Gambling Stories & the Future of Hollywood with Screenwriter Allan Loeb

Summary

Sharp or Square: Gambling Stories & The Future of Hollywood with Screenwriter Allan Loeb

Podcast: Sharp or Square
Hosts: Chad Millman & Simon Hunter
Guest: Allan Loeb (Screenwriter)
Date: June 30, 2026

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Overview

In this episode, Chad Millman and Simon Hunter are joined by acclaimed screenwriter Allan Loeb for a riveting conversation about the intersection of gambling, Hollywood, and artificial intelligence. Loeb, best known for films like 21, Things We Lost in the Fire, and Here Comes the Boom, shares his personal journey through gambling addiction, Hollywood successes and setbacks, and his evolving views on AI’s role in creative industries. The discussion weaves through stories of risk, addiction, creativity, and the future of both gambling and entertainment.

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Key Discussion Points & Insights

1. Allan Loeb’s Hollywood & Gambling Backstory

• Loeb’s Early Obsession with Numbers and Storytelling
  • Allan recounts inventing leagues, fake gamblers, and bookmakers as a kid:

    “I created fake leagues, fake gamblers... I kept these notebooks filled with these characters. I’d give them bankrolls, I’d give them stock portfolios... Many of them went broke, which should have taught me at a young age not to do this.” (07:36)

• Transition from Trading to Screenwriting
  • Worked on the Chicago Board of Trade, witnessing immense financial risk and ruin.
  • Realized his interest in creating characters and narrative outweighed love for pure numbers.

    “At the age of 12, I guess that trained my brain to create people that don't exist. And that's what was the road to screenwriting, possibly.” (08:58)

2. Hollywood High School Connection & Local Color

• Both Chad and Allan attended Highland Park High School, alma mater to many successful Hollywood figures.
• Community described as “where the John Hughes movies” were set and filmed.

  “If I could handle the winters, I would probably send my kids there. I don't have kids, but I would if I did.” (11:27)

3. Breakthrough with the Movie 21 and Gambling’s Role in Success

• Getting the Gig:
  • Loeb’s openness about his gambling addiction led Sony execs to tap him for the screenplay adaptation of Bringing Down the House (21).
  • He initially hesitated, concerned for his recovery, but ultimately accepted after consulting his therapist and mother.
• High-Stress Hollywood Moments:
  • He describes the drama leading to the last-minute re-write and the surreal experience of reworking the script in a Vegas suite the weekend before filming:

    “My Eyes would be bloodshot. I’d be an emotional basket case. But that’s because I was losing all my money. Now I’m in this suite... emotional basket case... because I’m doing my fucking job.” (15:03)

  • The gamble paid off; the script rewrite succeeded under pressure.
• Memorable Hollywood Anecdotes:
  • Breakfast with Kevin Spacey, who told studio execs to “leave Allan alone,” ensuring the creative process wasn’t derailed:

    “He looked at me and he goes, go. Fucking right.” (17:08)

4. The DNA of Flawed Characters

• Loeb’s experience with addiction and risk heavily influences his writing.

  “The best characters are super flawed. And anyone who gambles knows about being flawed... That’s what I try to do every time out.” (24:24)

• Simon reflects on money discipline, addiction, and the fine line between problem gambling and professional sharp betting.

5. The Evolution of Gambling and the Rise of AI

• AI’s Impact on Betting:
  • Simon explains how AI is revolutionizing the betting industry, automating tasks, accelerating model-building, and making sophisticated predictions.

    “Instead of taking me hours and hours to plug in data into my models, AI does this stuff already programmed for me, so it’s done within seconds and minutes.” (29:48)

• Shifting Markets:
  • Professional bettors are moving from traditional sportsbooks to prediction markets for more legitimacy and new liquidity.

    “Now they’re only focused on buying and selling and trading in prediction markets... It just feels like I’m treated as a legitimate executive, not as a degenerate better.” (34:46)

• The Addictive Drive Behind Success:
  • Panelists discuss the similarities between hedgers, traders, and gamblers—the compulsion to be “in action” runs deep in all high-achievers.

    “Anyone successful I’ve ever met in my entire life has an addictive personality. Seriously, it’s just the way it is.” (36:46)

6. Addiction, Rock Bottom, and the Road to Recovery

• Intense Lows:
  • Allan shares harrowing stories—blowing his portfolio in the 90s, lying to parents about being robbed, and literally losing (and briefly recovering) $100,000 on a Vegas tram, only to immediately lose it all gambling.

    “I remember getting on that tram and seeing the fucking Puma bag just sitting there on the bench with $100,000... and I immediately went to the casino and lost it all.” (48:42)

• Rock Bottom to Breakthrough:
  • The screenwriting breakthrough (Things We Lost in the Fire about heroin addiction) was inspired by the emotions and patterns of his gambling addiction:

    “I just moved it to heroin... No, Mom, I’m a gambling addict. Same same thing. But no, I’m not a heroin addict.” (42:20)

7. AI’s Place in Creativity & Optimism Toward the Future

• AI as a Creative Companion:
  • Loeb uses AI as a sounding board and editing partner.

    “I will give it a scene and I will say, what is your thoughts? Where could this scene be better? … It’s often really fucking smart, as if I had a kid Intern from a, you know, really smart kid from, from a college in the room with me.” (52:25)

• Industry Disruption & Opportunity:
  • Both Simon and Allan are cautiously optimistic that AI will create new opportunities and jobs, not just destroy old ones.

