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  • Big Island Blinks, CEO Exits, and TikTok Books More Rooms Than Your Sales Team - September 2025 Issue 2

Big Island Blinks, CEO Exits, and TikTok Books More Rooms Than Your Sales Team - September 2025 Issue 2

September 16, 2025

Aloha !

Welcome to this month’s Hawaiʻi Hotel Hui Insider!

A special thanks to Castle Resorts and Hotels for being our very first Issue Sponsor. They’ve been part of Hawaiʻi’s hospitality story for decades, and it shows in how they operate and who they sponsor. 😁 

This month we’ve got HTA déjà vu, a GM handoff at Marriott Waikīkī, more vacation rental delays (Big Island joins the club), and the hotel deal that… kinda wasn’t.

Plus: luxury’s recession-proof streak, TikTok’s OTA pivot, and a strong reader take on why HTA’s mandate might be broken beyond repair.

If you’ve been finding these updates helpful (or at least entertaining), we’d love it if you shared them with a colleague or friend. The more folks we bring in, the stronger this hui becomes.

Not on the list yet? You can join the hui below, no spam, no cost, just real talk.

Stay tuned, and as always, mahalo for being part of the Hui!

Let’s dive in.

Mahalo,

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

The Hotel Sale That Wasn’t: Oasis or Mirage?

Pacific Business News recently reported that New York’s Eagle Point Hotel Partners acquired the 96-room Oasis Hotel Waikīkī for $23 million. But I had a “wait, what?” moment, something sounded off.

After poking around and confirming with Ben Rafter himself (who knows a thing or two about these things), here’s what actually went down. Eagle Point partnered with Rafter to purchase the land under the Oasis, which had been held by the Japanese owner Hawaiʻi Sekitei Corp. The building itself is currently (already) owned by Rafter and Eagle Point.

So no, this wasn’t a full hotel acquisition, even though that’s how it reads. It was a land acquisition. 

As you might recall from a past issue, Ben recently merged his company, Springboard Hospitality, with Hotel Equities and took on the larger role as CEO for Atlanta-based Hotel Equities. And while Ben may be managing from Atlanta, you can see his heart (and wallet) are still here in Hawaiʻi.

Remember, as we’ve said before: hotels are complicated, and in Hawaiʻi, even more so. One Hotel can have a different landowner, building owner, manager, and brand. No wonder people get confused... even PBN. 😃

Ewa Hotel Waikīkī Hits the Market

Compare the Oasis land sale to the 92-room Ewa Hotel Waikīkī, which is up for sale at $21 million, and is unencumbered (as we mentioned last week, this means management and brand are at the discretion of the new owner). That is $228K per key for a leasehold property that runs through 2045. In our humble opinion, it seems like a steep price for a leasehold that will likely require a significant renovation.

Joe We Hardly Knew You!

A surprise announcement came last week (at least it surprised us). Hawaiian Airlines CEO Joe Sprague is out (retired, so they say), and Diana Birkett Rakow is stepping in, promoted from her role as Senior Vice President of Public Affairs and Sustainability at Alaska Airlines. Not the usual promotion path for a CEO, but with all the public relations challenges surrounding the acquisition, that skill set could only help. Aloha, Joe. Aloha, Diana.

They Said ‘No’ for Years, Then Quietly 4x’d Poolside Revenue
-Featured Partner-

For years, this luxury retreat on Oʻahu’s North Shore didn’t just avoid day guests, it avoided the idea of them.

With multiple pools, including an adults-only infinity pool and a family-friendly option, leadership questioned whether it was worth the risk to the guest experience. But in May 2025, curiosity (and FOMO) took over. Inspired by other Hawaiʻi resorts, they quietly rolled out limited pool passes through ResortPass and sold 30 in month one.

By June, they added one adults-only cabana and one family cabana per day. Both sold out, and revenue jumped 4x. Though inventory remains tight, ResortPass sales continue to grow, up 53% month-over-month.

It’s not headline-grabbing revenue, but it proves a point: even the most exclusive resorts can unlock new income without overcrowding the infinity pool.

Déjà Vu at HTA

HTA has named David Uchiyama as its new Chief Administrative Officer. He previously led HTA’s global branding from 2007 to 2015. Since then, he’s held senior roles at Island Air, Roberts Hawaiʻi, and HART.

He’s experienced, well-connected, and understands Hawaiʻi’s visitor industry as well as anyone. That said, some of his past roles, including during Island Air’s collapse and HART’s ongoing challenges, come with baggage.

Still, this appointment isn’t really about him. It’s about the agency. HTA is under increased scrutiny, has lost key staff, and is operating in a tough environment. Bringing in a steady hand like Uchiyama may help restore order, but it also feels more like a move to stabilize than to transform. We wish David the best of luck in the new role, and hope his experience helps guide the agency through this critical period.

Reminder: David will be taking on a role within HTA’s operating side, not the advisory board that has gotten all the press. As chief administrative officer, he’ll oversee the agency’s day-to-day functions.

Marriott Waikiki Swaps Out the Corner Office

We announced back in June that Jerry Gibson was leaving his post as GM of the Waikīkī Beach Marriott Resort & Spa to launch his own hospitality venture.

Jerry will continue with the property as an owner’s rep, but the hotel has now named Mark Weatherill (who surprisingly does not have a LinkedIn) as its new GM. A Marriott veteran with decades of leadership experience, Weatherill most recently was Complex General Manager at The Westin Galleria Houston and The Westin Oaks. Howdy and Aloha to Mark!

