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US singer Taylor Swift poses in the press room after winning six awards at the 50th Annual American Music Awards at the Microsoft Theater in Los Angeles, California, on November 20, 2022. –

Valerie Macon | AFP | Getty Images

Earlier this year, as the crypto meltdown was draining the industry of liquidity, FTX executives were begging company founder Sam Bankman-Fried to preserve cash and stop spending hundreds of millions of dollars on celebrity endorsements.

But the 30-year-old billionaire, who’d relied on branding and hype to rapidly take his crypto exchange from upstart to stalwart, was set on signing up one more big name.

Three people close to FTX and Bankman-Fried told CNBC that the former CEO lobbied aggressively for a partnership with 11-time Grammy Award winner Taylor Swift. The deal, which would have cost the now bankrupt company more than $100 million over three years, was close to coming to fruition before it fell apart in the spring, said the people, who asked not to be named because of confidentiality agreements.

The former executives, who had direct knowledge of the negotiations, said the partnership would’ve been a disaster for FTX because of the steep price tag. Bankman-Fried’s commitment to getting the Swift deal done despite the deteriorating business environment fit a pattern of ignoring his lieutenants and going it alone, a half-dozen former company insiders and business partners said.

The Financial Times reported earlier that FTX held talks with Swift about a potential sponsorship.

Bankman-Fried’s overconfidence was embedded into an organization that had few checks on its leader and no board of directors to hold him accountable. Meanwhile, Bankman-Fried portrayed a very different persona to the public, showing himself as a quirky young genius comfortable in shorts and a T-shirt or in a suit in front of Congress who repeatedly professed his belief in effective altruism, a philosophy that promotes the idea of earning a lot of money in order to donate it to the most important causes.

Valued at $32 billion earlier this year by private investors, FTX spiraled into bankruptcy last month after skepticism emerged about the health of the crypto exchange’s financials and customers began demanding withdrawals only to be told their money wasn’t available. Even facing potential criminal charges and the possibility of years in prison, Bankman-Fried has continued to shun advisers by speaking publicly, offering press interviews and tweeting his defense.

CEO Sam Bankman-Fried

Bloomberg | Bloomberg | Getty Images

“I have a duty to talk to people; I have a duty to explain what happened,” Bankman-Fried said in a video interview at the New York Times DealBook Summit last week, acknowledging that his lawyers are opposed to his current tactics. “I don’t see what good is accomplished by me just sitting locked in a room pretending the outside world doesn’t exist.”

Between his DealBook appearance, an interview with ABC’s “Good Morning America” and his commentary on various podcasts, Bankman-Fried has repeatedly claimed that FTX’s downfall was the result of sloppy management and excessive risk.

Bankman-Fried has denied committing fraud and said he was unaware of much of the intermingling of funds that took place between FTX and Alameda Research, Bankman-Fried’s hedge fund. At least $8 billion in FTX customer funds are now unaccounted for and were used to backstop billions in loan losses at Alameda.

Pursuing Swift NFTs

Bankman-Fried also ran fast and loose with company cash. Within just over two years of starting FTX in 2019, Bankman-Fried signed a $135 million, 19-year deal with the NBA’s Miami Heat for naming rights on the team’s arena. He also inked sponsorships with the Golden State Warriors, Major League Baseball and Formula One and got Larry David to promote the company in a Super Bowl ad. Gisele Bündchen, Tom Brady, Shaquille O’Neal, Stephen Curry, David Ortiz and Naomi Osaka were among the brand’s ambassadors.

Part of the Swift deal would have included the production by the singer of a collection of non-fungible tokens (NFTs), or digital items that can rise and fall in value. Beyond that, there was a lack of clarity over what Swift would be doing for the company, sources said. After the Swift agreement fell apart, talks emerged internally over a deal with Katy Perry as recently as August, one person said.

Representatives for Swift declined to comment, and Perry did not respond to CNBC’s request for comment.

