The $84 Trillion Wealth Transfer + The Real Value in Prediction Markets

Scott Galloway breaks down the biggest tax loophole in America, why the crowd beats the experts every time, and how to think about taking a pay cut for work you actually want to do. 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.

• 0:00Speaker 00

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• 1:36Scott Galloway?

  Welcome to Office Hours with Prof G. This is the part of the show where we answer your questions about business, 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 officehourswithprofgmedia.com. Again, that's officehourswithprofgmedia.com or post your question on the Scott Galloway subreddit and we just might feature it in our next episode. Question number one.

• 1:57Speaker 05

  Hi Scott, this is Pat from Boston. You talk a lot about how there's a greater concentration of wealth among retirement age Americans than at any other point in history. As someone who's both a well-off and a father who presumably leave an inheritance to his children, what's your thought on the current estate tax, given as a $15 million lifetime exemption, 30 million if you're married? Do you think that a more aggressive estate tax is healthy for a meritocracy? And secondly, do you think that given we're about to experience the greatest generational wealth transfer in history, we're currently in a unique opportunity to attack the federal deficit by taxing that transfer? Thank you.

• 2:35Scott Galloway?

  Thanks for the question, Pat from Boston. It sounds like we're brothers from another mother. Look, what do we know? We know that we are recklessly spending money. We're spending $7 trillion a year on $5 trillion receipts. That is, our government spends $7 trillion and collects $5 trillion. That's not sustainable. Leads to massive money printing inflation, and at some point, someone has to pay that money back, or it crowds out other investments in technology and education that have a greater ROI because we're busy sending so much money to seniors who keep electing other seniors to vote themselves more money. So just some data. The one big beautiful bill signed July of 2025 made the estate tax exemption permanent, 15 million per person, 30 million per couple. The bill's estate tax expansion is estimated to add $212 billion to the deficit over the next 10 years. Oh, yay, more deficits.

• 3:20Scott Galloway?

  The estate tax currently hits fewer than 1 in 1,000 estates and raises only around $37 billion a year against a $36 trillion national debt. And some estate taxes are meaningless now because of that exemption and the fact that you can put money in, and it grows well beyond that 30 million exemption. Research from Warden estimates the tax would have generated nine times more revenue under the 2000 era tax code, still roughly 85 billion versus the actual 9 billion. Baby boomers and the silent generation are set to transfer, God, I thought it was 50 trillion, it's not, it's 84 trillion by 24, oh my God, think about that. In the next 20 years, 19 years, $84 trillion is going to be transferred. The largest intergenerational wealth transfer in the history of the planet. Of that 73 trillion goes directly to heirs, and the wealthiest 1.5% of households account

• 4:03Scott Galloway?

  for 42%, almost half of expected transfers. So again, small number of people taking the greatest advantage of this tax loophole. And the ones who need it the least, quite frankly. Americans 70 plus currently control more than 30% of all US wealth, according to Fed data. And wealthier boomers are more than two times as likely to leave inheritances as poor Americans, meaning their transfer entrenches inequality rather than resets it. So, again, see above dynastic wealth. So that's where we are. So the key is with taxes is to try and find taxes that are the least taxing. And the idea of a progressive tax structure is that the wealthy, if they lose 40, 50, 60% of their income, it doesn't really impact their lives. Daniel Kahneman, the Israeli-American psychologist, has written a ton on this and done great

• 4:46Scott Galloway?

  research and said that above a certain amount of money, the happiness is really incremental. And that is, once you're making 3, 4, 500,000, or if you're in New York, a million or 2 million bucks and can afford to have kids and absorb an economic shock, have good healthcare. And by the way, it's not a lot of money. Above that, no real incremental happiness, which lends me to believe that, okay, if you're getting no incremental happiness from making 15 million versus 10 million a year, and the difference between universal childcare in a household and no universal childcare in a household, which is an incremental 10 or 15 grand in government services for that household, is enormous, then it just strikes me that we should have fairly aggressive progressive tax structure. Now, the problem is, once you become a superowner and stop making a lot of money but making

• 5:31Scott Galloway?

