It turns out Taylor Swift has better due diligence than half of Silicon Valley

Hiya! Dan DeFrancesco in NYC, but mentally I'm in the premium suites at Jimmy Buffett's Margaritaville in the Bahamas, which was reportedly a favorite of SBF's Alameda staff.

Today we've got stories on another fintech getting hit with layoffs, the biggest mistakes you're making with digital transformations, and how one of the most grueling races in the world is trying to soften the experience for the wealthy.

But first, nice to meet you, where you been?

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1. Taylor Swift has better due diligence than half of Silicon Valley

It's SBF.

Him.

He's the problem.

It's him.

Just when you thought the FTX debacle couldn't get any weirder, let's add Taylor Swift into the mix.

The now-bankrupt crypto exchange was reportedly in talks with the pop star about a potential sponsorship worth upward of $100 million before discussions eventually fell apart this spring.

Part of the deal, which was first reported by the Financial Times, was tied to sponsorship of Swift's upcoming tour, her first in four years, and included plans to offer tickets as NFTs.

I have so many questions:

• Could NFTs have actually prevented Ticketmaster's disastrous general sale of the Swift tickets?
• What was FTX, an exchange that specialized in the trading of complex derivatives, hoping to gain by marketing itself to Taylor Swift fans?
• What Taylor Swift album does Sam Bankman-Fried most identify with?

Perhaps the most pressing question, however, as pointed out by senior finance editor Michelle Abrego, is this: How does Taylor Swift have better due diligence practices than half of Silicon Valley? What does it say about venture investing in general that a pop star with no background in finance could vet a deal better than them?

It is worth noting that Swift might have a sharper eye in negotiations than your typical entertainer. Swift famously was in a very public dispute with talent manager Scooter Braun over his purchase of the masters of her back catalog. (Click here to read a fantastic profile on Braun.)

Part of me wonders whether this is the biggest indication of SBF wanting to get caught. Swift's fanbase is, to put it mildly, rabid. The so-called Swifties keep a keen eye on any potential slight against their star.

If a deal were to go through and malfeasance was uncovered on the part of FTX toward Swift, her fans might have personally extradited SBF from the Bahamas.

Also, was Swift trying to warn us about SBF all along?

Check out this lyric from "Anti-Hero," the first hit of her latest album, "Midnights."

Did you hear my covert narcissism I disguise as altruism
Like some kind of congressman? (Tale as old as time)

Swift has said the majority of the work done on the album was with Jack Antonoff while both their partners were filming a movie in Panama. Swift and Antonoff's partners — Joe Alwyn and Margaret Qualley, respectively — both starred in "The Stars at Noon," which shot in Panama last December.

And what else occurred in December, you may ask? A certain crypto executive, one who preached his belief in effective altruism, spoke before the House Committee on Financial Services.

By that point, Swift was already aware of SBF. According to the FT report, that fall was when FTX first approached Swift about a potential deal.

Was she calling out what she perceived to be a fake persona from SBF?

Click here to read more about the FTX-Taylor Swift deal that almost was.

In other news:

2. These are all the mistakes you're making during your digital transformations. Sumeet Chabria, a former top Bank of America tech executive who is launching his own consulting firm, detailed why the firm's tech overhauls end up going off the rails. Here are three key errors you should avoid.

3. A real-estate analyst who called the last housing crash is predicting a 20% drop in home prices if things don't turn around. Ivy Zelman, who famously called the housing market's peak before the 2008 crash, has a bearish view on the market as mortgage rates continue to rise and demand drops. Read more about her latest prediction.

4. Plaid is the latest fintech to get hit by layoffs. The startup, which plays a key role behind the scenes connecting financial apps to users' banks, is cutting roughly 20% of its staff. Read CEO Zach Perret's note to staff about the layoffs.

5. Bargain hunting for crypto companies is under way. Galaxy Digital has plans to acquire the self-custody arm of Celsius at a 60% price cut from what the bankrupt crypto lender paid for it a year ago, Bloomberg reports. More on the deal here.

6. Carvana's creditors are driving it crazy. The online used-card retailer saw its stock price plummet in the wake of some of its largest debt holders agreeing to work together on credit negotiations with Carvana. Read more here.

7. The job market isn't a complete disaster if you're a tech worker. Indeed mapped out the top 20 companies that have recently posted job listings for tech roles. Check out the entire list, which includes plenty of finance firms.

8. Meet 27 of the women who became executives at top VC firms in 2022. We mapped out women who were named investing or general partners for the first time in 2022 (including Yasmine Lacaillade, founder and managing partner at Sinefine, who is pictured above). Here's our list of the new women leading investing strategies at top firms.

9. Ironman is rolling out races specifically catered to wealthy executives. For when you want to push yourself hard, but not that hard. Read more about the races that cost nearly 25 times more than typical entry fees.

10. If you're feeling nostalgic, check out this Blockbuster pop-up bar. We've got plenty of photos from the bar, which is in Los Angeles. Grab a drink and take stroll down memory lane.

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Edited by Jeffrey Cane (tweet @jeffrey_cane) in New York and Hallam Bullock (tweet @hallam_bullock) in London.