The Lawyer Behind Elon Musk, Jay-Z and Megan Thee Stallion

0:00Join Bloomberg for the Canadian Finance Conference, proudly sponsored by National Bank of Canada Capital Markets, on September 29th in New York. Hear from influential corporate and government leaders as they discuss the strategies shaping Canada's economic future. Connect with senior decision makers, gain actionable insights, and be part of the conversations driving business forward. Register at bloomberglive.com slash Canadian Finance. That's bloomberglive.com slash Canadian Finance. I'm Emily Chang, and this is The Circuit. We're in Miami to meet with Alex Spiro, hotshot lawyer with a bevy of famous clients like Elon Musk, Jay-Z, Megan Thee Stallion, Alec Baldwin, Mr.

0:43Beast. He's part lawyer, part dealmaker, part fixer. What you think of Alex Spiro probably depends on what you think of his clients, some of whom are, let's just say, polarizing. With a background in psychology and an instinct for shaping public perception, Spyro has made a name for himself, defending the rich and powerful. He claims to have never lost a case, and that track record has carried him into the highest circles of American wealth and influence. And many see him as capable of delivering more than the typical lawyer can. I wanted to know more about his goals and motivations, the secrets to his success in the courtroom, and what his next move might be.

1:22Alex Spyro, please take the stand.

1:28we're going to start talking about your journey then we're going to get into your process then we're going to try to talk a little bit more about your clients to the extent that you can what was it like growing up alex spiro i'm not sure but i had a lot of fun played sports ran around caused trouble i think i did what most kids did were you the kids starting the fights on the playground or ending them i think maybe both tell me about your journey to law school How did you decide you wanted to be a lawyer? I was a pretty ordinary teenager, played sports, had fun, didn't really know what I wanted to be.

2:03And my mom started taking me to volunteer at her hospital that she worked at. And I started getting involved with different patient populations. I enjoyed that work. It was a psychiatric hospital, right? Yeah. And eventually there, you know, they sort of said, are you going to go to medical school? You don't seem like you want to go to medical school. you should go to law school. Because at that point, I had started to advocate for the kids and started to put my foot forward on things I thought needed to happen. Probably too big for my britches. Or maybe they wanted to get rid of me. I don't know.

2:35And they told me there was a test. I could take it. It wasn't too far from the hospital. They printed it out for me. I remember it like it was yesterday. And I went and I took it and I went to law school. I mean, it was literally like that. No lawyers in my family. Did you feel like you found yourself in law school? I think that the hospital, actually, is where I started to get a sense of who I would be as an adult and my professional life and things. And the law school thing didn't sound crazy to me because I had grown up watching a few good men and my cousin Vinny repetitively. Oh, my cousin Vinny.

3:04That's such a good word. And so I remember thinking, you know, it'd be pretty cool to be Lieutenant Caffey. There was at least something there that triggered it, and they pushed me over the edge. Your first job out of law school was at the Manhattan DA's office, and you cracked a couple of cold murder cases that had been unsolved for years. What did you see that prior lawyers didn't? I had a great mentor at the DA's office, Bill Mahoney, and he taught me by sort of pressure testing the way I thought and how I analyzed things to continuously check myself and rethink things in different ways. And I think pretty early on, I had a unique way of putting together facts and evaluating facts and putting together those puzzle pieces that allowed me to win trials early and solve cases early.

3:50What's unique about it? One thing is that I think of things psychologically. Why people do what they do, not what happened. And so if I think, well, why is this person doing this? It may then make better sense of the jigsaw pieces. The other thing that I try to do is continuously construct and reconstruct and move the pieces around a little bit. So one of the cases that was sort of unwinnable at the DA's office, I basically cracked by changing the angles by which people said that they were standing that would create a different view of the forensics. And then once I did that, it was sort of like a magic moment where everybody said, holy cow.

