At The Money: Tax Management for Investors with Bill Artzerounian, RWM (December 31, 2025)

There is still time to make some smart moves to reduce your 2025 taxes. You have to be proactive to take advantage of the latest changes in the One Big Beautiful Bill Act. But you better hurry – there is less than three weeks left in the year!

Full transcript below.

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About this week’s guest:

Bill Artzerounian is Director of Tax Services at Ritholtz Wealth Management, where he focuses on the specific steps investors can take to better manage their taxes.

For more info, see:

Personal Bio

LinkedIn

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Find all of the previous At the Money episodes here, and in the MiB feed on Apple Podcasts, YouTube, Spotify, and Bloomberg. And find the entire musical playlist of all the songs I have used on At the Money on Spotify

 

 

 

TRANSCRIPT:

 

Intro: Let me tell you how it will be
There’s one for you, nineteen for me
‘Cause I’m the taxman

Barry Ritholtz: It’s never too early to be thinking about taxes. April is only a few months away, but you have questions and we have answers. Let’s discuss how you can reduce or defer your taxes over the long haul.

I’m Barry Ritholtz, and on today’s edition of At The Money, we’re gonna discuss important issues for all investors about understanding how to lower their tax bill.

To help us unpack all of this and what it means for your money. Let’s bring in Bill Erian full disclosure. Bill is a director of tax services at Ritholtz Wealth Management, where I also happen to coincidentally work and have my name on the door.

Let’s start with the basics. Where does tax management sit in the hierarchy of priorities for, for investors. How does this look relative to things like asset allocation or security selection or even asset location and their own behavior?

Bill Artzerounian: Thanks for having me back, Barry. I’m biased. I’m a CPA, I run the tax practice here. I think about taxes all day.

But I’m a proponent of controlling what you can control. We can’t control the market. Asset allocation gives us. You know, we can run back tests, we can look at historical data. That’s very useful. Even security selection, that’s, you know, individual stocks are more volatile than say, uh, an index fund.

But taxes, we have a set of rules and we can, we can, we can define our behavior based on those rules, at least in the short term. We don’t know what tax law will look like 20 years from now. We have a set of rules for the foreseeable future. We have to act within those rules, but it gives us guidelines, and that’s where we can actually make a difference, because we don’t know what the market’s gonna do tomorrow, next week, next month, next year. but we do know what the tax code will look like, at least until probably 2028.

Barry Ritholtz: Let’s talk about tax aware portfolios. What are the core issues that investors can pull the right levers on? What moves the needle the most?

Bill Artzerounian: At it’s very basics. We have different buckets of tax assets. We have pre-tax money, like a traditional 401k. We have after-tax money, which is, say a brokerage account. And then we have tax-free money, which is your, which is your Roth account.

Asset location can be huge and we’re big fans of. Asset diversification and clients come to u  well versedin asset diversification, but not necessarily tax diversification.

Tax diversification to me means you have different levels of assets in each of these buckets, and that gives you a lot of flexibility when you need it. A lot of times this comes up in retirement. We have folks come to us and they stocked away money in a 401k their whole career. They have a couple million bucks. They feel great about it. And then we have to break the news like, “Hey, you’re gonna pay tax on every single dollar here, and there’s no flexibility in their plan.”

Every dollar that they distribute, every dollar that they need for the rest of their lives is going to be taxable. Whereas if you plan ahead and you can diversify those different buckets of tax money, that’s where that’s where you provide a lot of flexibility for yourself in the future.

Barry Ritholtz: Let’s talk about planning ahead and, and perhaps the thing that I find most fascinating, and I’ve been reading the most about, and I still feel like I don’t have a solid handle on it, is the Mega-Roth Backdoor conversion. Tell us what that is. What are the advantages of it? How do you make sure you’re doing that both correctly and legally according to the IRS?

Bill Artzerounian: Call it Super Roth. We can call it Mega Roth. It’s just a juiced up Roth option. In your employer retirement plan, let’s just use. Let’s just use 401Ks as an example. There are other employer retirement vehicles, but let’s use 401Ks.

The limit in 2025 for total 401k contributions is $70 grand. Now that can be employee, myself, contributing to a raw, uh, to contributing to a 401k, or that can come from the employer. Normally for a lot of plans, it’s a combination of the two.

Let’s say I’m 50 years old, I’m contributing $30K to my pre-tax, 401k in 2025. Next year, that’s gonna change slightly. We talked about that last time, but then my employer’s gonna kick in, let’s say 10 grand. That’s their match. So total we’re at 40 K, the remaining 30. If the, if the 401k plan allows it, that remaining 30 — 70k maximum minus 40k already contributed — that can be made on an after-tax basis. And then you have money that’s already been taxed in the 401k you convert that to Roth.

So now we have, we have 40K that went in pre-tax between employer and employee, and then we have 30 K that’s now in a tax free Roth bucket. So we started our discussion talking about tax diversification. This is a great way to do it. Now you have pre-tax money growing and you have tax free money growing.

And again, that’s gonna give you a ton of flexibility down the line. And even inside of those plans, you might want to structure the Roth money a little bit more aggressively because you know Roth money, imperfect financial theory is gonna be the last money you touch. So you might wanna be more aggressive in the Roth. If you have a bond allocation, you might want that in the, in the traditional or the pre-tax sleeve.

The mega backdoor Roth allows for these higher contributions. It’s a kind of an unlock for a lot of folks who are earning a lot of money. They want tax efficiency. A lot of plans are starting to pick this up.

So if you’re listening and you’re a high earner and you have some sway at your company, go ask your CFO, go ask HR. And see if you can implement the, the, the me, the mega backdoor Roth strategy.

Barry Ritholtz: And then what about the full-on Mega-Roth conversion? Do you take a traditional 401k? What does that look like when you convert that to a Roth?

Bill Artzerounian: The extra 30 K that I alluded to that goes in as in quote unquote after-tax contribution. When you convert after-tax money, you don’t pay tax on it. You don’t pay tax twice. That’s kind of a, a foundation of the US tax code. You don’t pay tax twice. Now, if you’re talking about taking money, you took a deduction on, that’s considered pre-tax money.

That 40 k of pre-tax money, if I wanted to convert that to Roth. That’s gonna be a Roth conversion and that one, that one’s gonna be taxable. That may make sense if you’re, uh, as an investor, you know, maybe you’re in your twenties and thirties and you have a long runway to retirement and you want full Roth money, that’s, that’s a great case to convert pre-tax money to Roth now and benefit from long term tax free growth in the Roth, uh, for, for decades to come.

Barry Ritholtz: What are some of the more common tax traps that you see around equity comp? Walk us through. RSUs, ISOs, NSOs, Employee Stock Purchase plans, et cetera.

Bill Artzerounian: We call that equity comp alphabet soup, Barry. It’s, it’s really confusing. A lot of folks out in the Bay Area or in other tech companies, they get employed by these companies, they’re like, here’s your package, and they have no idea what it means.

I think the first thing is just a, an understanding of. Of what you own and then an understanding of how it’s taxed.

RSUs are a little simple. These are restricted stock. Restricted stock is going to be paid on a stated vesting schedule, and it’s almost like a cash bonus. You’re just receiving stock instead of cash. Once you receive it, it’s yours to do what you want.

Options are a little bit more tricky. There’s two types of options. Non-qualified and incentive stock options, the tax treatment is different, but the way to think about it is: You don’t get anything for free. The IRS says, no, you don’t. You don’t get anything for free. So if there’s a difference in your option between what you pay for the share or your strike price and what the share is worth, there’s gonna be a tax component on that difference. We call it a spread or a bargain element, but that’s the big difference

At at the very basics, what folks that are paid in equity need to do is be proactive with a tax planner. I’ve seen far too often, uh, folks with RSUs or they exercise options and they have a big tax bill in April and they have no idea where it came from. Because in my experience, folks don’t feel stock. They feel cash. They know when they’re paid in cash. They don’t know when they’re paid in stock. So if you’re paid in stock and you recognize that as income, you’re not thinking about it. And then you’re left with a big tax bill down the road and you’re like, where I didn’t make a million dollars, I made 500 K. but then you realize, oh, that extra 500 K was stock, not cash. Therefore, I didn’t feel it.

Barry Ritholtz: What about some of the clients we have at some really high growth companies, Apple, Google, Palantir, Nvidia, they’re seeing their stock holdings go through the roof. What are best practices for those folks? How soon do they need to start thinking about managing capital gains?

Bill Artzerounian: Well, that depends. It depends how comfortable they are with the stock, both in the short term and long term. And there’s bias here, right? If you work for a company, in theory, you’re bought into what that company is doing, therefore you don’t really wanna sell the shares, but then you create some concentration risk.

When you’re, when you’re paid in equity, it accumulates. And if that accumulates to a point where. A small move in the stock is keeping you up at night because on paper you’re worth X and then the next day you’re worth X minus whatever, you might wanna diversify a little bit, and that’s where effective tax planning is gonna be crucial, because you don’t just wanna rip a bandaid off, you wanna strategically plan for capital gains based on certain limits.

It could be capital gain brackets, it could be salt limits last time on, on deductions. There’s a, there’s a very structured way to do this, but ultimately it’s gonna depend on. How comfortable you are with concentrated positions in your portfolio, and how much are you willing to pay tax to get rid of that concentration?

