Ira Judelson - Bail Street, with NYC's Leading Bail Bondsman - [Invest Like the Best, EP.40]

I know firsthand how complex the tech stack is for asset managers, and seemingly every new tool and data source makes the problem even worse, adding more complexity, more headcount, and more risk. Ridgeline offers a better way forward, one unified platform that automates away all that complexity across portfolio accounting, reconciliation, reporting, trading, compliance, and more, all at scale. Ridgeline is revolutionizing investment management, helping ambitious firms scale faster, operate smarter, and stay ahead of the curve. See what Ridgeline can unlock for your firm. Schedule a demo at ridgelineapps.com. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open-ended exploration of markets, ideas, methods, stories, and of strategies that will help you better invest both your time and your money. You can learn more and stay up to date at investorfieldguide.com. Patrick O'Shaughnessy is a principal and portfolio manager at O'Shaughnessy Asset Management. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'Shaughnessy Asset Management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of O'Shaughnessy Asset Management may maintain positions in the securities discussed in this podcast. This week's episode is very unique. It is the first episode devoted to bonds, just not the kind of bonds you might be expecting. My guest is Ira Juttleson, who is the leading bail bondsman in New York City. I met Ira through my friend and former podcast guest, Danny Moses, who is also a part of this conversation. I've always had a passion for understanding how different businesses work. In this case, this week we are exploring a different business, but also a different world. Ira's story is larger than life. He is as authentic and hardworking as they come. In both his book and this conversation, there is a lot about family, loyalty, and hard work. principles which really resonate with me. You'll emerge from this hour with an appreciation of hustle and what it takes to get ahead. I can't stop thinking about our discussion on how sources of power in any career morph through time, a framework that can help anyone think about their work and where to apply effort. The conversation goes all over the place, but suffice it to say we discuss Bond Collateral, Dominic Strauss-Kahn, and DMX, and that is but one small fraction.

Please enjoy my conversation with Ira Jettleson and Danny Moses. Before you came in here, Danny was telling me about a recent TMZ article at Rayos. And I was going to wait until later in the conversation to get into Rayos. But I figured maybe we'll start there. So I've actually never been to Rayos. You're missing out. I know. Most people listening either will have been or certainly know of it. So let's just start somewhere kind of interesting what Rayos has meant kind of to your business and your career. So Rao's is obviously the eatery in Harlem that you can't get a table. There's no reservation. And it's almost like owning your own condominium. It's your table for the night, and you get a certain amount of tables a year when you're on the books there. And being there and being in the business that I'm in, because I'm also in the title business, which I deal with a lot of developers, anybody could buy or use tickets to a Knick game or to a Yankee game to take your clients out. But when you take them to Rao's... You know, there's [redacted address]. And you're walking in and Leo DiCaprio's on one side. And you got Bo Dietl on another side. And in the back is Jason Gedrick. And then, you know, I was there one night with Tommy Mottola, Mariah Carey, Danny DeVito, Jim Carey. And then you got us in there. who basically just came off the streets. It's an unbelievable mix. And the people there, Frankie Pellegrino just passed away, who was just an icon, just a beautiful man, respected all over New York, a great actor and a great singer. And just being in there, the warmth and the family that they make you feel like you're eating in your kitchen with the greatest people that want to get into that place. And taking people there, I mean, I've taken... Every one of my friends there. And, you know, obviously I was there the other night and Fat Joe was there. And I brought Fat Joe with me. And Fat Joe is my partner. You know, we've done, we have a business called jammedup.com, which is a... It's supposedly we're going to do an app for the industry of criminality. So you can find anything you want on the app. You can find a lawyer, civil criminal, a bail bondsman, a DNA specialist, anybody you want in the legal field. And Joe jumped behind this. And Joe's a friend, and we went there the other night.

And next thing you know, they're playing all the way up and lean back. And Joe's dancing and singing. And the place is going wild. And it's 1 o'clock in the morning. And then next thing you know, TMZ hears about it. And they're calling. And they're like, tell us about it. And the next thing you know, the Daily News found out about it. And it's just wild. It's just a wild night. But Rayo is a great place. And I have to take you there one night. I want to make a comment on Rayo. So I've been there a few times, obviously, only with Ira. So the few times I've been, these are my memories. One. The hardest handshakes I've ever felt on planet Earth when you walk into a place, too. I ask Ira, can I look at that guy? Can I talk to that guy? Lastly, someone always sends over shots of something to us. And one time someone sent over shots and I didn't want to do it. I'm like, I can't do this tequila shot. Now I'm too full of meatballs. Ira goes, you'll do that shot. And you will do it now. I look over and I'm like, yep, love this tequila. It's great. Did that shot. So there's some etiquette there. There's a lot of very strong people that go there. It's a great place. And I love the people there. I love the staff there. friends. They've been to my home. I used to throw a white party in my backyard and they've come to that. And my kids' bar mitzvahs, they've made meatballs for both of the bar mitzvahs. And Dino, the chef, is a very good friend and a great cook. And I could actually say that hopefully I'll be able to pass the tables on to my son or my daughter one day because it stays in your family. Yeah. We talk a lot about brand as it pertains to companies on this show, looking as an investor at a company to invest in you on a strong brand. I can't think of a place that has has a stronger brand in the food world than that. There's nothing comparable in New York. And I've followed the food and seed pretty closely. Especially their sauces, which I believe, if you read in the newspaper, they've recently sold their business and their sauce business. And just the atmosphere. Now, they have other different places that they've done out in California and Vegas. But being in the New York one.

With the Christmas lights up, with my picture in there, with other people's picture in there, is just a special place to be. And it's a great place to really let loose and feel comfortable. Because you go into a restaurant a lot of times, you never feel comfortable. You're always looking around, asking for water. When are you going to get your meal? It's not like that there. So let's go all the way back to the beginning of the road that led you to get the table at Rayo's and talk about the bail bonds business, generally speaking. We talked a lot about bonds last time. This is a very different kind of bond. And I was completely, before your book, completely unfamiliar with the whole world, as I imagine most people listening will be. So maybe we could start with super basics. What it is, what the business is, how the economics work, how you earn fees, how you... as a business earn fees and we'll dive into some of the kind of interesting underwriting aspects and stories. Basically what a bail bondsman is in the terms of the court I basically put up a bond to secure the defendant's appearance in court and I take collateral behind that bond sometimes if I can get it and to make the court feel comfortable that that defendant's going to be in court and that they have something to lose if they. don't come back. As far as on the street terms, I could be known as a legal loan shark. I take a one-time fee as a rate to secure that the defendant will come back to court. And again, I take collateral to do that. As far as my fees go, in New York State, it ranges from 6% to 10%. Plain and simple. Of the value of the bond. Of the value of the bond. The smaller the bond, the higher the fee. I do a lot of large bonds. And that I try to get as much collateral as I can. There's other bonds companies that take jewelry and fur coats. And I know one bondsman in Arizona once took tables and chairs from someone's house. I normally take real estate as collateral. I feel that's the most. comfortable position for myself. And we secure it the best way we can. And I've built up relationships in the courthouses with DAs and judges who are on the other side. And I understand their business and I respect them 200%. They're doing their job and they have to do their job because they don't care about what I'm making. They want to make sure the defendant's there. But again, this is a business for me and everything is a business in life. And I want to make sure that they're comfortable. And we've built up relationships. And I have a lot of judges that I know and I respect.

talk to off the bench and we talk about a lot of different things. The same with DAs that, you know, are in there for, you know, sometimes they call them lifers. They're in there for a very long time. And then some of them are kind of, you know, like they're going to war. They're in there for a couple of years and then they're getting out. And, you know, those are the guys that are eventually going to come on the other side and we become friends and, you know, they bring me business. And we've talked about different things about that. Before we get back into the relationships and how important those are, because that built that slowly building a network and there's a phrase or I'll actually even quote. you in a little bit on this idea of sources of power within the business that are either kind of forced or just that kind of grow over time with these relationships. But could you first tell that story about when you learned that a pizzeria was a bad piece of collateral on a bond? I was in business. God, I can't even remember. I was just in business maybe a couple of years. And I was literally wet behind the ears. There was actually water behind my ears. And I... was so excited I finally got a big bomb and this guy came in and he brought all these documents into me and I look at it and I'm like oh pizzeria this is great god I mean I've been eating pizza my whole life you know look at all the people going in and out and what I didn't realize obviously if you when you read the book is that who I was actually bailing out was the guy that they actually had a KOS on, which is kill on the spot, which I had no idea, and that he was wanted on the street, and that he was actually cooperating with one agency, but meanwhile playing me in the other DA's office on another agency. So I take this pizzeria, and unbeknownst to me, I'm not even thinking that he doesn't own the building. Then I'm just taking pizza ovens and knock on wood that, you know, I'm sitting here saying, oh, wow, this is great. And I'm running it through my insurance company. Well, I do the bail. And obviously, you know what happens? The guy jumps. And now I'm stuck with a pizzeria. Oh, OK, I'll sell the pizzeria.