Sam Bankman-Fried faces possible bankruptcy after failed FTX deal

FTX insiders said that while some people in and around the company questioned Bankman-Fried’s decisions, he surrounded himself most immediately with a crew of yes men. Two sources used the word “insular” in describing his leadership style. Bankman-Fried mainly sought advice from a tight-knight group in the Bahamas, where he lived and where the company was headquartered, sources said.

One former FTX executive said Bankman-Fried had a tendency to chew out employees who disagreed with him in a way that deterred others from speaking up. When Bankman-Fried was angry, sources said his knee-jerk reaction was to immediately blame underlings. Some former insiders said Bankman-Fried put on an act for the public, portraying himself as an easygoing CEO.

Bankman-Fried said in a message to CNBC that he disagrees with the characterizations provided by those former employees. He declined to comment on details of the Swift negotiations.

“Partnerships were an area that was more contentious and on the margin I originally was in favor and ultimately started pushing back on new ones,” Bankman-Fried said in the message.

John Ray, the new CEO tapped to restructure FTX said in filings that in his 40 years of legal experience, which includes Enron’s liquidation, he had never seen “such a complete failure of corporate controls and such a complete absence of trustworthy financial information as occurred here.”

One of Bankman-Fried’s closest confidants was Caroline Ellison, the ex-CEO of Alameda Research, who he once dated. The pair would often go on lunch walks around FTX’s fenced-in Nassau headquarters, one FTX executive said.

Outside of his Bahamas cohort, Bankman-Fried went to great lengths to avoid speaking to others and he stayed away from face-to-face confrontations, preferring the encrypted messaging app Signal or Slack, one top deputy said. He frequently ignored messages from C-level executives if he disagreed with them.

Another former insider said employees were afraid of Bankman-Fried, adding that “there were very few people who were willing to challenge Sam.”

WATCH: Bankman-Fried said he didn’t ever try to commit fraud on anyone

I didn't ever try to commit fraud on anyone: Sam Bankman-Fried

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Etsy touts ‘shopping domestically’ as Trump tariffs threaten price increases for imports

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Etsy touts 'shopping domestically' as Trump tariffs threaten price increases for imports

An employee walks past a quilt displaying Etsy Inc. signage at the company’s headquarters in the Brooklyn.

Victor J. Blue/Bloomberg via Getty Images

Etsy is trying to make it easier for shoppers to purchase products from local merchants and avoid the extra cost of imports as President Donald Trump’s sweeping tariffs raise concerns about soaring prices.

In a post to Etsy’s website on Thursday, CEO Josh Silverman said the company is “surfacing new ways for buyers to discover businesses in their countries” via shopping pages and by featuring local sellers on its website and app.

“While we continue to nurture and enable cross-border trade on Etsy, we understand that people are increasingly interested in shopping domestically,” Silverman said.

Etsy operates an online marketplace that connects buyers and sellers with mostly artisanal and handcrafted goods. The site, which had 5.6 million active sellers as of the end of December, competes with e-commerce juggernaut Amazon, as well as newer entrants that have ties to China like Temu, Shein and TikTok Shop.

By highlighting local sellers, Etsy could relieve some shoppers from having to pay higher prices induced by President Trump’s widespread tariffs on trade partners. Trump has imposed tariffs on most foreign countries, with China facing a rate of 145%, and other nations facing 10% rates after he instituted a 90-day pause to allow for negotiations. Trump also signed an executive order that will end the de minimis provision, a loophole for low-value shipments often used by online businesses, on May 2.

Temu and Shein have already announced they plan to raise prices late next week in response to the tariffs. Sellers on Amazon’s third-party marketplace, many of whom source their products from China, have said they’re considering raising prices.

Silverman said Etsy has provided guidance for its sellers to help them “run their businesses with as little disruption as possible” in the wake of tariffs and changes to the de minimis exemption.

Before Trump’s “Liberation Day” tariffs took effect, Silverman said on the company’s fourth-quarter earnings call in late February that he expects Etsy to benefit from the tariffs and de minimis restrictions because it “has much less dependence on products coming in from China.”

“We’re doing whatever work we can do to anticipate and prepare for come what may,” Silverman said at the time. “In general, though, I think Etsy will be more resilient than many of our competitors in these situations.”

