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Taylor | Trap
This Week on The Floor
Taylor Swift’s buyback of her music: emotional move…or brilliant investment?
Is Jamie Dimon missing the real danger in the U.S. Treasury market?
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Markets Recap / Deal News
Interviewing this week? Here’s some content for your conversation.
Hot Take on the Bond Market: IT’S A TRAP!
Is the real risk in U.S. Treasuries…T Bills???
The financial press has been sounding the alarm for weeks. From Bloomberg to CNBC, heavyweights like Jamie Dimon and other trusted voices have been pointing to long-dated U.S. Treasuries as a risky investment.
Why?
Lack of fiscal discipline, inflation concerns, a recent ratings downgrade for the U.S., and a global selloff in the long end of other developed markets all point to concern for 20- and 30-year bonds.
And the institutional crowd is clearly listening. Recent positioning data shows that institutional investors have been piling into shorts — or at the very least, reducing their duration by moving further in on the yield curve.
Our former podcast guest Jamie Patton from TCW told Bloomberg: “We wouldn’t just look at the 30-year bond and say, ‘5%, let’s buy it’. We would look at it and say it’s actually still pretty rich vs. the rest of the curve.”
So, if you’ve been outright short 30s, has it worked out for you?

Source: CNBC
Nope. 30s have actually RALLIED more than 20 bps off their cheapest levels, which coincided with quarterly refunding, the launch of the “Big Beautiful Bill” and the Moody’s downgrade of the US.
Instead, the real impact has been a significant steepening of the Treasury yield curve: meaning, the difference between say 2-year Treasury yields and 30-year Treasury yields is growing.

The YTD steepening of the yield curve (as of end of May). Source: Bloomberg
For example, if 2 year US Treasury yields are 4.00% and 30 year US Treasury yields are 5.00%, the slope of the 2s30s curve is:
5.00% - 4.00% = 1.00%, or 100bps.
If 30s sell off by 10 basis points and their yields go from 5.00% to 5.10%, while 2’s remain unchanged, the slope becomes:
5.10% - 4.00% = 110bps.
We’d say the curve has steepened 10bps in this case. We’d call it a “bear steepener”, because the increase in that differential is driven by 30s selling off, not by 2’s rallying.
However, the steepening move we’ve seen in reality has been what we call a “bull steepener” — meaning, 2 year yields are rallying more than 30 year yields are.
What does that mean for the market?
1) It means that investors are still buying bonds. They’re just buying more SHORT-DATED bonds than long dated bonds.
2) Those who are outright short the long end of the curve are getting squeezed right now.
3) It puts investors at risk for something we call a “cash trap”.
Cash Trap
A cash trap happens when investors flock to short dated, safe haven instruments (like the T-Bills Warren Buffet so famously owns) at temporarily high rates. If the Fed cuts rates from current levels, that benefits your position…a little.
But because these are such short dated instruments, your price appreciation is minimal.
And then what do you do with all the principal you need to reinvest as those roll over and those formerly high yields are gone? Reinvest at extremely low yields? With minimal price appreciation potential, your returns start to look pretty bleak.
Whereas if you’d invested further out the curve, you would have benefitted from higher yields, higher duration, and most importantly higher price appreciation from a bullish move.
As always, when everyone in the markets is in agreement? Pay attention. Things can go very wrong.
Taylor Swift and Investing Collide
Is Taylor Swift’s purchase of her original masters an emotional move? Or a brilliant investment?
Last week Taylor Swift announced to the world that she had finally repurchased her masters for a reported $360 million, according to Billboard.
We don’t have many details. Billboard said she paid $360mm, while Matthew Belloni of The Town said her catalog was valued as high as $700mm. And simply saying bought her masters for $360 million doesn’t tell us whether that’s just what she paid (her equity check, excluding financing), or the total valuation of the deal.
Regardless, this is such a fun chance for us to talk about investing in music assets!
How do they work as an asset class? Why would a wealthy investor or private equity firm invest in them? And more specifically, was this a financially savvy investment for Taylor Swift?
Let’s get into it.
People invest in music assets for the same reason they invest in anything else: they want the value of the asset to go up.
From a portfolio theory standpoint, there’s also the benefit of diversification. Some assets are higher risk and higher return; others are lower risk and more stable. Then there’s the element of cash flows — what kind of income the asset generates while you hold it. With some investments, you’re just looking for asset appreciation; in others you’re relying on those regular cash flows (think about senior citizens living on a fixed income and relying on bond coupon payments).
Now if you’re a billionaire or a private equity firm, you might invest in a music catalog because:
a) You believe in the asset and think it’s undervalued / will appreciate.
b) The asset generates income.
c) When you add leverage, the returns can look even better.
Let’s look at Taylor’s catalog specifically. Her nemesis Scooter Braun bought it in 2019 for around $140mm. Technically, he bought her entire former label, Big Machine Records, for $300mm — $140mm of which was reportedly attributed to her masters.
There was a lot of drama at the time, because Braun and Swift have had beef going back decades. TL/DR: Braun was Kanye’s manager after the 2009 VMA mic-snatch, during the 2016 “I made that b*tch famous” fiasco. There’s a long, ugly history.
Many speculated that Taylor Swift should have just bought her masters then. But apparently Scott Borchetta (Big Machine’s founder) wouldn’t sell her masters separately. Instead, he would only include them in a package deal with the catalogs of other artists. Recall also that at the time, Taylor Swift was not yet a billionaire. Even if she’d been willing to buy the whole label, she simply may not have had the funds.
So let’s break down the investment since the drama began.
After Scooter Braun paid $140mm for Taylor’s catalog (ignoring the rest of the Big Machine Records purchase), he held them for 17 months. He then sold just Taylor’s catalog to Shamrock Capital (a PE firm with ties to Disney) for $300mm.
That’s a 70% annualized return based purely on price appreciation—before even factoring in cash flow or leverage.
When the 2019 deal went down, Taylor was furious and announced she would re-record all her albums (“Taylor’s Version”) to compete directly with the originals and devalue them. By 2024, she had re-recorded four of her albums, released three new albums, and launched her “Eras Tour,” all of which helped propel her into billionaire status. And with so much attention on her, the originals actually increased in value despite the competition. Starting in 2021, her re-records began to compete with the originals, bringing in up to 10x the streams of the originals. Yet the originals still doubled in income. They were generating $30mm annually by 2022–2024, up from $15mm when Scooter initially acquired them.
Shamrock held the catalog from 2020 to 2025 and reportedly sold it to Taylor Swift last week for $360 million. Ignoring leverage (which would only enhance returns) that’s a 12.5% annual return. And the actual return was likely even higher, considering Shamrock is a private equity firm that likely used debt financing and likely locked in low interest rates in 2020.
All of this happened while Taylor Swift herself was trying to destroy the value of the asset. As one fund manager told the Financial Times,
“To extract max value from music, you at least need the artist to not be actively angry.”
So the fact that Shamrock achieved that kind of return is honestly impressive.
Now that Taylor owns the masters herself, the prospects are even better.
We saw one hot take online calling it a bad financial decision, saying she would’ve been better off just putting the money in the S&P. But we have to disagree.
Not only does this consolidate all her masters under one umbrella, giving her full control over pricing, usage, and future licensing, but it also protects her rights in a future where AI-generated music is a real threat.
And strictly on financials, it holds up: the S&P 500 has returned about 12% annually over the past decade, with a 1.3% dividend yield. Shamrock’s investment in Taylor’s catalog returned 12.5% annually, all while there were a ton of headwinds.
So while this was clearly an emotional and symbolic move, it was also by all accounts a great investment.