  money from investments, you can defer all of your taxes. So this is kind of how billionaires work. They start companies, they own stocks, they never sell those stocks, they borrow against them, never triggering a tax liability. So if you think of yourself as a stock and you make $100,000 every year, every year, that $100,000 is taxed at 30%. And even though you're gaining 70,000 a year, instead of gaining 100,000, if you own stocks that were increasing $100,000 a year, they compound. And in 10 years, you have triple the amount of money on the tax-deferred ownership basis versus the earnings. Now, some people never make enough money to save enough money to become owners, but that's the key when you're young, is to find something you're focused on, or focus on something, live modestly, and start building that base such that you can transition from

• 6:16Scott Galloway?

  an earner to owner. That's a whole shooting match. It's not earning millions of dollars, it's transitioning from earner to owner because of the tax policy. Now, the problem is, when you can transfer ownership to new generations... And you never tax that money. That is probably the greatest tax loophole in sum. How do we raise revenues, increase taxes that are the least taxing? And I think you've zeroed in on it. One, I would have an AMT. The tax code's gone from 400 pages to 4,000 and all of those goodies are basically there to protect special interest groups, CEBF corporations and the rich. And there's all sorts of tax loopholes. So it's actually not the tax rates that kill us. It's tax loopholes. There's five Fortune 100 companies that pay no taxes.

• 6:58Scott Galloway?

  The average tax rate for the top 0.1% is, you know, single or low double digits. I paid my, I paid a much greater my ratio of my salary when I was making hundreds of thousands. And now that I've been fortunate enough to make millions some years, I pay at lower tax rates. Because CEBF, I'm an owner now, not an earner. Okay. So AMT tax on corporations, like, okay, take all your loopholes. But if you're not paying 30% of your income in taxes and you make over a million bucks, boom, and AMT kicks in and you pay that 30%. But what you're talking about is lowering the threshold on estate taxes. Generally speaking, in line with the American zeitgeist is that we don't build dynasties. And we've always traditionally had a pretty high estate tax. Because the idea is we want to invest in infrastructure, whether it's the internet

• 7:41Scott Galloway?

  or medical research or education or childcare. That creates opportunities for the next generation of people who demonstrate grit and hard work. And that you shouldn't just inherit wealth. We don't want to be like Europe and have dynastic wealth. So I personally would lower the estate tax exemption to a million dollars. Because of the $50 trillion in wealth, do you know how much was paid in estate tax last year? 20 billion. So what is that? Less than, I don't know, 0.2% or something? I mean, basically, not even that. What is that? 20 billion, 50, 2,500 times? So it's 0.04%? Jesus, anyways, my math is getting wrong here. 0.4%. Anyways, I don't know. I don't know. I did a lot of drugs in college and used to be very good at math.

• 8:25Scott Galloway?

  And now that part of my brain is just dying, along with calendars or ability to remember people's names. Anyways, I would absolutely pretty much go to 1 million from 30 million for estate taxes. And not only that, that number's misleading because if I put something, a stock into my estate, and it goes from being worth a million to 7 million, say, when I pass away in 40 years, it's not, it's not a 30 million tax exemption that it's, it's priced at that 1 million. So technically, that $30 million exemption could grow to be hundreds of millions or even billions that doesn't get taxed. And what do you want? You want a tax that doesn't decrease people's happiness. And if your kid inherits a million bucks or more, and they lose 40% of it, say, at 10

• 9:07Scott Galloway?

  million, instead of inheriting all 10 million, they inherit 6 or 7, it's not gonna, it's not in any way gonna change their life or their happiness. So I love the idea of lowering the exemption from 30 million for a married couple or 15 million from single to a million. Sure, you've, you've worked, you want to be able to pass along a decent amount of money, tax-free, I get it. But above a certain amount, we need you to reinvest in the, in the great things that made you rich to begin with, such that other future generations can be, can live up to what is truly an American dynamic. And that is have the infrastructure and investments and wind in their sails, such that if they demonstrate some grit and character and register some luck, they too, like you, can have a bunch of money.

• 9:47Scott Galloway?

