The contentious divorce trial of hedge-fund titan John Overdeck and his estranged wife Laura has offered the public a rare window into the mind-boggling wealth being generated on Wall Street.
To lawyers and other advisers, the case reads like a textbook example of how that wealth can come back to bite, especially when founders and other business owners don’t take steps to protect their companies.
“How many times is he kicking himself now?” said New York divorce attorney Lisa Zeiderman of John Overdeck. “Everyone knows what everyone’s pressure points are in a divorce. It’s a very dangerous place to be.”
It is a situation that many could one day find themselves in. Business formation so far in 2026 is happening at the fastest pace in years, according to Census Bureau data, thanks in part to artificial intelligence-driven innovation. And entrepreneurship comes with unique financial planning considerations.
John Overdeck, the billionaire co-founder of hedge fund Two Sigma, is offering his wife $723 million (NZ$1.3bn). Laura Overdeck says their marital assets should include his stake in the hedge-fund firm. Among other things, she wants about $2.2 billion—35% of what she thinks it is worth. The two have been fighting it out in a Newark, N.J., court for months.
The trial could produce one of the largest divorce settlements in history. It could also have a bearing on the power struggle at Two Sigma, where John Overdeck has been engaged in a long-running feud with his co-founder, David Siegel.
Here is how some careful financial planning might have helped avoid this saga.
Sign a prenup
John Overdeck proposed to Laura Overdeck in March 2002, a month before Two Sigma started investing with over $20 million in capital. By the time they married later that year, Two Sigma’s assets under management had climbed to about $350 million. Still, the couple didn’t sign a prenuptial agreement.
If they had, it could have started with something as simple as “the marital estate shall not include any interest in the business,” divorce attorneys say.
Laura Chickering, managing attorney at Fenchel Family Law in San Francisco, has recently been writing similar terms into prenups for founders of AI businesses.
“When the business is small, but you have an inkling that you don’t know what the potential upside is, that is the best time to sign a prenup,” she said.
Chickering tells founders to be prepared to negotiate and to make concessions. For example, a founder might agree to give up a home or another valuable asset in exchange for the business, in the event of divorce. She recommends their salary remain a marital asset to show that the marital estate is receiving a benefit from their employment.
Value your business before marriage
In New Jersey, as in other states, the growth of a business during a marriage can be subject to equitable distribution even if it was founded before the marriage, unless otherwise specified in a prenup. That is key to Laura Overdeck’s claim that she is entitled to a portion of Two Sigma.
John Overdeck has argued his stake in the firm is worth $4.5 billion, while Laura Overdeck has said it is worth $6.2 billion. A valuation expert hired by John Overdeck testified that his stake in the business was worth $50 million at the time of marriage.
Laura Overdeck’s side is disputing this valuation and has argued that her husband’s equity in Two Sigma didn’t vest until well after the marriage.
Having clear documentation of a business’s value—and the value of the founder’s stake—before the marriage can reduce some of the valuation gamesmanship if a once-happy couple later become adversaries, divorce lawyers say.
Pay yourself a market salary
John Overdeck testified that he had control over setting his own salary, a common trait among business owners that can open them up to scrutiny in a divorce.
An owner could be accused of intentionally underpaying themselves to withhold money from the marital estate, lawyers say. To avoid such accusations, they should engage third parties to help determine market-rate compensation and keep careful records on the methods used to determine it.
Robert Romanoff, a trust and estates lawyer at Levenfeld Pearlstein in Chicago, said he has included provisions in premarital agreements requiring that a business-owning spouse commission a compensation study.
“Should they make a change to their compensation upward if they’ve been underpaid?” Romanoff said. “You need to plan ahead of major life events.”
Separate your business from your family office
Up until around 2023, Two Sigma operated a multifamily office that managed the money of both John Overdeck and Siegel. Two Sigma employees provided personal services to Overdeck during that time, according to court testimony.
In one exchange, John Overdeck testified that he had a conversation with Matthew Siano, then Two Sigma’s general counsel, about removing Laura from their family foundation. Because Siano was representing Two Sigma and not Overdeck, the judge denied Overdeck’s attempt to claim attorney-client privilege.
To people who work with family offices, the blurring of the lines between business and personal are common.
“That’s the nature of the vast majority of family offices,” said David Handler, a trust and estates lawyer at Kirkland & Ellis. “It’s informal.”
Asking an employee to get involved in personal affairs puts a strain on that person and creates the potential for conflicts of interest, he said. They could end up doing something that helps their boss at the expense of other family members or shareholders.
Family offices should have separate advisers, keep clear records and be transparent by providing regular reports to all members of the family, said Kimberly Valentine-Poska, a former Deloitte partner who has served on the boards of public companies, private companies and family offices.
Valentine-Poska said family-office board work involves a closer working relationship with the owners than a public company, because she is helping to put governance in place and educating shareholders.
“You have to go in and set up a family office like it’s its own business,” she said.