Why Housing Is So Expensive, and the Myth of Timing the Market

Scott Galloway discusses what it would take to make housing affordable, how to handle regret after selling stock that later soars, the upsides of becoming a parent later in life, whether to leave a job you love to start a business with your dad, and how to navigate parenting disagreements with your spouse. Want to be featured in a future episode? Send a voice recording to [email protected], or drop your question in the r/ScottGalloway subreddit. Plus, you can now call or text Scott a question at our new Office Hours hotline: ‪(201) 472-3656‬. 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.

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• 1:54Speaker 00

  Welcome to Officer's with Prof G, where we answer your questions about business, big tech entrepreneurship, and whatever else is on your mind. Have a question? Send us a voice recording at officerwithprofmedia.com or post your question on the Sky Galloway subreddit. We just might feature it in an upcoming episode. Question number one comes from sure, why not 9876 on Reddit? Hey Scott, have you ever taken a reasonably deep wonky dive into what would really make housing affordable? I just keep wondering, what would it really take? Thanks for the thoughtful question. So what do we, first off, what do we get wrong around housing? Probably the worst thing we've done in housing is everyone complains about bureaucrats. The worst thing to happen to the housing market, especially for entrance, is we took

• 2:38Speaker 00

  power around housing permits out of the hands of bureaucrats, local civic officials, and we put it into the hands of homeowners. Now, what are the incentives of a homeowner? They live in a neighborhood. They like the fact there's not traffic. They like the fact there's not construction and free gift with purchase. And everyone, this is the atmospherics, is they know that the less housing that is built, there's, the greater the scarcity of housing, which creates their primary asset or incentivizes or fuels their, an increase in value of their primary asset. So the people in charge of issuing permits for economic growth and to provide more housing to meet the needs of new entrants who want to have their own house, the incentives of

• 3:23Speaker 00

  the people issuing permits is totally contrary to the needs of entrance. And that is a larger metaphor for the country the last 40 years. And that is the incentives have created regulatory capture such that the incumbents deny admission to the club such that their membership goes in value. This is a supply problem, not a demand problem. And the way we approach it and actually end up making things worse is the government provides tens of billions of dollars in what is a good intention, and that is creating more demand. Low-income housing tax credits, tax advantage on mortgage interest rate, which is tax deductible, right? First-time home buyers credit.

• 4:05Speaker 00

  All this does is create more demand when we don't address the supply side and maintain a national kind of NIMBYism as a, as a, as a public policy. We just again further escalate the price of housing. We need to address the supply side. We need federal legislation and local legislation that says, look, you cannot, or you're not, you cannot access federal funds if you do not, or if you create a NIMBY-like situation where it's very hard to issue permits. We need to provide tax credits to developers such that they have greater incentives to build. Some examples of places that have done a decent job, both Austin and Minneapolis,

• 4:50Speaker 00

  have increased affordability by getting rid of certain regulations such as height limits or a regulation that you had to have a car for every, a parking spot for every new unit built, which added on a ton of capital and expense to build sometimes underground garages in high-density areas. According to a 2020 Brookings study, local zoning regulation prohibit building anything other than single-family detached houses on 75% of the land in most US cities. High limits and minimum lot sizes can further restrict apartments. Smaller multifamily buildings have become rare. Duplexes, triplexes, and fourplexes accounted for 7% of new home completions in 1979. Get this, it's 1.1% in 2025. And why does that matter?

• 5:33Speaker 00

  Nationwide, 20% of middle-income renters couldn't afford to pay their full rent at least once during 2025, up from 14% in 2024. Let's look at that same number for low-income renters. It's 28%, up from 24% in 2019. So I think housing is, so Robert Shiller did a study, and in his study, he was able to prove that housing underperforms most other asset classes when you take into account taxes, maintenance, and all those things. Why do I think that study is incomplete? The psychic income and the component of wealth building is what is so powerful about housing.

• 6:14Speaker 00

  It is a step towards a key relationship, whether you're, have a serious boyfriend or girlfriend, whether you decide that you want a bigger house to take care of your parents at some point, whatever it might be, pride of ownership, something, you know, having that asset, owning your home, owning your nest is, has real psychic ROI. It just does. And while there are some cities where you're better off renting, essentially you take the yield, you take the, take the year-long cost of the rent divided into the cost to buy it, and if it's above, if it's above a certain return, you probably want to buy. If it's below a certain return, in other words, it's cheaper to rent, you want to rent. So I'm not saying everyone has to buy.