    “Anybody with a half decent idea... can create a business with agentic AI in two weeks. That would take $500,000 in five years, 20 years ago.” (56:07)

• Ray of Hope:
  • Allan: “I’m not really a subscriber to the dystopian 40% unemployment narrative... Entrepreneurship is going to be fascinating.” (57:24)
  • Chad: “I am always on the side of irrational optimism. So I’m with you.” (57:24)

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Memorable Quotes & Moments with Timestamps

• On childhood gambling creativity:

  "No, no, I didn’t make them go broke. The Dallas Cowboys, -6 and a half made them go broke." – Allan Loeb (09:26)

• On flawed characters and addiction:

  "Anyone who gambles knows about being flawed. There is a flaw to the DNA in a way." – Allan Loeb (24:24)

• On Hollywood under pressure:

  "He looked at me and he goes, go. Fucking right." – Kevin Spacey to Allan Loeb (17:08)

• On being in action:

  "You got to own a stock portfolio. Action. You own the ETF. Action. You’re in cash. Okay, I’ll just be in cash. You’re in action." – Allan Loeb (33:04)

• On AI as a partner:

  "It’s a tool, it’s a research tool. It’s a second pair of eyes… often is really fucking smart, as if I had a kid intern from a really smart college." – Allan Loeb (52:25)

• On entrepreneurship in the AI era:

  "Anybody with a half decent idea, a 19 year old kid... can create a business with agentic AI in two weeks." – Allan Loeb (57:07)

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Notable Segments & Timestamps

• [04:53] – Allan Loeb’s Hollywood intro and friendship with Demi Moore & famous crowd stories
• [07:36] – Loeb’s obsessions with numbers and inventing characters as a child
• [13:31] – How quitting gambling led directly to writing 21
• [17:08] – The Kevin Spacey "go. Fucking right" breakfast
• [24:24] – How gambling informs Loeb’s writing of flawed characters
• [29:48] – Simon on using AI for sports betting models
• [34:46] – The merging of betting and prediction markets
• [38:52] – Allan’s rock bottom stories and gambling addiction
• [48:42] – The lost $100,000 on the Vegas tram
• [52:25] – Loeb’s practical use of AI in screenwriting
• [56:07] – Optimism about AI and the new wave of entrepreneurship

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Podcast Tone & Style

Candid, humorous, and self-reflective, the episode is a blend of high-stakes storytelling and deep dives into craft and technology. The hosts and guest maintain a conversational, irreverent tone, often poking fun at their own pasts while drawing out serious insights about addiction, risk, and reinvention in gambling and Hollywood.

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Summary Takeaway

This episode stands out for its candid storytelling on gambling addiction, Hollywood pressure, and personal reinvention, as well as its open-minded, nuanced take on the risks and opportunities posed by AI in gambling and creative industries. Allan Loeb’s journey—from inventing characters and gambling as a kid, to Hollywood screenwriting success and battling demons—serves as both a cautionary tale and a beacon of creative possibility.

Transcript

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[Chad Millman]

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[Chad Millman]

Welcome to Sharper Square presented by Hard Rock Bat. We are part of the Voluum podcast network. This is the show that makes square sharper, makes the wise guys pay attention. I am Chad Millman. I am joined as always by my co host, my bff, my companion, my compadre professional better Simon Hunter. Hello, Simon.

[Simon Hunter]

Chad. How we doing, my brother?

[Chad Millman]

I'm pretty psyched today because one of my favorite people is coming on the show. He's got incredible stories, he's uber connected and he's written some of my favorite movies probably over the past 15 to 20 years. And it's been a long time since we had him on the show. He made a cameo name drop reference earlier this year. I will intro him in one second. I do want to remind our listeners, you know what, we've asked you to follow us on YouTube. Follow us on Instagram too. Harpersquare. All one word. We really appreciate it, Simon. Our guest today, back for the first time. He says it's been a decade. I can't believe it's been that long because that would mean it was back when we were in the ESPN days. Alan Loeb, longtime Hollywood insider, once called the most successful screenwriter in Hollywood by New York Magazine. He's written and produced, I think more than a dozen films. Things we Lost in the Fire, Here Comes the boom. Wall Street, Money Never Sleeps. That was the sequel 21, which was his breakthrough movie. Alan's gonna come on, we're gonna talk about Hollywood. We're gonna talk about AI. Alan and I have had many, many conversations about how we are using AI as creatives, which is a douchey term. He's going to talk about his long personal history with gambling. Alan Loeb, it's good to see you, buddy.

[Alan Loeb]

Hi. How are you guys?

[Chad Millman]

Dude, we're awesome. So I name dropped you because earlier in the off season of football because you, me and our other future guest, Michael Asker, who comes on every year for the Oscars, we had lunch and, you know, it was really fun. We had lunch at the All Star game in February and at NBA. And while we're sitting there, Demi Moore comes up to us and starts talking to you and you introduce her around like a classy guy. And the whole time I can't get out of my head like how long I've been watching Demi Moore. I didn't even know you were friends with Demi Moore. Why are you friends with Demi Moore?

[Alan Loeb]

She had her little dog with her.

[Chad Millman]

Yeah.

[Alan Loeb]

Yeah, she had a little dog and all that. No, I've been friends with Demi for. I wrote a short film for her to direct. Twenty years ago, Glamour magazine was doing something where they were allowing, like, giving actresses like 600k each to direct a short. And then she, through a intermediary, through a mutual friend, came to me and said, would you write this for me? And I did. And it was fun. And so we met then and we'd be pretty good friends since. And actually, yeah, I don't want to just name drop all the time, but I went to a bare. You'll appreciate this. I went to a Bears Packer game, Monday night game in Lambeau Field with Ashton when he was married to her and Jared Kushner. Oh, God, yeah, yeah, yeah. That was the crew. And we. We sat on the field. We were on the field for the game, which was, you know, for me and you, that's a huge deal. Lambeau and Bears fans, of course.

[Chad Millman]

Right? For just. People should know. You and I went to the same high school. We weren't friends in high school. You're a little bit older than I am. We became friends after high school when I was at ESPN and I was doing a lot of the gambling stuff for espn and we got connected through a mutual friend. Because what's interesting to me and Simon, I want you to jump in on this too in a second. You are very much a numbers dude, and you were able to translate that into screenwriting. I think people should hear, like, the evolution of that and how you used to, like, make up stats for Bears games when you were 10 years old. Because most people who are that into it don't all of a sudden become screenwriters. They go into finance or, you know, they go become traders at the, you know, in Chicago, at the Chicago Board of Trade or whatever. So explain to people how that happened.