4:25It didn't happen like everybody's been saying. When you do this and then you go look at the bullets and then you go to the medical examiner, It happened in just a different way that nobody could picture. How did it feel to put the bad guys in jail who'd gotten away with it? In the adversary system and as a young prosecutor, it's exciting. It's enthralling. There's something competitive about it. And I thought I was and believe still that I was keeping the streets safe and doing right always. It's a good feeling to win a case to solve a case. That being said, you know, given the way I look at the world and given what I had done before in psychology, I often felt bad.

5:00I felt bad with people sitting in prison. I mean, not so much the worst of the worst, but most of the arguments I had with my supervisors at the time were about leniency and psychological intervention and second chances. My understanding is that you were also, like, knocking on doors, saying, give me the cases you don't want. There's a sort of a relentlessness to your style. That's true, and it's not a metaphor either. I literally would go office to office and say, I've got nothing to try this week. Does anybody have a case they don't want to try? And I used to try them all. Why? Competitiveness, probably.

5:30desire to get better, I found it interesting. And I love being in a courtroom. You're defending people now, mostly, who are often controversial, seem difficult to defend. How do you decide what cases to take now that you have your pick? What cases to take started when I would evaluate social justice and civil rights cases. So people will send me, I get letters from prison, civil rights groups, human rights groups, celebrities, powerful people will send me, hey, will you take this case on? Will you take this issue on? And I realized pretty early on in my career, I need to have some sort of system, at least in my own mind, to siphon through it.

6:08So what I kind of look at is it's a bit of return on time. So is this case something that is going to happen in a location that I can get to easily versus not? Does it play to what I'm good at? Am I going to be in the courtroom? When I took on Pedro Hernandez to push the bail reform issue further, or I took on 21 Savage to release him from ICE custody, those were in the courtroom, every day, full action kind of situations. When people approach me about cases of actual innocence where someone's been sitting in jail for 20 years, those cases are very tricky, and maybe even five years later, you don't get a hearing.

6:41So you never have that magic moment where you can actually change the scope of the case. And then three, does it have an impact outside of the case itself? So if I take this case and make my point and win this case, am I setting an example for other cases? Am I changing the law? Am I moving society forward? So that's sort of how I look at that. I think similarly, I've now taken that blueprint and put it on trying to figure out which cases for corporations and individuals I should take otherwise. And at this point, frankly, unless I find it gripping or it's somebody that gets to me through somebody that knows me, I'm not taking lots of cases on.

7:16Do you have to believe in your client? Do you have to believe that every client is innocent or justified? I have to believe in my client and I have to believe in what I'm saying. It doesn't mean I believe in everything that my client does. It doesn't mean I believe my client is innocent in the truest sense of the word necessarily. But it means that the painting I'm going to put forth, what I'm saying, I firmly believe in or I wouldn't say it. So speaking of minds, you studied biopsychology before law. How do you use that to get into people's heads? Well, I use that when I cross-examine people, to read people and to understand what's motivating them and where they're going to get trapped and how, if they're trying to lie to me or mislead me or hide from certain things, how to sort of unravel that.

7:59And when I'm telling a story, I tell stories that are sort of psychologically based. When I say that, what I mean is, if somebody's going to say that some minor violation of law, like some, you know, an upgrade or, you know, somebody sends a tweet out or violated some horrific law. They have to ask themselves, well, what was in that person's mind at the time? Were they saying to themselves, I'm about to cross some bright line that subjects myself to prison? Were they really thinking that way? So you are known, a fellow lawyer said, you win unwinnable cases. What are the top three moves in the Alex Spiro playbook?

8:34Well, nobody can know that. But, I mean, the number one rule is that no one should ever know what I'm thinking. Because if anybody knows what I'm thinking, then they will try to pivot around me. And so that is for sure the number one rule. And it's often that not until opening statement or halfway through a cross-examination of a witness does anyone really know what I'm doing. The second thing is I am intentionally painting a picture as I go forward that does not reveal everything at the start. Part of that is for the element of the fact that nobody can predict what I'm going to do next. But it's also because a jury or a judge ends up having a eureka effect.