• 6:59Speaker 00

  That's a, you know, you never lose in real estate and the American dream. Those are all brought to you by the American Realtors Association. It does make sense in many cities now in this market to rent, not to buy. And you want to speak to people smarter than me. You want to use AI. You want to talk to friends in the real estate industry and see if it makes sense for you to buy a home. Having said that, real benefits, psychic benefit, and also the economic benefit not captured in Shiller's analysis is the following. If someone says to you, you need to spend $2,100 a month and put it into a Vanguard low-interest index fund, you get an opportunity to go to Cabo, you think, oh, you know, I really would like to upgrade my car, and okay, you don't put the $2,100 bucks that month into Vanguard.

• 7:43Speaker 00

  People typically make their mortgage payment, and that is it's a means of forced investment, which is good for younger people. It's good for all of us if we're trying, you know, you don't want to have your house repossessed. So you tend to plan and impose a certain amount of self-discipline around investing in an asset that does grow. It may not grow as fast as the S and P nationally over a long period, but if you get lucky in certain areas, it does grow as fast or even faster. And also, it's really tax advantaged. And when you sell it, you quarter of a million or half a million, if you're married, of tax-free income on the upside of the sale. And also, again, see above mortgage interest rate tax deduction. So there's psychic benefit, it's forced savings.

• 8:28Speaker 00

  So I do think housing is an enormous issue for the United States. The thought of unleashing kind of the private sector while also reducing If you will, the ability or the inability, you know, unshackling the housing market through economic incentives and also pulling down or lowering the bar on what can get built by national and local NIMBY laws. The big mistake we make in housing is believing it's a demand problem flooding the market or buyers with additional tax credits, which just gives them more money on a same base of supply, which drives up the cost. The issue is a supply problem and we need to refocus our attention on the supply side versus the demand side. I appreciate the question. Question number two comes from Jackson who emailed us.

• 9:13Speaker 00

  He says, hi Scott, you've talked about selling Netflix at a loss early on and selling real estate in Potrero Hill. And I imagine those kinds of missed opportunities haunt you differently than a straight up bad bet. I recently sold a large position in a big tech company I worked at for six years, forced to liquidate to close on a Brooklyn townhouse. The stock has since run up significantly. I know the sale was the right call for my family, but the number is real and it stings. How do you mentally separate I made the right decision with the information and constraints I had from the raw regret of watching the gains you left behind? My brother, get used to it. It's just, the cruel truth of capitalism is you're going to have a scarce amount of resources. At some point, you're probably going to decide that it's worth it to send your kid to a

• 9:56Speaker 00

  great school that he or she got into that just costs an arm and a leg and you're going to have to sell stuff. And some of the stuff you sell will go up in value. Now, the way you can console yourself on a very existential level, or how I console myself, is that the, something that's just changed my life is my colleague at NYU, Adam Alter, does studies regret, or one of the things he studies is regret. And he spent a bunch of time in palliative care and interviewed people who are at the end. These are people that have zero fucks to give, have real perspective around the end of their life. And their biggest regrets in reverse order are number three, not staying in closer touch with their friends, two, not living the life they wanted to lead, not one their parents or society or their spouse or themselves wanted to lead, or felt they should lead

• 10:41Speaker 00

  instead of living the life they actually wanted to lead. But the number one regret of people at the end are they wish they'd been less hard on themselves. I'm like you, I have a tendency to focus on all my mistakes. When I did a speech at UC Santa Barbara on Friday, it went so well and I'm happy about that, but I'm mostly fixated on the one or two things I could have done better, or I said something stupid or provocative, or I dropped an F-bomb where I really didn't need to. That's what I obsess about. And that's part of being, I think, successful is really trying to get better at something and recognize your mistakes. I have a tendency to dwell on them. What is it? Anxiety is about, you know, fear of the future and depression is about fear of the past or upset over the past.