Barry Ritholtz: What happens with someone who not only is getting their income from a company, but they just have so much concentrated risk in that equity? What sort of advice do we give folks like that?

Bill Artzerounian: There’s a couple options. Number one, you could just pay tax on it. That’s a win. Especially at long-term gain rates, you know, our clients are are pushing 35, 37% on their ordinary income, but their long-term capital gain rate is gonna be 20%. They’ll probably pay 3.8%, which is net investment income tax. But that’s a reasonable rate to pay for all this growth.

You’ve won! Now create some tax sell, sell the capital gain, and help yourself sleep at night because again, if that stock moves 10%. It’s gonna be material to your overall net worth. There are some other mechanisms.

We’re heavy with direct indexing here, we’ve had a lot of success with the O’Shaughnessy team [now part of Franklin Templeton] on direct indexing and creating tax losses to use against concentrated positions, or maybe use tax losses against real estate holdings or other stuff.

There are some newer things. Bill Sweet calls this late stage capitalism where there’s this, there’s this slew of new products to either avoid or defer taxes. 351 exchanges come, come into mind where you take a, you take a concentrated position, you find a group of investors, you bundle it into an ETF. And you have a diversified basket now rather than a concentrated position.

It doesn’t necessarily solve the tax problem because your basis is your basis. You can’t change that. So if I have a million dollars of stock with a $5,000 basis, even if I exchange that for a, a diversified ETF, my basis is still five grand.  So whenever I, whenever I wanna sell some shares of that new ETF, I’m still gonna have a pretty big capital gains bill. But it does solve the diversification issue.

Barry Ritholtz: This traces back to real estate. If you sold an investment property and rolled into another one, you got to roll over the tax obligation. It sounds like the SEC is finally caught up with real estate investors. Tell us more about how that operates. If you’re sitting in highly appreciated stock, and let’s be blunt, this is late stage of the bull market. People are sitting on giant, low-cost basis positions. How does this exchange work? Is it work? Is it just ETFs? What else can you do this with?

Bill Artzerounian: There’s a slew of products on the market to solve these quote unquote problems. They’re not problems at all. They’re, they’re, they’re, these are, these are champagne problems.

But just like in real estate where a 1031 exchange looks like, you have a piece of property real estate, for example, you find a bigger piece of real estate. You have a capital gain in the existing property, and you roll it into the new property.

Again, this is tax deferral. It is not tax avoidance. Your basis stays low. And so what you end up with is you, you, you push the capital gain down the line. In real estate, and what you could do with liquid assets and securities is if you exchange and exchange and exchange your whole life. Then you pass, let’s say you die – my favorite thing to say is, “Nothing solves tax problems like death” but when you, you pass on the assets to your kids. And what you’ve effectively done is you’ve deferred capital gains until you die, and then your errors get step up in basis. So there are more mechanisms now.

To replicate what’s happened in real estate with liquid securities and other assets, and that’s, that’s allowed folks to defer, defer, defer. And then, you know, eventually we’ll, uh, uh, inevitably we’ll see a bear market and this will solve itself. But right now we’re seeing a lot of folks explore these options because we’ve had a hell of a run for 15 years now, and a lot of folks are sitting on big capital gains.

Barry Ritholtz: To say the very least. There’s been a whole new set of rules passed last year in 2025. Tell us what the most significant tax law changes were? What should investors be aware of?

Bill Artzerounian: The biggest change is what didn’t change at all, and that was actually tax rates. If the tax bill that was signed into law, we call it OB3 (one big, beautiful bill), if that was not signed into law by December 31st, or if there were no tax changes. Tax rates were set to increase by about 3 to 5% across the board, For folks earning the highest incomes, that would’ve gone from 37 to 39.6% and that 2.6% difference, that is unlimited. In theory, that could be up to six figures, seven figures, eight figures, nine figures, and that 2.6%. Is now kicked into every dollar that exceeds that that amount. So the biggest thing that changed is what didn’t change. And that’s tax rates.

The other changes that we’re seeing come into effect are a lot on the deduction side. There’s more strategy around tax deductions, charitable giving, state and local taxes, how to bump from 10K up to 40K for certain taxpayers.

For most taxpayers, we talk about charitable giving quite a bit. And those are, those are what we’re focused on is, is controlling the timing of deductions to time with income, right? Your deductions are worth more when your tax rate is at its highest than when your tax rate is lower. We’re trying to time charitable gifts. We’re trying to time salt deductions to coincide with our client’s highest income years.

Barry Ritholtz: You mentioned earlier, death solves a lot of tax problems. Turns out it solves a lot of problems. But, um, how do you integrate tax planning into estate planning? Are they really one and the same? Tell us what the thought process is there.

Bill Artzerounian: They are one and the same with totally different rules. Estate tax as a whole doesn’t come up outside of the most wealthy individuals, right? Right now the estate exemption is gonna be like 30 million bucks for a joint family.

But Income tax plays a role throughout life, right? And so if we can, if we can integrate income tax planning with estate planning, it’s a, it’s a win for these families because at those levels of wealth, those are gonna be the folks that are most sensitive to big tax bills.

One thing we like to do. That combines the two is strategic Roth conversions. A lot of folks that we meet with, they have enough assets to live on. They’re thinking about  generationally, how do we take care of our kids within the bounds of the tax code? Roth conversions will allow, let’s say, parents to pay tax now rather than leave pre-tax money to their kids. Under Biden’s Secure Act 2.0, there’s now a 10 year rule for. Inherited IRAs. These are both pre-tax IRAs and Roth IRAs.

If I have a kid, let’s pretend I’m 80 years old. I have a 50-year-old daughter who’s a doctor in New York, right? Her tax rate is gonna be very, very high when I pass away. She’s gonna have 10 years to deplete my retirement accounts.

If that’s in pre-tax money, she’s gonna pay tax at the highest possible rate on that money. Whereas if I convert my assets, my pre-tax assets to Roth, maybe I pay tax at 24% instead of her 37% rate. I do that on her behalf, and now she has a lot more tax efficiency when she inherits my money.

Barry Ritholtz: What should people be thinking about as they start to organize their taxes, not just for 2026, but looking ahead to 2027?

Bill Artzerounian: It’s about timing income, right? Again, think about this, over the course of your lifetime, or if you have kids over the course of their lifetime, when can we pay tax at a lower rate than we might pay in the future?

That’s, that’s a lot of our work is just timing, income, timing, deductions to take advantage of fluctuations in, in tax rates and in, um, in, in lifetime income. And that’s where, that’s where you have to look forward. Again, look forward rather than backwards, is if you can time these things. These are gonna be marginal differences over the course of your lifetime, but marginal differences that can then compound, they’re really gonna add up over decades.

So to wrap up, there are a lot of steps investors can take to minimize what they pay in taxes, not only on capital gains. What they’re doing with their qualified accounts, where they locate their assets and changes they can make to make sure their kids aren’t saddled with the tax burden. Speak to your financial planner.

Speak to your tax professional. Make sure they’re working together so that you check every box that’s available to you to legitimately reduce and defer your taxes by as much as possible.

I’m Barry Ritholtz. You are listening to Bloomberg’s at the Money.

 

 

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Find our entire music playlist for At the Money on Spotify.

 

The post At the Money: Tax Management for Investors appeared first on The Big Picture.

My morning train WFH reads:

• The Unexpected Winner of Rising American Tariffs Is Mexico: Its exports to the U.S. have surged since President Trump imposed new duties on countries this year. (Wall Street Journal)

• Earth Is Running Out of Sand … Which Is, You Know, Pretty Concerning: Sand is the second most-used resource after water, but it’s unregulated and ripping environments apart. (Popular Mechanics) see also A huge cache of critical minerals found in Utah may be the largest in the US: The discovery could reshape the clean energy supply chain. (Grist)

• Car Payments Now Average More Than $750 a Month. Enter the 100-Month Car Loan. This fall, typical new car broke $50,000 barrier; ‘We don’t have $300 monthly payments any longer.’ (Wall Street Journal)

• Is the Federal Reserve truly independent? Who will be chosen as the chair of the Federal Reserve? (Washington Post)

• New York’s Congestion Pricing Is Working. Five Charts Show How: Congestion pricing is working as planned, with a significant drop in pollution and traffic declining by 11% in the tolled zone. The Metropolitan Transportation Authority is poised to beat its target of generating $500 million of revenue from the program after expenses. Despite initial concerns, the business impact in the district doesn’t appear to be as onerous as some had feared, with a 3.4% increase in visitors and a 6.3% boost in sales-tax revenue. (CityLab)

• The Santa Presidency: Trying to fix the economy by handing out cash. (The Atlantic)

• How diamonds are powering a new quantum revolution: By inserting tiny imperfections into the stones, scientists open up possibilities in computing, encryption, and sensors. (Financial Times)

• The Nordic diet can help you sleep better and live longer: The Mediterranean diet’s colder-climate cousin comes with the same health benefits thanks to its combination of anti-inflammatory- and antioxidant-rich foods. (National Geographic)

• Here Are 5 Wars Trump Started or Expanded in 2025: The U.S. military is fighting or preparing to fight in more countries than it was when the self-proclaimed “peace president” took office. (Reason) see also 25 Worst Villains of the Trump Admin: This most difficult part of this exercise was only picking 25. (Meidas+)

• The intellect of LeBron James: As the NBA great nears retirement he shows how the mind works. (Washington Post)

Be sure to check out our Masters in Business interview with comedian Jay Leno, former Tonight Show host, and creator of Jay Leno’s Garage.

