His method for securing premium hotel accommodations, which he shared in a TikTok on October 27, revolves around just a few things: genuine appreciation, recognition of the hospitality industry’s most glaring inequity, and a $20 bill, which, he says, “will pay for itself.”
Simon says if you walk into any hotel—reservation or no reservation, booked online or over the phone, it really doesn’t matter—go straight up to the front desk and chat up the staff there.
“You got your suitcase, and you go, ‘I am checking in, but before I do, I just want you to know I travel on business all the time. I’m always on the road. And it’s never ever made sense to me that everyone in the entire hospitality industry is being taken care of except for you people at the front desk,” Simon said.
“You look at the valet parking guys, these guys are morons. They can’t even fold their wallets at the end of a shift, they’re getting tips so much. Meanwhile, you probably have a degree in hospitality, right? Yet no one ever takes care of you. You’re on your feet for eight hours a day. You’re the front door to this organization. You’re running this hotel as far as I’m concerned.”
He then says to place a $20 bill on their keyboard. “I just want to let you know how much I appreciate everything you do,” he said. “My name is Tom Simon. I’m checking in. If you could get me a decent room, I’d appreciate it.”
Simon claims he has been using this technique for 20 years with consistent results. During his time as an FBI agent in Honolulu, where he investigated major financial crimes including Ponzi schemes and embezzlement cases, he traveled frequently to Maui and Kauai. “I would get these amazing suites overlooking the ocean,” he recalled.
Most recently, at a casino hotel, Simon said the approach yielded “the biggest hotel room I’ve ever stayed in my life”: a suite with a large living room, stocked bar, expansive bedroom, and bathroom “bigger than my first apartment.” He said the front-desk staff also provided complimentary parking and free breakfast coupons.
The strategy acknowledges a reality of hotel operations: Front-desk staff wield considerable discretionary power over room assignments. They determine proximity to noise sources like ice machines or late-night gatherings, and they often have latitude to upgrade guests when premium rooms remain available. Simon suggests framing requests in personal terms: “Put me in the room you would put your mother in if you wanted to show her a really, really special time here at the hotel.”
Tipping front-desk staff for upgrades is not a universally accepted practice, and policies vary by property. Some hotels explicitly prohibit such gratuities, with employees risking termination if caught accepting them. The practice appears most common in Las Vegas, where discretionary tipping can influence room assignments at Strip properties. In other markets, simply asking politely—without monetary incentive—often yields similar results when occupancy allows.
Simon’s technique differs from standard upgrade strategies recommended by hospitality experts, which typically emphasize loyalty program membership, elite status, booking directly with hotels, and traveling during off-peak periods. His approach introduces a transactional element that exists in a gray area between genuine appreciation and expectation of preferential treatment.
The broader context involves ongoing debates about tipping culture and worker compensation. Wait staff and bartenders derive more than half of their earnings from tips, but front-desk workers typically make their money through more conventional recognition programs in the hospitality industry.
Simon, now a licensed private investigator in Florida operating Simon Worldwide Investigations, continues to share investigative techniques and industry insights through social media. His hotel-room strategy reflects his investigative background: identify leverage points, understand human motivation, and recognize where power actually resides in organizational structures.
“The front-desk people have so much control over the quality of your stay,” Simon said in the video. “They know where the frat party is. They can put you next door to that, or they can put you not next door to that.”
You can watch Simon’s TikTok on the aforementioned hotel-room strategy below:
For this story, Fortune used generative AI to help with an initial draft. An editor verified the accuracy of the information before publishing.
