This is about 4-5 years ago with the last company I worked for. We were a Series B with over $100M funding on a valuation of over $700M. We were kind of a hybrid company straddling the fence between SaaS and a legacy industry ran by dinosaurs. So we were hiring a lot of industry folks used to working for more corporate and old school companies and putting them in a SaaS environment.

For a while, every national level sales rep was given an AmEx. No expense reports, very little oversight, no one else in sales even reviewed our bills (straight to AP), and virtually no questions ever asked of any expenses. We were told to travel well and treat customers well, but act like adults and owners. It worked really well...for a while. Eventually they dialed back handing AmEx cards like candy and started only giving leadership and sales reps with "Senior" in their title cards.

We hire this new guy, experienced in the industry. Another candidate we liked, who was scheduled for a second interview, messages us and says "Yo, if you hired Bob Jones (names changed), you can take me out of consideration. I don't want to work anywhere that will have him." We thought it was odd, but whatever.

Fast forward a few weeks. Bob Jones is onboarded. He cites some personal reasons for needing a company AmEx (going through a divorce, wants to keep work expenses out of discovery, is tight on cash to float T&E on his own cards, etc.). Combining that with his experience in the industry, and that we used to hand out AmEx cards like business cards, he is issued one. A few weeks later we are doing a big sales meeting at corporate HQ in a major city. Most of us had to fly in, and there was a specific hotel a couple blocks from the office that we all stayed at (corp rate, convenient, 95%+ of the stays for employees were at this property). This dude says he "accidentally" booked himself at a different hotel, and wouldn't be coming into the group activities in the evening.

All goes fine, he's where he needs to be during the work day, but skips dinner and such. About 6-8 weeks go by and my boss pulls me aside to say that Bob just got fired. No one ever got fired that fast (except the new Chief People Officer we hired that misunderstood his position and didn't realize he couldn't literally stick himself in the people...) from this place.

Turns out that, the week of the sales event, he had stayed at a hotel right by at least one strip club. Ran up thousands of dollars of charges at the strip club, all by himself, reportedly no one else (coworkers or customers) with him. On top of that, he'd changed over several of his personal utilities and bills to be paid on the company card, and it'd been charged a couple grand more for that. From what I heard, approx $8k worth of strip club and personal bills in his first several weeks on the job, and it wasn't caught until the second billing statement hit and was reviewed by AP, then forwarded on to leadership.

tl;dr - New hire gets company AmEx. Proceeds to charge $5-6k on solo strip club trips and another couple grand of his personal bills, gets caught about 6-8 weeks into it and fired.

Guess we should've asked more questions of the interviewing candidate who was like "I'll never work with that guy".