The ad opens with Trump, the presumptive GOP presidential nominee, boasting at an event about being "so good at business," before cutting to news reports of the fallout from his shuttered projects.
"Donald's businesses have been good for him, but not for everyone else," the ad says.
It features past Trump remarks about being the "king of debt" and "playing with" debt, with text in the ad arguing Trump wants to do the same to the U.S. economy.
The economy and jobs have consistently ranked as top issues for voters, and Democrats have focused on Trump's business record as Clinton, the presumptive Democratic nominee, looks to shore up support among blue-collar voters.
Clinton has been pounding Trump in ads online and on the airwaves, while the businessman is shuffling campaign staff and attempting to launch a fundraising push to close the financial gap heading into November.