9:14That is the point of the adversarial system, the idea that if we're fighting with each other, eventually the truth will break out. And I firmly believe that. So if I give an opening statement, I'm never going to say what ultimately the end of the movie is going to be. that wouldn't make for a very exciting movie. And three, I'm going to go away from whatever I think the traditional playbook is. It often comes back to predictability. If they're going to play checkers with me, I don't want to play checkers back. So it's almost like a show for the jury. It's the same way I would teach. It's the same way that I would write.

9:45It's the same way if I gave a speech. It wouldn't be so linear and boring and uninteresting. It would have twists and turns so that people remember it and so people are gripped by it. So when they get to the end, and I've had jurors come up to me and say, we believed in you, we believed that you believed in yourself, and we were going to follow you. And so they have to go on the journey that I went on when I figured out what the truth was. Again, my truth, the truth of the case. Gain insight on the innovators, disruptors, and tech-driven trends shaping today's complex economy. I'm Carol Masser.

10:21And I'm Tim Stenevec. Wrap up your workday with the Bloomberg Business Week Daily Podcast. We bring you deeper dives into the story shaping your world, from the evolution of AI to the shifting priorities of global business. Plus, Silicon Valley power players and the latest tech trends. Catch up on the conversations you miss during the day. Subscribe to the Bloomberg Business Week Daily Podcast on Apple, Spotify, or anywhere you listen. You really thrive in the courtroom. Is it like an adrenaline rush? Do you ever get scared anymore? Are you ever like sweating? or are you always in control? I sweat like all people.

10:56It's definitely an adrenaline rush. It's definitely sort of its own high, and it's the ultimate search for the truth. The search for the truth, there are great and curious journalists, and there are congressmen who are probably trying to get at the truth. The truth comes out in courtrooms. I've always believed that, and the longer my career goes, the more certain of it I am. And so I think it's very, very important. So if it's both exciting and important, that's a pretty interesting thing to do. Have there ever been moments where you felt out of control or that you'd lost control and you're trying to win it back?

11:27What do you do in those moments? There are never moments in a courtroom where I feel out of control. There are moments in a courtroom where I know I'm taking out water. And what I try to do is get control back, get the water out or change the direction of the boat, something. I think that's a testament to picking issues that are important that people misunderstand and the juries get it right. I read you charge$3 ,000 an hour. You're losing money as we speak. I'm always losing money. I don't talk about my hourly rate, but if I need more free time, it's getting higher. Moving to your clients, I'd love to hear how you describe some of your top clients in one word.

12:02Elon Musk.

12:07I didn't think this would be the toughest question of the day, but... In one word? You're speechless! I don't know that I'm speechless, I'm thinking. It's important to get answers to questions right. Groundbreaking. Megan Thee Stallion. Fearless. Jay-Z. Genius. Mr. Beast. Dynamic. Alec Baldwin. Hysterical. Yes, I agree. The victory you got for Jay-Z seemed like classic you. You got the case dismissed, you're coming back with a defamation suit, you called the accuser's lawyer a 1-800 lawyer. Why were you so aggressive in defending him? Because he was completely innocent. and because I felt that the system was being weaponized in an improper way.

12:54And what does that tell you about the system? The system is very broken. It's probably, you know, we spend so much time talking about other things, but it is one of the original problems in this country. It remains to this day. And what you can do, even by winning big cases for prominent people who have resources, is change the system for everybody. Where's that case going? You'll have to wait and see. Elon said at one point he didn't want white-shoe lawyers. He wanted hardcore street fighters, that there will be blood. Did that speak to you? Not particularly. But really, what does Elon Musk demand in a lawyer?

13:28You are someone who has survived in his inner circle for a long time. How? I, for better or worse, haven't changed that much since I was 10, I don't think. So what he gets with me is what everybody gets with me, which is I fight the right way, but I fight hard. Well, let's talk about that. Everyone thought Elon was screwed when it came to the SEC, and that hasn't happened yet so far. Is that thanks to you? Listen, the folks whose corner I'm in, I think owe some gratitude towards me, sure. I can stand up and protect people, I think, in a unique way and that goes for everybody that I represent and advise.