Go by the pizzeria. There's nothing there. Just dough. It's not even the ovens. The guy sold everything, got rid of everything, and I was out of a big number there. But it was a great learning experience, I guess. I had to learn a little bit about the business in the beginning and not to get so excited on a big bail, knowing that at that time in my life, there were some other bondsmen in the business, some old-timers, gentlemen I respected. And if they passed on this and it came to me, then something must have did not pass the sniff test. So now... Today, I'm in a different position where other smaller bondsmen, when they see bonds like this, say, well, wait a second. If Ira Juttleson's not doing the bail, what's wrong with it? So I ended up getting burned, and I didn't even get any pizza from there because I went by the place and there was nothing there. But I did get the defendant. We did actually get him. We got him before some alleged gang members got him on this KOS, and we ended up getting him back in, and I tried to deal with the agency that had the bail. bond and see if we could work out a deal. We ended up working out. some sort of a settlement. I didn't have to pay the full amount on the bond because we did bring them back, but we brought them back later than we were supposed to. Early in your career versus later, say now, what percentage of the time are you dealing with that issue with someone that's jumping? In the beginning, I would have to say that everybody jumped on me, including grasshoppers, because I had no idea what the hell I was doing. It was just unbelievable. I would take anything and everything off the street because I didn't understand the industry really that well. I would say back then, I would say probably 10 or 12% jumped on me. Now I would say... less than 2% jump and a lot of times when the less than the 2% jump a lot of these guys are actually in prison already under aliases and then when you run them through some different

Computer checks, you realize that they're under John Smith, but they're in Virginia, but his prints came up, so whatever. So you deal with, and that also goes back to the terms of relationships. I now deal with all the DAs who are on the civil side and say, you know, listen, come on, the guy's in Virginia. And they're like, okay, Ira, no problem. We don't want to break your chops, and we'll let you go. What do you say? You owe $25,000 on that bond. You want to settle for $15,000? And I'd say, ah, come on. But we work it out with them. They're good people. What's the size of the business in terms of? of the number of cases you're dealing with at any given time, the size of the open liabilities? How big are the numbers? I take 20 phone calls a day sometimes, and that's just me. On my cell phone, on my personal phone, my office takes maybe another 10 or 15. So you're dealing with calls all day long, ranging from a $500 bail to a $5 million bail. We might pick two that day, three that day that we feel comfortable with. Sometimes we pick none because people don't understand the world of bail bonds. And it's all risk to me. It's a risk factor. I'll take a 15-year-old kid that's never in trouble before, comes from a hardworking family. He might have got caught on a truck. train with six other guys, and they might have stole somebody's cell phone or allegedly stole somebody's cell phone, and they pinched all these kids, and the parents are hardworking people, and they got nothing. I'll take that bail. Then you give me some other gentleman that basically might be here for only a year or two and might be involved in the pharmaceutical business, and he's looking to do the dip, and I'm not taking that bail. And so the open liabilities, how long will these things typically last? I've had cases last six, seven years. Wow. Sleepless nights. Remember, I put a lot of money on the street, and these cases could last five, six years sometimes. So you could do $20, $25 million of bail a year. Now figure it out if these cases are going on. You've got $[redacted address]. I just thought of a great story, by the way. Ira and I are down in the Bahamas playing craps together. Ira's rolling the dice on one end of the table. I'm at the other end. So Ira's on a hot roll. He's actually rolling the dice. Some guy standing across from me actually looks up. He goes, Ira, and Ira's literally not paying attention. Six, mark the six.

Point hit six. Ira looks up at him and he goes, hey, man, what's up? He goes, yeah, I was the lawyer for this boxer that you bailed out. And Ira goes, yeah, where is that guy? Ira rolls point eight, mark the eight, points eight. Ira rolls, he goes, he was killed a couple weeks ago, literally in mid-flight of the Dice Ira. We got to exonerate that bail. This is an example of having money out on the street. True story. True story. I'm like, who's this? It's a great story. Yeah, we actually, actually, that was a promoter. And I actually, he called me on the phone. We did the bail. and I remember the open liability on that bell and I can't keep track of everything. I'm almost a savant in a way in my head and I'm sitting there rolling and we had a great roll going, didn't we? Yes. And I was like, there's no way anybody's going to break up this roll. And we started rolling the dice and I said, by the way, where is that guy? I haven't heard from him. He goes, I got shot the other day at a bodega. I go, wow, that's great. Lucky six, lucky six. I go, we got to exonerate that bell. And we were both dying laughing. Unfortunately, that boxer passed away. But these are the stories and the tentacles that reach this business because it's almost like Kevin Bacon, Six Degrees of Separation. You go somewhere and somebody knows somebody dealing with the business that I'm in. With those numbers, I kept thinking of this as I was reading the book. There's almost like a doctor-patient-like component where some aspect of it you can't help but get emotionally involved, whether it's someone you feel needs your help and is being wronged versus probably most of them which are pretty clinical. okay, what's the collateral? Let's see him out. If I tell you, and I mean this from the bottom of my heart, I'm a blue collar guy. I live in a white collar world because I want to give my kids everything that I didn't have. And sometimes it's very hard to ground my children because they'll go to somebody else's house and say, oh my God, did you see that basement? And I'm like, oh, we got a pretty good basement here ourselves. And daddy works 24 hours a day, seven days a week, and he deals with some very serious people. But I get very attached to my clients.

very attached because sometimes good people make bad mistakes and sometimes bad people just do what they do and if I told you that I trust when someone walks in my office and you can get somebody walking in your office or someone on the phone and what I do for a living I don't read very well sometimes I don't write the greatest but I am one thing I'm great at I'm a great judge of character I could judge you and I can read you right off the bat. And I basically hear when someone at their most vulnerable stage need me and if they're lying to me or they're telling me the truth. And when you get involved with your clients, you want them to feel like, hey, you know, that's my guy. Ira's my ally. And I have a lot of people that I don't know if they're listening to this now or who are incarcerated. today that will say, that's my guy. That guy went to bat for me. I had nothing. He took me out and he was able to keep me out for two years. And I was able to go and hang out with my family and watch my son grow up for that two years. And he helped my mom and he put commissary money in my place. And I get close to them and I become their rabbi. I become their priest. I become their employment agency. I become their doctor. I become their psychiatrist. I wear a ton of hats. And that's what separates in my opinion. opinion me from a lot of other people because I get invested in my people because number one I want them to feel like if you hurt me are you wrong me can I curse on this thing sure if they fuck me okay then they're they're hurting me and my family and I went to bat for you I fought to get you out you had nothing And I went to bat for you. And I gave you that two years or maybe even better. I cut time off because you were able to stay out and then make a better deal for yourself. Because if you were in, there's no leverage when you're inside. When you're inside and you're in jail and the DA makes you an offer, why would they give you a good offer? They got the leverage. They don't need to give you a good offer. But you get out and now your attorney's filing motions and you're looking at discovery.

