than certain people’s.

To some degree, everybody is broken and to be able to admit, whether it’s financial, whether it’s psychological or spiritual, that we’re wanting and that we’re hurting in some way. For people who have real trauma, and I don’t want to say real trauma, but have trauma, whether it’s bankruptcy, divorce, addiction or whatnot, to be able to speak to those people and show them that there is a way out. There is a way to overcome that and that in some ways these obstacles and struggles that we go through. I’m thankful for my struggle because I think without it, I wouldn’t find my true strength and I wouldn’t have been able to have the gratitude and perspective for everything I had now. I was the cliché before I went through what I went through and that I had as much money as I needed.

I had three beautiful children, a beautiful wife, a big house. I had sold a piece of my farm. I had a farm worth eight figures and I was miserable. I just wasn’t happy. It was a combination of feeling that I wasn’t put here on this Earth to be able to do what I was doing at the time. It was also my drinking. It was also hiding from myself in a lot of ways and trying to mask that pain through either exercise, drinking or distraction. The ability to have in some ways a near-death experience where I had everything taken from me. They took my firm, my career, my degrees, my law degree, my CFA degree, my securities licenses, it took all my finances and eventually, they took my liberty and to some degree, my marriage.

To be able to have that and be wiped away and came out with nothing but the clothes on my back and still then realized how incredibly wealthy I was and how blessed I was in comparison to certain people, whether they had health issues or lack of family or mental faculties. It was a valuable reset for me. It was a horrible thing to go through. I wouldn’t wish it on anybody else, but in some ways, it makes the rest of my life higher caliber because I understand and appreciate more everything I have now and I have a great deal of gratitude for that.

You said you read a whole bunch of books. Give me a book that stands out for you. Something that changes your life inside.

There are a ton of them. I’ll tell you a few of the favorites that you read in prison. Victor Frankl’s Man’s Search for Meaning is probably the biggest one. I don’t mean to in any way compare my situation or anybody else’s to his situation. It’s a book about surviving Auschwitz concentration camp, the depravity of man and what he goes through and how he gets by. It’s a brilliant book and it’s a testament to the human spirit and the fact that we have such an incredible ability to adapt and to overcome almost anything. We live in fear of so much but if you can get past that fear and accept where you are and what you have, it’s a book that inspires and also relative lets you know, “This is not that big a deal.

Sobriety is not the day after of not drinking. It takes a month or more to try to clear that fog. Click To Tweet

This guy survived circumstances that’s a thousand times worse and he was able to get through it. “I’ll be able to survive that,” that’s the biggest one. Then there’s a whole series of different books that are similar to that, whether it’s The Count of Monte Cristo and others where it’s people who feel they’ve been wronged and/or any book that tackles mental toughness and how to get through what you’re going through. People love that stuff away. As well as the classic, The Wolf of Wall Street, and all those big broad partying books.

I want to say I’m absolutely fascinated and inspired by your gratitude because I know personally when I’ve hit low points in my life. I try to look at the big picture and say, “At least I didn’t lose this or at least my kids are healthy and this will pass.” I always love being able to hear from other people who submerge themselves in gratitude and you are truly an inspiration for others who need to put things in perspective when they look at their life as a whole. It sounds like you’ve come out a solid individual who is an inspiration to many now. You should be very proud of yourself.

Thank you, Elsa. That means a lot to me, especially considering what you’ve been through and what Sean’s been through and you hit the nail on the head. Perspective and gratitude will get us so far and also that nothing is permanent. Everything is temporary to some degree. Failure isn’t falling down. It’s staying down. I think it was Cesar Chavez who said, “You can’t oppress somebody who isn’t afraid anymore.” Once you remove that fear aspect from your life, and that’s a very difficult thing, but the fear controlled so much of our lives and so much of our unhappiness and so many of the decisions we make. Once you tamper that or remove it, it unlocks a whole series of potential and opening that’s out there and keeping things in perspective.

AIH 23 | Creating Inner Strength

Creating Inner Strength: One thing you have to adjust to when you go to something like prison is there are people all around you who could care less about your life.