 

Almost no jobs have been added to the American economy since April 2025; 710,000 more people are unemployed since November 2024.

Source: Robert Reich

 

Sign up for our reads-only mailing list here.

 

 

The post 10 New Year’s Eve AM Reads appeared first on The Big Picture.

 

 

 

“The writing has “been on the wall for well over a year now” that SiriusXM wouldn’t be renewing Howard Stern’s colossal contract — and his employees have been taking advantage, “coasting” on the clock and trolling for new gigs, two current show staffers told The Post.”   –New York Post

 

Let’s delve into an example of declarative reporting predicting an upcoming event that ended up being completely, laughably wrong. You may have missed this one during the dog days of summer.

Supermarket tabloid The U.S. Sun reported on August 4th that “The iconic Howard Stern Show on SiriusXM is set to be canceled after a stunning 20-year run, [unnamed] sources exclusively told The U.S. Sun.” Four days later, The New York Post confidently reported that the Howard Stern Show’s 19-year run at SiriusXM was coming to its final and ignominious end.

Both papers, not coincidentally, are owned by the Murdoch family’s NewsCorp. Each relied on unnamed “longtime staffers” as sources. Both reported Stern’s audience had dwindled “from 20 million a day to 125,000” – if true, a 99.38% drop in listeners. Both misled their readers.

Data from Sirius (and elsewhere) puts Stern’s audience anywhere from 5x to 10x what was misreported –a substantial drop that requires no additional exaggeration. The more complete context would have explained the broader drop in all of SiriusXM audience numbers, and how its time-shifting and streaming app has affected broadcast numbers.

But the big error was simply the declaration that Sirius was finished with Stern. The satellite company just renewed his contract for another 3 years.

Instead, anonymous sources said things like: “Most of us have been coasting at work the last year,” because “we know he’s retiring, whether by choice or because he’s forced out…”

Perhaps motivated reasoning was at play at the Murdoch-owned properties: “The looming end of the once mighty radio personality comes after a sharp change in Stern’s politics.”2

I don’t know Sun/Post reported this in the manner they did; I only know they got the story wrong while engaging in poor journalistic practices.

Anonymous quotes are the stock-in-trade of gossip columnists; it would not surprise me to learn these quotes were entirely fabricated.1 Even with journalists and outlets with a sterling reputation for fairness and objectivity, you should treat any anonymous source with the utmost caution.

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Besides Sirius XM’s stock price, what does Howard Stern’s contract have to do with how we view coverage of markets or the economy?

Surprisingly, a lot. The parallels are there when you see people talking about things they don’t or can’t know about specific future events. The details in Stern’s negotiations are a minor example. There were a dozenish people – lawyers, agents, managers, corporate execs, perhaps board members – involved in the Stern-Sirius contract negotiations.3

Note that a lack of accurate inside dope did not stop reporting in an authoritative voice; was it trashing a political opponent that was so attractive? Might it have ironically been the broad interest in Stern’s activities?

This is the time of year when people confidently talk about things they cannot know. Turn on the TV, browse a website, read a newspaper, magazine, or Substack, and you will see authoritative predictions about what will happen next year, based on what is either unknown or unknowable. A lack of insight or knowledge doesn’t stop the speaker or writer from discussing a topic with great authority and conviction. Expressing doubt, acknowledging multiple possible outcomes, or admitting what you don’t know is considered unacceptable.

This is true regardless of whether the expression is opinion, commentary, speculation, or even wild guesses. Human nature favors precise errors over ambiguous accuracy. This is the default standard—lots of self-assured cockiness and very little humility. History informs us that this approach is flawed when talking about the inherently unknown and unknowable future, especially when capital is at risk.

Media malpractice is everywhere, but this one was exceptionally egregious. The Stern example goes beyond proof of how little we know about what the future holds; it shows how it manifests in supposedly authoritative sources.

We put a lot at risk when we ignore our own lack of knowledge and blind spots. This is especially true when we do not know what we do not know…

 

 

Previously:
“Nobody Knows Anything,” Wall Street Strategist Edition (January 2, 2025)

Nobody Knows Anything, DeepSeek Edition (January 28, 2025)

Nobody Knows Anything, The Beatles edition (September 26, 2024)

Let’s Say It All Together: Nobody Knows Anything (May 5, 2016)

Nobody Knows Anything (Full archive)

 

 

Sources:
BYE-BYE BOOEY The Howard Stern Show ‘to be canceled’ after nearly 20 years on SiriusXM as ‘$100m’ contract is up later this year
by Jessica Finn
The Sun, August 5, 2025

Howard Stern staffers prepping for show’s demise, withholding best material as future uncertain
By Chris Harris
NY Post, Aug. 9, 2025

 

 

 

__________

1. Beginning in the 1980s a wave of fabrication scandals of sources were perpetrated under the cover of anonymity. See, e.g., Janet Cooke at The Washington Post; Jayson Blair at The New York Times; Jack Kelley at USA Today; Stephen Glass at The New Republic, and others involving fabricated and unverifiable sources.

2. From the NYPost:

“I don’t know if its wokeness that alienated some of his audience, or if he just got tamer with age, but whatever it is, its apparent no one wants to hear it anymore,” the second staffer offered.

3. Anyone who has ever been involved in a large deal knows that the fewer people who know anything, the less chance of an accidental derailment…

 

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I extensively detail why “Nobody Knows Anything” in How Not to Invest: The ideas, numbers, and behaviors that destroy wealth―and how to avoid them.”

It’s on sale at Amazon for $18.01!

 

The post Nobody Knows Anything, Howard Stern Edition appeared first on The Big Picture.

 

 

The transcript from this week’s MiB: Jay Leno, Live Audrain Newport Concours & Motor Week, is below.

You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube, and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.

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Transcript:

 

This is Masters in Business with Barry Ritholtz on Bloomberg Radio.

Happy holidays, and We have an extra-special holiday podcast at the Newport Ordering Concourse, elegance. I sit down with Jay Leno talking about cars, comedy, watches, and pretty much everything else. Jay’s a fascinating guy who’s created an amazing career.

I thought this conversation was super interesting, and I think you will also, with no further adieu, my conversation with the former host of The Tonight Show, Jay Leno.

Barry Ritholtz: Jay, thank you so much for joining us.

Jay Leno: Thanks for having me. So let’s start out with a little bit talking about your background. Uh, born in New Rochelle, you grew up in, um, Andover, Massachusetts. Which interest came first? Cars or comedy?

Jay Leno: Well, when you grow up in a little rural town, you don’t think of comedy as a job, you know? And I was known to the neighbors as Kathy’s boy wants to be comedian. He’ll grow out of that. He’ll say, don’t worry, Kathy, you, that, that kind of, you know, that kind of mm-hmm. People just, it, it didn’t seem like a viable, you know, you go to Hollywood, you meet kids wanna be lighting directors or costumes or, ’cause they know people that did that. You know, but when you’re in Andover, it’s like, what?

Barry Ritholtz: What sparked your interest in comedy? How did you find the path.

Jay Leno: I had very good teachers when I was in high school. I had a English teacher, Mrs. Hawks, and being dyslexic, I was not the best student. And you know, she said, “Oh, I see making jokes in class and stuff. Do you ever think of writing comedy?” I said, well, I never, I never thought it’d be a job. Oh, you should take, oh yeah, that’s it. She said, “I’ll tell you what. Why don’t you, maybe you could, instead of writing a paper for the final, you give a talk, you know?”

And I said, okay. And I tried to. Put some kid style jokes in and that was the first time in my life I actually enjoyed doing homework and mm-hmm. Well, maybe I can make a living doing this. But as a kid, you know, I think people at a comedians, you tend to remember things that are funny, things that get a reaction, you know?, I was in the fourth grade and Mrs. Allen was my teacher. I always remember this. She was telling us about, Robin Hood. how cruel the Sheriff of Nottingham was, and he would boil Robin’s men in oil, and I’d put my hand up and I said, you, you know why he did that to Tuck? And she said, no. Why? Because he was a Friar. Okay. And then she does one of these. “that’s not funny. Just stop that.” I, oh, see. Oh, she’s kinda laughing, you know. But the real kicker was later in the day, I’m walking past the teacher’s lounge. No, no. Come here. Well, what did you say about Friar Tuck? I said, and I went, oh, she told my joke in the teacher’s lounge and I said, oh. I said, he is a Friar. Oh, that’s was a friar, that’s a very funny thing. I went, oh, that’s, that’s pretty good. And I thought, oh, and when you’re a kid, you, you know people that you tend to remember things that get a laugh.

You just sort of, a little bit of attention. Yeah. You put them in your mind, you try, it makes a little indentation, you know? So that was always something I enjoyed doing. Always remembered it. But again, I never thought. I could make a living doing it.

Barry Ritholtz: Who were your comedic influences when you were growing up?