Then the playing field gets even. And I gave you that opportunity. So don't hurt me. I'm there for you. You do right by me and I'll go the extra effort. You fucked me. Well, there's a different component. There's a different side to me. How did you get into the business? What was the initial, it's a great story in the book. It's a true story in the book. At that point, I didn't know one of my best friends who's sitting next to me, Mr. Moses. I was down and out on my luck to no extent. I tried to become a sports agent. I tried to basically, I own nightclubs and bars. I did some other things with people to try to make money. And I was playing professional softball. And you say, what the hell is professional softball? Well, I'll tell you what professional softball is. Arc softball, the arc, you would go around to all different types of. places to play. North Carolina, South Carolina, Florida, California, Vegas, Jersey, Connecticut, and anybody that's played arc softball understands those tournaments all over the country. And I had a sponsor, and this was his country club. You know, this was his, you know, Paul Newman, Minnesota Fats days where somebody would stake you to play. So he'd put up the fee, $300, $400 to get in the tournament, and we'd play for sometimes $5,000, $10,000 a tournament. And he'd pay some of the other players to play because I'd say to the guy, I'd say, listen, I can't play this weekend. What do you mean you can't play this weekend? I said, I got to work. I'm bouncing in a bar. I got to make the $150 that I'm going to make. But he goes, I'm going to pay you $350 for the weekend and you're going to come play for me. And I said, oh, $350? Jesus Christ, I'm going to play. And this is something I loved. And I couldn't have been more down on my luck. They didn't have chapter 7 and 11 where I felt at that point. I wanted to find another chapter. I was living with my parents. I mean, I was literally living with my parents. I was 29 years old. My ex-girlfriend comes to the door. She's married with three kids and she looks at me and says, oh my God.

You still live here? I used to come up here for, you know, to hang out with you. I'm like, yeah, well, you know, you're lying. You're like, I just moved back and da-da-da-da. And she's like, oh, you're going to go to the 10-year reunion for our high school? I'm like, well, what am I going to say? They repoed my car. I'm still living with my parents. I have no job. And my parents are paying the cable bill. And I basically, that's how I felt. So I'm playing this softball and we go and play in a tournament in New Jersey. But before that... I had a very close friend at the time, and he was a criminal defense lawyer. And I happened to be in his office one day, and somebody walked in, a Hispanic young man. And he was like, man, you know, I'm going to do my time. I got to lay up and do what I got to do. And I'm listening to him talk. And he's like, you know, can you get the bond, get my house released, my mom's house? And I'm like, he's like, man, I paid the bonds for $15,000. Man, that's down the drain. I was only out six months. And I'm like, clicked in my head. to my friend. I said, how do I get in this industry? He's like, well, there's one guy. He goes, I use one guy. Let me introduce you to him. You can get some lunch. So he sets me up for lunch with the guy. And I go to lunch with the guy and the guy basically, he ate for about 86 bucks. I had $100 on me. I couldn't even have a salad for myself. And the guy gave me absolutely nothing. He gave me the Oliver North, where you basically just go around in circles and my head is spinning. So I learned nothing. So I come back to him. He goes, well, how was the lunch? I said, it was great for him. He had chicken piccata. He had fried zucchini. He ended up having some tiramisu. We had coffee. He goes, what'd you have? I said, I couldn't even order grilled chicken over a salad. I was afraid in my mind, thinking in my head, I couldn't order the grilled chicken. So I had the salad.

So he says, well, I deal with another guy. And he gives me the number of this guy. I call that guy and I meet him for lunch and the same thing happens. I spent money on lunch and nothing. So I gave up on the business. So now we fast forward him out in New Jersey. We're playing in a huge tournament. And our sponsor used to say to me, hey, do me a favor. If we get to this Sunday, which a lot of times we did, and we're in the top 10, which he's going to collect money from. Please don't go out all night and drink and go crazy. And now you got to understand something. I'm single. I live with my parents. Okay. I'm playing second base and I could play hammered. So he would say 12 o'clock curfew. I'd be like, no problem. 1215, I'm literally leaving the hotel door. And I'm taking three other guys with me who are like unbelievable. And he hated me for that. But we would go out to all this. We came in like 430 in the morning. We walk into this Ramada Inn in New Jersey. We walk in, and I couldn't even stand. I think I might have had, at that time, Jose Cuervo. That was my drink because he didn't even have Patron or Don Julio at this time. And I come in, and I'm hammered. I tell the guy, can you give me a wake-up call? And the guy says, you know, yeah, sure. So I go back, and 7.30 to knock on my door. We have an 8.15 game. Finally, I wake up them all. I asked for a 7 o'clock or a 6.30 wake-up call. Nothing. So a guy comes, gets me a run out. We come back, and I think we went 2 and 3 or 3 and 2 that day. Came back in like 3 o'clock. We played game after game. I'm completely hungover. I'm in the sun. And I looked at the guy. I go, how could you not give me a wake-up call? He's like, oh, jeez, I'm sorry, blah, blah, blah. I go, you don't even have alarm clocks in the room. So he says, oh, my God, right. He goes, well, tell the owner he's walking in. And this little old man walks in. He looks like George Burns from the Sunshine Boys.

And he has on a, he has a little, you remember those little watches that used to sit, the pocket watches? It's one of them. He has a three-piece suit. I said, hey, I said, no alarm clocks in the room? He goes, who are you? I go, I'm the guy that didn't get a wake-up call, but I don't want to throw the guy under the bus. So he says, oh, he pulls out a little pad out of his little pouch, which he's sticking right by his chest. He writes down alarm clocks. And I said, blah, blah, blah. I said, where'd you make your money? Real estate now, right away. And he goes, no, bail bonds. And I go, bail bonds? I tried to get into that business maybe a year ago. I bring my friend over. I go, this is my friend. And he says, hi. He goes, I'm a criminal defense attorney. Where do you practice? He goes, Bronx, Westchester, Brooklyn. He goes, you know this one? You know that one? He goes, yeah. He goes, I'm the bank for everybody. I own the insurance company. I said, really? I go, could I call you? So I write his name down real fast on a Ramada Inc. card. And I told you I can't write very well. So that's why this story is going to get very, very funny. So I go home. So now I'm sitting in my house. And there's my Jewish mother who's sitting there. And she comes out. And she's in a little nightgown. And I'm like, should I do what you normally do when you get something? Like you meet a girl in a bar. You wait three days to call her. Or should I be 29 years old, college educated, living with your parents? Should I try to make something out of this? So I said, I'm going to call the guy right away. So I call up. And I hear, I go, hello. Yeah, hi. Can I speak to Mr. Phil? Yeah, hold on. He gets on the phone. Hey, what's up? I told you I met you tonight. What? When? What? And he's 85 years old, this guy. I don't remember. I go, yeah. Oh, yeah, yeah. Call this one. So I go, really? He goes, yeah. Call him. Tell him you don't miss the Phil. So I call the guy back up. I said, this is the guy I had the lunch with for 86 bucks. And he says, I go, hey, how you doing? It's Ira Jettleson. How are you? He says, good, good. What's up? I told you. I go, yeah. I go, you know Mr. Phil?

How do you know Mr. Phil? Tone changed. Totally changed. He says, well, I met him out in New Jersey. And then when he realized that I didn't really know him, he basically was like, well, but his tone changed right away. He's like, well, I told you whatever, this, that, whatever. I said, okay. So then I called the other guy up. Same thing happened. How do you know Mr. Phil? And I told him, he goes, listen, son, buy a hot dog stand. I go, hot dog stand? He goes, yeah, there's no money in our business. I said, okay. So I get off the thing and I leave the car down. And now, you know, I was very depressed at that time going from highs and lows. I mean, an elevator is nothing compared to what was in my world at that time. And my mother goes, you sure you wrote that name down? It took two years of frustration. All came out in that three minute. berate of my mother i know how to write a fucking name down you think i don't know how to write a name oh what i'm not college educated oh i went to school oh you're gonna make fun because i live and she's like whoa i just didn't know if you wrote that name down i go i'll prove it to you so i call up the bonding company And I said, hello, it was Mr. Phil. And now it's like a Gordon Gekko moment. They want nothing to do with me. They're like, no way. I told you we'd bind the two businesses together. Yeah, absolutely. It's Wall Street all over. And the secretary's like, I can't put you through. I go, please, please. She's like, I got to know. And she's like, whatever. I go, how do you spell his name? She goes, oh, it's K-O-N-V-I-T-Z. And I told you I don't write very well. I wrote K-O-N-V-I-Z when I ran out of the Ramada Inn. I go, whoa, whoa, whoa. It's not K-O-N-V-I-Z. She goes, no, it's K-O-N-V-I-T-Z. There's a T in there. I go, you sure? She goes, I worked for the man for 35 years. I think I know. So I look at my mother and I go, what are you, Dionne Warwick? What the fuck is this? And she goes up into our little co-op apartment. She pulls down a wedding album. And she goes, is that the guy? I go, oh, my God, that's the guy. She goes, oh, we're related to him.