Everybody has so much to be thankful for. Literally, people thought I was insane when I walked out of prison with nothing but the clothes on my back. I was practically giggling with laughter because I got to choose where I went, how I dressed, what I could eat, what I could read, when I can see my children. I have three healthy children. There are people who never had children and it’s the dream of their entire lives. That’s something they’ve learned to deal with or have had to deal with but that’s incredibly difficult. Here I had three of them and three healthy ones. Everybody knows somebody who has children that have either special needs or have ailments or whatnot. How could I be depressed or feel bad for myself?

They stripped my degrees and everything else, but they didn’t strip the knowledge that I spent or the training I spent acquiring those degrees. I don’t have my law license or my securities license or anything else, but I still have the knowledge and the training I got when I was getting those licenses. You got to take a step back and look at it. Think about it. Who do we know from a hundred years ago? Maybe a handful of people that are presidents or Albert Einstein or somebody like that. In 100 years, is any of this going to matter to a great degree? If you didn’t get the right salad dressing on your salad or if the girl you liked didn’t reciprocate that feeling. 100 years from now, it’s not going to matter. Concentrate on the big things and the important things.

Tell us what your book is and what things you’re working on right now.

The book is Confessions of a Wall Street Insider. You can grab it on Amazon or anywhere else. If anybody is interested in Wall Street finance, prison, criminal justice, they’ll enjoy it. It’s a very raw and true account of what it was like to be at ground zero of the biggest insider trading investigation in history. What it was like to go through the system and the toll it took on me and my family. I think you’ll enjoy it. I am editing and publish in a financial newsletter that’s geared around blockchain and cryptocurrencies. I do a lot of consulting in that space and it’s been great.

It’s an incredible technology and exponential technology that I think is going to have a big impact on the world. As somebody who has had not only my freedom and liberty taken from me but understands the dangers of a central authority when it comes to either technology or banking or government or anything else. I’m a very big believer in the concept of decentralization and Bitcoin and crypto are going a long way towards not only implementing that but given the two or three billion people in this world that the ability to have a bank account or to bank. The ability to do that is going to be revolutionary in many ways and it’s exciting to be in that field.

After what you’ve been through, I can absolutely see the appeal. Michael Kimelman, thank you so much for being with us in Adventures in Health. We wish you all the best.

It was amazing, Elsa and Sean. I loved being here and I look forward to talking to you soon.

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About Michael Kimelman

AIH 23 | Creating Inner Strength

We live in an age of disruption.  No matter where you are in society, or where you were, the unexpected can strike.  Loss of job, health, home, career, reputation, loved ones—or simply the lack of opportunity, can happen to anyone. Anywhere. At any time.

We look to others to guide us, inspire us, coach us through the mists to what we define as success. In an age of uncertainty, we look to those who have fought the battle and won.  For these are the precious few who can transfer their experience, wisdom, and momentum to our unique situations.  In short… A speaker or a coach cannot give you what they do not have.

If you are looking for someone to help you navigate, gain confidence and thrive, you cannot do better than Michael Kimelman. No one better exemplifies the quality of American Resilience.

Here’s his story.

It sounds like something torn from the pages of Grisham or Turrow.  Mike was living the American Dream.  A talented attorney running a successful hedge fund, Mike was married to a beautiful woman and they had three wonderful children.

But when fate, in the person of the FBI, knocked on his door in the middle of the night, it all vanished.   Not at once.  There were specious charges.  A questionable judge. An unjust trial followed by a 30-month jail sentence.

When Mike was released he had lost a lot.  His wife.  His money. His law license. His career. His reputation. Precious time with his children.  His world as he once knew it no longer existed.  This could have crushed anyone.

But Mike had gained something more valuable than he lost: an inner strength that gave him the peace and power to rebuild his life—and the compassion to help others, whatever their situation, do the same.

Newly empowered, Mike became a coach, an entrepreneur and the bestselling author of Confessions of a Wall Street Insider.  He is a founding partner in Crypto.IQ, a company that advises investors in crypto assets, hard money, and new markets.   He is a leader in prison reform.   And a sought-after speaker in all of these fields.

Mike has reestablished his role as father to his children and expanded his professional circle.  More than that, Mike brings to a chaotic and sometimes Kafkaesque world a calm and insight that reflects is the ability to tap and use his inner resources—and extend them to others.

Perhaps the simplest way to describe Mike’s journey is that he walked through the fire and came out a better person.   Today, he has the experience, the compassion and the resources to inspire and help others a speaker and a coach.   Or catch his podcast.

Remember, a person cannot give you what they don’t have.

Mike delivers.


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