$20 Hawaii Hotel Upgrade Hack Goes Viral: Here’s The Reality

It started, fittingly, in Hawaii. Former FBI agent Tom Simon claims his best hotel upgrades ever were right here in the islands. In a viral TikTok we share below, Simon reveals his go-to trick: a compliment, a short speech, and a folded $20 bill. The video, filmed from a casino suite, has sparked debate across Hawaii’s travel community about whether this old-school hack still works, and whether it belongs in today’s era of resort fees and tipping fatigue.

Simon’s pitch is simple and confident. He says it doesn’t matter how you booked, online, through an agent, or by phone. You walk up to the front desk, smile, and tell the agent that everyone in hospitality seems to get tipped except the people running the desk. “You look at the valet parking guys,” he says in the clip. “They’re getting tips all day long. Meanwhile, you probably have a degree in hospitality, right?” He sets down a twenty-dollar bill, introduces himself, and asks for a “decent room.”

He claims he’s done it for twenty years, including during his time in Hawaii. On trips to Maui and Kauai, he says he routinely scored “amazing suites overlooking the ocean.” His parting line in the video captures the tone perfectly: “Put me in the room you’d put your mother in if you wanted to show her a really special time here at the hotel.”

What’s behind the $20 trick: aloha or ambition?

Simon’s point is that the front desk holds more power than most guests realize. Staff decide who gets the quiet wing or the noisy floor. They can relocate you away from elevators, swap you into a brighter view, or quietly tag you for early check-in. A polite conversation with a small tip, he argues, simply acknowledges that human leverage.

In his Hawaii example, Simon says it often resulted in free parking, breakfast coupons, or upgraded ocean views. “The front desk people have so much control over the quality of your stay,” he says 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.”

What hotel staff say about the $20 tip.

The TikTok comments were as divided as you’d expect. “A $20 goes a long way for an upgrade,” wrote one front desk agent. Another added, “I’d have given you the room without the tip, I just needed the speech.”

But not everyone agreed. “It’s 2025,” one viewer wrote. “The $20 trick is now the $100 trick.” Others called it manipulative or outdated, while some said it was harmless and kind. One summed it up best: “Give the $20 if you want, but don’t expect magic. Just be nice.”

We also reached out to several Kauai front desk workers. Most declined to comment on the record, citing company policy, although one admitted off the record that small gestures of appreciation can sometimes influence room placement when occupancy allows.

Our approach to upgrading at the front desk.

In Hawaii, tipping isn’t just about money. It’s a cultural signal. A gesture offered with genuine appreciation may be welcomed, but one that feels transactional can fall flat or even offend. Hawaii’s hospitality culture values relationships and respect, and guests who come across as entitled risk missing the mark entirely.

Here are some strategies we use that may be helpful:

• Book your room direct. If you use a third party site, the hotel may earn only 70–85% of what you pay. That’s why direct bookings almost always get better room placement, more flexibility, and sometimes lower net cost once resort fees and loyalty perks are factored in.
• Join the hotel loyalty program before your stay. Staff often factor that into upgrades and satisfaction ratings.
• Don’t arrive too early and expect an upgrade. Housekeeping needs time to prepare the rooms, so it’s best to arrive at check-in time. Otherwise, let the front desk know you can wait.
• Early evening, around six or seven, is often when cancellations and no-shows free up better rooms.
• Consider a tip after being upgraded. If you stay at a luxury hotel with rooms starting at over $1,000 nightly, a $20 bill could land differently.

Why this still matters.

The $20 trick taps into a larger conversation about value and fairness in travel. Hawaii hotels already pile on resort fees, parking charges, and housekeeping surcharges, leaving many guests wondering who really deserves extra cash. Simon’s viral hack plays into that uncertainty, suggesting that even in a system full of fees, a personal gesture can still make a difference.

It also hits a nerve about service culture. In Hawaii, aloha in hospitality is still real but stretched thin. Guests notice when staff look burned out, and workers notice when guests act entitled. Somewhere between those extremes, a twenty-dollar bill might simply remind both sides of the human moment travel used to have.

Some readers will see this as simple appreciation. Others will call it paying for preferential treatment. Both arguments hit close to home in Hawaii’s hospitality economy, where fairness and aloha often intersect in complicated ways.

See the TikTok video below. Would you try the $20 front desk trick at your next Hawaii stay, or do you think it crosses a line in today’s travel culture?

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How can you maximize your hotel experience every time? Former FBI Agent Tom Simon, a frequent business traveller and private investigator, explains to @Matthew Cox | True Crime

♬ original sound – Tom Simon: Private Detective