I go, what? She goes, yeah, we're related to him. She goes, your grandfather went to jail. I go, what? My grandfather went to jail? So now I realize that I'm related to the guy and that my grandfather did time. So she goes, we went. I had no money. Your grandmother was dying of cancer. I needed money to bail my father out. And we went to him and he lent us money because he wasn't registered in New York at the time to do a bail bond. So he gave us money. I go, mom, please. Please tell me you gave the money back. She goes, no. I go, you didn't pay the guy back? She goes, no. I go, you got to be fucking kidding me. So now I got to get back. So I get back on the phone and I said to the secretary, please put me through. She goes, call back after five. So I call back after five. And lo and behold, she gets me and she's like, hold on. He gets on the phone. I go, Uncle Phil. He goes, what? I go, Uncle Phil. And he goes, who are you? I go, I'm his fucking. I'm family. He had no idea who the hell I was. I told him our relationship. I told him they were at my mother's wedding. He goes, wait a second. You're a cone, right? I go, yeah. He goes, your grandfather was Harry. I go, yeah. My great-grandfather. He goes, how you doing? I go, good. He goes, you want to be in the bail bonds business? I said, yeah. He says, I'll be out here next week. Now, Grant, there's a lot more in the book where I had to go out and I had some issues and he helped me through it, but that's how I got in the business. Crazy. Serendipitous. Unbelievable. So early on, you're taking anything pretty much, right? I take anything. And at that point, did you have kids yet? I did not have kids. So how long were you in the business before your daughter was born? My wife... now, who obviously was my girlfriend when I first got into it, is one of the main reasons how I was able to pass the state exam and get my license and totally supported me to no extent. You ever see the scene in Rocky II where...

Rocky has to read. He does his first ad in the morning. I put it on. It smells nice. Right. Blake is like... Blake's Talia Shire. Talia Shire, helping him read. I'll be right. Get him to the next level. She basically is like, you're not getting a piece of ass until we figure out you're passing this test. I want a ring. It doesn't have to be a big ring. And I'm like, okay, no problem. And she is my rock. She's my soulmate. She's my best friend. Without her, I'm not even here today. I mean, and I'm not saying this. And Danny knows her better than anybody because our wives... are very close. She's a bondsman's wife. She's the only Jewish girl from Long Island, has no money, and came into the relationship like that. But she is the most beautiful, genuine person and understands that if I have to go out in the middle of the night and I'm dealing with whoever I'm dealing with, she knows how to deal with it and understands how to raise our children and knows how to do the right thing. It's never a problem. And she was very supportive and understood that. I did not have kids, but I was pregnant. I think she was pregnant. We got engaged in 98. We got married in 99. I was in the business at that point. I'm fascinated by people's families and how they balance work and family. And obviously what you do at 24 hours. Have you ever met my kids? The most extroverted kids you've ever seen. I bet. My daughter won't get on a bus without looking to see. If somebody has a red or blue color on, she thinks they're a cripper of blood. I'm like, no, they're just wearing blue today. So how do you balance it all? I mean, I can't begin to imagine like the number of stores you've got. Where you're thinking about your family. Obviously, you're working hard for your family. That's the genesis of this whole thing, right? As you said earlier, and that's really what matters. But obviously, you're also in a very interesting line of work, right? Where I'm sure there's moments of fear, of danger, et cetera. So how do you think about that? How do you balance that? It's a tough balance. It really is. It's a very hard balance because, again, as I stated, I am a blue-collar guy. My father worked at Rikers Island Prison as a teacher. My mother worked in bond with Teller. I think the most money they ever made.

Together, it might have been $80,000 growing up. We lived in a tiny co-op apartment. And I want my kids to have everything. I want to give them what I didn't have. I want them to develop and meet people that will help them down the line. So if my son says, hey, Dad, I want to get into Wall Street, I call up Danny Moses. And Danny's like, well, where does he want to go? Or my daughter says, I want to get involved in broadcasting. And I call up Sarah Wallace from Channel 4 News now. Or I call up Dana Miles from Channel 7 and say, my daughter wants to get into that. And she just got out of the new school in Syracuse, wherever she ends up going. And those are my tentacles. I want to give them everything I didn't have. And more than anything, my kids are very good athletes. My daughter's a phenomenal soccer player and a great runner. My son's a great football player and a phenomenal baseball player and a good basketball player. He also fights MMA. And I want to be at every event. I don't want to miss a memory. And in my business, you know, there are times that people are staying in jail because I'm going to my kids' events during the season. Talk about balance. I think that Danny, you mentioned last time on the cast about how we're out to dinner and I'm trying to have fun and DSK got arrested. And, you know, here's possibly the new French president of the world and, you know, they're pulling him off a plane at JFK and I'm eating dinner, you know, over at Trediche, you know, and I want to have fun. And, you know, and that balance comes into effect because now I got to go on my cell phone. I got to go outside. I got to start putting it together. And, you know, it's very tough to do everything. I will say that Ira is the most efficient phone person. You know, if you go out to dinner with people, you have to expect that someone's going to take a phone call every once in a while. It could be a kid. It could be with Ira. You kind of know. And I was cognizant of not being rude. And I would say 95 percent of the phone calls that he takes at dinners, which are business related, last no more than 12 seconds. It's three questions. Where is it?

Who's the guy? Does he own anything? And then he just hangs up or he just moves on or he, you know, he assigns it to one of his juniors. But when there's a big one, he stands up and leaves the table because, you know, he goes, I got to take this. My attorneys, my attorneys, the ones that I've been with me for the longest time is the, you know, the Jerry Shargels, the Ben Brothmans, the Murray Richmans, the Frank Rothmans, the Peter Frankles of the world. I can go down the line. Ronnie Fischetti, Jimmy DiPietro, Joe Muri, Mario Romano. I can keep going on and on. These guys. When they call me, they expect me to get it done. I am the fixer. I am going to fix the problem. Because when I walk into a room, as somebody stated in the courts, there could be chaos. I become the volume in the room because I am going to make sure that everything gets settled down. And when someone expects me to do it, I'm going to do it. I take my job very serious. And with experience, as Danny mentioned, I know right off the bat, I'm reading you on the phone. I could hear you. That's another thing. That's why I have the flip phone. I don't have an email. You could not understand in an email what's really going on, the sensitivity of the case. You know, I got a phone call from a wife who says my husband got arrested. I don't know where the checkbook is. I hear the dog barking in the background. My sister has to pick up my children because my husband's now in jail. She doesn't know where to go. She has no money because she doesn't even know where the money is because her whole life has been basically taking care of the family and now her life gets turned upside down in what, five minutes? And now she's coming to me. And now I'm a social worker and I'm also a therapist. Then I also deal with him because now he just lost his job. Now I'm an employment agency. And now next thing you know, he's telling me allegedly what took place. Now I'm a priest and a rabbi. So, and help me. fix this for me. And I come in and I fix it. I want to read a quote from the book that I mentioned earlier about this, the sources of power, because one of the things that I talked about with Danny a lot, I talked about with every investor is like, what's your edge? Why are you going to be better than the competition? Why do you have the market share you do in the New York area? Probably the most competitive, I imagine the most competitive kind of bail bond scene in the world. So in the book, you say,

This is again about sources of power. On some days, it works out that you draw your power from your clients, meaning you get it by association, meaning you're protected because you've done business with someone big, someone important. On other days, the power is earned. It's more active than passive, which means it has more to deal with who you are than who you know. So how has that balance shifted over time, the sources of power? I imagine early on, it's very little about who you knew. It's what you were. It was your hustle. It was your grind. But it strikes me that you still do all that, and now that other source has just grown and grown. It's absolutely true. In the beginning, it was nothing but just a set of balls. Ben Brofman one day, and I came out of, I had a Today's Man suit on for about $99, and he's walking off of an elevator, and he looks impeccable, and he's so amazing in court, and I want his work, and he's like, well, I got somebody, and I kept staying with him, staying with him, staying with him until Ben trusted me. So, you know, I still keep those balls together, but it's experience, and it's times, and you realize what the world of... Criminality is what the legal world is really about. The clerks that run the courthouses, the court officers, the correctional officers, the judges knowing what they want. Criminal defense lawyers, as I explained to you, the edge is that they get the phone call too. Now remember, the client, if God forbid they don't get out of jail, they don't blame the bondsman. They blame the lawyer. So that lawyer is banking on me to get that guy out the door because he wants that X amount of money retainer. So he's like, Ira, make this happen. Retainer. Retainer. But he just understands that he needs me. And the same thing, I'll get a call from a judge and he'll say, I want you to take this case. I'll get a call from a DA and says, you can get involved. And we trust you're going to do the right thing. And I've had DAs over the years that say to clients, we respect his work. We know who he is. And again, this is a business for me. And they get what they want. They worry about the case. That's where people lose thought. They worry about the case. The defense attorney could do the case. The DA could prosecute the case. And the bondsman is going to get the defendant to court and make sure that everything's on the up and up. And I have a ton of...