• 11:25Speaker 00

  And by the way, okay, the stock has gone up, you've sold, but so likely has the value of that Brooklyn home you purchased. It's not like you took the money and put it in treasuries or invested in another stock or invested in Nike, which got cut in half in the last year, or Netflix, which got cut in half the other year. You invested in Brooklyn real estate, which I think over the last 12 months has gone up. In addition, you've invested in your family. Working at a tech company and selling the stocks, let's say you can buy a home in Brooklyn or a Brooklyn townhouse. My brother, it's good to be you. That's what you call the mother of good problems. That means you're in a relationship. That means you probably have kids. It means for God's sakes, you had the money in the stock to afford a townhouse in Brooklyn,

• 12:10Speaker 00

  which probably puts you in the top 1% of Americans. So this is a really good problem, my brother. Whenever you sell stock, it's just very unlikely that you can time the top and time the bottom. You need to time your life and that's what you've done here. You needed the money for your family, for a townhouse. You've probably made money in that townhouse already, maybe not as much as this tech stock you sold, but okay, it sucks to be an adult. This is not, this is not, this is an inconvenience, not a problem. And again, don't be hard on yourself. You did the right thing. Thanks for the question.

• 12:48Speaker 00

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• 15:37Speaker 00

  Welcome back. Our next question comes from a listener on Reddit. AliveShallet6780 says, greetings Prof G. I'm a 35-year-old man and my wife and I left New York to move to Portland, Maine to start a family. We've been trying to start a family for three years now and I can say that infertility has been the hardest experience of my life. While we're blessed with financial security thanks to good luck and hard work, two rounds of IVF have been unsuccessful and we're considering pursuing surrogacy. The most challenging part of this experience has been the social aspect as it is quite frankly painful and dull to hang out with parents and their young children. As someone who became a father in his 40s, what kind of advice could you offer someone who's likely to become a parent later in life? Thanks for everything you do.

• 16:20Speaker 00

  I'm choosing my words carefully because I think this is so important and, and I don't know if my experience is the same experience as anyone else's. So according to the CDC, about 1 in 5 married women ages 15 to 49 with no prior births are unable to get pregnant after a year of trying. It's so weird, we spent so long trying not to get pregnant. And then what's strange is as we get into our 30s or our 40s, then we have trouble getting pregnant. It's, it's, so this is something that as people are having kids later and later, this is something that is very common across households. And people are becoming parents later. The average age of first time fathers rose from 27 in 1972 to 31 in 2016.

• 17:04Speaker 00

  And I just read a crazy stat that there's more women having babies over the age of 40 now than under the age of 21. Teen pregnancy is way down, which is a good thing. Lower birth rates are, they just are, they're a bad thing for the economy. If you want to look at a country that goes into recession, just look at the ratio of young people to old people. We do better actually than most nations because people are still having kids here and immigration is a means or a pressure valve. If things get really serious, you let in more immigrants, although our current administration doesn't seem to get the memo on that. But demographically, the US is, is quite frankly, is less screwed than many nations in Europe, Japan and China.

• 17:43Speaker 00

  Anyways, what is the advice for having kids later in life? I got lucky. I think it was really good for me. I had kids at 42 and 45. I didn't want to have children. I like being selfish. I'm a naturally selfish person. I didn't like enjoy other people's children. So I wasn't against it, but I just wasn't for it. And I liked my life. And I met someone who I fell very much in love with, who wanted kids. And I said, I don't want kids. She said, I'm not going to be with someone, or I can't be with someone long term that doesn't want kids. I said, wait, I've reconsidered. I want kids. And we got pregnant almost right away. I said to her, I don't want to get married. She said, I don't need to get married. It's

• 18:23Speaker 00

  kind of called my bluff. And in the next three years, we had two kids. Look, I feel like there's never a good time to have kids, whether you're in your twenties, you're too young, in your thirties, you're working your ass off, in your forties, you start to feel like you're too old. I liked having kids a bit older for the following reasons. One, I just think I'm a better dad. I'm older. I realize that life isn't about getting a return on your relationships. It's about being on the right side of the ledger. And then if you exit this world, having given more than you've gotten from your relationships, which sounds weird, but you know, a pretty good obituary might be, the vast majority of people in his life felt there's no way they could be as good a friend, as good a spouse, as good a son as this guy was. You