[Alan Loeb]

Well, I was actually down at the Board of Trade out of college. Yeah. But I worked there for a year and I knew I would d if I stayed there. That was an insane place. When we had graduated high school and college, we had friends whose fathers were there. We have friends whose fathers. And you probably know what I'm talking about, put guns in their mouths. After being worth in 1991 worth $150 million and a year later owing 10 million. I mean, that was what it was like down there. And I digress. But as a kid, I was always obsessed with numbers. So I created fake leagues, fake gamblers. When I learned the points read at about nine, eight years old, I would check this Chicago sometimes and Then I would have like six characters and notebooks. I kept these notebooks filled with these. With these characters. I'd give them bankrolls, I'd give them stock portfolios, I would bet their weekend gains. I would look at real estate listings and buy them houses and cars. And many of them went broken, which should have taught me at a very young age not to do this. But the. But then, so out of college I worked at the Board of Trade. I didn't know what I wanted to do, so I kind of. It wasn't the numbers part of it, but it was the creating of characters, the creating of human beings, giving them children, giving them issues, marital issues. Some of them were divorced, some of them were living in the city, some of them were living in the suburbs. You know, at the age of 12, I guess that trained my brain to create people that don't exist. And that's what was the road to screenwriting. Possibly.

[Chad Millman]

But as a 12 year old, how are you making characters go broke? Like you gotta be thinking in a darkish place to have the understanding that, oh, with gambling, these guys are gonna go broke.

[Alan Loeb]

No, no, I didn't make them go broke. The Dallas Cowboys, -6 and a half made them go broke. All right.

[Chad Millman]

I mean, come on.

[Alan Loeb]

They just, by the way, these were mushes. These guys were old. Cause I was, I was a 12 year old. I was always taking the favorites. I was always taking the most public team. I didn't know what that shit was at that age, so. And my characters were betting way more. They were revenge trading. They were revenge gambling. And of course, many went broke. There were no sharps in the group.

[Chad Millman]

Simon, you gotta respect the creativity for a 12 year old who's already figuring out you shouldn't be betting the favorites and these guys are going broke.

[Simon Hunter]

Yeah, I would say I was so far on a different spectrum. I think at 12, I just joined my first fantasy football league in America with my American friends, and I drafted Dan Marino, who had retired the year before. That just shows where my football knowledge was at that age as well. Can you name drop your high school? I feel like this high school produces an absurd amount of millionaires.

[Chad Millman]

Al and I went to Highland Park High School. There are like crazy amounts of successful people that went to Highland Park High School.

[Alan Loeb]

Al.

[Chad Millman]

I don't remember Jonathan Gray, who is the president, future CEO of Blackstone. He might have graduated in Alan's class. My close group of friends. The amount of success just from that group is kind of absurd.

[Podcast Host (Guaranteed Human Ad)]

I.

[Chad Millman]

It's a school that just has had a lot of connections. The entertainment business al like, has been connected to those guys.

[Alan Loeb]

More than one studio head from our high school. There was also directors. F. Gary Gray went to our high school. He was a. He's a very famous, successful director. The high school, every two years would take a week off from classes and just do these symposiums like TED Talks and alumni who were very successful normally in the arts would come and speak. And that was just an amazing thing. And then I came back multiple times and spoke at Focus on the Art. Did you do Focus? You must have, Chad.

[Chad Millman]

Many, many times.

[Alan Loeb]

Yeah, yeah, yeah. And it was just a very nurturing. And it still is. It's a very. Just a very good high school. If I could handle the winters, I would probably send my kids there. I don't have kids, but I would if I did.

[Chad Millman]

For context, the school, the area, it's all the John Hughes movies, Simon. They were all shot in our hometown. Ferris Bueller was shot there. Risky Business was shot there. Breakfast Club.

[Simon Hunter]

I was like, breakfast Club? Was that your high school breakfast club or. No,

[Chad Millman]

it wasn't shot at our high school.

[Simon Hunter]

16 hallway scenes. That's your high school with the library somewhere else.

[Chad Millman]

I don't think they shot it there, but it's all sort of the same North Shore community. You know, it's pretty.

[Alan Loeb]

The ravine. The ravine where the Ferrari fell into. And Ferris Bueller stayed off. That was just a few blocks from my house.

[Chad Millman]

That was across the ravine from my house. I could see it from my house.

[Alan Loeb]

I want to do a plug right now. I just did a movie last summer that's coming out, I believe, in the spring, called the Best Is Yet To Come with Matthew Broderick and Alan Ruck. So it's Cameron and Ferris. I was up in Vancouver with them last summer, multiple dinners and hung out with them and just did a movie with them. So I brought them back. We brought them back together, coming out next spring.

[Chad Millman]

So I think it's important, you know, we talked a little bit about your experience as a better that did help you as much. And I want to get to the Free Press story that you wrote because I do think there's some really interesting perspectives from you as someone who has been a big better and is now moving on from that. But first, explain to people how you ended up writing the movie 21, which was based on Bringing down the House, the Ben Mezrich book. Because that is really what kicked it off. It was gambling and gambling story that kicked it off for you.

[Alan Loeb]

Yeah, I Had recently, a few years prior to finally quit gambling. You know, this one took. It was probably the 50th time I quit, but this one took. I was in. I was. I was in good therapy in the program, whatnot. And I had then really, really broken through in Hollywood because I had struggled in Hollywood for about 12 years. Really struggled, Couldn't break through. It's a very hard business to break through, as people know. And I had broken through. I was kind of a younger, hot, for lack of a better term writer. And I got a call from my. An executive I knew at Sony, and he said, I have a very personal question to ask you. I had heard through the grapevine that you're like a compulsive gambler. And I said, yeah, I'm totally open about it. Yeah, I am. And he's like, would it be crazy for you to write a movie about counting cards, blackjack? Because we have the rights to this book, Bringing down the House. And I had read the book. I knew the book. So I said, I know the project well. I mean, I know the story well. He goes, well, would you want to come on and write that for us? And I didn't know. I'm like, let me talk to my therapist. Let me talk to my mother. Let me see if this is right for me. And I had those conversations, and I came back to him like, you know what? I think I can do this. And I did, and I wrote that. But the funniest part of the story is, you know, as these things go in Hollywood, you're close to production, and suddenly everyone, like, for whatever reason, freaks out about the script. And suddenly it needs a ton of work. When it was perfect the week before and they might pull production. Like, it was a really dramatic thing. And we're in Vegas, and I was in one of those suites at the Wind. You know, those big suites.

[Chad Millman]

Yeah, yeah.

