PayPal's CEO search amid an uncertain economy will be no easy task

Welcome back! Dan DeFrancesco in NYC.

On tap, we've got stories on another creative way the rich are avoiding paying taxes, how much top hedge-fund managers got paid in 2022, and how Tiger Woods spends his, now, billions.

But first, there are some big shoes to fill.

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1. Who's next?

Wanted: CEO of a payments company with an $84 billion market cap.

In case you missed it, PayPal CEO and President Dan Schulman announced his plan to retire at the end of 2023 earlier this month.

Schulman, who has been at the helm of PayPal for more than eight years, said in a release, "I'm at a point in my life where I want to devote more time to my passions outside the workplace."

Good for him! Schulman accomplished plenty at PayPal, from navigating its spinoff from eBay to championing his employees' financial wellness. And after a difficult 2022 that saw his company's stock crater, along with the addition of a particularly aggressive shareholder, why bother sticking around?

Which takes us to the more pressing question: Who's going to take over when he leaves?

Insider's Paige Hagy and Bianca Chan spoke to industry insiders to get their picks on who would make for a good candidate to run PayPal.

The list, which features six executives, noticeably includes only one person currently at PayPal. Many of the people who were suggested, however, spent a time at PayPal at the most senior levels.

It's an interesting dynamic. On the one hand, you could view that as a testament to Schulman's leadership. He's done such a good job of grooming his deputies that they are constantly getting poached. On the other, it could be a sign that strong executives didn't stick around because they felt there was always a ceiling under Schulman.

Either way, it has put PayPal in a bit of a precarious situation. Coming off an extremely difficult 2022, and with competition seemingly coming at them from every which way, PayPal has to find a new CEO. And if all that wasn't hard enough, a notorious activist investor also holds a significant stake.

I hesitate to compare this to the seemingly never-ending CEO search at Carlyle, but it's easy to see how a difficult quarter or two could complicate this entire search.

Click here to read more about about the people experts think would be strong candidates to run PayPal next.

In other news:

2. The rich stay rich thanks to another loophole that helps them save on taxes. Charitable remainder trusts are a way the ultra-rich can benefit from tax savings but still guarantee themselves income for life. Here's how they're doing it.

3. A hedge-fund exec you've never heard of got PAID in 2022. Elliott Management's Paul Singer and Two Sigma's David Siegel both played second fiddle to Haidar Capital's Said Haidar in 2022 when it came to comp. Here's how much Haidar, along with other top hedge-fund managers, earned last year.

4. How's your PE fund doing? One of the largest US endowments has put $14 billion in private-equity funds recents. We got a look at their returns, including how investments with Thoma Bravo and Clearlake have done. Check them out here.

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6. Cutting down on cloud costs. Lots of talk about shifting to the cloud is about saving money. But Snap is pushing to cut expenses by pulling back on cloud costs. Here's what it could mean for the larger industry. Meanwhile, top Wall Street tech execs detail how they keep costs down while using the public cloud.

7. Go out on your own, they said. It'll be fun, they said. Plenty of investors set up their own funds when times were good. But as the market has turned, some are reconsidering. More on why it's time to adapt or die.

8. Millennials are so broke we can't even afford to have a mid-life crisis. The only Corvette I'm going to be able to buy when I'm 40 is a Matchbox. Here's a Bloomberg report on why millennials can't pay for a crisis.

9. Tiger Woods just joined the three-comma club. The golfer has now made more than $1.4 billion since turning pro in 1996. So what do you do when your job is everyone else's hobby? Check out how he spends his money.

10. We've got air fryer recipes. This chef has 13 eay-to-make recipes for you. Get cooking here.

Curated by Dan DeFrancesco in New York. Feedback or tips? Email ddefrancesco@insider.com, tweet @dandefrancesco, or connect on LinkedIn. Edited by Jeffrey Cane (tweet @jeffrey_cane) in New York and Hallam Bullock (tweet @hallam_bullock) in London.