The DAs were DAs at that point and now defense attorneys that I've grown with. They were young kids when I was a young kid and I've been in the business almost 20 years and now they've been out and we've grown together and we laugh and we joke and we say, look at your office now. Look what it's become. So that power, that source of power comes with experience and time but you can't lose where you came from and that's a big part of it. I mean listen. Danny's in this room and you're in this room, and you guys have been in the investment world. People, when they come to you, they expect your experience and your knowledge. You're not going to get them into a Madoff situation. So they come to you knowing that they could trust you and they could respect you and you're going to get the job done. Too bad that was federal Madoff. You could have really used that one. I actually got called on that case. Really? Yeah, I got called on that case. I was going to do a bond for one of the people. I don't want to mention the name, and she didn't have enough. And she was incarcerated. And the attorney came to me and said, put something together. Now, I've written before in the federal bureaus. It's not often, but I've written in there where they come in and they've asked a bail bondsman to piece off the rest. And I've done it. And I have the highest respect for those people, too. I almost got involved in that case. Back to just to round out that edge. You know, it's such a freaking powerful lesson, which is it seems like. Intense reliability, consistency, and empathy. People know that they're getting that from you. And that would be true of anyone in any job anywhere. And it's amazing how few people are that reliable all the time. I take phone calls at one in the morning. I take phone calls at all times of the night. And you, again, with the flip phone that I have, you could hear. I spoke to a woman today that spoke broken English. She was Hispanic. And I couldn't understand a word she's saying, not because she was speaking bad English. She was crying for the whole whole time of our conversation that her 21 year old son was with six guys. They got pulled over. There was drugs in the car and all six of them got arrested and he had nothing to do with it. And she's like.

I couldn't understand. And finally, I had to calm her down. I'm like, I will take care of this for you. I will figure it out. But after the tears, you feel that. You feel the empathy. You know what that client in an email, you're not hearing the tears. You're not reading the tears. You're not sensing the moment. And that's the part of my business that I think is different than anybody else. Because I, hey, listen, people look at me and they might say, well, wait a second, Ira. You're taking out a bad person. And I'm like, well, everybody has the right to bail. But, you know, sometimes you talk to, I've had people walk in my office and basically, man, I sell guns. That's what I do, man. I grew up in the hood. And, you know, this is how I make my living. My mom's strung out. I don't even know who my dad is right now. My grandmother raised me. And, you know, this is how I got to earn. And I'm slinging. And that guy, I trust him more than anybody I grew up with. Because that guy, if I need anything, has my back. And that guy, if I say to him, don't fuck me, he goes, you think I'm jumping, man? If I got to go lay up and lay up is a turn of going to due time, I'll go lay up. Now I call that guy when he's inside because when a hedge fund guy gets arrested for stealing $20 million from a company and he goes inside and he walks on the yard and he's shitting in his pants and I reach out to that guy's mother and I say, make sure that he's okay for his two year stretch. And then he's in the law library doing all these other people's appeals, but he's being. protected inside and he comes out and he looks after me and says I'll never forget that you saved my life and I say well don't just remember me remember the guy that was inside watching your back all the time and I you know and I send his mother three four hundred dollars and say you know tell Carlos thank you very much I mean that means everything because he didn't forget me and and that respect goes a long way because I tell you right now I trust people more in my industry than people I grew up with tell me about

a case in which you got extremely emotionally involved, maybe more than what you had expected going into it and kind of how that played out? I'll tell you there's a story. A lot of the sexual components of the stories I get involved in where young kids are involved always grabs my heart a little bit. And I'm trying to go back to a story where A guy came into my office, hardworking iron worker in the union, and he had a young daughter, and he was away for a little while himself. And his daughter was living with the wife, and he was a hardworking, strong guy. And it turns out that the daughter became very quiet around him after a period of time and he couldn't figure out where it was. And he ended up, he ended up finally, he got the daughter on the weekends. And he ended up finally getting the daughter and the daughter said, says, listen, mommy's boyfriend's been touching me, molesting me. And this guy could not believe it. And the guy got pinched for it because finally after a while, the girl kept making complaints and making complaints to the school. and the school's the one that called because the mother never did anything because the mother wanted the guy to stay because he was paying the bills. And this guy walked in my office and he was steaming. And we bonded, no pun intended, with the fact that I'm a father and he was a father. And he felt so guilty that he was away during the time that his daughter needed him. Now he's this iron worker and he's working his ass off making X amount of money and he's got his kid and now his kid's molested by this animal. And he wants to do something. So he wants to bail the guy out to go to work on him. And I sat with him for about an hour expressing to him that the first thing they're going to do is come back to you. You can't do this. You can't do it this way. So a plan was devised where somebody else bailed this gentleman out. And this guy got out.

something happened to this gentleman, which I don't really know exactly, but allegedly he was canned, where the word canned means is you put a certain amount of soda in a pillowcase. The movie Bad Boys with Sean Penn. Yeah, yeah. And this guy was hurt pretty bad. In fact, he was in the hospital for a very long time. I don't know what happened. I don't know how it happened. And then he was actually convicted. And he's doing time upstate. And the craziest thing happened to him when he was upstate. He was shanked. Again, I don't know what happened. But I had heard that he was shanked inside. And then I heard he was in protective custody. And I have a relationship with that gentleman to this very day. And this guy got custody of his kid. I think his kid is doing well. I haven't spoke to him in quite a long time. Situations like that, it's almost where you don't have control. There's a part in the equalizer. I don't know if you've ever seen the movie The Equalizer. When Denzel is sitting on the porch with the former CIA person. And she says, Robert, why? And he goes, because you can. And at that point in my life, the street part came out of me. And also the father. part came out of me. And I just looked at this man's eyes and this guy was a tough son of a bitch. You saw it. His hands were huge. You want to talk about getting gripped? And he was a baby. He was in tears because he couldn't protect his child. And he knew that this guy was going to get out. And we talked and we talked and it ended up working out for him. He was able to move on and get his kid. And unfortunately for the other gentleman, it really didn't work out. I think he had a bad road in the beginning. And then, again, I had heard that he had got shanked inside, which is a terrible thing. Anybody see Richie? Anyone want to know where Bobby Lupo is? Exactly. But, I mean, listen, every bail that you do, you get attached to.