[Alan Loeb]

With the massage room off to the side when you walk in. The studio was kind enough to put me in that. And I'm rewriting the script, not knowing if they're going to make the movie on Monday. Like, our first day of production was Monday, and they were going to maybe pull the movie. And I'm rewriting all throughout the night, and I've got room service trays. I'm bloodshot. It's 4 in the morning. And I remember the next day I called my mother and I said, you know what, Mom? Like, eight years ago, when I would come here, I'd be in this exact suite with room service trays, my Eyes would be bloodshot. I'd be an emotional basket case. But that's because I was losing all my money. Now I'm in this suite, it's five in the morning. I have room service trays. I have an emotional basket case. That's because I'm doing my fucking job. So it was a return, but it ended up working. The script worked and the movie gets made. And I'm pretty proud of that movie. Movie did well, and I think people like that movie.

[Chad Millman]

What do you remember what all of a sudden fell apart that weekend? And how did you.

[Alan Loeb]

I do.

[Chad Millman]

What triggered you to get back to it?

[Alan Loeb]

Get back to the script to what?

[Chad Millman]

Sort of. I know you had a very important breakfast with a guy who is now infamous, but in the moment, he wasn't infamous. What was the problem with the script? And how did you sort of turn yourself around?

[Alan Loeb]

So, yeah, basically it was the read through. The read through. In Hollywood, the read throughs can be very treacherous. And often movies, more than TV actors, will not perform during the read through. They don't want to be directed by the director. So they read really, really monotone. And it sounds horrible. Like all the jokes don't land, all the lines don't land. And you would think that the executives would know that, but they. So they hear a rough read through, then they freak out. And that's what happened. And they were all freaking out. It was a terrible read through. We were all in. We were at the Planet Hollywood in a suite, all of us. The producer, Mike DeLuca, who now runs Warner Brothers, and Kevin Spacey, who was the producer in the movie and starred in the movie. And Amy Pascal, who ran the studio, Sony and whatnot. And everyone's yelling at me and freaking, you need to put this in there. What we really need is this. And everyone's freaking out. And Kevin Spacey leans into me. Do you guys remember Swimming with Sharks? The Kevin Spacey from Swimming with Sharks. Okay, so it was that Kevin Spacey. He was literally that character. He leans into me and he goes, this is a clusterfuck. Meet me tomorrow for breakfast in the Mirage and we'll figure this out. And he left. And everyone's yelling at me. I didn't know what to do. I was freaked out. I was young. It was like my first big movie. And so I thought it through and I kind of rewrote the script in my head. And I went to this breakfast and I laid it out to him. I go, I think I figured out how to fix this. And I laid out the whole thing to him. And it was just this great moment. It was like a Hollywood moment with literally out of Swinging Sharks, he called Amy Pascal, who ran Sony, and he said, hey, it's your movie star and your producer of your movie. Alan has pitched me his new take. It's going to work. He is going to do it now. Nobody from the studio allowed to call him at all. And we're gonna make this movie. And he hung up with her. And he looked at me. I'll never forget this. This is a movie moment in real life. And he looked at me and he goes, go. Fucking right. And that's when I did. And I went to the suite to get five in the morning, room service trays and all that. But it did work.

[Chad Millman]

How long did it take you?

[Alan Loeb]

It was just literally a weekend. It was. It was Bears super bowl, by the way. That Sunday was Bears, Indianapolis, cold Super Bowl. Rex Grossman, Devin Hester opening kickoff.

[Chad Millman]

Touchdown.

[Alan Loeb]

That was the Sunday of the super bowl. And I had handed in the script literally five minutes before kickoff and then watched the Bears lose.

[Chad Millman]

And you watched it in Vegas.

[Colin Coward]

Yeah.

[Chad Millman]

As a recovering gambling addict.

[Alan Loeb]

Yes.

[Chad Millman]

That's testing yourself. That's testing yourself right there, brother.

[Alan Loeb]

Yeah, it was a monumental moment in my life. But we did get the movie made. That was. That was the key.

[Simon Hunter]

I love that the studio exec was like, yeah, you're a gambling addict. You'd be perfect to rewrite this script. And let's send him to Vegas while we're at it. It's like, oh, my God. Temptation. I can't even imagine.

[Alan Loeb]

That was a real moment in life that I am proud to say I survived.

[Chad Millman]

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[Jeff T]

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[Colin Coward]

hi, it's Colin Coward from the Colin Coward Podcast. Every goal starts with an assist. As Official partners of U.S. soccer, this team is ready to deliver Sensodyne Dentist recommended defense of your sensitive teeth. Centrum Fueling your day with science backed nutrients. Advil, of course. Powerful inflammation fighting pain relief. Voltaren Arthritis gel helps penetrate deep, keeps the joints moving and tums ready to counterattack with fast heartburn relief. Learn how Halion can assist your game day [e-mail] Colin Bro, from the show

[Alan Loeb]

last night to this drive, why is it never chill?

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[Jeff T]

Good thing.

[Alan Loeb]

Nissan builds for that kind of chaos.

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[Chad Millman]

Yeah, you can tell.

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[Chad Millman]

I do want to ask you, like you've written a ton of movies, whether it's comedies, dramas with a lot of big name people, but I do feel like you have a very specific ear for movies that are about risk, temptation, people who are unafraid to sort of live on that edge. Is that something that you think about a lot? Is that something that you recognized early on was a gift?

[Alan Loeb]

Yeah, I would say beyond risk and beyond what you said, there's. I think the real truth is the best characters are super flawed. And anyone who gambles knows about being flawed. You know, there is a flaw to the, to the DNA in a way. I mean, maybe it's not. There's very few gamblers who are just always clean and happy and perfect. Like, I think we all know that. So I think early on in my writing I did and I specialized in writing very flawed characters who we can still get behind. You know, not clean, but having real issues and demons that we can connect with as an audience is what I try to do every time out.

[Chad Millman]

Simon, you can attest to it not being a clean, perfect, happy life. I feel like you are the personification of someone living with demons who we all can connect to and root for.

[Simon Hunter]

I would say I'm as close as you get to a clean gambler, to be honest with you, Chad, like I'm disciplined. Like I can watch World cup games and not bet on it. You would, I would say 99 of the people that do what I do don't have that type of restraint, whether it's five bucks or ten bucks. They're getting action down pretty much on everything. And that just comes with the territory of addiction. Right. It's like, whether you know it or not, you're addicted to it. Right? And someone like me, I am addicted to it. Like, I literally went to a buddy's little kids little league baseball game the other day. We, we gambled on sixth grade baseball. So it's like, do I have an addiction? Yeah, of course. But I can control it, which is half the battle, right? That's a mental battle of in. And you know, I just think all the time about people that do what I do. It's Right. There's plenty, plenty of people that are great at math that can build models that can do sports betting. But can they control it? Can they unit size? Right, right. Can they take the right bet on the right edges and sit out other times where they're kind of missing things? That's, that's half the battle. So, yeah, that's what I talk all the time. Money discipline on this show.