• 19:08Speaker 00

  know, that wouldn't be a bad obituary, right? So you just get more perspective. I think you get more generous. I think you get more patient. And also, just to be blunt, having kids later in life meant I could spend more time with them, and I wasn't as freaked out because I just, I had more economic security. Now, when my kids were born, it was, my first kid was born in 07, and just as the market was crashing, came kind of marching out of his mom. And the first thing I felt was economic security. Had I felt that economic security when I was younger, and I didn't have kind of currents in the marketplace, I just think it would have been incredibly stressful raising kids in a home, not of economic stress, but

• 19:52Speaker 00

  where I'm basically working all the time, trying to build economic security, and didn't have a lot of money. I was pouring all my money back into the business. So more perspective, more maturity, more generosity, and some economic security. You know, the downside is the following. I may or may not be around to see my grandkids. I think I will. It's an incredible motivation to try and stay healthy. I do think kids keep you younger. And there's some studies that show that having kids in the house kind of slows the aging process. And you do, you know, picking them up and running them around and playing football in the backyard is just good for you. And it's incredibly motivating for me in terms of staying healthy. Also, I think it just makes you a better person. You know, that

• 20:35Speaker 00

  saying, be the man your dog thinks you are? That's nothing compared to, I really want my sons to admire me. And I had Senator Murphy on the show a few years ago, and he just said something. I asked for his advice around what he tells his sons or his kids. And he says, I don't really tell them much. They don't, they don't listen. They observe. I try to, I try to just model good behavior. That sounds very simple, but it's just so true. And that's made me a better man. Trying to be, trying to just set a really good example, right? Try to be polite, kind, try to walk the walk, you know, be good to their mom,

• 21:16Speaker 00

  be really respectful of women, constantly talk about and model and give money to people less fortunate, such that they realize their privilege. It's great to have kids when you're young, if you, if you have the support system and a great partner, because it would be awesome to have kids my age and be in my 40s. It would just be fantastic. I would love that. But at the same time, you know, life is just trade offs. At the same time, being a little bit more economically secure and generous with my own emotions is also a huge advantage. In sum, my brother, what I am sure of is that despite the anxiety, despite

• 21:56Speaker 00

  the resource commitment, despite the real moments of, you know, having kids is a surgical procedure, as Jimmy Carr says, and that is, you're going to have your heart taken out, and it's going to live outside of your body for the next 18 to 25 years. I worry, I'm never worried about anything a fraction as much as I worry about my kids. But at the same time, I love the saying, grief and anxiety are receipts for love. You're just never going to have something that you feel, in my opinion, or most people, more purpose and more investment in. It's a long-winded way of saying, there's a trade off, there's some good, there's some bad about having kids when you're older. But the one thing I can tell you, or recommend

• 22:39Speaker 00

  and urge, is if you have a good partner, some economic security, oh yeah, for God's sakes, don't think about that stuff. Just do what you can to have kids, even if it means IVF, even if it means a surrogate, you know, adoption is a wonderful means of participating. I just, I am shocked, literally shocked. Not how much I enjoy, but how much reward and purpose I've had from having kids. All of this is to say, my brother, don't overthink it. Just get on with it and have kids. Our next question comes from Jake, who texted us. He says, hi, Prof G. I'm a 27 year old guy living in Chicago. I work at a job I absolutely love, and I'm fairly well compensated. That said, I've always had the entrepreneurial bug. Recently, my dad came

• 23:23Speaker 00

  to me with a genuinely intriguing business idea in his field. He has been a practicing physician for 20 plus years. I'm excited at the prospect of starting this company and working closely with my father. That said, I'm struggling to take the leap because of how much I generally love my current job. Any advice for someone in my shoes, or insights on starting a company as a father-son duo? Appreciate the consideration. Okay, this is where I likely am going to give you a different answer. And that is, we romanticize entrepreneurship, and people are really generous with your economic security and your money. And we'll say, go for it. Start a business. I think it depends on what type of, if it's a raw startup with your dad, no matter how good of an idea it is,

• 24:03Speaker 00

  startups, the infant mortality is just crazy. So many moons, no business makes sense. No new business makes sense at the time. Otherwise, it would already exist. So it's crazy, but sometimes it ends up being crazy genius and carves out a niche. And in exchange for taking that incredible risk, there's more incredible upside. But be clear, five to six out of seven new businesses aren't around in like seven or eight years. So if it's a raw startup, that's a different, that's a different risk scenario. If it's your dad has a business that's already going, and he wants you to take it over, you want to go into the family business. I teach a lot of kids at Stern, who are going into the family business, but first, they and their parents want them to go work at IBM or somewhere else, get some

