The Crackdown on Free Speech, How to Handle a Bad Boss, and Why Scott Took Down His AI Clone

Scott Galloway answers listener questions on the rise of free-speech arrests in the UK, navigating a toxic boss, and whether AI can (or should) act as a therapist. Want to be featured in a future episode? Send a voice recording to [email protected], or drop your question in the r/ScottGalloway subreddit. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Scott Galloway?

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• 0:48Speaker 01

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• 1:19Speaker 02

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• 1:51Scott Galloway?

  Welcome to Office Hours of Prop G. This is the part of the show where we answer questions about business, big tech, entrepreneurship, and whatever else is on your mind. If you'd like to submit a question for next time, you can send a voice recording to officehoursofpropgmedia. Again, that's officehoursofpropgmedia.com or post your question on the Scott Galloway subreddit and we just might feature it in our next episode. First question.

• 2:14Scott Galloway?

  Our first question comes from user Armadillo Can on Reddit. They say, "Hey Scott, with the pressure on free speech in the US lately and you living in the UK, what are your thoughts on people getting arrested in the UK for social media posts?" So around 12,000 people a year are detained in Britain for online speech-related offenses. That's more than 30 arrests a day, under the 1988 Malicious Communications Act and the 2003 Communications Act. Under these laws, it's a crime to send messages deemed grossly offensive and decent, obscene, or intended to cause distress or anxiety. The original laws were written before social media and are widely seen as outdated. One clause written to stop nuisance callers is now being used to monitor private WhatsApp

• 2:55Scott Galloway?

  messages, since there is technically no concept of a private conversation online in English law." Okay, so I am blissfully ignorant of UK politics. I see that Joey Bagged Donuts idiot Nigel Farage, who scored the biggest own goal in history with Brexit, and then I hear about Nondom, where theoretically it makes sense to charge people who are moved here for tax avoidance, increasing their taxes, but guess what? 10,000 of them have left and your treasury is going to be smaller now. And you know what? I mostly don't care. I'm here sort of as an extended tourist, and I like the break of not thinking about politics every fucking minute, which I do anyways, because unfortunately I have the

• 3:39Scott Galloway?

  internet and I see the shit show descent into fascism that is the United States. Okay. I generally think the hallmark of a democracy is that almost anyone should be able to say almost anything about almost anybody. In the US, there's some laws, you can't defame somebody. You can't say that somebody is a pedophile when you know they're not, or there's no information that they are, which decreases or harms their ability to make a living. That's defamation. You also can't incent violence. You can't spread rumors saying, "Oh, so-and-so is the head of a rape gang and this is his address," and if people show up and harm that person, and that was a false statement

• 4:23Scott Galloway?

  and you incited violence, yelling "Fire in the theater," that's wrong. 99.9%.

• 4:30Scott Galloway?

  That speech does not qualify as that. Saying offensive things online, I don't think, in my view, that warrants a police response, even if it's ugly, even if it's vile. Now, having said that, I think 90% of the problem, what's the problem? The problem is it tears at the fabric of a society. This weekend, I got very upset. Someone said something so wrong, false, and incorrect, and just mean about me. And if you didn't know me, you would have taken this teaspoon of propaganda and turned it into a tsunami of bullshit lies. You would have thought, wow, what a bad person this guy is. And I wanted to weigh in, and of course, you don't want to weigh in because that's what the algorithms want.

• 5:14Scott Galloway?

  But they, I believe they should have the right to say that. Now, having said that, where I think 90% of the problem goes away is that if the platforms where all this shit is taking place, no longer are protected by Section 230 for algorithmically elevated content. I think 90% of it goes away if we just hold these platforms to the same standards we hold the BBC or the Times of London. So what is the answer here? I believe that free speech is a function of when you, people are allowed to say really offensive, fucking stupid things. And falsehoods. You can circulate conspiracy theories because sometimes the conspiracy theory ends up being right.

• 5:59Scott Galloway?

  What you shouldn't be able to do is that if somebody says mRNA vaccines alter your DNA, which they do not, if the platform wants to elevate that content beyond its organic reach, then they should be subject to the same standards as traditional media companies. But where I ultimately net out on this is that I think you err on the side of free speech. Platforms shouldn't engage, shouldn't connect profit to elevating this stupid, false, and defamatory content beyond its organic reach. I think there are easier ways to, to reduce this while not encroaching on people's free speech rights. Thanks for the questions.