Jay Leno: Oh, Robert Klein, George Carlin. Richard Pryor, primarily Klein. ’cause Klein was like me, middle class white kid. You know, most comedians at that time tend to be, uh, grew up during the depression. Mm-hmm. And Youngman, uh, all those kind of guys, you know, kids today with the long hair, you know, all that kind of stuff.

Then all along comes Robert Klein. And, and, uh, and, and once again, George Carlin. Richard Pryor, Bill Cosby before the recent turn of events. Uh, you know, so it, it was, yeah, those were my influences.

Barry Ritholtz: Since we’re at the ordering Concourse and Motor Week, let’s talk a little bit about cars. (Good transition, right?)

Your first, your first car was a 34 Ford stock. What’d you do to it?

Jay Leno: I saw my dad and I were driving past the tip top miniature golf in North Reding, Massachusetts. It was parked at the Shell Station with a sale sign. I went and I bought it. Um, what’d you pay for that? $350. Mm-hmm. Which was a lot of money in Yes, in 1965.

But I had been working at McDonald’s and I’d saved some money and, you know, so, and then we dragged it back to my house and I took a couple years to get it running, and then I got my license and I drove it every day to school.

Barry Ritholtz: Self-taught mechanic. What do you mean? You took a couple years to get it?

Jay Leno: Oh, self. Self. Well, yeah, I mean, just. You know, you’re a kid, you’re playing with it after school, you know, that kind of thing. Uh, yeah, it took me a couple of years to learn how to do. Yeah, I guess self-taught would be the fair way to say it. Yeah.

Barry Ritholtz: So 34 Ford is the gateway drug. At what point did you realize this is more than a hobby, something of a passion.

Jay Leno: Well, when I had a garage full of cars, I Perhaps this is, uh, more than a Yeah, yeah.

Barry Ritholtz: Well, how many cars is too many? At what point do you need help?

Jay Leno: Just maintain, well, I have 214 on the road now. Plus the motorcycles.

I watch the show hoarders, and go, the guy’s fine. It’s a problem, man. You can still get to the bathroom. Look, but that’s old newspapers. You have motorcycles and cars. Something a little more reasonable when your parent did the same thing.

Barry Ritholtz: How do you decide of the 214 cars, which one you gonna take that day?

Jay Leno: That’s the first world problem. Mm-hmm. That’s not very much. So people don’t want to hear a rich guy go, how do I decide? I just can’t decide which guy. No. I mean, whatever I’m working on. If I do one oil change a day, it takes 18 months. So, right. You have to look at it that way. Right.

Barry Ritholtz: Watever you’ve just worked on, you say, let me drive it home to see if it’s okay.

Jay Leno: So that’s what I enjoy.

Barry Ritholtz: You’re a little bicoastal, you’re in L A but you also have a place here in Newport?

Jay Leno: I do have a place, and I also have a house in Andover, Massachusetts, where I grew up here.

Barry Ritholtz: Do you, do you keep any cars out here as well?

Jay Leno: No, I don’t. Because of the weather and mm-hmm. You know,

Barry Ritholtz: What do you drive when you get here?

Jay Leno: I’m one of these people. Really my car, you know? If my car was on another coast, oh, that would be horrible. Like, we go out to eat if, if I can’t see the restaurant from my table, we’re not eating here, honey.

Barry Ritholtz: I’m curious how Leno’s Garage came about. I have this fantasy that your accountant says to you…

Jay Leno: No, no, no. I have a garage, I have friends with cameras, I’m on TV already. This seems like a fairly natural transition.

Barry Ritholtz: Why don’t you take the TV hobby and put it on tv and this way you try to mo, um, you know, monetize it as much as you can?

Jay Leno: I did it for nothing for the first, I guess, 15 years. Really? Yeah. You know, just because I enjoyed doing it. It was fun. Um, and it just opens up another, you know, you should have something. I’m not a particularly interesting person. Uh, you know, so if you have other things of interest that other people like, then you have something in common, you can talk about it. So, cars, motorcycles. Anything that rolls, explodes, makes noise is interesting.

Barry Ritholtz: Do you know what the cars, uh, that are top of the list here are gonna be?

Have you walked around, seen much so far? Oh yeah. This, you have some of the best cars in the world here. This is quite an event. You are. And inevitably you see something you’ve never seen before or, or never even heard of.

Jay Leno: You know, the, uh, all countries are working on automobiles. In different, you know, you had cars from Czechoslovakia, the people on the other side of the mountains never heard of. Mm-hmm. You know, like a Tatra, a very unusual car. Most Americas never seen one, but it’s very popular in Czechoslovakia or what was then Czechoslovakia at the time.

So, yeah, so it’s a fascinating hobby and the nice thing about it is it’s no more than really 150 years old. You know, if you, if you like Egyptology, well now you gotta go back 6,000 years and stand in hot sun and dig in the sand. And, uh, you know that with cars, I only have to go back a few years. We, we took a walk down, um, the Boulevard earlier, the two that kind leapt out to me, aside from the Gulling, I know you have one of those was the Talbot Lagos.

Yeah. Spectacular. Yeah. Very interesting guy. They’re very art deco, you know? Yes. It’s only in recent years, cars are seen as kinetic artwork. Right. You know, it used to be just an old car. Mm-hmm. But now people are looking at them and I mean, it’s. You know, you can buy a painting that this for a hundred million dollars.

Right? You get something that rolls down the road, looks pretty, has a practical element to it. So, and only cost a 10th as much. Yeah. Only cost a 10 or sometimes, almost as much you Right. I mean, Ferrari go for the, I think the last Ferrari sold for $75 million. Yeah. I mean it’s pretty crazy. That’s a one of one though, right?

No, no, that’s one of 13. 13, wow. Yeah, I also saw, um, uh, and there wasn’t a sign on it, so I’m doing this. By sight, but a Mercedes SK 500, the giant front fenders has Yeah, yeah. Spectacular. Also, they are, they, I try to enjoy the, the, the, some suspicious things happen in Germany, even. Thirties to the mm-hmm.

Middle forties. I tend to avoid those for obvious reasons. Mm-hmm. But the early ones I love. Yeah. So let, let, let’s talk about some of these classic designs. What do you think has aged especially well? What looks good? Uh, perhaps that wasn’t thought of so well, when it first came out. Oh. Oh, what his age?

Well, I wasn’t thought when it first came. Well, two different court, I mean. Uh, shapes evolve. I mean, uh, cars used to change just for the sake of change. Mm-hmm. Now they change mostly because of aerodynamics and efficiency and, and things of that nature. You know, uh, I mean, a Prius is about an efficient shape as you can get, but it’s not, it’s attractive enough, but it’s not striking.

It doesn’t take your breath away the way. Mm-hmm. Some Ferraris by pin or whatever, you know, back in the, in, in the twenties, thirties, forties, fifties. Things are drawn by hand. So there’s a, there’s a, a flow. Yeah. Flow. Yeah. Like now everything is sort of computer design. You have all these sort of weird angles and things like that, but.

Uh, you know, the best looking cars are both masculine and feminine, like an XKE. Mm-hmm. I don’t know any women that don’t find Jaguars attractive. Even women that don’t know anything about cars, there’s something about, because it has a feminine element to it, but then it has the rear haunches and, and so it has a masculine, so it’s a little bit of both to it.

Mm-hmm. You know. A lot of cars look too brutal. You know, Lamber, goodie, Kosh? Mm-hmm. Those look like guy cars, right? You drive, one of the girls go, how old are you? Yeah, boy toy. You pull ’em a jag, you’re like, Ooh, I like that guy. Yeah. So sometimes the proportions, the shapes, the lines, they speak to everybody.

They’re universal. Yeah. I mean, it’s trick is. Well, if it speaks to everybody, then you have a Corolla. Mm-hmm. You know, the, the best. Cause people, some people love it, some people hate it. Anything that gets emotion going is probably gonna work on some level. You know, I remember talking to Bob Lutz about this when the Viper came out and said, A lot of people think it looks like a cartoon car.

It’s a bit over exaggerated because we’re not trying to sell it to them. We’re trying to sell it to the people who think it looks good and there’s enough of ’em out there, you know? For sure. So, so let’s talk about, um. People have to ask you questions about cars all the time, but they don’t have to.

Actually. Most of ’em just, people must assume. Lots of people do. Yeah. Yeah. When someone asks you for a recommendation, what, what, what do you recommend as a good, cheap set of wheels for a budding enthusiast? Well, you know, there are almost, or for an enthusiast mm-hmm. Or for transportation. Transportation is easy.

I mean, someone who wants something fun for the weekend, well, first they tell me what it is they’re looking for. You know, I, I, I mean obviously el cars, Mustangs, Camaros, things of this nature. Any sort of two seated sports car, uh, yeah, there’s plenty of choices out there. You don’t need me for that. Mm-hmm.

So this event is sponsored in part by Alanga and Sauna. Mm-hmm. Um, we’re both wearing Longa watches. What drew you to watches? See, I paid for mine. So did I. Oh, you did? I paid for mine also. So, so, and you probably have access to more of these than I can get, so, well, it’s interesting, you know, I, I, watchmaking and automotive things have a lot in common ’cause they’re both extremely mechanical.