[Alan Loeb]

That's.

[Simon Hunter]

We preach it all the time, right, Chad? It's, it's a big part of what we do. And if you can't control your money, you probably can't control your addiction.

[Alan Loeb]

My question, though, I have a quick. Can I ask a question? Of course. Now, most people in your position, including you, did they get there? Were they always that way or was there always a crucible? In probably their late teens or early twenties they went through to get there. Scared straight, as it were.

[Simon Hunter]

I've talked about, I've gone, I went broken, I went broke betting before I got into it. Right. I live right down the road from Atlantic City, so my youth was Texas hold' em poker. Boom, right. Chris Moneymaker. That was a huge thing for me. I was playing in tournaments at the Tropicana at 16 with a fake ID. So like I was all in into gambling. Sports betting is a little different. Like I did it, but I didn't. I just was like you. I'd bet on favorites. Especially was in college, Chad News, where I basically had gotten a job that took me out to Vegas and I met professional betters and he put me on as a runner. That's what I started as. And even as a runner, I was building out models and like going on Reddit and trying to take other people's models and trying to get really good at it. I went broke as well. Like got information off guys that was really good. Like, hey, not only does your model back this up, I know this other group that's Putting say a million dollars on it at the time. I put 20k, which was all my money. I was like all in on this one side. It lost. I told the guy I worked for, he's like, jesus. He's like, just because I told you this group loved it doesn't mean it's a sure thing. Like, it's sports. Anything can happen. So that again, was a big learning curve, which is like, don't put 100 of your pot into one game. So, like building back up a bankroll after that. Yeah, it was very humbling. But again, it's any sports player. If a sportsman comes to you says, I never went broke doing this, it does happen. I know plenty of guys, they're servants, way ahead of it. Right? They didn't have the pains of their teens. They were always winning in their teens. They built a model of 13 that's better than guy who's been for 50 years. So it's when I first got into this in 2011, if I would have told you what a life is like in 2026, using AI and all this other shit, you would think you're lying. It doesn't sound real. It's just moved way far away from gut feeling and inside knowledge to computer models and AI prediction. So it's totally shifted that someone like me, like I said, I'm on the show. I, I think I'm the clean version of many people like Chad is. I've never missed a show. I know pros who, they'll lose big on a game. They'll disappear for a month. Like, I lose big. I'm on this show Sunday night talking about it. You're not going to find too many guys. I want to do that. Right. It's, it's, it's a very unique job, this, especially talking sports betting, living life. So I, I, I agree with your sentiment of it though, that, yeah, it's, People say they never went broke. Everyone goes broke. And like you said, like, it's, there's something wrong with all of us. That's what got us into this. Right? We're not some normal guy who, you know, a good time to us is having ice cream and watching the news at night. That's just not how any of us here are wired.

[Chad Millman]

Al, do you want to say something?

[Alan Loeb]

No, I, I agree with everything. I was, Simon answered my question for me. I was going to ask him about AI and in the world of handicapping and groups, I was also going to ask him if he ever remembers the movie the Runner. Do you remember The Runner.

[Simon Hunter]

I do. I do. I. I watch any terrible movie. I watch. I watch another. Another one with what's his name, Elijah. The guy that into the Wild. It was some gambling movie that was just. I recently just watched. It was horrible, Absolutely horrible. But I'll watch any gambling. I will watch it. Yeah. AI, me and Chad talk a little bit about it. AI, AI, there's some stuff I can't talk about here because of contractual stuff, but I will say I've been very upfront about it. Instead of taking me hours and hours to plug in data into my models, AI does this stuff already programmed for me, so it's done within seconds and minutes. So it's like shaving off a ton of time of prep for me. But, yeah. Are people using AI to win big? Yeah. Like, I talked a little bit about the Super Bowl. A group I really respected had a model that gave, basically said that Seattle Seahawks were going to win by more than two touchdowns, right? Which anyone has a model that says that you would get rid of that model. There's something wrong with that model. So because it's all new and it's AI again, it's a model maybe two years old, they were giving out the information. Everybody, they're saying, hey, we have a model that's projecting this to be a bluff for the Seahawks. And a lot of arguments, a lot of discussion for those two weeks lead up to the game. I don't know if they did win by two touchdowns, but the Seahawks did blow them out, right? They were the much better team. That group now is out trying to sell that model all off season. That's why they're giving out that information to people, because it's all. People are trying to sell their models right now because people are trying to be ahead of AI. I know plenty of guys in their 70s and early 60s that are just like, hey, if I can spend 500k on a model and rather than hire some kid out of college to do it for me, I'm going to do that. So that's what's really shifted right now is there's a big influx of selling AI models in the gambling sphere.

[Chad Millman]

You know, I do want to talk about the AI stuff, but speaking about addiction and guys who can sort of live in this space, you know, I just finished this book, the Number, which we're going to start talking about during football season. I follow these professional betters. They're all very successful. None of them were losing money. They are tops in their field. Whether it's a prediction markets Whether they're betting up with bookies, whether doing it legally. And I was always trying to figure out where was the line between addiction, obsession, focus, concentration, what is the difference between the better in New Jersey who can't let go when he's on vacation, and the trader who's on his vacation with his family in Japan and he's up all night while the family is sleeping because he's trading currency markets in the United States. Like, where does that line end? Is it just because of betting? It's got to be an addiction. I do think there's some language differences here. And if you are a trader who feels that way, it's different than if you are a gambler who feels that way. Al, as someone who has lived all of those lives and written stories about those lives, whether it's in movies or about your own life, do you sometimes feel that is a distinction without much difference?

