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60-Day Sprint, Miami Moves, and a $2.5B Tech Bet

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Aloha {{first name |}}!

Welcome to the latest edition of HHH. This issue, we have a lot in store for the hui.

The legislative sprint is officially on, and while we are watching the clock at the Capitol, some of our industry’s biggest players are quietly packing their bags for the continent.

Before we dive in, a big mahalo to our quarterly title sponsor, Allana Buick & Bers (ABB). While we talk strategy, ABB ensures your HVAC and mechanical systems don’t fail you. They help Hawaiʻi owners shift from “fixing what’s broken” to proactive CAPEX engineering, allowing your team to stay focused on the guest experience.

In this issue, we look at Trinity’s quiet exit to Florida, cover the 60-day sprint at the Capitol, and the results of our Michelin Guide debate. We also explore a $2.5 billion tech valuation that could reshape hotel operations (or just the math in pitch decks) and why 85 million people are suddenly panicking about AI.

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Let’s dive in.

Mahalo,

Dan Wacksman
Hawaiʻi Hotel Hui Insider Editor-in-Chief 😄

Trinity Says “Aloha”… From Miami

Honolulu-founded private equity real estate firm Trinity Investments has relocated its headquarters to Miami, calling it a strategic move to position the firm closer to capital, partners, and key hospitality markets.

Founded in 1996, Trinity grew from a small three-partner shop into a global hospitality investor that has deployed more than $10 billion. Over the years, it owned marquee Hawaiʻi properties including The Ritz-Carlton Kapalua, Hyatt Regency Waikīkī, Fairmont Kea Lani, and The Kahala. Today, its only remaining Hawaiʻi hotel is The Westin Maui, acquired in 2017, while recent transactions have focused on Europe and the U.S. Sun Belt.

Trinity operates under a classic private equity model: raise institutional capital, acquire hotels to increase profitability, and eventually sell them for a return. Other PE companies active in the islands include KSL Capital, Blackstone, etc.

The firm says it remains interested in Hawaiʻi and will maintain a local presence. Fair enough. But zoom out, and the pattern is hard to miss: Hawaiʻi still hosts the hotels. Increasingly, the capital allocation and strategic decisions are made somewhere else.

Read More

Speed Lawmaking, Hawaiʻi Style

Before we dive into this year’s bills, a quick refresher on how the game works.

Hawaiʻi’s Legislature doesn’t sit year-round. It’s constitutionally capped at 60 “working days,” which stretches from mid-January to early May. That puts us on the shorter end nationally. A few states meet most of the year. Most others compress their lawmaking into 30 to 120 days.

We’re in the compressed window now. Hundreds of bills. Hard deadlines. Limited runway.

Plenty touch on hospitality and tourism. Here are a few worth watching:

  • TAT Marketing Dedication (HB 1950) – Earmarks funding specifically for marketing.

  • $25 per comp room (SB 241) – Would charge hotels for complimentary nights.

  • Vacation Rental Enforcement (HB 1590) – Expands tools targeting illegal operators.

  • Destination Management Restructure (HB 1947 / SB 2807) – Shifts tourism governance again.

  • Michelin Guide Support (SB 2072) – Backs payment to bring Michelin recognition to Hawaiʻi.

If you feel strongly about any of these bills, or even just have a perspective, you can submit testimony directly through the links provided. Look for the orange “Submit Testimony” button.

At a recent conference, Tourism Committee Chairs Senator Lynn DeCoite and Representative Adrian Tam both noted how closely testimony is read and how it can influence discussion and amendments. It’s not symbolic. It’s part of the record, and in a 60-day sprint, it is a real way to have influence.

👉 List of Hotel and Tourism Bills to Watch

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Sheraton Waikīkī Says A Hui Hou to Tom Calame

After more than 30 years with Marriott International, Sheraton Waikīkī Beach Resort is bidding farewell to General Manager Tom Calame as he retires.

Tom’s career began in 1988 and took him through leadership roles across Latin America, Europe, the Caribbean, and Hawaiʻi. Since 2018, he has led not only Sheraton Waikīkī but the full Kyo-ya portfolio, including The Royal Hawaiian, Moana Surfrider, Sheraton Princess Kaiulani, and Sheraton Maui. He guided the group through COVID, major repositionings, and some of the most turbulent years our industry has faced.

Thirty-plus years. Five iconic Hawaiʻi resorts at the finish line. Not a bad run. A Hui hou, Tom.

Hotel Performance

Quick Summary (So You Sound Smart in Meetings): Demand is slightly up statewide, with the rate flat. Maui filled more rooms by cutting the rate. Hawaiʻi Island pushed rate and won (7.4% rev par growth!) Oʻahu is steady but uninspiring. Net result: modest RevPAR growth (2.5%), no breakout story.

Hotel performance data will be published in the first issue of each month.