And then, just so you know, there's other sides to it where you realize you're taking somebody out on a vehicular manslaughter on a DWI. And that person just killed somebody. And that's, you know, there's been, I'll tell you a great story. I almost left the business. I had been involved in the beginning. I did a bail for John Taylor. I don't know if anybody remembers that name. Well, I did a bail for him. And it was a $3,500 bail. $3,500 bail, right? That's like urinating on the street. And it was a gentleman that had a gun, but the gun wasn't loaded. It was a first arrest, never in trouble. The defendant was a manager of a restaurant. And he did this bail. So I did the bail. Unbeknownst to me, he went in, got out on bail, and he went and shot. a few people at Wendy's. I don't know if anybody remembers that years ago. And when the DA's office called me up and said, hey, we need that file. I said, sure. What did he do? And I put two and two together. And it killed me that I had done a bail. And I remember speaking to my wife about it. And I said, Blake, I said, I just, I just, look what I did. She goes, listen, she goes, it was a 35. If it didn't go to you, they went into somebody else. I said, I just don't know if I want to be in this business anymore. I don't know if I can handle that. She goes, you're providing a service. Just don't get attached. But unfortunately, I get attached. So it killed me because I had a tremendous amount of guilt and a lot of sleepless nights. Because you do business and you do bail for people and that could happen. And it's happened before. I always thought that I would be nervous if I was Ira because one of the people that he... bailed out that they think they owe Ira the money would come after Ira and they're on the run they're like if I can get rid of Ira I get rid of the trail because people would think short-sighted things like that like to me I always like Ira you got you got some guys that are out there right now are you guys are you concerned at all he's never really concerned about it I'm not concerned because even though I turn down a lot of bails all the time the people in the alleged gangs people in the alleged underworld I'm their

Get out of jail card. I'm their guy. And I'm their bank. You know, I'm their Willy Wonka. So you got to take care of me. And they do. I've walked into rooms. You know, I've actually walked into a funeral once. And I'm ready to pay my respects. And a guy comes up and goes, Ira, listen to me. And the cops came in. I go, whoa, whoa. Can I just go pay respects to John over here? He goes, yeah, but after you pay respects to John, I got to go. I'm like, all right, well, let me go through the line. All right. Let me pay my respects. Then we'll go talk about your case. I do that. And he's looking at me over there and I'm not even online. And he goes, hold on, hold on. He actually came and pushed me to the front of the line so I can pay my respects and go back out. And I'm like, all right. And he's like, don't worry about it. This guy's not going anywhere. And I'm like, oh, you're right. But I just want to pay my respects. I think not to run any type of question you have, but I think the best story, which kind of says it all, was when. Blake was in labor with a child, with a child where you had to go to court and they all waited for you an extra day in prison. That was the first time where I actually, it was my first big payday in the business. And my wife, Blake, was pregnant when I first daughter. And we had it at a hospital in the Bronx, which we would never do again. And I'll tell you a great story about that too. And we're sitting there and we're walking back and forth. And we had already had Mexican food that night just to get this baby out, you know, because, you know, my daughter now, who's a pain in the ass, became more of a pain in the ass that night. And the phone rings at like eight o'clock in the morning after a huge, huge, like laborious. My wife was in labor for a long time. And it's Murray Richmond. And I love Don't Murray Murray. And, you know, he says, Ira, I said, what's that? He says, listen to me. A big case broke in the Javits Center. And there's 15 defendants. I'm representing three or four for arraignment purposes only. Jerry Shargel's down there. He's got some. Now, you got to remember some. These are the gurus.

of the industry. These are the guys that you want to know. These are the best lawyers around. And what did I? I was taking pizzerias as collateral. So now I go down and I go, Mara, my wife gave birth. I can't get down there. And all I hear in the background is, Well, the kid that I use for bail bonds, his wife just gave birth, and I hear throughout the echoes of all the hallway. So he gets back up and goes, they're going to wait for you. I go, what do you mean they're going to wait for me? He goes, they're going to wait for you. He goes, they're going to wait a night. They'll stay in. They'll get away from their wives. They don't mind. I said, okay, what do I do? He goes, I don't know. We'll talk later. Go back to your wife. And I went back and I stayed with my kid and da-da-da-da. And now I'm sitting there and I'm trying to put all these bails together. So I'm on the phone with my insurance company trying to put all these bails together. I have like nine bails and I'm getting properties and I'm like properties now and it's great. So now the next day I come to court and Literally, I got to be honest with you. I get to court. I'm so nervous. And I got all these bonds in front of me. And all the defendants, like I said, the ones that I had, I think it was a 13-person indictment, are sitting in the jury box. And the place is packed. And I'm not going to mention any names. And I basically sit in there and I got my Today's Man suit on. Because me and Blake are just starting out. And I'm sitting there. And the first guy gets up. supposed to come out of the jury box, go straight in front of the judge. You got the prosecutors on one side, defense attorneys on the other. And he comes up and he's handcuffed. He looks at me. He goes, how you doing, Ira? It's Paulie. How are you? My wife, my wife, Sharice is in the back over there. He goes, congratulations on your baby. It's awesome. We got a little gift for you. And I'm like, I look up and I'm like, oh. Okay, thank you, whatever. And he goes in front of the judge, and the judge sets a bail. And then the next guy up, and he goes, how you doing, Ira? That's my wife, Connie, in the back. Congratulations on the baby, blah, blah, blah, blah, blah. And I'm like, oh, thank you. And this went on for another seven defendants.

And then, and I'm like, holy shit. Now you got to understand a regular indictment should take no more. And this took like two and a half hours, you know, back and forth. And I'm like, Oh God. And I go, now I got to go in front of the judge and give him all the bonds. And I know he's going, he is looking at me and he takes, and I'm sitting in front of a microphone now and he pushes it to the side. He goes, what'd you have? I go, I had a girl. He goes, I got two girls and a boy. He goes, by the way, I upped all the bails. He goes, so you can send your kid to college. So I basically finished that day. I go back to my office and in there was homemade wine, cheese, balloons, all gifts from the family. And I'm like, meanwhile, it was my biggest payday ever. So now my wife is calling me. It's like 630 and I finally did all the bells, blah, blah, blah. And she's like, this place stinks. You got to get me out of here. There's bedpans all over the place. Nobody's speaking English in this hospital. Get me the fuck out of here. So I basically go back. Now, I don't even know how to put a car seat in. So I get the car seat in, which was so she says, bring the car seat up. You got to get me out of here. I'm not staying here any longer. And I take the whole piece of the car seat out. So I took the whole piece out. So I'm walking through the hospital with the car seat. And the nurse is like, and now there were bedpans in there that were sitting in there for all day. And she's like, look, I took the bedpans. And I put him on the front of the nurse's table. I go, she's like, that's disgusting. I go, that's what my wife's been sitting in all day. And I go, I'm taking my kid out. She goes, you ain't taking your kid out. I go, yeah, I'm taking my kid out. So I walked in and I grabbed my daughter because my wife is holding her. I go, I'm leaving. They go, she has to pass a hearing test. I go, really? I walk up to my kid. I go, ah! And she starts screaming and crying. I go, she can hear fine. We walked out of the hospital. My kid cried all the way downstairs because I yelled in her ear.

She has implants now, right? She never forgot, but she has Miracle here, actually. My father hears better. He's 81. So let's go to a total different end of the spectrum. I've always been a huge hip-hop junkie, and so I was shocked to see, towards the end of the book, a story about Ja Rule, a story about DMX. Maybe pick one of those two and walk through that experience. Well, first things first, Ja, obviously, is going through a tough time right now, but he's a good man. He's a good guy. And in the hip-hop community right now, he's going through a tough time. But he's a good guy. And hopefully he gets out of this. Are you talking about that thing in the Bahamas? Yes. And he's a good man. And I know him. He's not that type of guy. He's not that type of guy. If something went south... He had no idea what was going on. He's not that type of person, and I hope he gets out of this because he's a good man. He really is, and he was coming back, and he owned up to everything he did. He's a good guy. DMX, well, Earl is a whole different guy. I mean, I love... Earl, you wouldn't believe, man. I mean, I'm on speed dial with Earl all the time, and I get upset. I really do. I get upset for Earl, aka DMX, because he had it all. And Ensign. He had it all. I mean, Earl was doing movies, and he had a great voice. I called him Surf and Turf because he could have done movies and sang. And he had the whole thing going on. He got hooked, obviously, on some bad stuff. And, you know, his wife is a sweetheart and we became very friendly. In fact, in the book, we talk about how I was at, you know, my daughter's, excuse me, my niece's birthday up in Connecticut where we are today. And I told DMX, you know, he owed me money. And he was supposed to make an appointment with me three times to pay me. But he has a little bit of a time management problem. And finally, he basically said, okay, I'm going to pay you today. I said, all right. He goes, I'll be there at 1 o'clock. And I said, okay, Earl, what time are you coming? 1 o'clock. So I'm sitting there and it's 1.30, 2 o'clock. And my wife comes out at 2.30. She's like, we got to go. We got to be at your niece's birthday at 3.30 up in Build-A-Bear in Danbury, Connecticut.