[Alan Loeb]

I do. I do. And I think the, it's, A lot of it is semantics. A lot of it's semantics because if you, if you're, if you're a compulsive gambler or not, or maybe a problem gambler, and there's specific definitions for each one of those things. But if you have an issue with gambling and you make any money, you have any money, you're gonna have to be in action. You're gonna buy a house, you're in action. Mortgage rates are action. You got to own a stock portfolio. Action. You own the ETF action, you're in cash. Okay, I'll just be in cash. You're in action. If you're in cash and inflation is 6% and the markets go up 40% because you're losing every day, your dollar is losing, you can't avoid being in action. So there's different words for these things. If you're an investor, you're fine. If you're, you know, playing nickel slots, you're, you're a degenerate. I mean, it's whatever, whatever these things are. So delineation between these things, it's all personal. And it's just for me, my, my ending up definition is, is how are you emotionally? Like, how is your marriage, how are you as a family, father? If it's controlling your life, if it's destroying your life, you have a problem. If, you know, even if you're a trader and you're trading all the time, but you're a good provider and you're with your kids emotionally and you're present and you're with your family, you might not have a problem. I mean, at the end of the day, it might not be a popular opinion because I know the medical establishment around these things. And the addiction industrial complex likes to, you know, have their definitions and make their dogma, and that's fine. But that's just what I've come to learn at, at this point.

[Chad Millman]

Well, look, it is interesting, especially with prediction markets. Betters have always looked at themselves as doing something that is no different than trading. Right. The language is even the same. They want to get the best price, they want to buy low, they want to sell high. Regardless of whether you're talking about buying a stock or buying a number in a betting market, the prediction markets have sort of merged those worlds. And I know a lot of people, and I wrote about this in the book, a lot of people who are completely moving their betting operations from offshore books, from having networks of runners sign in and betting at DraftKings, FanDuel, Hard Rock, all over all the books around the country. And they're moving all of their liquidity into prediction markets, shutting down their entire network of runners. And they're only focused on buying and selling and trading in prediction markets. And it feels. And they. One of them just said to me, he's like, it just feels like I'm treated as a legitimate executive, not as a degenerate. Better.

[Simon Hunter]

And that's all in the last year. Like, that's not. Yeah, this is all new. And Chad knows, like, I. It was hard for me to shut down what I had. But like, we talked a little bit about the show. I haven't got too much into it, but New Jersey is the only state that outlawed runners. And it just so happens that this show is probably one of the biggest gambling shows. And I've talked at news ad nauseam about how I have runners in this state. So, like, do I feel attacked? Am I a little egomaniac in that way? Of course I am. But it's like, okay, lucky for me, this other market has opened up and it's really changed in a lot of ways. I don't know if you saw the bet the other day, Chad. A guy basically, basically bet on Spain just to win against this small country.

[Chad Millman]

And they million dollars on Polymarket.

[Simon Hunter]

Yeah. So guy had basically made what I always called the sucker of sucker bets. Right. You're placing a bet on something you think can never happen, but it's sports. And when anything can happen, something will eventually happen.

[Colin Coward]

Right.

[Simon Hunter]

The old saying. So, yeah, it goes back to the addiction thing where it's like anyone successful I've ever met in my entire life has an addictive personality. I've never met again. I've met all walks of life through my career. They all have addictive personalities. Seriously, it's just the way it is. How you be successful in life if you're not addicted to it, right?

[Alan Loeb]

I agree with Simon, and I know a lot of people in different walks of life, many of whom are extremely successful. And what I realized is it's one carrot on a stick for. For these guys or women, and it's one of a few things. Often it's money, but even it's beyond money. It's winning. So if you have a hedge funder who's worth $4 billion, the money journey's over. Whether they want to admit it or not, it's over. But they are still going from five in the morning till midnight, neglecting their kids or whatnot, because they want to keep winning. So it's either winning, money, power, sex. And I know guys who are just like, that's. It's always one thing. And they are just so motivated by that one thing. And I thought about my thing, and I know what my thing is, and it's none of those things, to tell you the truth. I mean, I do like winning. I enjoy money, and I don't hate sex, obviously, but for me, it's freedom. It's just freedom of time and activity. I am just. I am very greedy with my freedom. And like Simon just said, I'm not married. I have no kids yet. And one of the reasons is because I'm just selfishly greedy with my freedom. And that could be a very big thing. Flaw. That could be a horrible thing. I'm not saying it's a great thing, but it's always one thing for each one of these guys. It's just. It's. It's never four. It's just one. And that thing they can't get enough of, and it's compulsive. And almost every very successful person I know has one of those things.

[Chad Millman]

So you mentioned earlier in the show you had a few times where you went through rehab for gambling. What were some of the things that sent you into rehab each time that made you think, oh, my God, this is. This has got to be the bottom?

[Alan Loeb]

Yeah, no, I. Throughout my 20s. It was mostly in my 20s, in my early, too, like, late teens. I like, got in with my father, had to bail me out with bookies at college, like, four times. And that's always brutal. I wrote about in my Free Press essay That I went to the Bahamas with friends during college. And within, I don't even know what, within two hours, I had lost all the money I brought to gamble in the bohemian casinos. And then I told my parents I was mugged and they needed to send money to which I lost that right away. And then out of college in my 20s, I just blew through and I was in a crazy time. That was the time where the text that. Similar to now, by the way, not much different than now with AI and the AI stocks and the semiconductor stuff stocks in those days it was the mid-90s, so it was the Internet stocks. And I went crazy on that shit. And I maxed out multiple, multiple credit cards and built a portfolio and then just was going crazy on margin with the JDS uniforms. Cmgi. I don't know if you guys remember these. Lucent. I mean, there were so many of these. And I did really well. You couldn't not do well in a bull market like that. If you're long, you have to be the biggest moron in the world to not do well. So I made hundreds of thousands of dollars. And then I go to Vegas every weekend and blow it. Or with a bookie, blow it. And that was my life for six, seven years. I was still screenwriting, trying to break through in Hollywood and sell scripts, which I wasn't selling. And that was just a crazy period in which I, you know, I had made a lot of money and I inherited some money from, from a grandfather and I had money and I made money and I, and I. And I had a lot of money for a kid in his late 20s. And then by 32, when the bubble burst, lost it all. 0. Had to sell a car to pay rent. So now I'm taking the bus in LA at 33. My friends, a lot of the guys that we knew, Chad, were in real estate in Chicago. They started making real money in real estate. So now they're buying houses, marrying women. I mean, I couldn't get laid like you wouldn't believe. And so I'm sitting there broke, taking the bus blue. You know, I blew seven figures at 28 years old, 29 years old. I think I two or three million dollars within three months of the market crashing and bubble bursting, which is interesting is now we are in a situation where people are, I don't know if you follow the markets, but everyone's saying, are we in a bubble? Are we in a bubble? I think we are in a bubble, but it could be another five years. Is it 1993 or is it 1999 is the real question. But when these things end, they end really, really badly for many people that get caught up in it. And regular people with a 401k or just people with. And I'm a little nervous now right now. We are. It's feeling. It's giving 90s to me, mid-90s, late 90s. And I watched it all go away. And then I was, you know, decimated in very dark times. And that was the time that I really, really. That's the time I quit. And then. And then subsequently, a few years later or within a year, found the Hollywood success that I had been trying for so badly. And these things are correlated. They're not. They're not. It's not correlation. It's causation. It's causation, not correlation. I think I got that right.

