tech, startups, internet

What it will take to defeat TurboTax

“It’s taking consumer finance companies with massive distribution, combining them with a tax preparation API and real-time visibility into users tax position. Tackling TurboTax head on is probably a waste of money. Tackling TurboTax asymmetrically has a real shot.” | learn more

oh, chicago

A tax on all your boxes

“With the pandemic bringing a host of financial problems Chicago’s way, 11th Ward Alderman Patrick Daley Thompson proposed a ground delivery tax.” The city’s never-ending search for ways into residents’ pockets goes on. Not content with taxing the contents of […]

fun facts

Ikea is a nonprofit (technically)

“Ikea is a nonprofit dedicated to furthering the advancement of architecture and interior design–a cause they give a pittance of $2 million or so to a year.” Click through for an overview of their clever tax avoidance structure. | learn more

oh, chicago

Uber suing Skokie, but the real target is Chicago

It seems like a clever strategy to sidestep a battle with the big city with more legal resources. “The firm contends the north suburb’s ride-hailing tax violates state law. Its arguments could apply to the mayor’s proposed $40 million tax […]

oh, chicago

CPS is getting taxed. 

Not literally, but, “The rate on the [school district’s] bonds, which are supposed to stay extremely low because investors can resell them to banks periodically, jumped to a maximum 9 percent on March 1 from 4.64 percent the week before […]