Love and Deceit: Work-From-Home Era Spawns ‘Pillow Talk’ Insider Trading
Lawyers say recent securities-fraud cases have a new twist: they are the product of the daily humdrum of two adults doing their jobs remotely
4 min
Steven Teixeira’s use of his girlfriend’s laptop began innocently enough when she asked him to keep an eye on her work email while she went to fitness classes and ran errands.
As they weathered the pandemic from their apartment in Queens, N.Y., he gave in to temptation. His sweetheart worked as an executive assistant at Morgan Stanley, and her calendar invites included meetings about planned mergers and acquisitions that involved the investment bank.
Teixeira, a compliance executive at a payment-processing company whom she intended to marry, used the information to trade in advance of the deals. It netted him thousands in profits, promises of Rolex watches from friends he tipped off, and the scrutiny of federal officials probing insider trading. He pleaded guilty to a dozen fraud charges in June.
There is a rich history in securities fraud of “pillow talk” cases, in which insider traders glean confidential information from romantic partners. The Covid era offered a twist: Secrets weren’t spilled in the bedroom or over a bottle of wine, but during the humdrum routine of two adults working from home.
“During Covid, there was an uptick in brazen conduct,” said Edward Imperatore, a defence lawyer at law firm Morrison & Foerster. “In a work-from-home environment, people acted with more impunity.”
Another recent case snared a boyfriend who was training to work for the Federal Bureau of Investigation. Seth Markin pleaded guilty in December to trading on information he purloined from his lawyer girlfriend, an associate in the Washington office of law firm Covington & Burling.
In 2021, she was working on a pharmaceutical acquisition from her one-bedroom apartment, where Markin spent days at a time. According to prosecutors, she trusted him because he told her he had a security clearance, was going to be an FBI agent, and wanted to marry her.
Prosecutors said Markin passed on tips that led to at least 20 people trading based on confidential information. “I knew that my behaviour was wrong,” Markin told the judge during his plea hearing. He is scheduled to be sentenced in March.
Representatives for the FBI and Covington declined to comment.
In Teixeira’s case, he was aided by a mouse-jiggler he bought that ensured his girlfriend’s laptop wouldn’t lock when she wasn’t using it, according to court documents. He has been cooperating with prosecutors and is scheduled to testify this year at the trial of his former friend, Jordan Meadow, who at the time was a stockbroker with Spartan Capital Securities. Meadow made more than $700,000 trading on Teixeira’s information and used the tips to advise clients who made millions, prosecutors allege.
“Yo you see UFS,” Meadow texted Teixeira, referencing the stock symbol of a company involved in a $3 billion deal, according to the indictment. He then asked for more nonpublic information, texting, “Feed me.”
Meadow has pleaded not guilty to the eight charges he is facing. Lawyers for Meadow and Spartan declined to comment, as did a spokeswoman for Morgan Stanley, and a lawyer for Teixeira didn’t respond to requests for comment.
In 2022, the Securities and Exchange Commission settled with a New Jersey man who it accused of illegally trading on inside information he heard when his domestic partner, who worked in marketing for an IT company, participated in calls from home, including an 11:30 p.m. videoconference in a home-office adjacent to their bedroom. Although he typically discussed his trades with her, in this case he hid them, executing the transactions from his work office, the SEC said. The man, who didn’t admit wrongdoing, paid $180,000.
One thing hasn’t changed since the earliest days of pillow talk: It is usually the men who can’t resist the urge to take advantage of their confidential information.
“Insider trading is an equal opportunity crime,” said Dixie Johnson, a partner at law firm King & Spalding who advises companies on how to avoid such situations. “But the cases we see usually have involved men doing the trading.”
Not that female romantic partners have always been innocent bystanders. In 2002, adult-movie actress Kathryn Gannon, known on screen as Marylin Star, pleaded guilty to trading on tips from an investment bank CEO with whom she was having an affair. She was sentenced to three months in prison.
A decade later, former beauty queen turned hedge-fund consultant Danielle Chiesi pleaded guilty to securities fraud for her role in a sprawling insider-trading ring. In a sentencing submission, she blamed a toxic relationship with her boss—and lover of 20 years—who urged her to get inside information.
One challenge for prosecutors is determining whether the partner who is privy to the information was in on the crime, said former federal prosecutor Brendan Quigley.
“Do they say, ‘Oh, my God, I would never give information to my spouse or significant other?’ It depends not only on what actually happened, but also on the nature of their relationship,” said Quigley, who prosecuted insider-trading cases in Manhattan.
For defense lawyers, pillow-talk cases can be difficult to handle at trial, particularly if one partner testifies against another. “To a juror, this is the bad boyfriend,” said Imperatore, the defense attorney. “He’s acting badly in a relationship in a way that goes beyond the four corners of insider trading.”
Not surprisingly, many such relationships don’t survive. Teixeira and his girlfriend split up, as did Markin and his.