Click here for the full DBEDT breakdown: Seats, stays, and then some.

Cartels, Conflict, and the Domestic Advantage

You’ve all seen the news out of Mexico. Following cartel violence, travel advisories were issued, and headlines moved quickly. Officials say order is being restored and major resort areas remain operational.

First and foremost, we hope for safety and stability for residents, visitors, and industry colleagues. No destination benefits from instability, and neither does our industry.

Tourism demand is highly sensitive to perception, but recovery depends on how contained and how prolonged the disruption is. In prior Mexico advisory spikes, where incidents were not directed at tourists, resort markets often saw short-term softness that stabilized within a booking cycle.

Closer to home, the Maui wildfires showed how quickly headlines can disrupt demand, even when impacts are geographically concentrated.

Mexico remains Hawaiʻi’s biggest West Coast leisure competitor. If coverage lingers, perception alone can influence booking behavior. Layer in U.S. involvement in Iran and rising global tension, and the travel picture gets murkier.

Historically, when Americans feel uncertain about the world, they don’t stop traveling. They adjust. International trips may get deferred. Familiar domestic destinations often benefit.

Hawaiʻi sits in that space. We are far, but we are still home.

This isn’t about rooting for instability elsewhere. It’s about understanding how sentiment shifts and working to our strengths.

Not so fun fact:

  • The annual risk of being murdered in the United States is roughly 1 in 15,000.

  • The annual chance of an American being killed in a terrorist attack abroad is approximately 1 in 2–4 million.

There’s a name for this: dread risk. We overreact to dramatic, unlikely threats and underreact to familiar ones. Think fear of shark attack vs. car accident.

Payroll as a Percent of Revenue? That’s Cute.

A recent hotel industry white paper made a point we’ve been circling for a while: The old staffing model is gone.

A few highlights that stood out:

  • Wage elevation is permanent, not cyclical.

  • Turnover is now a predictable operating expense.

  • Luxury properties face the biggest mismatch between service expectations and available talent.

  • Extended-stay models are outperforming in part because weekly housekeeping aligns better with workforce realities.

  • Forward-looking operators are shifting from payroll as a percent of revenue to payroll per occupied room.

None of this should shock anyone operating in Hawaiʻi. We’ve already talked about hotel wages and benefits and an aging workforce pipeline.

The takeaway isn’t that labor is expensive. It’s that the operating model many of us built around abundant labor no longer exists.

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Ron Reads Hawai’i Hotel Hui

If you read the last issue of HHH, you may have seen my piece on Classic Vacations and its founder, Ron Letterman.

I was amazed that one of our readers forwarded it to Ron… and he replied!

I didn’t expect he would remember our conversation (which he didn’t), but it was definitely a good reminder of the impact you can have, even if you are not aware of it. Below is his email to me. (Published with Ron’s permission.)

Aloha Dan ,

A former employee of mine… sent me the article you wrote about our meeting so many years ago. I appreciate being remembered after all this time, and also appreciate the compliment, even though I do not really remember the specifics of our exchange. At the time of our meeting, the hotels were trying to adjust to the entrance of online booking agencies like Expedia and Priceline, and the traditional travel agency community was paranoid with fear, with many in the industry predicting the end of brick-and-mortar agencies. Now, companies like Expedia and Priceline are trying to adjust to the entrance of AI into their industry, and many are predicting their demise.

Click To Read The Whole Email.

Hotel Tech Bubble or PMS Revolution?

Hotel tech money is flowing again, this time it landed squarely on Mews. The cloud-based PMS (property management system – AKA brains of the hotel) just raised another $300 million, valuing the company at $2.5 billion. For context, that’s more than double what Sabre sold its entire hospitality business for.

The investor story is polished. Mews is positioning itself as a full hospitality operating system, not just a PMS, leaning hard into AI-native, agent-driven workflows. The press release cites 15,000 customers across 85 countries. If my back-of-the-envelope PMS math is even close, it’s hard to justify a $2.5 billion valuation on topline alone, never mind the bottom line.

PMS companies don’t win on funding rounds or vision decks. They win on reliability, integrations, and how rarely the front desk has to make an angry call at 2 a.m. 

Maybe Mews really is building the future of hotel operations. Or maybe this is venture math getting ahead of hotel reality. 

Either way, the valuation bar has officially been raised.

Why 85 Million People Stopped Scrolling

A recent AI essay titled Something Big Is Happening exploded online, pulling over 85 million views. It didn’t come from a household name. It came from a startup founder arguing that AI is moving faster than most people realize and that white-collar disruption may arrive sooner than expected.

This is not a new sentiment, but it went viral because it captured a real and growing anxiety. A sense that something is accelerating, and most people aren’t fully participating yet, and are getting left behind. The essay went on to give real and specific examples that people can relate to (and freak out about). 

The takeaway isn’t panic. It’s participation. 