Mm-hmm. Most watch people don’t really like electric watches the same way they don’t like quartz watches. Mm-hmm. Quart watches are obviously the most accurate you can get, but there’s, don’t appear to have a soul to ’em, you know, with these kind of things, when you turn, you hear the, the, you know. Mm-hmm. It is, it’s a sort of a.

The car, the watch needs you. If you don’t wind it, it won’t run. So there’s a human element that needs to be attached to watch, to get it to the run, you know? And if you flip it over, you can see the absolute spectacular mechanicals on the other side. Yeah. They do a beautiful job. So, so very parallel the, the precision and intricacy of a mechanical watch and a classic automobile.

Yeah. Yeah. I, I, I seen them as somewhat similar. I mean, I like things that need me, you know, my, my cars need me because I need to do certain things to make sure they run correctly. Electric cars kind of run them out of who the master is. Mm-hmm. You know, it’s about like that screen door. After a while, you learn it has to be shut a certain way.

Normal people can’t do it, but you know that you lift it and turn it just a quarter of an inch, oh, it’ll click in. Coming up, we continue our conversation with Jay Leno, live from the Newport, a Drain concourse, the elegance, discussing how a career in comedy. And car collecting led to a fascination with mechanical time pieces.

I am Barry Ritholtz. You are listening to Masters in Business on Bloomberg Radio. My extra special guest this week is Jay Leno, comedian, car collector, timepiece enthusiast. Let’s return to our conversation live at the Newport or drain concourse Gonz. What, what are your thoughts on, on the new EVs and hybrids that are coming out?

What, what does this do to the collectible market? I, I believe you have a Tesla plaid, is that right? A Tesla plaid’s a great look. I used my electric card during the week. I mean, sitting on the freeway in a 40, a 1966 Hemi, 4 26, it gets three miles per gallon. Doesn’t really make a lot of sense. You’re not going fast, you’re not, you’re just annoying people and, and poisoning the atmosphere.

So you take your electric car then on the weekends. If there’s a car rally, you drive your Mustang or whatever car you have to the rally, you sit around and you tell lies about it to other people and they tell you lies about their car and you know, it’s a sort of, a little bit of interaction, you know, so, so I mentioned the precision of automobiles and the precision of watches.

You have famously been touring for 40 years, 40 plus years. Um, when you put together a standup set, do you put the same sort of precision into structuring that set as you do? Well, I think, I like to think so. Mm-hmm. I mean, you, you, you, you want to have a joke every six to nine seconds. It’s a bit like spinning plates of the Sullivan show, and then, then you want to keep it going, you know?

So you wanna make sure that the people, you’re not wasting people’s time. I hate when people are, how y’all doing? Woo. Anybody from Boston? Woo. Boston? Yeah. Okay. That’s not comedy. You’ve wasted 40 seconds. You know, get right. Yeah. Keep it moving. You know, when you watch Rodney, Rodney was a, I was a big fan of Rodney Dangerfield, and it was, it was the economy of words.

It’s getting the funniest words you can in the shortest amount of time. You know, Rodney had jokes I loved, like, uh, I worked practice strip joint. It said topless and bottomless. I went in. There was nobody there. I mean, it’s, it’s a funny joke. I mean, ’cause I didn’t waste your time. It wasn’t a three minute setup.

You know, one of his favorite jokes, it’s so stupid. My doctor wanted a semen sample, a stool sample. And a urine sample. So I gave my underpants. I mean, okay. But it’s quick. Boom, boom, boom. You’re not, you’re not wasting people’s time. Really. Interesting. So you’ve been known as somebody who just has toured his whole career, even during, what was it, 22 years of the Tonight Show?

You still were doing standup on a regular basis? Well, when you’re on television, you rely on 175 other people. Mm-hmm. They really can’t do the show without all the elements to it. And when you go out on the road, you’re by yourself. You rise the fall strictly on your own ability. And I, I, I like that you get all the blame, but you also get all the glory.

And, and I, I like that. Plus it’s piecemeal, right? Joke, tell joke, get checked, boom. Next show nobody says, you know the joke she told two months ago, they’re not working out. Come back. You gotta come back and do the show again. You don’t have to do that. You know? Mm-hmm. On tv you get, there’s so many irons in the fire and whatnot.

You’re dealing with. You know, and my, my favorite TV line of all time when NBC was letting me go, I said, you know, I’ve been number one for 23 years, well for 18, 18 of the 23 years. And they said, we want what’s above number one? I said, okay, what, uh, what is above? What is above number? I mean, just made me laugh.

And even they realize how stupid that song. I said, what do you mean? How can you have, what’s a above? Just tell me, somebody tell me what it, yeah. Just made me laugh. Sorry. So since this is Bloomberg, a financial network. Yeah, let’s, let’s talk a little bit about money. Alright. You are known as someone who is savvy with your money.

You only spent the money you earned doing standup. Well, I’m not savvy. I’m dyslexic. Yeah. Okay. So consequently I don’t really understand it. All I know is money. My I work and my money relaxes. That’s my, I don’t want my money out working for me. Because he’s gonna screw up somewhere. I don’t want that.

Right. Whenever I hear, and there’s minimal risk, and I hear the word risk. Mm-hmm. And minimal. So that means I’m gonna lose something, right? No, no. I, no, I don’t. I always had, even as a kid, I worked at Wilmington Ford, I worked in McDonald’s. Whichever job made the most I banked and the other money was my, you did the same with The Tonight Show.

You banked The Tonight Show. I never touched a check in 22 years from The Tonight Show. That’s amazing. I banked everything and I lived on the money I made as a comedian. Then when I, when I, uh, when the show ended it, oh, I opened this little pass book. Oh look, this. It’s quite a bit of money here, you know?

This is good. Yeah. So when you started collecting cars, did you ever envision this collection would get this large No. No. Or this valuable? No. I never thought that, no. When I, I remember I would sleep in the alleys in New York and it was the most depressing. I remember sleeping on the alley. It was one of those alleys where guys would come with hookers and I’d be in the back just hiding behind some trash cans and they were doing whatever.

Really, this is my life now. I mean, it was like. It’s the most horrible that really on the road you were that hard travel. I remember on 44th and ninth it was Dikes. Lumberyard, right across the way and from from the alley where I slept a couple of nights I could see dikes lumberyard. I always had that in my mind, and hookers would come in and they’d just, just horrible.

It’s a terrible, they just hear terrible sounds horrible. I said, really? This is my life. This is what it is now. You know? So everything better than that was gravy. Yeah. Well, it’s been a little bit of gravy. You recently had a, uh, gulling, you found in a barn you’ve had a number of barn. No, no. I, no, I didn’t.

I didn’t buy that. I didn’t buy, that car was found. It was sold for $10 million and we had the owner You had it on the show? We had it on the show, yes. I did not. I, I would like to have owned that car, but no, I didn’t buy it. Didn’t you find a number of barn fines, cars? Oh yeah. Sure, sure. What, what are some of the more memorable ones?

Um. Well, the most recent one was a 1963 Jaguar XKE. Uh, the guy bought it in 62, started drinking about 66, 67. He became a hoarder, just had trash piled on top of it. Uh, when he died, the family called me, they said, uh, cars right across the street. Uh, my uncles had some kind of car. We didn’t know what it was.

And it was a Jaguar. And I, I said, and, and this is really the best way. I said, look, Google it. Find out what’s it worth. Okay. Find out what they’re worth and let me know and I’ll pay you that. And that’s what I did. Seems fair. Yeah. I, I mean, I paid more than a fair price. Mm-hmm. Because I, I don’t flip cars.

I don’t sell cars. So to me, this way, nobody goes, you wanna rip me? I don’t, you don’t want any of that? Any cars on your list that you’re still, uh. Hunting for anything you’d like to have? No, you know, I buy, I buy the story as much as I buy the car. Really? Yeah. I mean, to me the fun, you know, I had a lady call me 94 years old, and she and her Hudson, her and her husband bought a 51 Hudson Hornet in New Jersey.

They drove it to California with their two kids. He bought a gas station. He ran that for the next 30 years. He died sometime in the early nineties. She calls me about 2000, I guess. Three, four. Uh oh. My husband died like 20 years ago. We got this car. I say I already have a 5,300 will come look at it. Okay, so I gotta look at it.

She’s 94, no hearing air, no glasses, right? And she said, would you gimme $5,000 for her? Okay. So I bought it. I take it back to my garage. It takes about a year and a half. We get it off and let me see if she’s still alive. I call her up. Hello? Oh, it’s jaylenn off. I said, the car’s all finished. You want to go for a ride?

She goes, okay, now she’s 96. Okay. And she says, can I bring the kids? I said, yeah, bring the kids. So I get there and the kids have got a blindfold and the kids are 74 and 72 and they’re blindfolded or right. And she’s like touching the car. Oh, the paint feels so smooth. Oh, it used to be so rough. We’ll take the blind.

Oh, she starts crying. We wanna go for, let’s go for araj. So the kids get in the back. Right. So we’re driving along and we’re talking, and the two kids start doing this to each other, poking each other, right? And, and she turns around. I, I told you kids, and she’s whacking the crap out of me. Mr. Leno was nice enough to take us a ride in his car, and you kids can’t be here.