• 6:44Scott Galloway?

  Question number two comes from user don'tcare12345 on Reddit. They say, "Scott, at the beginning of the year, I was moved out from under my long-term manager and mentor of five-plus years due to an organization flattening. My new manager, I feel, has it out for me. For context, I have eight years of this company under my belt, and I'm a strong performer. Recently promoted about a year ago under my old manager. I punch above my weight with no history of performance issues. I feel my contributions are acknowledged from top to bottom and am well-liked. Is there any way to successfully navigate these waters? I am in my 40s and still ambitious. I feel like I don't have the time to tread water under someone who isn't going to be my advocate." Oh, my gosh, welcome to the work week.

• 7:27Scott Galloway?

  Your ability to navigate assholes, or bosses, or people who don't agree with you, or maybe they're right and you're the asshole, who knows? But your ability to navigate and learn from these issues is really important. I think there's a couple of things. One, I think you continue to perform strong. And also, at some point, I think the truth has a nice ring to it. I think it's okay to sit down with this person and say, "I feel as if some of our interactions, or the way you approach me, it feels biased and it feels unfair." And highlight, in a very sober, unemotional way, some examples of that. And say, "Is there something I can do to improve this relationship? This job is important to me. I've been here a while. I like it. I want to succeed here."

• 8:10Scott Galloway?

  But I think that, you know, I think important relationships need to be open and honest, and this is an important relationship. At the same time, keep your eyes out for an opportunity to move to another manager, right? I mean, if this is a dynamic situation, and you're probably gonna have another manager in a year, you may not even want to have that conversation, you just may want to suck it up. Everyone has a bad boss. That's the only... Or at some point, will have a bad boss. That's the only thing I can guarantee you in the corporate world, is a series of injustices throughout your corporate life, and your ability to navigate them is kind of as important as doing a good job, almost. So... See if in fact, how long you're gonna have to endure this. Consider having a very open, honest conversation with them.

• 8:51Scott Galloway?

  Make sure you have an open and honest conversation with them before you ever go to someone senior to them. Otherwise, they're really gonna have a bias against you if you sort of go behind the back or tattle on them. Be honest and straightforward with them. I think people appreciate it, and if it's true, it will hit hard and they'll probably check back a little bit or reconsider. I don't think it's, if you're doing well after eight years, I don't think it's a bad idea to a market check and see what else is out there. People tend to advance further, faster, and make more money when they job switch every kind of five to seven years. But what you are going through is what I think almost everyone goes through at some point in their career. And the fact that you've been somewhere for eight years and have done well means that you're in a position of leverage because you've done well there for eight years, they don't want to lose you, and you have currency in the marketplace.

• 9:36Scott Galloway?

  Very much appreciate the question. We'll be right back after a quick break.

• 9:48Scott Galloway?

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• 10:30Scott Galloway?

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• 10:48Scott Galloway?

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• 11:33Scott Galloway?

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• 11:55Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch-up when audit season comes around again. Vanta works differently. The Regentic Trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year-round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

• 12:40Scott Galloway?

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• 13:04Scott Galloway?

  Welcome back onto our final question, which is from Reddit user DC10-50, who says, "Hi Scott, I'm curious what insights you have into the emerging trend of AI's role in providing relationship advice or acting as a replacement for a human therapist. I recently discovered my partner of over 10 years engaging with ChatGPT as a way to seek help with an internal conflict she was facing. I'm concerned this addictive, godlike technology will drive people further into isolation and depression. How would you recommend bringing this up with my partner?" Oh my gosh, I'm dealing with this firsthand and I'll come back to that. So some data, OpenAI says ChatGPT now has nearly 700 million weekly users, more than 10 million people pay $20 a month for it. It's not clear how many are using it for mental health,

• 13:48Scott Galloway?

  but for a lot of people, it's become the easiest kind of support to access. Actually, I've heard the number one use is therapy. Important to note, the US currently faces a widespread shortage of licensed therapists. So I have some personal experience with this. About a year and a half ago, I mean, it was two years ago. A guy came to us and said, "I can build Prof AI on top of an LLM." Now, I get about 10 to 30 emails a day from mostly young men, sometimes their mothers, asking for advice. It's almost always professional or investment advice. And I got a very long thoughtful email and I think, "That's such a nice kid, I need to respond."

• 14:27Scott Galloway?

