
Loading summary
Adobe Acrobat Studio Advertiser
Adobe Acrobat Studio so brand new. Show me all the things PDFs can do. Do your work with ease and speed. PDF Spaces is all you need. Do hours of research in an instant with key insights from an AI assistant. Take a template with a click now your prezo looks super slick. Close that deal. Yeah, you won. Do that, doing that, did that, done. Now you can do that. Do that with Acrobat. Now you can do that. Do that with the all new Acrobat. It's time to do your best work with the all new Adobe Acrobat Studio.
Strawberry Me Advertiser
Support for this show comes from Strawberry Me. Be honest. Are you happy with your job or are you stuck in one you've outgrown or never wanted in the first place? Sure, you can probably list the reasons for staying, but are they actually just excuses for not leaving? Let a career coach from Strawberry Me help you get unstuck. Discover the benefits of having a dedicated career coach in your corner. Go to Strawberry Me Unstuck to claim.
Scott Galloway
A special offer Every story you love, every invention that moves you, Every idea you wished was yours. All began as nothing. Just a blank page with a blinking cursor asking a simple question. What do you see? Great ideas. Start on Mac. Find out more on apple.com Mac welcome to office Hours of Prop G. This is the part of the show where we answer your 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 officehoursofigmedia.com Again, that's officehoursofgmedia.com or post your question on the Scott Galloway subreddit and we just might feature it in our next episode. Our first question comes from Karen Chan on Reddit. Karen says, hi Scott, if a surge in unemployment caused by AI were to occur, what do you think the impact on US Health care policy would be? Since most working age Americans rely on employer sponsored insurance, widespread job losses would mean millions losing their coverage. That could create significant public pressure for a public option. What are your thoughts? Okay, so about half the population get health insurance through an employer plan. About 8% of Americans, or 27 million people were uninsured in 2024, according to the latest census data. And premiums for employer plans hit $26,000 a year for family coverage in 2024, up 7%. These plans always seem to go up more than inflation. Why? Because they're a fucking cartel with regulatory capture and so that's faster than inflation or wage growth. Small Firms are especially vulnerable. Only about half offer benefits at all. By the way, here at Propagate, we do offer health benefits. The average worker still pays 19% of single plan premiums out of pocket. Deductibles average about 1800 bucks. So it's bad for the economy because losing your job oftentimes means losing health insurance. You're not able to allocate your human capital to where it would be best served. Entrepreneurship or moving or taking time to care for a loved one for fear that you will lose your health insurance. So if AI driven unemployment rose by 5 percentage points, roughly 8 million people would lose their coverage. At least I think I'm doing the math right. And about three and a half million would likely move to Medicaid or ACA marketplaces. And around three million people would become uninsured, at least temporarily. By the way, the uninsured are really fucking expensive. Because when people lose insurance, they don't stop getting sick. They just delay their care until they're in the emergency room, oftentimes putting much more of a burden on the healthcare system than if they'd had health insurance. And hospitals then shift those unpaid costs to everyone else through higher premiums and fees, driving up the overall healthcare spending. The result is a sicker population and a more expensive, less efficient system. See above the American healthcare system that spends $13,000 per capita and the other six of the G7 spend $6,500 for better outcomes. Look, I think this is a bit of a moot market. I believe that. So I'm coaching and I'm bragging because I'm desperate for your affirmation. I'm coaching the Democratic Party or some constituents, including some people running for president, on messaging. And I think it's time to move beyond the indignance and the pearl clutching and the outrage to ideas. And one of the big ideas I think the Democratic Party, or potentially the Republican Party should embrace is the following. Healthcare is not working in the United States. Or let me put it this way, it's like everything else in America. It's been optimized for the top 10%. If you're in the top 10% of income earning households in America, you have the best healthcare in the world. You have access to the best doctors, the best pharmaceuticals, the best treatments. People in the top 10% on average live, get this, between 7 and 12 years longer than people in the bottom 10%. Literally, being wealthy means you're gonna is life, money is life in the US now. So we have this healthcare system that's been optimized for the top 10 or the top 1%. And I think the model is the following and it's the UK model and people don't like the NHS here. And the reason why is because it's underfunded. Because the UK has not grown in 10 years. There's just not enough money to go around. They don't have the resources. That's not the problem in the US. We've grown our economy, I would bet by 30 or 40% in the last 10 years. So we have 30 or 40% more money