And the three of them are just laughing. I mean, they’re just falling down. And she, and she’s not holding back. I mean, she’s really hitting them, but she’s laughing while she’s hitting them, you know? And it was just so funny. It was just so funny. She lived to be 106. Wow. And every time I get in that car, it makes me laugh.

’cause it was just so fun to see these, these two old men and they all look the same age. You know, she’s 96, they’re 74, and, and she just whacking the crap out of hilarious. So more stories than there’s a hole in your collection or you’re enamored with this? No, don’t have a hole. I know. I have enamored with this.

No, it’s just about the stories. You know, my key to success is low self-esteem. I’ve heard you say that before. Yes. Yes. Because. If you have low cycle esteem, you never assume you’re the smartest person in the room. I assume one of the dumbest person in the room. So let me look around and see what the other people are doing here, and that’s what you do.

You know, I have so many friends that do TV shows and they really think, I don’t like, I wanna change these lights. And the lighting director who’s been in the business 40 years, I don’t think, no wait, I wanna change. Well, no. Why? Why don’t just let the lighting director do his job? You know, the fun thing about the Tonight Show was when I did it, anybody could pull, pull a cord and stop the train because I don’t like this.

I don’t think this is funny. Did it get to be annoying sometimes? But everybody felt they had a, a say in what was going on. It felt like they were part of the whole system. This idea that, you know, do not make eye contact with the star and just all that kind of nonsense, you know? So to me that was always the key to, to, to being successful.

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I am Barry Ritholtz. You are listening to Masters in Business on Bloomberg Radio. My extra special guest this week is Jay Leno, comedian, car collector, timepiece enthusiast. Let’s return to our conversation live at the Newport or drain concourse Gonz. So, so let’s stay with, um, the Tonight Show and comedy.

All right. Um, you’ve interviewed a few presidents, right? Right. Um, you interviewed Barack Obama. Who, what other presidents did you interview? Uh, was Barack Obama. Was Reagan before you, uh, started on, no, I, I interviewed Reagan. They had dinner with Reagan at the White House a couple times, but he wasn’t ever on the show.

Barack Obama was the first sitting president ever to do the show. Mm-hmm. Um. Uh, Barack Obama, Hillary had the nomination locked up and then he announced he was running for president. So I called him up and said, wanna come on the show? Oh, we’ll call. Thank you so much. You know, he rented a car, drove himself to the show, you know, walks out.

I goes, Hey, my name’s Barack was saying Obama. I’m running the president of the United. I said, okay, black guy from Chicago named Hussein. I said, you know, you shouldn’t even have to campaign. I just think you, you’re shooing with that. And you know, he got the joke and he’d laugh and he was very funny. And we got to be friends.

And so next time he came on the show, I asked him, it was the first time a sitting president and the whole parking lot was tented. Mm-hmm. So a satellite could not see where, when it came in, where it came in, couldn’t tell. Yeah. And I mean, I’ve told this story, but this is. I have the same idiot friends I had in eighth grade, so I’m telling him I had Barack Obama on the show and he gave me this phone number.

Nah, Uhuh Uhhuh. Uhuh Uhhuh. You don’t get it. You said you now, alright, let’s call him up. I go, I’m, it’s surprising the United States, I’m not gonna call him up. No, you don’t have it now. Uhuh Uhhuh now Uhuh Uhhuh. So I, I take out my phone book and I cover the phone and they go, see what it says there. Barack Obama president, the United States, his phone number is right under here.

You you? I said alright. Alright. I’ll call him. You want me to call him? Ill call. It’s like three o’clock, I figure. Okay, what can go wrong? Yeah. Hello, Brock Here. Mr. President. Yeah. Jay Leno. We’re gonna do vj. I’m just here with some of my friends. Lose this number. Jay, click. So your reputation has never been, uh, a very political.

Uh, comedian, you play it straight down the middle. Well, I used to get, we used to get quoted every day in the New York Times. We, we, we tried to make fun of both sides. Yeah. Mm-hmm. But yeah, that’s the way we did it. That’s not the way everybody else does it, but that’s okay. So, so recently Jimmy Kimmel mentioned on the air that you called to check in on him when, when he was temporarily suspended.

Uh, is what do you think the future of late night looks like? And and what does that say about the comedians have to watch what they say. Well, apparently they don’t have to watch what they say ’cause he’s back on tv. Mm-hmm. Okay. I mean, you either believe in free speech or you don’t, you know, free speech.

It only becomes annoying when it says something you don’t like. Mm-hmm. Other than that, it’s fine. And that that’s really the only, the only problem. And there’s always something somebody doesn’t like, whether it’s banning books or Huck Finn or whatever it might be. Uh, so to me, I, I always support street. I mean, I support Jimmy as a comedian, but also just the whole premise.

You don’t have to agree with him to realize. I mean, I, I, I had people that tore me apart every day. But they had the right to do it. I, I, I didn’t like what they said, but I agree with their right to say it if they chose. Yeah. You, you have Dave Chappelle speaking at the comedy festival in Saudi Arabia.

Mm-hmm. Saying he feels like, uh, free speech is under assault in the us. Uh, not that Saudi Arabia is a hotbed of free speech. Well, yeah, yeah. Again, I, I don’t like this new thing of comics criticizing other comics. We’re comedians. Okay. Just, you know, I believe in free speech. I, I shouldn’t have to say any more than that and I will defend it.

To the end, but, you know, and how about when he said this again, whatever, I don’t have to agree with it. Mm-hmm. You know, it’s like the Nazis marching in Skokie. Okay. They, they have the right to do that. I don’t agree with it. Well, I He like to see someone punch them in the face. Yes. But I don’t want that to be police doing it.

If some angry Jewish guy was about, well, okay, it’s fine with me, you know, I might even cheer him on, but I’m, no, I, I, I, again, I think you hit. It’s America. You have the right. And what about the, in the era of streaming, what about the future of late night? We heard Colbert is supposedly not profitable. I don’t know how true that is.

We heard similar threats about Jimmy’s show. How do you look at, you were a steward of the Tonight Show for 22 years. What do you think the future of this looks like? Well, I, I, I mean, when you could turn on streaming. And see Harrison Ford talk for half an hour saying whatever you want unscripted. Or you could watch him do a seven minute segment on a talk show, which you gonna do?

Or Jay Leno for 45 minutes unscripted. Yeah. But yeah. Well, I mean, to me, I think it just, the nature of television, it, it changes. It goes from one thing to another. I mean, it’s like going from CD players to cas cassettes, to CDs to it is just another. It’s another format that, that you can, that you can use.

So, uh, the thing that really kills late night is the incessant number of commercials. Mm-hmm. After 1130, you can run like nine minutes at 12 o’clock where some crazy. Yeah. It’s crazy. It’s wild. Yeah. So, and when you realize you’ve just watched all three Godfather movies in a row without one commercial, suddenly seeing Jake from State Farm again.

You know, okay, enough with this guy, you know, to me that’s the thing that’s really hurt. Late night. It’s not necessarily what people say. It’s the fact that people, oh God, another commercial, you just, you know, reading through. All right. So we don’t want to keep you all day ’cause we know you have a lot of places to go, cars to see.

Alright, I wanna, I wanna do a speed round, uh, a speed round, right. A dozen questions in under a minute. I’m just gonna throw these at you and, and gimme your answers. Alright. Starting with, what’s your favorite car to drive a dusenberg, what’s your favorite motorcycle in your garage? Uh, brush superior. What car offers the best bang for the buck?

Corvette, what’s your favorite car in your collection? Not necessarily a driver, but just the favorite car. Uh, McLarin one. That’s, that’s tough one to argue with. What’s been the biggest maintenance annoyance in your collection? Uh, my 1925 Doble Steam car. The one that kind of blew up. Is that the one we’re talking about?

That blew up, but that wasn’t the one that actually blew up in my face. No. Any cars you have any regrets passing on? Oh yeah. Was all. What modern car features do you find most annoying? Uh, probably the infotainment system. Uh, you know, I have my 51 Hudson. I reach out, I press a button, I get a station. I don’t have to stop and look at it.

Are you happy this thing? Yes. Would you make this election again? Yes. Others have made this election. Would you continue? Yes, I would. You know, would you pick your language? English is good. Thank you. You know, I it annoying. Um, what car do you drive the most often from your collection? Oh, I don’t know. Uh, well, hmm.

I drive a lot of them. Cardo. Uh, that’s what they were made for. A model t’s kind of fun, I guess I don’t drive it that much. Uh, probably the Mustang. That’s pretty good. Well, actually the Tesla won’t have to go to the airport and all those kind of things. What, what’s the rarest car in your collection? Not necessarily the most valuable, but one of very few.

Well, that would be the double steam car. Yeah. Mm-hmm. Um, is there any one brand you would never buy that you stay away from? No, no, not everyone breaks you. You don’t have a lot of Ferrari, right? No, I don’t have any Ferrari. But it has nothing to do with the cars. The cars are excellent. You know, for the longest time you had to buy two Manial before you’re allowed to buy the car.

You, you know, so I just never took part in that. What car surprises people the most, whether driving it or just the way it’s put together? Well, I have the kind of cars people. Not surprised that I got there earlier, late. They’re surprised I got there at all. When you show up in a 1906 Stanley Steamer and it’s on fire, people like, oh my God, your car’s on fire.