Still, American shoppers may face higher prices on Etsy as U.S. businesses that source their products or components from China pass some of those costs on to consumers.

Etsy shares are down 17% this year, slightly more than the Nasdaq.

WATCH: Amazon CEO Andy Jassy says sellers will pass cost of tariffs on to consumers

Amazon CEO Andy Jassy: Sellers will pass increased tariff costs on to consumers

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Google hit with second antitrust blow, adding to concerns about future of ads business

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Google hit with second antitrust blow, adding to concerns about future of ads business

Google CEO Sundar Pichai testifies before the House Judiciary Committee at the Rayburn House Office Building on December 11, 2018 in Washington, DC.

Alex Wong | Getty Images

Google’s antitrust woes are continuing to mount, just as the company tries to brace for a future dominated by artificial intelligence.

On Thursday, a federal judge ruled that Google held illegal monopolies in online advertising markets due to its position between ad buyers and sellers.

The ruling, which followed a September trial in Alexandria, Virginia, represents a second major antitrust blow for Google in under a year. In August, a judge determined the company has held a monopoly in its core market of internet search, the most-significant antitrust ruling in the tech industry since the case against Microsoft more than 20 years ago. 

Google is in a particularly precarious spot as it tries to simultaneously defend its primary business in court while fending off an onslaught of new competition due to the emergence of generative AI, most notably OpenAI’s ChatGPT, which offers users alternative ways to search for information. Revenue growth has cooled in recent years, and Google also now faces the added potential of a slowdown in ad spending due to economic concerns from President Donald Trump’s sweeping new tariffs.

Parent company Alphabet reports first-quarter results next week. Alphabet’s stock price dipped more than 1% on Thursday and is now down 20% this year.

Why Google's antitrust woes endangers its AI momentum

In Thursday’s ruling, U.S. District Judge Leonie Brinkema said Google’s anticompetitive practices “substantially harmed” publishers and users on the web. The trial featured 39 live witnesses, depositions from an additional 20 witnesses and hundreds of exhibits.

Judge Brinkema ruled that Google unlawfully controls two of the three parts of the advertising technology market: the publisher ad server market and ad exchange market. Brinkema dismissed the third part of the case, determining that tools used for general display advertising can’t clearly be defined as Google’s own market. In particular, the judge cited the purchases of DoubleClick and Admeld and said the government failed to show those “acquisitions were anticompetitive.”

“We won half of this case and we will appeal the other half,” Lee-Anne Mulholland, Google’s vice president or regulatory affairs, said in an emailed statement. “We disagree with the Court’s decision regarding our publisher tools. Publishers have many options and they choose Google because our ad tech tools are simple, affordable and effective.”

Attorney General Pam Bondi said in a press release from the DOJ that the ruling represents a “landmark victory in the ongoing fight to stop Google from monopolizing the digital public square.”

Potential ad disruption

If regulators force the company to divest parts of the ad-tech business, as the Justice Department has requested, it could open up opportunities for smaller players and other competitors to fill the void and snap up valuable market share. Amazon has been growing its ad business in recent years.

Meanwhile, Google is still defending itself against claims that its search has acted as a monopoly by creating strong barriers to entry and a feedback loop that sustained its dominance. Google said in August, immediately after the search case ruling, that it would appeal, meaning the matter can play out in court for years even after the remedies are determined.

The remedies trial, which will lay out the consequences, begins next week. The Justice Department is aiming for a break up of Google’s Chrome browser and eliminating exclusive agreements, like its deal with Apple for search on iPhones. The judge is expected to make the ruling by August.

Google CEO Sundar Pichai (L) and Apple CEO Tim Cook (R) listen as U.S. President Joe Biden speaks during a roundtable with American and Indian business leaders in the East Room of the White House on June 23, 2023 in Washington, DC.

Anna Moneymaker | Getty Images

After the ad market ruling on Thursday, Gartner’s Andrew Frank said Google’s “conflicts of interest” are apparent by how the market runs.

“The structure has been decades in the making,” Frank said, adding that “untangling that would be a significant challenge, particularly since lawyers don’t tend to be system architects.”