and we have the money. The problem is the prosperity, similar to the future. What William Gibson described as the future is here, it's just not evenly distributed. So what you have with NHS is it's nationalized healthcare. You get sick, you go in, you get treated, you don't get bills, you find out you have lung cancer. It doesn't also mean you're going to go bankrupt. Now the wait times are longer. People complain about it, especially if it's elective or non urgent surgery, you have to wait too long, it's underfunded. What I like about it is that people like myself who have some money opt out and go private. You think, well that's a douchebag rich thing. No it's not, because it takes some burden off the system and then they can offer better services to the bottom 90, if you will. In sum, what needs to happen in the U.S. i believe, is that if you want to have greater mobility, we have to have portable health insurance. People shouldn't stay at their job because they're worried that they have a melanoma when they would be better off at another job. Also, it creates greater pricing because the key to pricing is to connect the consumer with price and shop. I never look at the, I literally never look at my insurance or my medical costs because if you have health insurance paid for you by your employer, you don't give a shit what that MRI costs. You might have to go through tons of hoops, but you don't care. So you're not shopping around, you're not calling around or going on chatgpt to saying where can I get the cheapest MRI in soho? So we've disconnected what is the key to keeping prices down and that is consumer scrutiny. Because if it's offered by your employer, you don't care. You just go wherever there's in network. There's tons of administration. 40 to 50% of all health insurance premiums go to administration and profits, meaning that if you spend $100 on insurance, you're getting 50 to 60 bucks of healthcare. So what to do? What to do? I think we take Medicare, which by the way, Medicare is the healthcare programs and services offered to people over the age of 65. And guess what? Unlike the rest of healthcare, it's actually quite popular. And this is what we do, folks. We lower eligibility for Medicare by two years every year for the next 10 years. Where does that get us next year? If you're 63 or over, you're eligible for Medicare. If you want concierge or high end, you go out of pocket. Fine. Rich people, old people, of which there's a lot less burden on the system. Good for you. You get better service. You can get your colonoscopy the next day. If you wanted from a nicer facility with better looking people wearing figs instead of just traditional scrubs. Fine, have at it. And then what do we have? And then in two years the eligibility is 61. And then in 10 years the eligibility is 45. What is that? Effectively socialized medicine. Why? Because the vast majority of medical care costs happen to people over the age of 45. Because guess what? Young people, unless they're having a baby, don't need healthcare. I think I went to the doctor three times before the age of 40. Yeah, I said it. Nationalized medicine. It's time, folks. It's time. 40% of America has medical or dental debt. You want to talk about stress and anxiety on a household? I have to borrow Money so my 22 year old daughter can get a root canal. Can't sleep at night, is in screaming pain and we don't have the money for a root canal so we have to go into debt. Can you imagine how humiliating and stressful that is for people? Almost half of households have medical debt enough already. Lower Medicare eligibility by two years every year for 10 years and then boom. Better health care, better pricing, less stress, less anxiety, less debt. A healthier America. Thanks for the question. Question number two comes from Freda Bloogs on Reddit. Okay, Freda, they say. Hi, Scott, how does a high net worth individual manage their money and their investments? I can't imagine that you log into Fidelity or Schwab like the rest of us to sell your covered calls. Or maybe you do. Do you make sure that credit cards and rent are paid on time out of pure nosiness? Can you allow us to peek behind the curtain of daily money management, tracking your net worth and following your investments at this different scale? Okay, I try to be very transparent about my wealth and how I manage my money. One is because I think I'm a narcissist and I want people to know I'm successful. I think some of that is there. I think it makes me more interesting to other men and more attractive to women. Is that wrong? Is that wrong? Anyways, it's there. But also I do think it's important to talk about money and create financial literacy. If you want to understand something, you need to talk about it. Talk to your friends about taxes and investments and diversification. You need financial literacy. You know, I think Roger Federer thinks about and talks about tennis all the fucking time. How do you ever get good at anything without talking about it and thinking about it? Okay, so I have been wealthy three times, which means I've gone broke twice. And the primary learning for me is that the reason I went broke twice is because I wasn't diversified. I grew up in an era where VCs and the media taught you you go all in on something, and if you're a real baller and good at what you do, as long as you throw yourself at it, you'll be really successful. So I