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The Weekend

Heroes, Villains and a Startup Spy

Art by Clark Miller
By
Abram Brown
[email protected]Profile and archive

Welcome, Weekenders! In this newsletter:

• The Big Read: Inside the Deel-Rippling spy drama

• The Arena: Exclusive new database! Meet all the techies who own sports teams

• The Top 5: The people who help Silicon Valley hone its taste in art 

• Politics and Policy: Why Section 230 may finally get changed 

• Biotech: The woolly mammoth gets ready for its close-up

• Plus, our Recommendations: The emperor richer than Bezos; Robert De Niro, cyber crusader; and breaking bad in Montana


When I first met Parker Conrad and Alex Bouaziz a couple years ago, they were both Silicon Valley heroes: Their fintechs had just soldiered through the Silicon Valley Bank crisis, helping keep a wide swath of the startup economy functioning. 

“We literally went into war mode,” Bouaziz told me in an interview shortly after the tumult concluded. Conrad put it in even more dramatic terms. “I thought the world was ending,” he said. 

But that was then, and the perception of the two now is distinctly different. Silicon Valley’s instinctual tribalism has kicked in, and as a remarkable feud between Deel and Rippling has deepened into allegations of corporate espionage by Deel, Bouaziz has quickly become persona non grata. Rippling’s investors have rushed to publicly support Conrad, while Deel’s have been mute.

Is it over for Bouaziz? It’s tempting to assume so after the past week, but perhaps the only narrative Silicon Valley loves more than a villainous turn is an eventual redemption tale, something Conrad himself knows very well. 

“From a professional perspective,” Conrad acknowledged to me in a 2023 Big Read, “I’ve had a lot of really big ups and downs. Some really big highs—some really low lows.”

Before Rippling, Conrad was ousted from his previous unicorn, Zenefits, over a compliance scandal. But Conrad has always attributed the defenestration to pressure from Andreessen Horowitz, which was a major investor in Zenefits—and is now a major investor in Deel. 

Like the other Deel investors, the Andreessen Horowitz crowd hasn’t said anything much, which I find unusual—and potentially quite telling. Generally, Andreessen Horowitz is a firm that enjoys a fight, and its reluctance to come out swinging against Conrad and Rippling seems a likely indication of how unhappy Deel investors are with Bouaziz. (The venture firm declined to comment for this column.) 

Another group involved in this mess might be in the most uncomfortable position in tech at the moment: the investors with stakes in both Rippling and Deel—firms caught between the warring sides. I counted eight of them, including Coatue Management, Y Combinator and Ron Conway’s SV Angel, by reviewing PitchBook data. (None of these investors would comment either.) 

Generally, venture capitalists don’t invest in rival startups, since once you’ve given money to one startup, it’s generally not a great idea to then go fund its competitor. But sometimes it happens, because startups change directions over time and end up in a rivalry that wasn’t apparent at first, which is arguably what happened with Deel as it evolved over the years. And for a firm like Coatue, the options are few: It needs big deals with big startups to possibly see a meaningful return on its capital. That limits its potential pool of investments. 

Regardless, maybe these firms stuck in the middle can play a necessary role: as peacemakers between Conrad and Bouaziz. Certainly no one would have more incentive to find a truce.

Disney’s Next Megadeal

Stop and picture Disneyland or Disney World. Who’s there: Pluto? Minnie? Cruella de Vil? Snow White? In other words, all characters owned by Disney.

Yet Disney’s new partnership with Epic Games, the maker of Fortnite, is what got the headline treatment in a new Bloomberg profile of Josh D’Amaro, the company’s theme parks boss and a possible successor to CEO Bob Iger whenever he decides to retire again.

The details of exactly how Disney will install Fortnite at its theme parks remain unclear, but the tightening relationship between the two companies is striking: Despite Disney’s historic reluctance to use characters it doesn’t directly control, it’s poised to do exactly that with Fortnite’s array of heroes and villains. 

Right now, Disney just has an investment in Epic, a stake it took last year that valued the videogame business at $22.5 billion (a figure scooped by our Cory Weinberg). D’Amaro led the deal and has joined Epic’s board as an observer.

Melding Epic and Disney in a lucrative, drama-free way would certainly further position D’Amaro as Iger’s heir. At the very least, I could see D’Amaro pushing for further Disney investment in Epic, and it’s not extraordinary to think Disney might purchase the entire videogame business. Such a blockbuster move could be what puts D’Amaro fully on the throne—or something he saves for a big early moment as CEO. 

The deal would pose some challenges. Epic has been a longtime adversary to Apple, a longtime Disney ally. And affording the deal would require some real Disney magic, since the media conglomerate already has substantial debt from buying much of 21st Century Fox a couple years ago.—Abram Brown


The Big Read 

How the Nasty Deel-Rippling Feud Became a Spy Drama

A tale of corporate espionage is a rarity. What’s even more extraordinary is for a reporter to find himself caught in the middle of the chicanery. But that’s exactly what happened to our Michael Roddan. 