14:04So the SEC sued Elon again just days before Trump took office. You have said the agency has been engaged in a multi-year harassment campaign against him. What is the status of that case? Or this campaign, as you've called it. Well, the case, which, let's be clear, is a pretty ticky-tack technical violation, still pens. I don't think it's going anywhere, but it's pending. But what about the campaign? Will the SEC's stance on Elon change now that he's playing such a prominent role in the administration? I'm hoping that the stance of the SEC will change because it should change, which is that, you know, we shouldn't be trophy hunting and celebrity hunting, especially as government lawyers.

14:44And that is a major concern that I've raised over the years and have been raising a lot lately. The Twitter takeover. That one got real messy. You were in the trenches. What worked? What didn't work? Well, his decision to acquire the company obviously worked. The company is worth more than it was worth then. He is glad he bought it. Elon is very much experimenting as he goes. And that's part of his genius. It may, at moments, look, as you put it, messy. But this is what the great experimenters have always done. It's just that Sir Isaac Newton and Albert Einstein and others were not doing it live on Twitter and for the world to say.

15:25You only remember the experiments that worked. You don't remember what it says in their journals, which is that it almost never worked until it worked. What about the method? Like, you know, there was this report that you guys were yelling at each other in a conference room. How does someone like that respond to pushback, especially when it comes to legal advice? Like, how do you set expectations for someone like Elon Musk? My clients are all used to my pushback. Everybody advised is used to my pushback. I don't know how they take it. They probably curse me out at times, but I think ultimately when the movie's over, people will be thankful that I told them the truth.

15:59The critics say he thinks he's above the law. Does he? No. How do you know? Like, is there a practical response when you're saying, no, we cannot do that? Yeah. Whenever I've said, and people often ask me, well, if this world leader or this person or that person, because again, 95 % of the people that I've advised over the years, nobody even knows that I have. What if that person were going to do something crazy? What if that person had their finger on the nuclear button? What if that person was going to break the law? Could you stop them? I get this question seemingly every day. I have faith that I could.

16:36I have faith that none of them would run me over or break the law, and that I have the kind of relationship and hopefully respect that if I flew in and said, don't do something, I think people are going to listen to me. Elon tweeted, if any judge anywhere can block every presidential order everywhere, we do not have democracy. We have tyranny of the judiciary. This is a direct challenge to the legitimacy of the courts. How does that stand in your eyes? as a lawyer? I don't... It would take a lot of time to go through every tweet. But this one particularly has to do with the law. I'm not so sure it has to do with me.

17:14I have my own views on the system being broken. They're not going to be the same as his views and other views. But I respect the system. I'm just trying to change it in my own way. Okay. So how about this? Tapping your inner biopsychologist. What do you think it is about Elon and Trump that they get on together so well? You'd have to ask them. Do you think it could all end in a bad breakup? I think they'll be fine. You have had such an unprecedented seat to this moment in business and politics. What have you learned from this vantage point? Well, I've learned that my initial instinct to stay away from politics was a wise one, even when I was 25 and thought, geez louise, I would never go near that.

17:58because it does infect and distort things in a pretty impactful way. I mean, I always have been able to, no matter what the media sensationalization is of something or how out of favor somebody is, be able to pull everybody back to reality and facts and just bring everybody back to a courtroom, tell the truth, do the right thing, and convince the world that I'm right. Politics is seemingly the fifth rail. and I'm watching it infect the search for truth on all sides. It's not taking a side here. And I'm sort of waiting to see if I'm going to be able to cut through that level of political chaos.