poured everything, everything into my first brand strategy firm, Profit. Then I poured everything into my e commerce company, Red Envelope, which went public in 2002. And then I poured everything into tech because I was a genius. And if I could throw myself at everything and your VCs are telling you, are you in it to win it? Don't sell shares in a company, even though I should have. And what happens is that as I got older, I realized market dynamics will always trump individual performance. It didn't matter how fucking smart you were on the Internet in 2000. Amazon lost 90% of its value between 99 and 2001. And I didn't learn that lesson. And I was rich in 99, broke by 2001. I was rich again in 07, broke by 2009. I am not going back. I've crawled my way back. I'm now worth kind of low, whatever, nine figures. And what I've decided the key attribute is diversification. And that is I try not to have more than 5% of my assets in any one investment. The exception is real estate. My kind of general investment strategy is, I believe, leave. I think of someone who is a student of demographics. What I see is that income inequality is only going to get worse globally. I think that America is giving everyone a hall pass to be corrupt and for regulatory capture and cronyism and oligarchy, meaning you're going to have the greatest boom demographically is going to be an increase in billionaires. We've gone from 500 to 2,500 in the last 10 years. I think we're going to go to 10 or 20,000. And these people all want to live in one of the same five places. Dubai, London, Palm Beach, New York or Aspen. So I have bought homes in each of those places except for Dubai. And I bought two homes in Aspen and I'm fixing them up. And I think it's good intergenerational wealth. It's very tax advantaged. So I have a disproportionate amount of my net worth in what I'll call 0.1% real estate. Some of these places I'll live in for a couple years, but then I'm planning to sell them and then use our tax code which disproportionately advantages real estate to roll into rentals and create intergenerational wealth. And if one of my kids is a total fuck up, as long as a good kid, he can bang on doors for rent and just try and, or I don't know, manage a mini mall with a Chipotle in it. I don't know. I used to be one of those guys, like I'm going to pay for their college and then they're on their own. And now I see how hard it is for young people and I'm kind of changing my tune. Anyways, now we asked intergenerational wealth transfer. So the key for me is diversification. I spend at least a day to a day and a half managing my money and thinking about investments. I have found. Unless you're all over it all the time, you're going to lose money. And that is unless you're all over. Goldman Sachs manages my money. I have a law firm managing my taxes. Unless I'm constantly asking them questions, I find that stuff falls in the cracks and they will figure out a way to jack up fees. Generally speaking, what you want is low cost index funds. If you have access like I do to kind of better deal flow where you can get additional equity for going on the board because they think you're smart, fine, have at it. If not, you want to be diversified and you want to be in low cost index funds. I have the ability to hire really talented people. I probably spend 100 to $300,000 a year just on the people who manage my money. Why? Because the tax code's gone from 400 pages to 4,000. Why? So that 3,600 pages could fuck the middle Class and transfer money to the wealthy. Because if you've got gps, you want to run races at night. Because the people without GPS, the bottom 99, crash into the fucking rocks. And the rich people just keep on cruising because they've got really smart tax lawyers and Goldman Sachs managing their money and finding the lowest interest rates on things, charging the lowest fees, figuring out ways how many days I should be in Florida or not be in Florida such that I have lower taxes. All that shit, right? All of these things I leverage. One, because I have the capital. But two, I am thinking about it all the goddamn time. Keep track on what you're spending. A lot of it's just discipline. What's the algebra of wealth? I'll go to my book. You gotta focus and get good at something, right? Specialist economy. Get really good at something. Find something you'd be in the top 10 or 1% in. It's probably not a vanity industry to be in the top 1% of acting. You gotta be fucking Meryl Streep, right? It's just very difficult. And then apply some stoicism and some discipline. Get used to spending less than you make. Start saving from an early age. Even if it means getting money taken out of your paycheck. Try and find tax, advantage or matching things. Any matching thing. Your employer. Max it out. Find out wherever you live, what are some tax advantage savings vehicles. Max it out. Try and find savings or investment vehicles where it's taken out of your check. Because most of us don't have the discipline not to spend money once it comes into our hands. So that sort of stoicism. The next is time. Start early. Recognize a little bit of money every month. Discipline. That's why buying a house is so powerful. But it's not because it outperforms other asset classes. But it's for savings. And then also the power of diversification. Focus equals the product of stoicism and discipline. Right? Time. Right. And then diversification.