For Weekend’s latest Big Read, Michael delves deep into the latest chapter of the bitter rivalry between Deel and Rippling and explains exactly how he got swept up in it. It has the elements of a real potboiler: a honeypot trap, a private detective and a phone hastily flushed down a toilet.

The Arena

All the Tech Moguls Who Own Sports Teams

The basketball world received shocking news this week: The Boston Celtics have a new owner—a little-known techie, Bill Chisholm, co-founder of Symphony Technology Group, a private equity shop specializing in software. 

You know who wasn’t all that shocked? Our Sara Germano, who has spent several weeks assembling The Information’s latest exclusive database: a definitive list of the tech founders, investors and executives who’ve become sports moguls. Sara limited the list to people who have controlling stakes, but she otherwise took an expansive view, examining both traditional and emerging U.S. sports leagues. What she has captured is an eye-catching snapshot of how sports and tech have become increasingly intertwined.

Politics and Policy

Why Section 230 Reform May Finally Happen

Over the last few years, lawmakers have increasingly talked about altering Section 230, the bedrock legislation that has allowed the tech economy to flourish by giving websites broad immunity over what their users post. That talk could swiftly turn into action amid new, true bipartisan support for reforming the legislation, our Paris Martineau reports.

The Top Five

The Art Advisers Who Help Tech Moguls Buy Masterpieces

Need something to hang in the hall? Or maybe the boardroom? I’d suggest getting some expert advice on exactly what to put there: It’s not just about spending a ton of money on art—it’s about spending a ton of money on the right art. And as luck would have it, frequent Weekend contributor Todd Plummer has a list of Silicon Valley’s favorite art advisers, who function as both brokers and tastemakers.

Biotech

Why the Woolly Mammoth Startup Felt It Needed to Hire a Hollywood Director 

“It’s been one of the most rewarding experiences of my life: to meet and learn from all these scientists,” filmmaker Michael Dougherty told me recently as he described his recent job switch to biotech executive. “They’re objectively intelligent. Whereas a lot of people in Hollywood—their intelligence is questionable.” 

Dougherty (“Godzilla: King of the Monsters,” “Krampus,” “Trick ‘r Treat”) is the new executive vice president of entertainment at Colossal, a startup that intends to resurrect an extinct animal: the woolly mammoth. It hired him to publicize and document its mission, which, obviously, sounds a lot like a Hollywood screenplay.

Truthfully, Abram Brown, editor of The Information’s Weekend section, has always been more of a mastodon guy. Reach him at [email protected].


Listening: “Empire of Gold” (Sony Music Entertainment) 

For anyone who has outgrown a fascination with ancient Rome and wants to learn about another opulent, bloodlust-ruled realm, “Empire of Gold” puts a spotlight on just such a place: Mali, a West African kingdom more than twice the size of California that lasted many centuries and grew wealthy from Arabian trade. The podcast focuses mostly on Mansa Musa, the empire’s ninth leader, who journeyed across the world at the head of a caravan of more than 1,000 people and 100 camels laden with 300 pounds of gold. The dude was riiich—like, richer-than-Bezos rich, notes Luke Pepera, the pod’s amiable host, a Ghana-born, Oxford University–educated expert on African history.—A.B.

Reading: “Beartooth” by Callum Wink

A universe away from the Yellowstone Club or Whitefish Lake is the Montana in “Beartooth,” a place deep in the impoverished backcountry where the smell of cut cottonwood and bear shit hangs in the air. There a pair of young brothers, Thad and Hazen, eke out an existence as loggers, handymen and novice criminals. As the bills mount after their father’s death, they feel the pressure to increasingly break bad and eventually set out into the wilderness on a desperate caper, talked into the scheme by a more experienced felon known just as The Scot, who is eager to reap the rewards of the dangerous plan. 

Given the novel’s setting, there’s a constant sense of the dynamics around predators and prey: the old elk chased down by wolves, the hapless hikers who might wander into a grizzly’s path, the desperate lower-level crooks put in harm’s way by a villain higher up the food chain.—A.B.

Watching: “Zero Day” (Netflix) 

There’s a lot happening in Washington these days both in real life and on the screen. In addition to Hulu’s “Paradise” and Netflix’s forthcoming Shondaland murder mystery “The Residence,” there’s “Zero Day,” in which Robert De Niro really has his hands full. De Niro plays a former president, George Mullen, pulled out of retirement to investigate a nationwide cyberattack that shuts down hospitals and sends airplanes hurtling out of the sky. Was it the Russians? The Chinese? Homegrown terrorists? In a world this fractured, there’s no shortage of suspects.

Mullen gets chosen to lead the investigation because he’s the last living politician who managed to draw bipartisan support, and the only one who can be trusted to manage the suspension of civil liberties required in such a national emergency. Adding to the collection of eerily familiar themes, he also appears to be battling signs of dementia as he attempts to crack the case.

Sure, the dialogue can get a little bit cheesy. (“Cocktails and canapes for the 1% while the world burns down!”) But hey, if the script was good enough for not only De Niro but also Angela Bassett, Jesse Plemons and Connie Britton, it’s good enough for me, too.—Julia Black


Final Thought

Maybe next time Deel will just go with the crazy doppelgänger masks.

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