  And I can't. I just, if I had 2,400 or not 2,000, if I had 72 hours in a day, I still couldn't get all these emails. So great. Built a Prof AI, it ingested all of my blog posts, my books, my podcasts, my media experiences or appearances, and then it gave what was 70, 80% of the answer I would give. And so I thought, "This is great." It was used, I think, a couple hundred times a day. We ultimately decided it was an experiment, we took it down. And then a graduate student instructor came to me, or who was my TA at business school, who works at Google, super smart, impressive woman, came and said, "We're doing something at Google Labs with characters and we want to launch ProfGAI."

• 15:10Scott Galloway?

  And we'll do a much better job than what you did. I said, great. They spent about six or eight months developing this thing, getting my voice, an avatar of me right, et cetera, et cetera. And they launched it. Now, between the time I thought this was a good idea, about nine months ago, and when it launched earlier this week, my view has entirely changed on this. And that is, I worry that these synthetic relationships are making us less mammalia, that they are sequestering us from each other. And that is, people are going down a rabbit hole and leaning on AI for things they typically lean on other humans for. And the idea that I had these kind of horror fantasies that I would read about

• 15:55Scott Galloway?

  some young man who hurt himself and he had, he had sequestered from his parents and role models and teachers because he had a series of synthetic relationships. And I don't want to be on that list. I don't want to participate. On a less evil level, but equally frightening for me is the idea that young men are going to use synthetic relationships to replace real world relationships. And that it reduces their mojo and motivation to establish a relationship with a coach, their dad, dad's friends, go to their friends with, with concerns. And I see a little of that happening, it sounds like, with your partner. So what do I think? I think a lot of it is age. I don't think anyone under the age of 18 should be allowed

• 16:39Scott Galloway?

  to enter into a synthetic relationship. I don't think they have the maturity to handle it. I think there's a lot of really horrific examples of self harm where people thought they were in a relationship and that person or that synthetic relationship gave them permission to harm themselves, easy to sequester from friends. So I just hate synthetic relationships for anyone under the age of 18. I think that What I have found about when I go down a rabbit hole and start asking these things for advice on issues, they're way too supportive, empathetic, and don't give it to you kind of real. Don't say, oh, shut the fuck up, buck up, welcome to the real world. I think occasionally you need to hear that. And while I, it's important they're supportive, I don't

• 17:20Scott Galloway?

  know, I wonder if we're just gonna become less depressed. And that is, real victory comes from the complexity and difficulty and friction of real world relationships. It is difficult to establish, or figure out, or navigate the pecking order of friends and approach people and express friendship. It's, it's hard to figure out the corporate bullshit you have to navigate and get good at it. It is really difficult to establish a romantic relationship with someone and, and maintain that type of commitment. People are messy, complex, and that is why it is so fucking rewarding, right? To figure out how to navigate all the bullshit at work and get promoted, it feels amazing. To have

• 18:01Scott Galloway?

  a good group of friends and put up with their shit and they put up with yours and you get to my age, I can't tell you how much joy I get from my friends, even the ones I didn't get that much joy from when I was in my twenties. I just, I just get so much reward for them. And my God, figuring out a way to wanna hang out with someone and make them feel loved and supported and make sure that they wanna love and support you and figure out a way to have sex with them and then have kids with them and then support that kid. And so hard, right? So much friction. And when you figure it out, it is like, the universe just says, all right, you matter. This all makes sense. You're here for a reason.

• 18:43Scott Galloway?

  So what I would do is I would have a very open and honest relationship and just say, look, using this as a resource is fine.

• 18:52Scott Galloway?

  Using it as a relationship is not cool and it's dangerous. It's dumb and you're going to be more depressed. I generally think that. I would be wary of the fact that you don't want them going down a rabbit hole and deciding they're in a relationship with someone and start taking that advice over the advice of real world people who understand them, care about them, care about them enough to say, no, that's wrong, or you're not thinking about this correctly, or stop this, I love you, I'm worried about you. Thanks for the question and by the way, I decided to take down my character AI after 12 hours. I just got increasingly uncomfortable with it.

• 19:31Scott Galloway?

  I, I want young men to figure out a way to engage with other men. That's all for this episode. If you'd like to submit a question, please email a voice recording to [email protected]. Again, that's [email protected]. Or if you prefer to ask on Reddit, just post your question on the Scott Galloway subreddit and we just might feature it in an upcoming episode. This episode was produced by Jennifer Sanchez. Our assistant producer is Laura Janer. Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from Prop G Media.

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