[Chad Millman]

But don't you think it was ironic that the thing that gave you the most public success after you quit gambling was a huge movie about gambling?

[Alan Loeb]

Yes and no. Because what really broke to just what really broke me through to the Hollywood establishment, the people that were rejecting me for 10 years, and suddenly I was their favorite. You know, golden boy was not 21. It was a script I wrote that subsequently became a movie called Things who Lost in the Fire with Benicio Del Toro and Halle Berry. That script is really broke through and got me noticed. And that script's about heroin addiction. But all the heroin addiction that the Benicio character played and suffered through was all inspired by my gambling addiction. I just moved it to heroin. I remember I sold that script for a lot of money for, like. And it was a weird little drama. In those days, they paid money for weird little dramas. Sold for over a million dollars in 2004, I think it was. And then my mother, you know, was like, shocked and proud of me and happy. They were really, really worried about me, obviously. And then proud and happy. But she read the script and then she freaked out again in Jewish mother way. She's like, are you a. Are you a heroin addict? I said, no, Mom, I'm a gambling addict. Same same thing. But no, I'm not a heroin addict. But that was what broke me through, and that was inspired by my gambling addiction. And then 21 came about two years later.

[Chad Millman]

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[Jeff T]

This is Jeff T from the Club 520 podcast. Oh my goodness. Now this is a performance you do not want to miss. The Dell xps. Powered by Intel Core Ultra. It's got the sauce. We're talking speed, style, stamina, bam. And a long lasting battery life unheard of in this league. So whether you're using it for the next level, creativity, never ending productivity, or the entertainment that has you on the edge of your seat, this laptop is your mvp. Just look at the hustle. Is there anything you can't do? From the first second of the action all the way through to overtime, this thing is a powerhouse. The Dell xps. Built for those with all the right moves. Built for you. Find technology built to take your game up a [e-mail] XPS

[Colin Coward]

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[Alan Loeb]

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[Alan Loeb]

And it got some kick too.

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[Chad Millman]

Your story about the Bahamas and calling your parents and saying you did money, you had been robbed. I just actually used that on my kid, believe it or not. My younger son, who's in between his freshman and sophomore year in college, he wants to go to Japan with his buddies at the end of the summer. And his buddies are able to pay for it either through jobs or whatever. And so we told him, all right, but you got to figure out a way how you're going to pay for. Where are you staying? What are you eating, like. And so he's got to, you know, he's working this summer. He's got to use some of that money. And I said to him, I go, by the way, you call me three days in and say you got mugged and you're out of money. I'm not falling for it. Just so you know, like, you better not lose your goddamn money.

[Simon Hunter]

Chad all mark no bite. You would. You would. You would break so quick, Jeff, by

[Chad Millman]

the way, I'm totally. By the way, my wife. I could be taken in two seconds. My wife and I, you know, our kid graduated from college and earlier this month. And talking about, like, you know, he wants to be a video game designer. He wants to make the dungeon next Dungeons and Dragons, either for video games or in real life. And, like, he's really good at it, and he's won a lot of awards for it, but it's a hard business to break into, as Al knows, just from screenwriting. Right? And so. And like, we both have a lot of friends who were in that business who needed help for years before they broke through, and then they broke through big. And he's trying to figure out where he's going to live. Is he going to stay in Philly? Is he going to go to the west coast? Where's. And I'm whispering to him, guy, I got you. Just follow your dreams. Don't worry about it. On the other side of it, my wife can't hear me. She's like, well, you're going to have to get a job, and if you're going to have to bartend or do whatever. And I'm thinking, like, when I moved to New York, my dad left town, I had my bar mitzvah money, and he gave me a bartender's manual. And I'm, like, still a little soft. And I'm like, guy, we're going to help you out. No problem. You do have to tell the story of when you left $100,000 on a train.

[Alan Loeb]

Yeah, yeah. By the way, it's all in the Free Press. Can you do a link to the Free Press piece to this? I don't know how you guys do that, but it's a good essay. But in the essay, I tell a story of another bottom I was chasing. I owed a bookie. I had to sell some stocks. Not to pay the bookie. The plan was this. I was living in la, and the plan was in the gambler's brain, my brilliant, genius brain. The plan was I had owed the bookie maybe 100 grand. So it was real money. I owed a lot of money, but I had money in this market, so. So I sold some stocks, roughly 100 grand, and went to. I did what's called the Chinese water torture of going to 10 banks to get $9,800 in each bank, because over 10,000, you have to fill out the forms and then you don't know, or they know. And plus, the banks don't even have that much on hand unless you call them. I mean, we all know these particular issues. So I went to 10 banks around LA, got 100 grand in cash, put it in the Puma bag, flew to Vegas to bet a weekend's Sunday slick, basically, and try to get enough money out of that hundred to pay back the bookie as opposed to just pay the bookie. Chasing. I got to the cab line at the Vegas airport and realized I didn't have the Puma bag on me. I had left it on the tram. And I remember just running to get back to the tram and telling myself this is a sign from God if that bag. Crying, like, literally just freaking out, panicking. If that bag. If I find this bag, if I find the hundred thousand dollars is a sign from God, I fly back to la, I give that hundred thousand to the bookie, and I'm done. I'm done gambling. And I remember getting on that tram and seeing the fucking Puma bag just sitting there on the bench with $100,000. And it probably left unattended for 17 minutes or who knows what it was. And I immediately went to the casino and lost it all. The other way? Yeah, of course the other way. You know, so it didn't matter, by the way, what the. Did it matter that I found it on the tram? It was going. You know, I think the Treasure Islander Bellagio in those days was the. The Steve Wynn properties were the ones that benefited from me finding that bag. On the, on the train. That was the fact.