And I'm like, all right. And all of a sudden, three o'clock comes and we're on the highway and it's Earl. Where are you fucking at? I'm at your house. I said, Earl, you said one o'clock. I said, I got my niece's. Where's your niece's birthday party? I said, it's up in Build-A-Bear in Danbury. And he's like, I'm coming. You got to understand something. My sister, I mean, there's just no way she wants DMX and his family at my niece's birthday party. And all of a sudden, we're in traffic coming off of the Danbury Mall. And all of a sudden, I just see, and he shouldn't even be driving because most of the time, he's out for traffic violations. And I see him fly on the shoulder. And my kid goes, isn't that DMX fucking flying on the shoulder? I go, yeah, what are you doing? And I get to the mall, and there he is. And he gives me my money. He's like, I'm coming. I'm like, I go, Earl, you can't come to my niece. Come on, I'm coming. I'm like, all right, come. So you walk in. And at that time, he was the man. And the mall shuts down. You want to talk about a frenzy. And I'm in Build-A-Bear. And so is his kids. And so is my niece's, all her friends. And there's Earl's kids. And we're sitting there. And he goes into, I think, Toys R Us and spends like $300 on my niece. And my assistant's like, who the fuck is this? You know, she's listening to Kenny Chesney. I'm like, oh, this is DMX. You don't know Earl? And he sat there and Earl was at my niece's birthday party. And we have... We have a great relationship. He was in Vegas one night, and he was all jammed up, and he called me, and I was like, I'll do what I can for you. He was in New York on his child support stuff, and he called me. And, you know, I have a lot of great relationships. I have a great relationship with, as I said, Fat Joe. I was close to Earl. Still am. I would do anything. You know, Ja, you know, obviously I've been involved with Lil Wayne, doing some work for him down the line, the former ODB, old dirty bastard who, you know, passed away. I've done Plaxico Burris and, you know, I've done Cat Williams. We can go down the line. Lawrence Taylor. Lawrence Taylor. Wow, Lawrence Taylor. I don't remember that one. Lawrence, you know, Lawrence wanted to play golf in the Bahamas. And I said, yeah, you can go. Good luck. And I called his house and, you know, his wife started screaming at me. But one of the greatest linebackers of all time. Good man. Good guy. You know, and again, I'm glad everything worked out for him. What now, 20 years in?

gets you excited most? What do you enjoy most? Is it still just the relationships? Is it helping people that? It's the action. It's the juice. It's taking the bell from the beginning and putting it together. It's knowing that it's going to be a very difficult ride, but more than anything is seeing the face of the family when they get their loved one out the door. Because as I said before, sometimes it's good people making bad decisions. And we're in a world every day where people just do a lot of stupid things. A lot of people don't get caught. I always say to my kids, You see a lot of people driving 75 on the highway in a 55 mile zone. They just don't get caught. Eventually they will. But I think it's the relationships. And it's also more than anything, it's the relationships that I've built over the years. I mean, I have judges that I know very well that, you know, have gotten sick. that I care about, you know, and we talk off the bench. I've had DAs that I'm very close with whose, their families are looking for jobs and I try to help them, you know, call my buddy in the Wall Street world or call my buddy over at JP Morgan or whatever or call my friend that's in the Garment District. And it's like, I enjoy helping people. I don't know if the word fixer, I'm living that world because as you know, I help everybody, and it's not just in my world. It's in other parts of the world because my tentacles reach to places that no one else could reach to. Ira has. I mean, he could spin off and do a consulting business where he's one person. He puts out a bail for someone. That person gets out. There's a court order that they can't go near someone else, but the wife doesn't trust it, and she wants a bodyguard. She wants someone to watch this guy, and Ira can do that. I'm doing that now. I'm protecting. Somebody right now with some guys that I know, you know, she's going through a very bitter situation in her life. I don't even want to say it. It's a domestic situation. And I don't like bullies at all. I teach my son and my daughter. And they've been on the bus before. And I got a phone call. And it's, you know, the principal of school says, Mr. Jettleson. I'm like, please call me Ira. Oh, Ira, listen, your son.

hit somebody on the bus and i said my son went to work this went went to work on somebody in the bus and he goes yes can you come in go in and they say you know whatever and i get my son and he's like dad i'm on the bus and this kid was being really mean to this other guy i told him to knock it off he wouldn't knock it off and he said what are you gonna do and i did something and i looked at the principal i said well i got no problem with that So I don't like bullies. I really don't. I don't like people taking advantage of people, and especially a man taking advantage of a woman. Really, it eats me alive. And there's a lot of people who I've bailed out and a lot of people that I've been involved with and a lot of my friends, who I call friends today, that don't like that either. So I'm watching after this woman and making sure that... she can go to work and that she can make sure that her son is safe because she's fearful of her life. You think he'll ever stop? My business? You know, it's funny. My father is 82 years old and going through a very difficult time in his life right now. And he worked there, as I said, at Rikers Island Prison in Spotford in the juvenile detention center there. And he had all these jobs. And I think the worst thing in the world for him was retiring. I think that I always want to work. I like it. Now, don't get me wrong. I enjoy watching my kids play sports. I enjoy being with my wife all the time. I enjoy my friends. I love my friend here. But I love what I do. I could actually say that I get up in the morning and I love what I do. If you get on the train tomorrow. and you look at people going down to the city or anywhere in the country, how many people really love what they do? I love what they do. Not enough is right. And the answer is, I don't know. If I found another passion, we talked about it, about doing some different things together. I might want to pursue some other opportunities. I wanted to do a TV show. I was talking with some gentleman out in California right now. We're talking. He wants to do a TV show with me.

I thought about maybe writing another book. I don't know. I want to do, as I mentioned to you, somebody wants to option my book. And I was talking to you guys about it before. And he keeps pursuing me, pursuing me, pursuing me to option a book because he wants to do a feature film. I've actually thought about going around to other bail companies around the country and being consultant to help them get their brand going, help to get their business going. I've got a lot of ideas. But again, you talked about balance. I also love my family. And I don't have enough time in the day sometimes. You know, I'm on the field and watching my kids play sports and the phone doesn't stop. And the funny thing is when it does stop, I get upset because it's not ringing. And when it rings, I get upset because I'm like, well, I'm doing something. So it's a catch-22. But I don't think I would want to get out right now. You never know. I have been approached to get out and stay involved and let somebody buy my business. I don't know if I would want to do that now. I asked Danny when we had our conversation to describe the things that he would look for in somebody young that he might potentially hire. And it was a really popular answer. And so I actually pulled and stuck it right at the front of the episode because, you know, I think people really enjoyed hearing that. So I'll ask you kind of a version of the same question, which is a lot of people early in their careers that listen to this podcast. What advice would you give people that are still kind of in that feeling it out mode, trying to figure out what they're passionate about, or if they found it, trying to figure out how to do a good job? What are the things from your own experience that you think contributed most to your success or maybe said differently, people that work for you? That's a great question. We're in a day and age right now, and I'm trying to teach my kids this, where you play a sport and everybody gets a trophy. And I fucking hate that. Okay, more than life itself. Oh God, little Jimmy, he's playing baseball. He's going to get a trophy. He's in fifth, sixth grade. No, those days are over. Okay, there's a time when everybody plays and there's a time when you have to earn it. And there's a time when you get to seventh or eighth grade where you start to play a modified sport where they, you, and then you get, and everybody's got to make the team, they say. But then in ninth grade, they may cut. So you're setting your kid up for failure. And I hate that because I think that you have to earn it.