• 24:48Speaker 00

  skills, learn how to navigate a place where people aren't going to kiss your ass because of your last name, right? So if it's an existing business that's already succeeding, I think that's a different risk profile. Now, what I'm going to tell you is, I'm going to assume this is a raw startup and a great idea, but you have a great job. I would stick with the great job for a while. I think there's no wealth creator like the US corporation or existing platforms on a risk adjusted basis. If you're kind of on, I won't call it a rocket ship, but a plane that's ascending, and they like you, and you have senior level sponsorship, you have stock options, you have good benefits, you like it, you don't go into a deep funk on a Sunday night, I think you want to ride that out. I think

• 25:30Speaker 00

  if you're fortunate enough to be at a platform that brings resources, intellectual property, other people, an environment and culture where it leverages the whole to make it greater than the sum of its parts. I think we romanticize entrepreneurship and diminish the value and how much reward psychologically and economically you can get from being associated with a, with a bigger platform that is doing really well. Also, you need to speak to a bunch of people about this. Be very honest and open about the opportunity with your dad. Be very open and honest about what you're doing right now, your compensation, how you're accelerating. Also, family businesses, especially a raw startup, raw startups are so emotional and

• 26:12Speaker 00

  so stressful. And I worry that if things don't go well, through no fault of your own, the market is bigger than any individual. But if things don't go well, then it might put stress on your relationship with your father, both the opportunity you gave up, you know, disappointment, the thing you're doing together isn't working. Family businesses make me a little bit, or starting a business with a family member makes me a little bit nervous, because you're putting a lot of eggs in one basket. So I have a bias towards, if you're out of corporation and doing well, to stick there as a young man, and see where it goes. And then if things begin to flatline, maybe revisit. I would imagine this opportunity

• 26:52Speaker 00

  with your dad will be there for a while, that it's not perishable. But I think, again, we inflate and romanticize entrepreneurship, and don't appreciate how powerful it can be if you have figured out a way to be good in a corporation. I worked in Morgan Stanley in the, in the late 80s, right out of college. That was an incredible opportunity, a growing platform. But I was awful at it. I was politically immature, and I wasn't good at the source material. I mean, I, I wasn't good at it. It just was so obvious. I did not know how to operate in a big company. It sounds like you have those skills. And those are real skills. Navigating the bullshit of a corporation, of which there's going to be an infinite

• 27:35Speaker 00

  amount, establishing the right relationships, getting along, playing well with others, living in a state of disinformation or misinformation. I remember once my company got acquired by Gardner, they shut our website down. I couldn't even find out who made the decision. And that was very frustrating for me. Anyways, long-winded way of saying, pull together a kitchen cabinet, outline both scenarios. But I personally have a bias towards sticking with the greatest wealth generator in history on a risk adjusted basis, and that is platforms called US corporations. Anyways, it sounds like you're cursed with opportunity. And a great problem is the problem of not what to do, but what not to do. I appreciate the question.

• 28:20Speaker 00

  We'll be right back after a quick break.

• 28:27Speaker 00

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• 32:19Speaker 00

  Welcome back. Our final question comes from a listener who emailed us. Hey Scott, my wife and I don't see eye to eye when it comes to child versus marriage dynamic. Her highest priority is to respond to his every want, not just his needs. She's been told by Instagram, "Child development experts to one, distract and show affection to the child to stop their crying ASAP, regardless of the situation. Get used to the idea of roommate syndrome with your spouse as the child should be your primary focus. How do millennial fathers navigate what some might call overfeminization, especially when raising boys? Thanks for your time and wisdom." Oh, gosh, I'm just not an expert here. I just, like, some, just some data. Millennial and Gen Z dads are spending twice as much time with their kids