Caller / Listener
Whew.
Scott Galloway
That was a tour around the world. Anyways, thanks for the question. We'll be right back after a quick break.
Brex and LinkedIn Advertiser
Support for the show comes from Brex. These days, every business leader is under pressure to save money. But you can't crush the competition just by cutting costs. To win, you need to spend smarter and move faster. You need Brex. Brex is the intelligent finance platform that breaks the trade off between control and speed with smart corporate cards, high Yield Banking and AI powered Expense Management. Join the 30,000 companies that spend smarter and move faster with Brex. Learn more@brex.com grow support for the show comes from LinkedIn. We say this all the time on our show, but it bears repeating. Running a small business isn't just a full time job. It's about a dozen full time jobs that you rarely, if ever get to clock out of. At least until you get to the point where you can start hiring the dream team. And if you've made it that far, you already know there's no time to mess around. That's where LinkedIn Jobs comes in. LinkedIn makes it easy to post your job for free, share with your network and get qualified candidates that you can manage all in one place. And LinkedIn's new AI feature can even help you write job descriptions and then quickly get it in front of the right people with deep candidate insights. And if you decide you want to go the extra mile to find the perfect candidate, LinkedIn says that promoted jobs get three times the number of qualified applicants. It's all these little things that let you find help fast without compromising on quality, which add up to you finally having extra time in the day for, I don't know, relaxing or knowing my listeners. You'll probably use that extra time to expand your empire even further. Post your job for free@LinkedIn.com Prof. That's LinkedIn.com Prof. To post your job for free. Terms and conditions apply. Support for the show comes from Betterment. Nobody knows what's going to happen in the markets tomorrow. That's why when it comes to saving and investing, it helps to have a long term approach and a plan you can stick to. Because if you don't, it's easy to make hasty decisions that could potentially impact performance. Betterment is a saving and investing platform with a suite of tools designed to prepare you for whatever is around the corner. Their automated investing feature helps keep you on track for your goals. Their globally diversified portfolios can smooth out the bumps of investing and prepare you to take advantage of long term trends. And their tax smart tools can potentially help you save money on taxes. In short, Betterment helps you save and invest like the experts without having to be an expert yourself.
Scott Galloway
And while you go about your day.
Brex and LinkedIn Advertiser
Betterment's team of experts are working hard behind the scenes to make sure you have everything you need to reach your financial goals. So be invested in yourself. Be invested in your business. Be invested with betterment. Go to betterment.com to learn more. That's B E T T E R m e n t.com investing involves risk.
Scott Galloway
Performance not Guaranteed welcome back onto our final question.
Caller / Listener
Hi Prof. G Hannah from Georgia here. How do you recommend a couple decide how many kids to have, especially when partners want different things. You've mentioned on a few episodes that you wish you've had a third child. I'd love to hear your perspective on how to navigate this decision for context. My husband and I have two boys, ages 3 and 1. I'm incredibly grateful and feel content with two kids, but I'm also exhausted. My husband, meanwhile, really wants a third. I'm 36, so time isn't exactly on my side career wise. I was on a strong trajectory pre kids and a high paying, high growth career. After our first, I shifted to a more flexible lower growth role. It still pays well, but doesn't feel fulfilling long term. Lately I felt a strong pull towards entrepreneurship and I'm ready to leave my comfortable corporate job, but a third child would likely delay this dream by several years. My husband is in the military and plans to retire in about 10 years, which adds another layer of complexity. A large part of me feels guilty for not wanting to give him something he so deeply desires. I know that's a lot of context, but I really value your opinion. Thanks for the thoughtful advice. Each week I never miss an episode of Office Hours.