What I'm saying today is that you got to have heart and you have to have a set of balls and you got to know that to be a winner, you have to be a loser. You have to fail to win. And I failed a lot in a lot of my businesses. And I finally found a great niche for myself in this industry. And if I said to somebody young out there is that, you know, it's funny. You go to college and unless you're going to be a doctor. or go to MIT and become a space engineer, you're going to come out in this world, and this world is not as what you think it is. Everybody, oh, whoa, wait a second. This guy's making millions. I'm going to go to Wall Street. Well, no, no, no, no. You've got to pay your dues, and you've got to basically get in there, and these clients have to believe in you. It's hard, and I'm telling a young guy nowadays that you get that degree, and that degree basically is a key. A key into a door to get you an interview, to get you a job. Then it's what you know. Okay, but before that, it's who you know. And you got to keep striving and striving and striving, and you can't quit. Because if things come easy, okay, if things come easy for you your whole life, and then you get to a certain level, and then all of a sudden it doesn't become easy, there's two ways you can go. One, you can go and become basically a little spoiled brat and live off mommy and daddy until they cut the lines. Or two, you can work harder. So I only hire, like I have a guy in Brooklyn. He's an Arabic kid. And this kid is as hungry as they come. He calls me at 2 o'clock in the morning with a call. Can I go do a bail? Of course you can go do a bail. Okay? And that's the guy I want. That's the guy that says, because if I go work, he's making money. And he's got five kids. And he's got to support those kids. And he's got to worry about everything in this world. And he's got to go home to his wife. And his wife believes in him. But if you get somebody that basically says, well, my job ends at 3 o'clock. I'm not taking that phone call. It's actually the same answer I gave in a different format. And we didn't talk about that at all. But it's funny that that's the exact same. Yeah, I've heard similar versions of the same answer from a lot of people. Listen, I mean, again.

I'm not, obviously I'm not the brightest guy in this room right here amongst you guys, but I think you got to have a mixture of street and legal in your world. You got to know what you're, you know, you got to have some sort of a, listen, I'm a chameleon. I could talk to a Harvard grad. And I could also talk to the guy that basically has a third grade education. And that's what I think you also need in a guy that's coming out today. You've got to be able to be a chameleon. You've got to be able to talk and speak different languages to get where you want to get to. You need passion. That's the overline. 100% passion. It doesn't matter what you do. 100% passion. And you've got to work hard. Look at Derek Jeter. Derek Jeter did not get married. until he was, what, is he 40? He was doing okay. Well, we know he was doing okay, but the point is that Derek said, my career is my career. I don't have time to really right now raise a child. I don't have time to get married. I want to focus on this. There'll be time. And, I mean, for him it worked. You know, for other people, you know, but Derek's passion for the game and doing what he did was incredible. And, you know, it's a great foundational format. I wanted to highlight two things you said because I've been thinking a lot about them lately, which is first the willingness to fail. I think that's maybe the most important part of that answer. But the passion part... allows that to happen, right? Like if you have the passion, then failure kind of can feel like nothing. If you're doing something for an impure motive or for, you know, because other people expect you to do it or, you know, whatever, you're following the Harvard. I mean, let's call a spade a spade. I mean, Danny is in the hedge fund world and invests every day. Not everything is a winning investment. So he has to lose money in a deal to know that he's going to gain money later on. And if everybody was going to gain money all the time. We'd see him in O'Connor County Jail in North Carolina as we see Madoff there now. So, I mean, you know, you can't win all the time. I mean, I've had people that jump on me and I've had great bails. And listen, I was in the bar business. I was a sports agent.

I went down to the Fulton Street fish market. I bought fish upstairs. I was a bouncer. You know, you gotta, you know, I live with my parents now. You know, you gotta fail and you gotta understand what failure is, you know, and say, you can go one way or you can go the other. I'll just add to that. I think the other thing, which I didn't mention when we spoke, is you've got to enjoy life to what it gives you. And if there's the points where you get an opportunity to do something fun and experience something, maybe it costs a little bit of money to do. Maybe it's a trip somewhere with a group of people that really opens up your horizons. And I think experiencing the highs is important so that when you hit the lows, you can realize how great it is to get back to that. I'm going to give you another thing that I'm going to talk about. This is something I could talk about with one of my best friends right here. to be about six, a little over six years ago. I had lumps on my body. I didn't know what it was. I was trying to lose weight and I went to a doctor and the doctor says, when was the last time you went to your, who's your primary doctor? And I said, why do I need a primary doctor? I'm coming to you, you're my urologist. So I want you to see a primary. And I went to the primary and the primary says, I want you to go to this doctor. I said, okay, was there anything wrong? Nothing's wrong, you're fine. So I go to the Take my wife, and I walk in, and I see this word on top of the doctor's desk that says oncologist. I'm like, Blake, what the fuck am I doing on an oncologist? I walk into the doctor's office, and they say, okay, we want you to do this. We've taken blood. We think you have lymphoma. I'm like, what? They're like, we think you have lymphoma. I'm like, we want you to do this biopsy. So I go and I do a biopsy and it comes back negative. So we're jumping for joy. Go back to the oncologist and she says, I want you to do this bone marrow and don't want to take a piece out of your stomach. And my wife's like, he's not a fucking cadaver. We're not taking pieces. Well, we think he has lymphoma. We just don't know where the primary is. Long story very short, I turned around and a buddy of mine turned me on to another doctor. It turns out that I have an autoimmune disease. I didn't have lymphoma. I was supposed to start chemo, but I didn't. I have what is called sarcoidosis.

And sarcoidosis is an autoimmune disease. And it's very rare, but people have it. And it affects your lungs. And when I have a common cold, it can turn into pneumonia. You have a common cold, and you guys are taking NyQuil and going to sleep. So I always got to watch that. But it goes back to that day. And he left a message on my voicemail. He's almost in tears. And he's like, I'm not going to let anything happen to you. I love you and I'm going to take care of you. And our relationship has always been like that. But I realized that day that life is very short. And at any time, health could grab you. And I want to live the moment. We were just talking about, you got to live the moment. I've been to the Kentucky Derby with Danny. I've been to crap tables with Danny. I've been out to dinner with Danny. I've been to softball games with Danny. We've been just out to just sitting, smoking a cigar in his backyard. And you got to live your life. Never was sarcoidosis so celebrated. By the way, I just wanted to say, we got sarcoidosis for 90 years, but good. You can beat that, right? Yeah, and we were... I think we went out and celebrated the sarcoidosis. We did, we went to Pascual's. We did, but that goes back to my point. You gotta live your life. You gotta live your moments. Oprah said one time, die poor, live your life. She's easy for her to say. She's fucking got everything going for her. She loses weight, she makes fucking money. It's unbelievable. Another, see, wait, watch your stock. Maybe we could have, you know, jumped in on that one. Yeah, exactly. But I really believe that. So that's why I don't want to miss any of my kids' sporting events. And, you know, I want to spend as much time with my wife and laugh and joke and more than anything, be with my friends. And I think Ira loves what he does. It's back to the passion. So the thought of even leaving it wouldn't even cross his mind because, again, he'd be bored. He'd be worried about what he would do. So the minute that he doesn't enjoy it. Yeah. Listen, there's a lot of things that I don't enjoy about my business. Sometimes fighting with the other side to get somebody out the door and them using the bail as a way not to let the client out. I disagree with that because you want to win your case, you win your case. And you really can't take a break. I went to Italy, I want to say, a couple years back and I'm in the middle of the sea. I don't swim. I'm with a friend of mine. I don't know how to swim. He throws me a noodle. He calls me noodles now.

That's my boy, Mikey Cohn, and he basically, the phone is ringing. I'm in the middle of the sea in Capri, and a huge case breaks, and I'm on the phone. They're all swimming in the ocean. I'm on the phone going, all right. Get the house. Find out the appraisal value of it. Let's get a confession of judgment against the house. Have Michael write the bail. Have Joey write the bail. Call the insurance company. How many people are on it? Okay, who's the DA? Who's the defense? And I'm in the middle of the sea doing this. And they're all dancing and singing, you know. But that's my bit. And I love that. That half hour of putting that deal there was great. Well, you had to buy the ticket home, so you were able to do that at that point. Thank God. Yeah, exactly. Thank God. Well, this has been an absolute blast, as I knew it would be. Thanks for all your time, all the great stories, and maybe we'll do it again sometime. Well, listen, we're going to do... This is the official launch right here. This is the official pilot episode of Bale Street. I'm telling you, Danny's world and my world collide all the time. I will tune in, and I'll promote the hell out of that one. There you go. Thanks, guys. You got it. Hey everyone, Patrick here again. To find more episodes of Invest Like the Best, go to InvestorFieldGuide.com forward slash podcast. If you're a book lover, you can also sign up for my book club at InvestorFieldGuide.com forward slash book club. After you sign up, you'll receive a full investor curriculum right away and then three to four suggestions of new books every month. You can also follow me on Twitter at Patrick underscore Oshag, O-S-H-A-G. If you enjoy the show, please leave a quick review for us on iTunes, which will help more people discover Invest Like the Best. Thanks so much for listening.