In the three-minute, documentary-style video, the New York City-based architect Andrew Tesoro says the real estate mogul "bullied" his firm out of "many thousands of dollars."
Tesoro details how Trump hired him to design a clubhouse at the National Golf Club in Westchester County, New York, then refused to pay the bill. After some back and forth with Trump and his attorney, Tesoro decided he had no choice than to accept what he describes as "way less than half, barely more than a third" of the amount billed. The deal, he says, nearly had him seeking bankruptcy protection.
Peppered with clips of Trump touting his experience and business-friendly policies, the ad reinforces the Clinton campaign's narrative of Trump's unfair and harmful treatment of small businesses. As such, it echoes what's likely a key theme of the Clinton campaign: to damage Trump's populist appeals by pointing out ways in which he's hurt ordinary people.
But will the business community agree?
Not likely. Molly Day, a public affairs spokeswoman for the National Small Business Association, says while it's hard to watch this ad without feeling sympathetic toward Tesoro, it's unlikely to sway entrepreneurs.
Trump supporters, Day says, will see the ad and think: What do we not know here? They'll likely take into consideration that contract negotiations are tricky and nuanced. Clinton supporters will simply have their notions of Trump confirmed, Day says. Those on the fence will be left wanting more.
"What resonates is actual plans," Day says. "How is Clinton going to fix the wildly burdensome tax code and cost of health care for small-business owners?"
The video doesn't mention Clinton's policies.
In one entrepreneur's opinion, the ad misses the mark when it comes to connecting to the business community.
"If you're a politician and you have very little business experience, you might think it was a powerful statement," says Carey Smith, founder of Big Ass Fans, a manufacturer in Lexington, Kentucky. "From a business person's perspective, it was weak."
What's more, he says, Clinton chose the wrong subject for the video. "Showcasing a professional, an architect or doctor, is not the way to reach the business community," he says.
Telling more stories of this nature--related by small-business owners rather than Clinton herself--could have a significant negative effect on Trump's campaign, says Ari Ginsberg, professor of entrepreneurship and management at New York University's Stern School of Business.
Trump's response is equally as important, Ginsberg says. The least effective reply would be to attack the character or integrity of Tesoro. Instead, Ginsberg says, "Trump is more likely to be successful with counterattacks that shine a negative spotlight on Hillary Clinton herself."