Yeah, I know. It’s supposed to. It’s supposed to be. You carry open flame in. Um, what’s the most recent addition to the collection? A Mustang, GTD. What’s the best sounding engine you own? Uh uh, um, Porsche GT V 10. And final question. Oh, is, is there one dream car you’re still hunting for? No. No. I’m, I’m, I’m.

Quite happy with what I have. Like I said, be happy what you have. Just make sure you have enough. There you go. Thank you Jay, for being so generous time. Alright, well thank, thank you. Thank you.

That was my live interview with Jay Leno at the Newport Audrey Concourse Elegance. If you enjoyed that conversation, check out any of the 592 we’ve done over the past 12 years. You can find those at iTunes, Spotify, Bloomberg, YouTube, wherever you get your favorite podcasts. And be sure to check out my new book, how Not to Invest the ideas, numbers, and Behavior that Destroys Wealth and how to avoid them at your favorite bookstore or book seller.

I would be remiss if I did not thank the correct team that puts these conversations together each week. My videographer at the live event was Sebastian Escobar. Alexis Noriega is my video producer, Anna Luke is my podcast producer. Sean Russo is my researcher. Sage Bauman is the head of podcast here at Bloomberg.

I’m Barry Ritholtz. You’ve been listening to Masters in Business on Bloomberg Radio.

 

 

 

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The week between Christmas and New Year’s Eve Monday morning reads:

• Charles Schwab CEO Explains Why Investing Works—and Gambling Doesn’t. Rick Wurster, Charles Schwab CEO,  says the firm manages $11.8 trillion in assets across 46 million client accounts, serving both retail and independent advisors. Schwab is attracting younger investors, with one in six new clients being Gen Z and 60% of new-to-firm clients under 40 years old, he said. Wurster says Schwab plans to launch spot crypto trading in 2026. (Barron’s)

• Data shows the ‘Made in USA’ brand still suffered under tariffs: Fewer shoppers are return customers of ‘Made in USA’ products. That’s because it still sends the wrong brand signal: expensive. (Fast Company) see also US Trade Dominance Will Soon Begin to Crack: Savvy countries will discover there’s a way to mitigate the harm incurred by Trump’s tariffs—and it’ll boost their own economies while making goods cheaper too. (Wired)

• Family Offices Have Become the New Power Players on Wall Street: Wealthy families are launching offices to manage their money at a record clip and are getting a seat at the table in significant deals. (Wall Street Journal)

• The boomer-doomer divide within OpenAI, explained by Karen Hao: There are two sides to the AI debate, and both are perpetuating the idea that AI is “inevitable, all-powerful, and deserves to be controlled by a tiny group of people,” says the Empire of AI author. (Big Think)

• After three decades of pretty constant growth, the consultancy boom just hit an AI-shaped wall: A partnership with AI may be good for consultants looking to decorate their LinkedIn profiles with AI badges, but it also reflects a deep shift within the industry, as the traditional model built on adding more people to bill for long hours begins to unwind. (Sherwood)

• The Sleeper Issue That Could Destroy the Economy: Trump may have stopped threatening Jerome Powell—but he’s still got designs to control the Fed. (The Bulwark) see also Historic Shift Underway in China’s Economy as Investment Slump Deepens: Investment in manufacturing, infrastructure and property is expected to fall this year, a remarkable turn for an economy whose growth reshaped the world. (New York Times)

• Societies with Little Money Are among the Happiest on Earth: Wealth and well-being go together in many studies, but certain communities complicate this link. (Scientific American)

• Trump’s Own Mortgages Match His Description of Mortgage Fraud:  The Trump administration has argued that Fed board member Lisa Cook may have committed mortgage fraud by declaring more than one primary residence on her loans. We found Trump once did the very thing he called “deceitful and potentially criminal.” (ProPublica)

• 4 surprising, proven rules to avoid getting sick this winter: We all know the basics of avoiding winter bugs, but science is uncovering lesser-known tricks that make a real difference. (BBC Science Focus Magazine)

• Jack Black and Paul Rudd: ‘I had a traumatic experience when I was a kid’ Hollywood’s comedy kings talk about the movies that shaped them and joining forces for Anaconda, a satire about a giant snake. (The Times)

Be sure to check out our Masters in Business interview this weekend with comedian Jay Leno, former Tonight Show host, and creator of Jay Leno’s Garage.

 

Stocks are spending less time in the S&P 500

Source: TKer

 

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Avert your eyes! My Sunday morning look at incompetency, corruption and policy failures:

• Scams, Schemes, Ruthless Cons: The Untold Story of How Jeffrey Epstein Got Rich: For years, rumors swirled about where his wealth came from. A Times investigation reveals the truth of how a college dropout clawed his way to the pinnacle of American finance and society. (New York Times)

• How Did DOGE Disrupt So Much While Saving So Little? The group’s biggest claims were largely incorrect, a New York Times analysis found. And its many smaller cuts added up to few savings. (New York Times) see also A Year In, the MAGA Labor Market Story Has Fallen Apart: The administration bet on government cuts, tariffs, deportations, and a gendered theory of growth. The data say otherwise. (Mike Konczal)

• How Starbucks Came Undone: In the ’90s, it became a once-in-a-generation triumph. Then it fell apart. What happened? (Slate)

• The latest government inflation and GDP figures are worthless, and will be for months to come: The federal government’s monthly releases of economic statistics — especially the inflation rate and growth as tracked by gross domestic product — have long occasioned partisan preening (or denunciation) and for a general public stock-taking of the health of the economy. Not this month. This time, they’re the occasion for doubt and confusion. (LA Times)

• These kitchen items may be contaminating your food with chemicals: See the thousands of plastic chemicals in what we eat. These chemicals act on the body in multiple ways — confusing hormones, disrupting immune systems and boosting cancer cells. But they all have one thing in common: They are intimately linked to plastic. (Washington Post)

• 15 People Have Died in Crashes Where Tesla Doors Wouldn’t Open: There are no official statistics on the dangers of electric handles. So Bloomberg did its own analysis. (Bloomberg)

• There’s a 92 Percent Chance Trump Is Making It Up: When riffing, the president exhibits an unusual tell. (The Atlantic) see also Here’s how Trump gets away with using dubious numbers: Trump doesn’t use numbers the way most of us do, as “things that can be added, subtracted, multiplied, and divided,” as Columbia University statistician Andrew Gelman put it. Rather, he uses them as rhetorical objects. (Los Angeles Times)

• The Florida Divorcée’s Guide to Murder: Hit Man: A Technical Manual for Independent Contractors inspired a triple murder and led to a major First Amendment case. Still, the book is just one chapter in the bizarre story of its author, “Rex Feral,” a 77-year-old great-grandmother wrestling with decades of guilt and living anonymously—until now. (Vanity Fair)

• Bari Weiss spiked a major migrant story — and told on herself: Weiss’ catch-and-kill puts her editorial incompetence at CBS News on public view. (Salon) see also Bari Weiss is Not on the Level: When Fairness Becomes Permission for Lawlessness. (Notes from the Circus) see also Here’s the 60 Minutes Segment Trump and CBS News Executives Don’t Want You to See: Hours before it was set to air last night, CBS News executives pulled the segment, but Canada’s Global TV app received it prior to broadcast. It’s now all over the internet… (The Reset)

• Russia’s Puppet Tulsi Gabbard Strikes Again: How the Director of National Intelligence Is Laundering Kremlin Lies, Undermining NATO, and Endangering U.S. National Security. (Unmasking Russia)

Be sure to check out our Masters in Business interview this weekend with comedian Jay Leno, former Tonight Show host, and creator of Jay Leno’s Garage.

Have tariff policies been benign for the economy? The data implies otherwise

Source: LinkedIn

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This week, I speak with Jay Leno at the Audrain Newport Concours & Motor Week. They discuss the future of late night comedy after The Late Show with Stephen Colbert was canceled. They also discuss Jay’s classic car collection, watches, and his approach to wealth.

A transcript of our conversation is available here Tuesday.

You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube, and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.

Be sure to check out our Masters in Business next week with Stephanie Drescher, Apollo’s Chief Client and Product Development Officer. She oversees everything from the global wealth business to portfolio management, product development, and client marketing. She is a member of the firm’s leadership team. Since 2020, Barron’s has named her annually to its list of the 100 Most Influential Women in U.S. Finance.