[Simon Hunter]

God said, either you can lose it right now in this tram or you can go lose the casino in 20 minutes.

[Chad Millman]

Yeah, see, but when I remember that story, I thought that had been the signal. Like I'm just getting out of here. I forgot that you actually lost the money.

[Alan Loeb]

It's in the essay. Yeah.

[Chad Millman]

How quickly did you lose the money?

[Alan Loeb]

Probably on that SL Sunday slate, you know, I would assume it was that Sunday of football. I, I think I, you know, I don't remember. I know myself to know that I probably was gonna. I probably put down a lot of parlays going for the lottery ticket win to pay the bookie back and make a profit or whatever it was, you know, 5000$3 game or 5000$2 game around. Robbins with the three, all that and lost, you know, probably went two and four and lost the whole hundred thousand.

[Chad Millman]

Those are the signals. Right. By the way, before we get out of here, you and I have talked a lot about AI and we just talked a little bit about it and I wanted to close that loop because I feel like you and I are much more pro AI as a tool than I think a lot of other people in our collective industry, whether they're in journalism or in screenwriting, are. Explain to people your theory and feelings about AI and how it's useful to

[Alan Loeb]

you at the moment. And it's a, it's a very, you know, it's an ever changing landscape. These things are iterative and they're advancing so fast. And it's such a. It's such a wild time right now. We don't, no one knows what they don't know. We don't know. But in terms of creativity and screenwriting, I find AI to be a great tool. It's a tool, it's a research tool. It's a second pair of eyes. I use it, I use it all the time, the way that I use Google. When Google first, I mean, I remember writing scripts before Google and then Google came along and that was mind blowing. And this is a very similar thing to me where it's just an amazing tool and it 10x is 100x is what Google can do and you can, you know, I will give it a scene and I will say, what is your thoughts? Where could this scene be better? What. What about. I'm thinking about getting rid of this line of dialogue or replacing with this line. And it gives me its opinion. And it often is really fucking smart, like shockingly smart, as if I had a kid Intern from a, you know, really smart kid from, from a college in the room with me and he was reading the script and he was like, someone. I'm like, I have to promote this kid. Like, I don't want to lose this kid at the moment. It's really helpful. Now what happens when it writes the scene better than me and the studios don't have to pay me because all they need is a subscription to Claude? Well, you know, then I can, then I can, you know, just maybe go back to betting a lot of games and do what Simon does for a living and be successful.

[Chad Millman]

Baby, you can work Simon's AI. I don't want to tempt you there

[Simon Hunter]

same fear in my industry though. Like I, I told Chad, I used to have to have a team of guys, sometimes 10 deep. Now I need three guys at most. And that's overkill because a lot of the grunt work is just done by AI. It's. I, I just feel bad for the younger generation. It's like we, we're, we're lucky we've seen this happen before, right? I, I remember the dial up, getting onto AOL and Ask Jeeves, like you said before Google, like we remember all the iterations of this thing. I can see exactly what you're seeing ahead of me. It's again, we know the future is going to happen, but I can promise you we're not gonna have an 80 year old in the White House that's gonna just let all these things happen. Like there's gonna be laws in place, in my opinion, to protect creative people like yourself, right? Like this is, there's gonna have to be something because you, you just nailed it. Like, I, AI is better than anyone I can hire right now out of college. That's the honest truth. Like, if I hire some kid to write code for me and to help work on models, it's gonna be like talking to a puppy. This kid, maybe he's a genius when it comes to computers. He knows nothing about sports betting. AI, it's getting better, it's getting smarter and it's, it's understanding these odds. I mean like this guy right now who does our, he's doing our soccer stuff, our World cup stuff, talking to him and the programs he's using right now. It is so fascinating because of AI and he's using a tool that basically is predicting these ties and that's been a big moneymaker. Ties happen all the time. We all know that. His whole thing right now is he's ahead of, is there's these little breaks in between these games, right? I don't know if you've been watching the World cup taking these water breaks, which is not normal. And it just, he's basically proven out how, if there's any type of momentum, right? If the, if a team that's not that good scores before these water breaks, it's already played out. These better teams that they come back from the water breaks, they, they have a strategy to combat it. And it's like he's taking advantage of that right now. Again, he'll be able to do that without AI, but instead of having three other guys under him, we're all making money, it's just him. And that to me is the biggest difference right now. I think you're talking a little bit about that.

[Alan Loeb]

I do think I'm a little bit more, and I've said this before, I'm a little bit more optimistic. I think this whole narrative that's been very, very pervasive that AI is going to cause 10, 20, 30, 40% unemployment eventually. I don't know if that's true. I think there is going to be many interesting new positions created because of it as well. It's just a transfer, it's a change. It's a Cambrian moment of change which is terrifying for many people. But I'm not really a subscriber to the dystopian 40% unemployment. We need universal basic income narrative, especially with agentic AI and I. Entrepreneurship is going to be fascinating. Anybody with a half decent idea, a 19 year old kid, a 23 year old kid with a kind of interesting idea can create a business with agentic AI in two weeks. That would take $500,000 in five years, 20 years ago, 15 years ago. And that's going to create a whole new economy which is going to be very disruptive for many brands and legacy businesses. But it's going to create a lot of new wealth in interesting places and a lot of new jobs in interesting places. I'm hopeful Al.

[Chad Millman]

I am always on the side of irrational optimism. So I'm with you. Alan Loeb, thanks for coming on the show. Running the freaking gamut of topics. Outstanding. That's our show. This has been Sharper Square part of the Volume podcast network. Watch or listen on YouTube @Sharpersquare. Like this video. Subscribe to the channel. Download us from Spotify, Apple Pods, wherever you get your pods rate review. Subscribe. Leave us. Five stars. Say whatever you want. Feedback is a gift. Until next time. Love you.

[Colin Coward]

Winner, winner, chicken dinner.

[Chad Millman]

Those words have been dancing around my head all night.

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[Chad Millman]

That phrase.

[Alan Loeb]

Just ask any of the old time pit bosses.

[Jeff T]

They'll know.

[Colin Coward]

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