• 33:04Speaker 00

  as they did 40 years ago, and working dads are now spending more time than working, with their kids than working moms did 40 years ago. So dads, dads are actually stepping up, and I do believe that probably the most accretive thing for society in terms of crime, the deficit, mental well-being, is if more dads were more engaged in their kids' lives. And we're doing that. And I think that, that has indirect, but very strong correlation with plummeting crime rates and the fact that suicide, opiates, deaths of despair are all on the, on the decline in the US, which is a great thing. And I realize there's a lot of different factors,

• 33:44Speaker 00

  but more engaged fathers is, I think, just an incredible, if you will, I don't know, antidote, steroid, fix, neosporin, whatever you want to call it. It's good. Let's just say it's good, right? It's a good thing. I think, as it relates to your relationship, I think you have honest conversations if you think your, your partner about parenting. But brother, for the most part, when it comes to parenting, I think you're, when people ask me why I'm in London, I say, because it makes no sense. 98% of my business in the US. I say honestly, around life decisions, I'm an influencer, not a decision maker.

• 34:29Speaker 00

  Because your wife, and this is sexist, is just going to have greater intuition around the kid, around how to behave, around how to treat the kid. Mothers are elemental. Dads, in my opinion, for the first, at least first few months, are supplemental. That's not to say they're not important, but the mom is essential. And I know with my partner, she'll come down and say, I'll say, we will have dinner with our youngest, and she'll say, something bad happened at school today, I can tell. And I'm, what are you talking about? He's fine. And then we find out later, he bombed his test, or he didn't make the, you know, did or didn't make the [inaudible]. She has just, if he gets up, when he was little, if he would get up in the middle of the night, she would, she would sense his feet getting out of bed

• 35:13Speaker 00

  and be like, and immediately pop up and be, and say, oh, he's awake, or he's up, he's about to come into our room. And I'm not suggesting you shouldn't make an effort. I'm not suggesting you shouldn't be there. I'm not suggesting this should absolve you of any responsibility to be engaged in how you raise your son. But I think when it comes to child rearing, you defer to the mom. I think she's just going to have better intuition. Also, I think our job as dad is not only to be a great dad, but be an incredible partner and be super supportive of the mom, who has a tendency, or usually, society just expects so much from women during these years. Be a great mom, be nice. But also, we need you to be a baller, maybe a semi-baller

• 35:57Speaker 00

  while you have young children at home, but we need you, you can't just be a mom. You need to also, or the expectation is also, you know, potentially be great at work. I mean, and, oh, and if you can, do Pilates and stay very attractive. And also be just a nice civic-minded, I mean, the expectations on new moms in a capitalist society are enormous. Not that there aren't huge expectations on dad or on being a good provider, but this is all a long-winded way of saying, okay, have open and honest discussions around parenting. That's healthy, be generous with each other. But my approach, and maybe it's, it's my way, it's maybe not the right way, has been to provide my viewpoint and then say, okay, the decision model is I give you my viewpoint,

• 36:40Speaker 00

  but as it relates to the kids and their school and the approach to discipline, I'm going to defer in most cases to the mom and recognize part of being a really good dad is your kid seeing how good you are and how respectful you are of mom. And I defer to her judgment sometimes in front of them on purpose, so I, they see that mom, you know, mom is sort of the, you know, she's the sheriff in town, so to speak. That's not to say I don't get involved in disciplining. That's not to say that the discipline I provide, quite frankly, let me make another sexist comment. I think dad has a different form of discipline that, quite frankly, the kids take more seriously. I'm not talking about, you know, I'm not talking about being physical with them, which I am not.

• 37:25Speaker 00

  I'm talking about, the reality is you're bigger and have a deeper voice, and oftentimes, the kids just take dad more seriously when he weighs in. So this is something we all struggle with. There is no owner's manual. Every book I've read on parenting contradicts the one before it, but a couple of things I am certain of is, or that's worked for me, defer to the mom on key decisions around the kid as she has better intuition than you. And remember that part of being a good dad is being just a fantastic, supportive partner. Appreciate the question. That's all for this episode. To submit a question for next time, email a voice recording to [email protected]. That's [email protected], or post it on the Scott Galloway subreddit.

• 38:09Speaker 00

  This episode was produced by Jennifer Sanchez, Laura Janier, and Asher Schwartz. Our editor is Brad Williams. Kami Reek is our social producer. Juberos is our technical director, and Catherine Dillon is our executive producer. Thanks for listening to the Prop G Pod from Prop G Media.

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