Former Playboy CEO Christie Hefner and her husband, William Marovitz, divorced about a year after the SEC accused him of illegally trading Playboy stock based on information gleaned from his wife—despite her explicit instructions not to. Marovitz didn’t admit wrongdoing in a 2011 settlement.
One woman whose husband recently settled insider-trading charges involving confidential information related to her employer said coping with the allegations strengthened their bond.
“It felt like an injustice,” said the woman, who wasn’t identified in court papers. “It brought us closer together.”
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Selloff in bitcoin and other digital tokens hits crypto-treasury companies.
3 min
The hottest crypto trade has turned cold. Some investors are saying “told you so,” while others are doubling down.
It was the move to make for much of the year: Sell shares or borrow money, then plough the cash into bitcoin, ether and other cryptocurrencies. Investors bid up shares of these “crypto-treasury” companies, seeing them as a way to turbocharge wagers on the volatile crypto market.
Michael Saylor pioneered the move in 2020 when he transformed a tiny software company, then called MicroStrategy , into a bitcoin whale now known as Strategy. But with bitcoin and ether prices now tumbling, so are shares in Strategy and its copycats. Strategy was worth around $128 billion at its peak in July; it is now worth about $70 billion.
The selloff is hitting big-name investors, including Peter Thiel, the famed venture capitalist who has backed multiple crypto-treasury companies, as well as individuals who followed evangelists into these stocks.
Saylor, for his part, has remained characteristically bullish, taking to social media to declare that bitcoin is on sale. Sceptics have been anticipating the pullback, given that crypto treasuries often trade at a premium to the underlying value of the tokens they hold.
“The whole concept makes no sense to me. You are just paying $2 for a one-dollar bill,” said Brent Donnelly, president of Spectra Markets. “Eventually those premiums will compress.”
When they first appeared, crypto-treasury companies also gave institutional investors who previously couldn’t easily access crypto a way to invest. Crypto exchange-traded funds that became available over the past two years now offer the same solution.
BitMine Immersion Technologies , a big ether-treasury company backed by Thiel and run by veteran Wall Street strategist Tom Lee , is down more than 30% over the past month.
ETHZilla , which transformed itself from a biotech company to an ether treasury and counts Thiel as an investor, is down 23% in a month.
Crypto prices rallied for much of the year, driven by the crypto-friendly Trump administration. The frenzy around crypto treasuries further boosted token prices. But the bullish run abruptly ended on Oct. 10, when President Trump’s surprise tariff announcement against China triggered a selloff.
A record-long government shutdown and uncertainty surrounding Federal Reserve monetary policy also have weighed on prices.
Bitcoin prices have fallen 15% in the past month. Strategy is off 26% over that same period, while Matthew Tuttle’s related ETF—MSTU—which aims for a return that is twice that of Strategy, has fallen 50%.
“Digital asset treasury companies are basically leveraged crypto assets, so when crypto falls, they will fall more,” Tuttle said. “Bitcoin has shown that it’s not going anywhere and that you get rewarded for buying the dips.”
At least one big-name investor is adjusting his portfolio after the tumble of these shares. Jim Chanos , who closed his hedge funds in 2023 but still trades his own money and advises clients, had been shorting Strategy and buying bitcoin, arguing that it made little sense for investors to pay up for Saylor’s company when they can buy bitcoin on their own. On Friday, he told clients it was time to unwind that trade.
Crypto-treasury stocks remain overpriced, he said in an interview on Sunday, partly because their shares retain a higher value than the crypto these companies hold, but the levels are no longer exorbitant. “The thesis has largely played out,” he wrote to clients.
Many of the companies that raised cash to buy cryptocurrencies are unlikely to face short-term crises as long as their crypto holdings retain value. Some have raised so much money that they are still sitting on a lot of cash they can use to buy crypto at lower prices or even acquire rivals.
But companies facing losses will find it challenging to sell new shares to buy more cryptocurrencies, analysts say, potentially putting pressure on crypto prices while raising questions about the business models of these companies.
“A lot of them are stuck,” said Matt Cole, the chief executive officer of Strive, a bitcoin-treasury company. Strive raised money earlier this year to buy bitcoin at an average price more than 10% above its current level.
Strive’s shares have tumbled 28% in the past month. He said Strive is well-positioned to “ride out the volatility” because it recently raised money with preferred shares instead of debt.
Cole Grinde, a 29-year-old investor in Seattle, purchased about $100,000 worth of BitMine at about $45 a share when it started stockpiling ether earlier this year. He has lost about $10,000 on the investment so far.
Nonetheless, Grinde, a beverage-industry salesman, says he’s increasing his stake. He sells BitMine options to help offset losses. He attributes his conviction in the company to the growing popularity of the Ethereum blockchain—the network that issues the ether token—and Lee’s influence.
“I think his network and his pizzazz have helped the stock skyrocket since he took over,” he said of Lee, who spent 15 years at JPMorgan Chase, is a managing partner at Fundstrat Global Advisors and a frequent business-television commentator.
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