Scott Galloway
I think this may be one of my favorite questions ever. Hannah from Georgia one For a weird reason, I have never related more to a question and never known less what to tell you. These decisions are so deeply personal and I wouldn't trust anyone that's like go for it or don't do it. I'll tell you what we went through. We have two kids and I never wanted kids. I was very selfish. I loved going to brunch when I wanted to go to brunch, going to Equinox when I wanted to go to Equinox, taking off for St. Barts when a friend said, hey, let's go to St. Playing Bart. And then I had kids and it's not like there was bright lights and angels speaking. I was mostly just really nauseous because I was worried about money. But kind of, you know, 15 and 18 years on, it's my purpose. I've never had purpose in my life or I thought I had goals. I wanted to be rich. I wanted to be awesome. But I never really felt like I had purpose. I now have purpose. My purpose is to raise two good men. It is the greatest source of joy and contentment I will ever discover. Not to sound too macabre, but I think about death a lot. One of the comforting things about death for me is that because my partner is 14 years younger than me, knowing that I'll go first, that gives me comfort. I never feel more relaxed than when I'm up late with my dogs. I know my kids are safe and I know my partner's happy and they're taken care of and they're warm and looked after. That is the only time in my life where a box has been checked in. Indelible ink, not a, not a pencil. Where I want better colors or bigger colors. Anyways, we had two. I didn't want the first one. My partner said, I want to have kids. I said, I'm not getting married. She said, we don't need to get married. She called my bluff, had kids. I literally basically looked at her and she was pregnant, had a second one and she wanted a third. And I was so freaked out about money and logistics and it was hard and she didn't feel tired. I felt tired. Having two young kids, boys in Manhattan, always having their hands for fear they're going to run out in the street. Also, our boys, they're not without their issues, but on the whole they're super healthy, happy and wonderful boys, young men. And I know a lot of people who have kids who struggle. You know, name the acronym ADHD or whatever it is, learning disabilities, health issues, and it brings the house down. And I thought, let's cash out. We have two that are great. I don't want to have a third because I'm worried we're pushing our luck. Having said that, my biggest regret, my biggest regret now and I, and I'm scared to say this out loud because my partner just gets infuriated when I say this now is that we didn't have a third. Specifically, I would just kill to have a little girl. And as I've gotten older and I see not the end, but I see myself getting older, I would just kill to have a little girl. I feel like there's this weird void in our household now that our two boys, my 18 year old's applying to college. Our 15 year old is really into his friends and I feel like there just needs to be another kid in the house. So hands down, my biggest regret, not having a third. Having said that, a lot of this comes down to money, comes down to support system. And the only thing I would say is that. And again, my bias is coming out here. The only thing I would say is that having kids early, you know, giving birth, by the way, you said you're 37. That's still really young. If you're in decent shape with today's technology that's still in this day and age kind of fertility years. So I wouldn't let that get in the way. Having said that, women bear a disproportionate amount of the responsibility. They just do. What I would say is no doubt about it, it's a pain. It's hard, especially with babies. But I find as they get older, it gets easier, it gets funner. It's like making that sacrifice now, future reward. But I like the idea of sitting down and from a position of generosity saying, your happiness is really important to me. These are my concerns. How important is this to you? Let's talk about the logistics, but also looking at through the lens of how you'll think about things in 10 or 15 years, because that 10 or 15 years is going to be here in a instant. Literally. Yesterday my oldest was coming into bed with me on Sunday mornings and snuggling with me for 10 or 15 minutes and then sitting up and saying, let's make a plan. I mean, it was like there was a Hallmark movie, where are the cameras? And then yesterday I'm arguing with him about him taking the act for his college apps and he's just rolling his eyes and like trying to avoid me around the house. It was yesterday. He was, he was saying, dad, let's make a plan. It goes really fast. Again, hugely personal decisions. But the fact that you're with a loving partner, you have two healthy kids, and an issue right now is whether you have three or you just stick with two. And you both have jobs and what sounds like healthy careers. Your problems are a function of you being in the most fortunate 99% and the most fortunate 99.5%. So, you know, well done. Congratulations to you and I trust that you're in these conversations, taking pause to realize how lucky you are to be thinking this way about a loving partner and having a healthy family and children and just being in a position to be considering a third. Such a such a nice place to be in. Thanks for the question. That's all for this episode. If you'd like to submit a question, please email a voice recording to officehoursoffertymedia.com Again, that's officehoursopropertymedia.com 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 Gennar. Drew Burrows is our technical director. Thank you for listening to the propg POD from Propg Media.