Start using it! Draft an owner update. Analyze a STR trend. Build a sales outline. Test prompts with your revenue team. Play with it now, before your manager quietly replaces you with a prompt. (Half joking).

You don’t need a strategy deck. You just need to start.

Industry Events

Full list of 2026 Hawaiʻi Events 

*If you have industry events to share, please email me at Dan@hawaiihotelhui.com.

Spotlight on Hawai‘i Hospitality Opportunities

  • National Sales Director / VP (Remote) – Hawaiʻi travel platform with surging traffic is hiring a senior ad sales leader to build partnerships across hospitality and tourism. Independent contractor role with uncapped earning potential and real runway.

    • Confidential retained search. Qualified candidates can email dan@sassato.com for more information.

  • Hotel Assistant Manager – Prince Waikiki (Honolulu)

  • General Manager – Grand Wailea, A Waldorf Astoria Resort (Wailea)

*If you happen to have any job openings, let us know. We will be glad to include them in the newsletter, space permitting; send the job link to Dan@hawaiihotelhui.com.

Last issue, reported on Senate Bill 2072, the proposal to use state general funds to pay for a Michelin Guide. We asked if Hawaiʻi should be footing the bill, and the results from our LinkedIn and newsletter survey are in.

The “Yes” camp edged it out at 52%, with 40% opposed and 8% on the fence. The vote was close. The commentary? Not even a little. Many of you made it clear that while our culinary scene may deserve the spotlight, taxpayer dollars might have higher priorities.

Here is what the Hui had to say this week:

The Michelin Drama

  • “Just an update that the bill [Michelin Guide (SB 2072)] was deferred, and most likely will die. The oral testimony [was] embarrassing.”

    • HHH Note: After reading this comment, it piqued our curiosity. We found the testimony online and quickly understood the reader’s concern. The presenter appeared unfamiliar with how Michelin actually operates. I suppose the old expression about two things you never want to see made, sausages and laws, still holds.

  • “I don’t see the need for an investment (bribe) to bring the Michelin Guide to Oʻahu. There are far more important things for the legislature to spend money on. Visitors are generally not looking for haute cuisine, and locals know where to go. Your list should suffice for most people!”

  • “There are some great chefs in the Hilo area, and striving to earn a Michelin star would only up the competitive game in my opinion.”

The “Hui Approved” Must-Eat List
Since some of you think my list is better than a tire guide anyway (your words, not mine), here are a few more local spots recommended by the hui:

  • “Regarding your restaurant list, I would include Mitch’s and Kats Sushi in the sushi section.”

  • “If you haven’t tried Izakaya Tenkichi on King Street, you should. It’s fun. And delicious.”

Classic Memories: Ron Letterman
Our piece on Ron Letterman and Classic Vacations brought back some serious nostalgia, and some reminders that Ron usually knew what was coming.

  • “I recall sitting in meetings when Ron said, ‘The internet will never completely replace travel advisors.’ That was in the late 90’s; crazy, right?”

  • “Loved your article on Ron Letterman/Classic. After working with Ron… for several years, one thing I learned: Ron was always right. Always. It paid to listen to him. I was so fortunate to have him as a mentor for so many years.”

Strong Opinions & Industry Notes

  • On the AI Threat

    • “Very interesting; Hilton and Marriott view AI Chatbots as [a] potential threat to direct bookings. At the same time, many experts claim that these AI agents will open opportunities for hotels to increase direct business at the expense of the OTAs. If these bots don’t book with the large brands and also don’t book on OTAs… will there be new middlemen, which currently don’t exist?”

  • On the North Shore Dilemma

    • “The folks on the north shore need to decide if they want to be Lanaʻi or Molokaʻi. Few places are more rural than either island, but one supports an affluent population, and on the other, close to 35% are on public assistance.”

The Virtual High-Five

  • “Another great newsletter, thanks for the updates.”

  • “As always super!”

  • “I have to say I was impressed with the quality of [the] articles and would enjoy continuing to receive them even though I am happily retired…”

  • “Great newsletter, again!”

Agree? Disagree? Have a hot take of your own? Fire back at dan@hawaiihotelhui.com, and your response might be featured anonymously in the next edition.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective.

Our team brings decades of experience across operations, marketing, revenue, tech, and finance, all aimed at helping hotels and travel companies make smarter decisions and move faster. Whether you need additional expertise, extra horsepower, or just someone who thinks like you and moves things forward, we’ve got you. From local independents to global brands, we show up with a no-nonsense, results-focused mindset. To be blunt: we get sh*t done.

Learn More

Recent projects include brand transitions, system selection (PMS, CRS, CMS — all the acronym soup), implementations, project management, feasibility studies, training, audits, and everything in between.

A lot of organizations deal with stretched teams, siloed processes, and messy tech stacks that quietly stall important work. We fix that. Happy to chat if this hits close to home.

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