  But I'm writing a book on public policies or kind of ideas on how to increase the health and prosperity of America. And one of my kind of, I think, no-brainer ideas is to pretty much do away or dramatically lower the exemption on estate taxation. Very much appreciate the question.

• 10:06Scott Galloway?

  Question number two comes from a listener who emailed us. "Hi, Scott. I'm a 28-year-old veteran from Minneapolis, currently transitioning from active duty into marketing. You've mentioned your interest in data from prediction markets, including calcio to gauge your wisdom of crowds. I'm curious how you think young professionals might leverage this type of data to strengthen the storytelling in their work? Are there any industries or use cases where you think this approach could be especially impactful going forward?" Hmm, okay. So just, so I love the data from prediction markets. We use it here at PropG all the time. Kalshi secured exclusive deals with CNN and CNBC this year within 48 hours of each other alongside closing a $1 billion funding round. The CNN deal is exclusive. It says that they won't work with any other prediction markets. CNN pays zero licensing

• 10:51Scott Galloway?

  fees. Polymarket struck a deal with Dow Jones in January 2026 for their data to be displayed across W S Street Journal, Barron's Market Watch, and Investors Business Daily, including in print. Polymarket data was also integrated into the Bloomberg Terminal in 2024, the first signal that Wall Street was taking prediction markets seriously. And Polymarket also has deals with X, Yahoo Finance, and Substack. Okay, so what's going on here? Why is this data so powerful? There is a phenomenon called the wisdom of crowds, that if you ask one person to make a bunch of predictions across different subject material, and then you ask 100 people their prediction, and you take the prediction that is most prevalent among those 100, the wisdom or the crowd will beat the individual almost every time. So there's a wisdom of crowds, and that is

• 11:35Scott Galloway?

  it balances out all emotion, super smart, not super smart, biases, et cetera. So I find this data is absolutely just powerful and insightful. And if you look at the elections, the prediction markets have gotten, have gotten elections correct more often than any pollsters. As a matter of fact, Kalshi has, has predicted Fed rate cut decisions correctly 100% of the time. And that is, the crowd on Kalshi has predicted what is going to happen with respect to Fed interest rates and the amount of that cut or not cut. Its track record is 100% right now. So I think that looking at this data, using it

• 12:15Scott Galloway?

  as just another data stream, is really powerful, and just to incorporate into your own analysis. I don't see it as, I'm trying to think.

• 12:26Scott Galloway?

  Is there specific businesses based on the data? Probably. But I would just think of it as another data source. And when you go into a meeting where you're, you know, you're talking about an issue that might be impacted by an issue, I think it's interesting to go to one of these markets and see if a market has been started and what the market or the crowds are saying about the likelihood of something happening or not happening and incorporate that into your data set. And some, I just think of it as another arrow in your, in your toolset. It's also just interesting to go on to these platforms and just look at the data set and see how things are forming and how things are going up or going down. You know, what it thinks oil is going to do, what it thinks the Fed's going to do,

• 13:08Scott Galloway?

  what it thinks earnings are going to do. I personally would be careful not to engage in this type of gambling personally, especially if you're a younger man who's more prone to this type of addiction. But using it as a data source, gosh, I think it's powerful and I use it every day. So again, it's just another tool, another data set. Get facile with it. Find out if you're in an industry where there's a lot of markets being formed, providing predictions, then check on them and incorporate them as a data set. A second order thought here might be, could you potentially use it as some sort of interesting insurance market? That's a little esoteric and generic, but the idea is that there might be, so in Florida, it's near impossible now to get hurricane insurance.

• 13:53Scott Galloway?

  So the feeling is there might be markets started where they make bets that a hurricane will hit and that you make a, the insurance market invests a small amount of money that the hurricane will hit. And if it does, it pays off and that's the equivalent of insurance because maybe you incurred damage from that hurricane. I think there's a lot of different applications for how this might be used to insure or hedge certain bets. If you're worried that the market's going to go down because Trump is elected, then maybe you bet on Trump being elected. And if he is, that hedges, hedges what you think might be downside risk in your stocks or what have you. So that's probably pretty esoteric and for specific industries.

• 14:36Scott Galloway?