18:40Well, on that note, is your role evolving? As Elon's spending more time in Washington, do you have any interest in getting involved with Doge? My role is going to be the same always, okay, which is I'm going to take on the issues I want to take on, I'm going to advise the people that I want to advise on the issues I want to advise, and I'm going to move on to doing other things with myself. So how about this? It looks like he's taking a hacksaw to the federal government. It looks like Twitter takeover 2.0, but the stakes are higher. How do you view that from a legal perspective? That's too vague of a question.

19:16I don't have a legal opinion on sort of the generality of this. I will say that he has been successful in every business venture he's ever done with unprecedented success in human history. I try to not watch the day-to-day, hour-by-hour reporting on the chaos or the reporting on the perceived chaos or the reporting on whatever's motivating the reporting. I'm going to continue to watch, but obviously that's not my mandate. My mandate is not to produce music for musicians and write the movies for the movie directors. I'm here to take on the issues that I think are important and to fight against what I think is legal momentum and legal overreach that shouldn't happen.

20:03And I'm hoping that that changes the system for the better. One last Elon question, if you'll humor me. Hi, I'm Barry Ritholtz, inviting you to join me for the Masters in Business podcast. Every week, we bring you conversations with the people who shape markets, investing, and business. I speak with CEOs, Nobel laureates, market innovators, and legendary investors. Whether you own stocks, bonds, real estate, commodities, even crypto, these are discussions you absolutely need to hear. Subscribe to the Masters in Business podcast on Apple, Spotify, or anywhere you listen. Speaking about the rise of lawsuits, they're a big part of his playbook.

20:43Lawsuits are a big part of Elon's playbook. He's suing OpenAI. He's trying to take over OpenAI. Like, sometimes it's hard to take that seriously. What would you say to people who don't believe it or understand it or feel like it's not real? Well, this idea that Elon and his orbit have a lot of lawsuits, you know, the size of his entire empire is a nation state. It is bigger than most countries. It is more complicated than many. And so it's inevitable that it leads to lots of litigation. I'm sure that the percentage of cases against Elon and his companies versus the ones they start is something in the order of 98 % to 2%.

21:21You got to remember that. And third is he's just not going to back down if he thinks he's right. That's just the bottom line. How much are you two still working together? What's your relationship status? Elon and I work closely together. Okay. You're a lawyer. You're a sworn officer of the court. How do you tell the line when it comes to pushing the boundaries on legal theories? Easily, which is that I don't ever argue something or say something in court that I don't believe to be true and supported by the facts and the law. But I'm also not afraid to make a creative argument or tell the truth when it's otherwise unpopular.

21:54Exactly. Let's talk about the creativity. Tell me about that process. Like, I know you do a lot of research. You're on the front lines. You're reading stuff that maybe other big-time lawyers wouldn't read or they have their team do it. You're very in the details, in the weeds, aren't you? Yes. And all I can say is I'm an idea minute kind of person once I'm getting sort of in my creative environment, and that is trying cases is my creative environment. And so I'm trying to come up with creative ideas, and a lot of them don't work. The only ones everybody sees become public are the ones that are legal, ethical, factually accurate and proper, and that I think are going to win.

22:34And so on the cutting board, if I say, well, what if I did this or what if I did that? If it's not allowed, not supported by the law, not proper, it's not going to come out. You also represent Mayor Eric Adams. Was that creative? I think everything that I do has a touch of creativity. I'm not just following some playbook. I think the fact that they tried to run him out of town and take him down for this stupid case, I think my ability to stand my ground and stand my ground for him is forceful, whether creative or not. There was a public outcry in response to the result there. Mass resignations, people who say they've lost faith in the justice system.

23:14What's your response to the response? Well, when you say mass resignations... Lawyers resigned. Lawyers resigned. Yes, the small group of lawyers that were involved in this case effectively decided together to resign, right? And I don't begrudge them their resignations. I also don't take much from it. But they resigned in a blaze of glory. I mean, there was quite a letter to accompany the resignations. They may think or have intended to resign in a blaze of glory. I don't see it that way. I frankly would have resigned by just simply saying, I'm not going to dismiss this case, that actions speak louder than goodbye letter words.