Interesting story on a company and owner that seems to be betting against itself in the stock market to game the tax system.

https://www.propublica.org/article/jeff-yass-susquehanna-tiktok-tax-avoidance

Meet the Billionaire and Rising GOP Mega-Donor Who’s Gaming the Tax System by Justin Elliott, Jesse Eisinger, Paul Kiel, Jeff Ernsthausen and Doris Burke

Susquehanna founder and TikTok investor Jeff Yass has avoided $1 billion in taxes while largely escaping public scrutiny. He’s now pouring his money into campaigns to cut taxes and support election deniers.

Series: The Secret IRS Files Inside the Tax Records of the .001%

One day in July 1985, three young men from Philadelphia, their lawyer and a burly Pinkerton guard arrived at a horse track outside Chicago carrying a briefcase with $250,000 in cash.

Running the numbers on a Compaq computer the size of a small refrigerator, Jeffrey Yass and his friends had found a way to outwit the track’s bookies, according to interviews, records and news accounts. A few months earlier, they’d wagered $160,000, gambling that, with tens of thousands of bets, they could nail the exact order of seven horses in three different races. It was a sophisticated theory of the racing odds, honed with help from a Ph.D. statistician who’d worked for NASA on the moon landing, and it proved right. They bagged $760,000, then the richest payoff in American racing history.

…

Four decades later, the firm he and his friends founded, Susquehanna International Group, is a sprawling global company that makes billions of dollars. Yass and his team used their numerical expertise to make rapid-fire computer-driven trades in options and other securities, eventually becoming a giant middleman in the markets for stocks and other securities. If you have bought stock or options on an app like Robinhood or E-Trade, there’s a good chance you traded with Susquehanna without knowing it. Today, Yass, 63, is one of the richest and most powerful financiers in the country.

But one crucial aspect of his ascent to stratospheric wealth has transpired out of public view. Using the same prowess that he’s applied to race tracks and options markets, Yass has taken aim at another target: his tax bill.