  But I think it's just a way, I think it's an interesting way to think about, you know, how you use different types of markets. Anyways, thanks for the question.

• 14:54Scott Galloway?

  We'll be right back after a quick break.

• 15:02Scott Galloway?

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• 16:03Scott Galloway?

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• 17:13Scott Galloway?

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• 18:22Scott Galloway?

  Welcome back. Question number three is another email from a listener. Hi, Scott. I'm seven years into the corporate FPNA, Financial Planning and Analysis, at a tech company. Good money, zero soul. I want to move into sales, but the company is asking me to start at a lower tier, essentially a demotion, for a year before I get to the level I'm actually targeting. That means a 20% pay cut at a time when my wife and I are relocating to Chicago. She's starting grad school. I'll be the sole owner for three years. The financial logic says stay put. Is the short-term sacrifice for the long-term career alignment a reasonable trade-off? Or am I rationalizing a bad decision at the worst possible time? Thank you for everything you do. Okay, so the retail advice is do what you love and take the risk now. But the reality is, these people providing advice don't have to pay for your kid's night

• 19:07Scott Galloway?

  nurse or give your wife some semblance of financial security. So I don't know your financial situation. If you have rich parents, that solves everything. Or if you have a couple, if you have some money saved up? You're in a position to take more rest. But if you're like most people, young families and not living, not living hand to mouth, but not a ton of cushion, then I think it's really hard to take a pay cut. And I empathize with that. The silver bullet here, if there's a silver bullet, if it gets fired, is to go find an equivalent job, an equivalent position at the better pay, and then be able to go back and say, I want to stay, but I have an offer at this. I find that generally speaking, corporations don't value you until they believe there's a non-zero probability

• 19:52Scott Galloway?

  or a credible possibility you're going to leave. And then all of a sudden, they really decide what your net worth is. And then I would, I would also potentially go to someone in your organization, your trust, your boss, and just explain the issue. I really want to be in this, in this field. I think I'd be good at it, but I'm struggling with how to do that while supporting my family. I think transparency is a really good,

• 20:18Scott Galloway?

  you know, is the best way to communicate, you know, be authentic. The truth has a nice string to it. So let me summarize. One, if you, like many new families, are really focused on, or don't have a lot of cushion, I would say stay put, just because money is important. And it's especially important in terms of your mental well-being with a new kid. When my first child came marching out of my partner, all I felt was financial anxiety, quite frankly. And it really fucked with me mentally because I was worried about how to, you know, it was no longer just taking care of me. I was taking care of a kid. We were living in New York. I was not broke, but had gone nearly broke in the 08 recession. And it was just tremendously stressful. So you need to be, it sucks to be a grown up and you might just have to suck it up for a while and stick with the higher paying job.

• 21:01Scott Galloway?

  Two, go to someone internally, your trust, your boss, or someone in HR, be very transparent about the struggle. And maybe you've already done that and they've said, sorry, this is what there is. But they might be able to find some sort of creative solution for you, tell you to wait a year and then you'll transition at a higher level or something like that. Finally, the silver bullet here is to be able to walk in and say, you got another job in the department you want, at the pay you want. So that's sort of the three legs of this stool, of this decision, if you will. But look, I don't want to say this is a good problem, but what it means is it sounds like you're making pretty decent money. You have a job and you have a new kid. And, oh, and also make sure you get alignment with your partner around this. Talk to your

• 21:43Scott Galloway?

  partner, get her view. Make sure that whatever decisions you make, these are joint decisions and you have alignment with each other. Otherwise, if something goes wrong or it doesn't work out, you don't want her to feel as if you're surprising her or, you know, you just need alignment here. That way you guys own the victory or the mistakes, own the decision together. Thanks for the question.

• 22:04Scott Galloway?

  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, post your question on the Scott Galloway subreddit and we just might feature it in an upcoming episode.

• 22:20Scott Galloway?

  This episode was produced by Jennifer Sanchez and Laura Janer. Kami Rieck is our social producer. Brad Williams is our editor. Andrew Burrows is our technical director. Thank you for listening to the Prop G Pod from Prop G Media.

• 22:39Speaker 06

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