However, the uncertainty that comes with a potentially years-long appeals process means many publishers and advertisers will be waiting to see how things shake out before making any big decisions given how much they rely on Google’s technology.

“Google will have incentives to encourage more competition possibly by loosening certain restrictions on certain media it controls, YouTube being one of them,” Frank said. “Those kind of incentives may create opportunities for other publishers or ad tech players.”

A date for the remedies trial hasn’t been set.

Damian Rollison, senior director of market insights for marketing platform Soci, said the revenue hit from the ad market case could be more dramatic than the impact from the search case.

“The company stands to lose a lot more in material terms if its ad business, long its main source of revenue, is broken up,” Rollison said in an email. “Whereas divisions like Chrome are more strategically important.”

WATCH: U.S. judge finds Google holds illegal online ad-tech monopolies

U.S. judge finds Google holds illegal online ad tech monopolies

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Discord sued by New Jersey over child safety features

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Discord sued by New Jersey over child safety features

Jason Citron, CEO of Discord in Washington, DC, on January 31, 2024.

Andrew Caballero-Reynolds | AFP | Getty Images

The New Jersey attorney general sued Discord on Thursday, alleging that the company misled consumers about child safety features on the gaming-centric social messaging app.

The lawsuit, filed in the New Jersey Superior Court by Attorney General Matthew Platkin and the state’s division of consumer affairs, alleges that Discord violated the state’s consumer fraud laws.

Discord did so, the complaint said, by allegedly “misleading children and parents from New Jersey” about safety features, “obscuring” the risks children face on the platform and failing to enforce its minimum age requirement.

“Discord’s strategy of employing difficult to navigate and ambiguous safety settings to lull parents and children into a false sense of safety, when Discord knew well that children on the Application were being targeted and exploited, are unconscionable and/or abusive commercial acts or practices,” lawyers wrote in the legal filing.

They alleged that Discord’s acts and practices were “offensive to public policy.”

A Discord spokesperson said in a statement that the company disputes the allegations and that it is “proud of our continuous efforts and investments in features and tools that help make Discord safer.”

“Given our engagement with the Attorney General’s office, we are surprised by the announcement that New Jersey has filed an action against Discord today,” the spokesperson said.

One of the lawsuit’s allegations centers around Discord’s age-verification process, which the plaintiffs believe is flawed, writing that children under thirteen can easily lie about their age to bypass the app’s minimum age requirement.

The lawsuit also alleges that Discord misled parents to believe that its so-called Safe Direct Messaging feature “was designed to automatically scan and delete all private messages containing explicit media content.” The lawyers claim that Discord misrepresented the efficacy of that safety tool.

“By default, direct messages between ‘friends’ were not scanned at all,” the complaint stated. “But even when Safe Direct Messaging filters were enabled, children were still exposed to child sexual abuse material, videos depicting violence or terror, and other harmful content.”

The New Jersey attorney general is seeking unspecified civil penalties against Discord, according to the complaint.

The filing marks the latest lawsuit brought by various state attorneys general around the country against social media companies.

In 2023, a bipartisan coalition of over 40 state attorneys general sued Meta over allegations that the company knowingly implemented addictive features across apps like Facebook and Instagram that harm the mental well being of children and young adults.

The New Mexico attorney general sued Snap in Sep. 2024 over allegations that Snapchat’s design features have made it easy for predators to easily target children through sextortion schemes.

The following month, a bipartisan group of over a dozen state attorneys general filed lawsuits against TikTok over allegations that the app misleads consumers that its safe for children. In one particular lawsuit filed by the District of Columbia’s attorney general, lawyers allege that the ByteDance-owned app maintains a virtual currency that “substantially harms children” and a  livestreaming feature that “exploits them financially.”

In January 2024, executives from Meta, TikTok, Snap, Discord and X were grilled by lawmakers during a senate hearing over allegations that the companies failed to protect children on their respective social media platforms.

WATCH: The FTC has an uphill battle in its antitrust case against Meta.

The FTC has an uphill battle in its antitrust case against Meta: Former Facebook general counsel

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