 

 

 

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The weekend is here! Pour yourself a mug of Danish Blend coffee, grab a seat outside, and get ready for our longer-form weekend reads:

• How Warren Buffett Did It: The most successful investor of all time is retiring. Here’s what made him an American role model. (The Atlantic)

• The Last Human Edge: In an age of machines, Henry Ellenbogen’s alpha comes from reading people, patterns, and the painful transition where certain companies either compound for life or die trying. (Colossus) see also The war is over. Human advisors won. Wildly wrong predictions from a generation ago are laughable today. (Downtown Josh Brown)

• The 20-something billionaires ushering in a betting bonanza in Trump’s Washington: The CEOs of Polymarket and Kalshi were facing off with the federal government one year ago. Now they’re new power players in Washington. (Politico)

• Stanford’s star reporter takes on Silicon Valley’s ‘money-soaked’ startup culture: “How to Rule the World,” out May 19 — three weeks before he graduates — promises an explosive look at how venture capitalists treat Stanford students as “a commodity,” wooing favored undergrads with slush funds, shell companies, yacht parties, and funding offers before they even have business ideas in their hunt for the next trillion-dollar founder. (TechCrunch)

• The United States of Klarna: Want to understand the state of the economy? Just look to all the shoppers flocking to “buy now, pay later” services. (Businessweek free) see also America’s hidden economic crisis: From healthcare costs to layoff worries, the country’s under-the-radar problem is personal financial chaos. (Business Insider)

• We Might Not Be So Strange: Perhaps intelligent life wasn’t so unlikely after all: It seems a rather odd coincidence that in the 4.6 billion years since Earth formed, humans have emerged now. For us to be here, first life itself had to get started, of course, and then develop more complexity. Then enough oxygen had to accumulate in the atmosphere. And habitability had to continue for a further 2 billion years or so while complex animals evolved. But here we are, now, thinking about such things, on a world that seems uniquely hospitable to us. (Nautilus)

• The 26 Most Important Ideas For 2026: Modern trends and history lessons—across culture, politics, AI, economics, science, and the long story of progress. But first: an announcement! (Derek Thompson)

• Melissa Hortman Died in a Shocking Act of Political Violence. This Is the Story of Her Life: The Minnesota Speaker’s closest friends and family open up for the first time. (Rolling Stone)

• An amateur codebreaker may have just solved the Black Dahlia and Zodiac killings: To attack the problem, Baber used artifical intelligence and generated a list of 71 million possible 13-letter names. Using known details of the Zodiac killer, based on witness descriptions, he cross-checked those names against military, marriage, census and other public records. (L.A. Times)

• 21 Facts About Throwing Good Parties: Parties are like babies, if you’re stressed while holding them they’ll get stressed too. Every other decision is downstream of your serenity: e.g. it’s better to have mediocre pizza from a happy host than fabulous hors d’oeuvres from a frazzled one. (Atoms vs Bits)

Be sure to check out our Masters in Business interview this weekend with comedian Jay Leno, former Tonight Show host, and creator of Jay Leno’s Garage.

 

Sentiment remains nearly 30% below December 2024

Source: Bloomberg

 

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I love this short, sweet version of what to do with your capital; its an updated version of the index card strategy, via @buccocapital::

 

Few thoughts on retail investing since it’s popping up again on FinTwit:

– As I’ve said before, I think it’s probably the lowest ROI activity you can do if you’re trying to get rich. Focus on your career
– You should index 90% of your money
– You have zero edge day to day. Your…

— BuccoCapital Bloke (@buccocapital) December 19, 2025

 

 

 

Previously:
The advice to ensure financial ruin? It fits on a 4×6 index card (September 13, 2015)

How to ruin your financial life, #badadvice (Washington Post, September 12, 2015)

 

 

 

 

 

 

Few thoughts on retail investing since it’s popping up again on FinTwit:

– As I’ve said before, I think it’s probably the lowest ROI activity you can do if you’re trying to get rich. Focus on your career

– You should index 90% of your money

– You have zero edge day to day. Your advantages are that you have duration, no mandate, and nobody forcing you to sell

– It follows that the fewer trades you do, the better. The more trades you do, the worse you will do

– Process is the only thing that matters. How rigorous is your process? How do you reflect on what worked and what didn’t? Do you even know why it worked? Otherwise it’s just luck. For most people is still probably just luck.

– Your biggest enemy is yourself. You have no institutional guardrails to stop you from doing stupid things

– If you are thinking of it YTD you have already lost. That’s not your game, and is a recipe for failure. Trying to beat the market every single year will cause you to overtrade, where you have a structural and insurmountable disadvantage

– It’s OK to just do it for the love of the game. Because it’s the greatest game on earth!

 

 

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My Boxing Day morning reads:

• Playing Santa Does Strange Things to a Man. What It Did to Bob Rutan Was Even Stranger. Bob Rutan is legendary among the tight-knit fraternity of Macy’s Santa Clauses. Like many of these men, playing Santa changed Bob. Profoundly. His story is one of struggle and failure, heartbreak and grace and—yes—the magic of Christmas. (Esquire)

• Can Netflix Help Save the American Mall? The entertainment company’s new “Netflix House” experience is bringing the brand’s shows into former department stores. Will streaming TV fans follow? (CityLab)

• King of Cannibal Island: The tulip bubble​ is the most famous financial bubble in history, but as historical examples go it is also, in one crucial respect, misleading. That’s because anyone can see the flagrant irrationality which was at work. At peak tulip madness in 1637, rare bulbs were so expensive that a single one was worth as much as a fancy canalside house in Amsterdam. You don’t have to be Warren Buffett to see that the disconnect between price and value was based on delusional thinking. (London Review of Books)

• No one knows anything. Let’s ask them about that: It’s never obvious what to do with thematic surveys. Is it positive or negative that 0 per cent of investors expect a new pandemic in the next 12 months? Should we assume their guess is probably right and buy airline stocks, or should we assume the consensus has underpriced the possibility and sell airline stocks? (FT Alphaville)

•  The Untold Story of Charlie Munger’s Final Years: The Berkshire vice chair was making gutsy investments, forging unlikely friendships and facing new challenges to the end. (Wall Street Journal)

• It turns out that CBS forgot to cancel the broadcast of the piece in the Canadian market…  Here’s the 60 Minutes Segment Trump and CBS News Executives Don’t Want You to See Hours before it was set to air last night, CBS News executives pulled the segment, but Canada’s Global TV app received it prior to broadcast. (The Reset)

• The Most Important Thing We Learned From Susie Wiles: Ever since the publication last week of a two-part article in Vanity Fair in which Susie Wiles, the White House chief of staff, said all of that and more, political observers have been asking: Why did she do it? Why discard her usual discretion and speak so frankly, on the record, about her cracked compatriots in the Trump administration? (New York Times) see also 5 turning points that explain MAGA’s civil war. Today, the movement’s most consequential fights are unfolding beyond the control of its term-limited president — empowering rival factions to shape MAGA in their own image. MAGA entered the year with a sheen of invincibility, riding the high of Trump’s victory and united in his promise of a new “Golden Age.” It’s ending 2025 locked in an existential war over the future of conservatism. (Axios)

• How Willie Nelson Sees America: On the road with the musician, his band, and his family. (New Yorker)

• James Webb Space Telescope confirms 1st ‘runaway’ supermassive black hole rocketing through home galaxy at 2.2 million mph: ‘It boggles the mind!’ News By Robert Lea published December 17, 2025 “The forces that are needed to dislodge such a massive black hole from its home are enormous.” (Space.com)

• How How the Grinch Stole Christmas: Behind the scenes of the lavish, painful, wigged-out movie that should have won Jim Carrey an Oscar. (Vulture)

Be sure to check out our Masters in Business interview this weekend with comedian Jay Leno, former Tonight Show host, and creator of Jay Leno’s Garage.

High market concentration isn’t a sell signal

Source: TKer

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My jolly X-Mas Day reads:

• Santa might be Christmas’ main man, but Mrs. Claus would like a word: Don’t look now, but here comes Mrs. Claus, right down Santa Claus’ lane. While St. Nick might be the season’s marquee draw, Modrzejewski and others say Mrs. Claus’ popularity is on the rise as clients look to break from routine, enlist the character’s motherly qualities and highlight positive female role models. (USA Today)

• Societies with Little Money Are Among the Happiest on Earth: Wealth and well-being go together in many studies, but certain communities complicate this link. (Scientific American)

• Forget the Bond Vigilantes. It’s the Gold Vigilantes You Need to Worry About. The bond vigilantes, as first coined by Wall Street veteran Ed Yardeni, sniff out government largess, corporate profligacy, geopolitical tremors, and inflation risks long before other financial assets and respond in kind. And by the sheer brute force of its size, bond markets force both the subjects of its wrath, and the investors that rely on them, into submission. (Barron’s)

• Crypto for Christmas? Gen Z-ers Are Cautiously Open to the Idea. Despite recent volatility in the crypto market, younger generations are still open to receiving digital currencies as gifts. (New York Times)

• Is the Tao smarter than the Dow? A high-return investment hiding in plain sight. (The Leading Edge)

• How to create a home that appeals to all five senses: The way a couch feels matters as much as how it looks. (Washington Post) see also Scent Makes a Place: How the desert taught me to smell. (Nautilus)

• America’s Tiny Airports and the People Who Love Them: Small-airport devotees brag about cheap parking, minimal TSA waits and friendly employees. (Wall Street Journal)

• The Doomsday Glacier Is Getting Closer and Closer to Irreversible Collapse: An analysis of the expansion of cracks in the Thwaites Glacier over the past 20 years suggests that a total collapse could be only a matter of time. (Wired)

• The Truth Physics Can No Longer Ignore: The fundamental nature of living things challenges assumptions that physicists have held for centuries. (The Atlantic)

• Four Perspectives on Bing Crosby: We hear him sing “White Christmas” every December, but the most inspiring stories about Bing are hidden from view. (The Honest Broker)

Be sure to check out our Masters in Business interview this weekend with comedian Jay Leno, former Tonight Show host, and creator of Jay Leno’s Garage.

 

Which states contribute the most and least to federal revenue?

Source: USA Facts

 

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