Strawberry Me Advertiser
The Pumpkin Spice Latte is back at Starbucks. Crafted with our signature espresso and real pumpkin sauce, then topped with whipped cream, cinnamon and nutmeg, the PSL get it while it's hot or iced. Only at Starbucks.
Adobe Acrobat Studio Advertiser
Adobe Acrobat Studio so brand new. Show me all the things PDFs can do. Do your work with ease and speed. PDF Spaces is all you need. Do hours of research in an instant with key and insights from an AI assistant. Take a template with a click. Now your preso looks super slick. Close that deal. Yeah, you won. Do that, doing that, did that, done. Now you can do that. Do that with Acrobat. Now you can do that do that with the all new Acrobat. It's time to do your best work with the all new Adobe Acrobat Studio.
Adobe Express Advertiser
Nobody knows your customers better than your team, so give them the power to make standout content with Adobe Express. Brand kits make following design rules a breeze, and Adobe quality templates make it easy to create pro looking flyers, social posts, presentations and more. You don't have to be a designer to edit campaigns, resize ads and translate content. Anyone can in a click and collaboration tools put feedback right where you need it. See how you can turn your team into a content machine with Adobe Express, the quick and easy app to create on brand content. Learn more@adobe.com Express Business.
Episode: How AI Could Reshape Healthcare, How the Wealthy Manage Money, and the Case for a Third Child
Date: October 20, 2025
Host: Scott Galloway
Podcast Network: Vox Media Podcast Network
In this thought-provoking Office Hours episode, Scott Galloway fields listener questions spanning the future of healthcare in the age of AI-driven unemployment, practical wealth management strategies for the affluent, and the deeply personal decision-making process behind having a third child. With his trademark candor, humor, and occasional profanity, Scott offers insights into the intersection of policy, personal finance, and family life, drawing on his own experiences, hard-won lessons, and a deep sense of empathy.
(Starts at 01:01)
Listener Question:
Karen Chan asks about the potential impact of AI-driven unemployment on U.S. healthcare, especially since employer-based insurance is prevalent.
Current Healthcare Landscape:
Problems with Job-Linked Insurance:
The Costs of Being Uninsured:
Policy Prescription:
Scott’s Proposal:
(Starts at 11:50)
Listener Question:
Freda Bloogs inquires about daily money management and investing at high net worth levels.
Transparency in Wealth:
Lessons from Going Broke Twice:
Philosophy & Tactics:
On the Tax System:
Advice for Most Listeners:
(Starts at 19:05)
Listener Question:
Hannah from Georgia seeks advice on deciding whether to have a third child, balancing her career aspirations with her husband’s strong desire for another child.
Personal Connection:
On Timing and Sacrifice:
Advice on Navigating the Decision:
On Healthcare Inequality:
On Diversification and Wealth:
On Family and Regret:
This episode encapsulates Scott Galloway’s distinctive blend of sharp analysis and heartfelt reflection. Whether unpacking the economics and politics of health insurance, demystifying the daily reality of managing significant wealth, or meditating on the emotional intricacies of family planning, Scott offers practical advice rooted in personal experience, honesty, and empathy. This episode is essential listening for those rethinking career moves in a world rapidly changing due to technology, reconsidering their own financial strategies, or weighing some of life’s biggest personal decisions.