Dane Wilcox had come to Boston for two reasons: hot sauce and Dota 2. Getting into a months-long courtroom fight with the world's largest startup was never in the plan.

The former IT consultant had become a hot-sauce entrepreneur in 2014, after a surprisingly successful Kickstarter campaign to launch his brand, "FYM Hot Sauce." He picked a quirky method of advertising that suited his own interests: Wilcox sponsored a team that played a popular video game, Dota 2. Wilcox played the game himself and had tired of seeing ads for gambling websites. So looking for a different and fun way to promote his product, he got a team on board and became its flagship sponsor.

After a long flight from his home in Portland, Oregon, Wilcox landed in Boston on December 5, 2016. He was looking forward to getting straight to the Airbnb he'd rented and getting some rest. But then he made a fateful decision—to use the Uber app to get a ride from the airport. It was the first Uber ride he'd ever taken.

Wilcox had two big suitcases as checked baggage filled entirely with hot sauce—more than 100 pounds of it. All of his personal effects—including his laptop, clothes, an extra cell phone, and blood pressure medication—were in his backpack. The Uber car was squeezed into the narrow Boston street between other cars, and Wilcox had to shimmy out. So he hauled out just the suitcases, telling the driver he'd be back in a minute to grab the backpack. But when he reached the curb, the Uber car immediately drove off with his backpack still sitting in the back seat.

"Initially, I just thought it was a mistake," Wilcox said. "I called the Uber support line and told them, 'I have to take my medications daily.'"

Uber gave Wilcox a number to call that would ring the driver's phone through a third-party proxy service. Wilcox waited a half-hour outside. Then he went inside and unpacked his stuff, continuing to call the driver every half-hour, until about 2:30 in the morning. He got a generic voicemail message and left messages explaining his situation. Ultimately, he got a message that the voice mail box was full. The next morning, he started calling again at 8:00.

At around 1:00pm, Uber called Wilcox and told him the driver didn't have the bag and never saw it.

"They said, 'We're not responsible for that,' and that was the end of it," Wilcox recalls. "I was pretty frustrated when the driver wouldn't respond to me. But when he dodged me but responded to Uber, I thought, 'OK, this guy is intentionally dodging me.'"

At that point, Wilcox went to the police and filed a report. He had the driver's first name, a picture of him from the Uber app, the car's license plate number, and confirmation of his ride details.

Wilcox knew that it was possible that a later passenger, and not his driver, had taken the backpack. But he wanted an answer and not to simply be blown off. Uber wouldn't even tell him if there had been additional rides that night after him, citing "driver privacy." He needed police help to get even that information, so Wilcox filed the report.

He spent the next two days working the Dota 2 tournament and handing out samples of hot sauce, as planned. Meanwhile, he felt like "garbage" without the blood pressure medication he takes daily. By that Thursday, it was time for him to leave town. He had been stonewalled by the driver, blown off by Uber, and the police hadn't done anything. Between his laptop, extra cell phone, FYM swag, and personal effects, he had lost more than $4,000 of stuff.

Wilcox decided the smart move would be to file papers in small claims court before he left town. At this point, he was confident the driver had ripped him off. He had positively hounded the man for a week, leaving dozens of messages, and the driver refused to even respond. So Wilcox went to Boston's small claims court and filed a case asking for $3,900. He flew back to Portland, still confident at that point Uber would hear his plea and help him out.

But Wilcox wasn't going to get his $4,000 from Uber—not without a fight. Instead of compensating Wilcox, the $59 billion company said it wasn't responsible for his backpack. Instead of compensation, Uber was going to give Wilcox a drag-out court fight that would cause him to fly across the country twice.

Listing image by Dan Wilcox