Big Island Pulls Up a Chair to the Delay Table

Last issue, we flagged how Oʻahu and Maui’s short-term rental reforms are stuck in neutral. Now Hawaiʻi Island is drifting the same way. Ordinance 25-50, the county’s new law for hosted short-term vacation rentals, was set to take effect December 20th, 2025, but is now expected to be pushed back to March 2026. 

The law requires owners to register their rentals, pay fees ($250 hosted, $500 unhosted), renew annually, and comply with health and safety regulations, with fines of up to $10,000 for violations. Platforms like Airbnb and Vrbo must also register and report monthly data. The delay is meant to give operators more time to comply, but it leaves yet another county in limbo on STR enforcement.

Recession-Proof, or Just Enshittified?

If your industry feed looks anything like mine, you've seen the flood of takes about the “recession-proof” luxury market. Powell and Aucello just reported that Hawaiʻi luxury RevPAR is up 9% year-to-date, even as upscale and upper-midscale properties are each down 14%. Nationally, STR shows the same pattern: luxury is holding, while the middle softens.

Then there’s Rafat Ali’s recent “Enshittification of American Travel” post on LinkedIn (worth a read), where he argues the industry has shifted from democratization to pure extraction.

Put that all together, and the questions get sharper: How long can the luxury tier stay insulated while the middle gets squeezed? Are middle-income travelers trading up, and taking fewer trips or going into debt to do it? Or is the wealth gap simply showing up in hotel performance?

Whether it holds or cracks, luxury’s outperformance is starting to feel like a signal.

BTW- My word for 2025 is now “enshitification.”

If AI Can’t Read You, Guests Can’t Find You
-Featured Partner-

Most hotel websites were built for human eyes, not machine brains. But that’s changing. Soon enough, your next guest won’t “search” - they’ll ask AI.

And AI doesn’t care if your site is pretty; if your content isn’t structured, strategic, and human-friendly, you’re invisible.

That’s where three&six comes in. They build brand, web, and content ecosystems designed for discovery - for guests and machines. It’s the happy medium between tried-and-true and what’s next.

Built for humans. Structured for AI.

Jump into the conversation with three&six - they’re having a lot of fun with this new era of digital marketing.

Brand USA’s Shrinking Stage

Brand USA just axed 15% of its staff after Congress gutted its federal funding this summer, cutting it from $100M to $20M. Inbound U.S. tourism is still hovering around 80% of pre-pandemic levels and slipping month-to-month. If D.C. can’t get its act together, no amount of glossy branding will fix the bigger problem: politics scaring off visitors.

Tick Tock… There Go Your Direct Bookings

TikTok is moving from dance trends to room sales. The platform has launched TikTok Go, an affiliate program where creators tag hotels in their posts and earn commissions on bookings. Combined with the new Booking.com integration, users can now watch a video, check rates, and book without ever leaving TikTok.

The mechanics are simple. Creators pick a hotel from TikTok Go, see the commission rate, and post content with auto-tagged booking info. Followers tap, book, and get confirmation in their TikTok inbox. Creators earn, TikTok gets stickier, and Booking.com captures the reservation.

Each booking that flows through TikTok and Booking.com means less direct control and more OTA reliance. Booking.com is covering the commissions for now, but does anyone want to take odds on how long before this becomes a “pay more, get featured” product?

The question is not whether TikTok can move rooms. The real question is whether hotels will let the middleman continue to own the funnel.

Industry Events

Vendor Pop-Up: three &six Is On-Island

Looking for a new digital agency, curious about 2026 trends, or want to see how our clients show up in AI search? three&six will be in Hawaiʻi next month (Oct 26th, 2025 - Oct 31st, 2025), visiting partners on Oʻahu, Maui, and Hawaiʻi Island.

We’d love to stop by your property or host a pau hana with your team. Reach out if you’d like to connect and set something up.

*If you have industry events to share, please email me at [email protected].

Spotlight on Hawai‘i Hospitality Opportunities

*If you happen to have any job openings, let me know. I will be glad to include them in the newsletter; send the job link to [email protected].

Asia Travel Tech: A Blast from My Past

Before I planted roots in Hawaiʻi, I spent years bouncing around Asia during one of the most explosive periods in travel tech. I launched an OTA startup in Beijing, then led the Asia region for a major wholesaler based in Hong Kong. It was a wild time: scrappy, chaotic, and moving fast.

That’s why this new documentary from Siew Hoon Yeoh hit home. She’s long been one of the sharpest voices in the industry, and she does a great job capturing the energy of the era. It’s a thoughtful, well-produced look at how the Asian travel industry grew from stitched-together systems and faxes into the dynamic digital giant it is today.

Now, fair warning: this one’s a bit nerdy and definitely geared toward the travel industry crowd. But if you’ve ever sat through a GDS demo, dealt with room mapping drama, or remember when taking payment online was considered cutting-edge, you’ll probably enjoy it as much as I did.

It’s a fascinating watch, especially if you care about how fast travel is evolving and how much is still up for grabs.

I always say feedback is welcome, unless it’s about my typos.

Kidding… Mostly. 😉

This month, a reader emailed me to say, “Great issue! And excited for twice monthly! Keep up the great work.” Mahalo!

One lucky reader was bold enough to send me an email asking me if I had any more invites to the perplexity’s browser Comet, and it so happened that I did!  Which shows you my grandmother was right, it never hurts to ask! 

You might recall in the last issue, we asked in a Poll if you agreed with State Senator Wakai's LinkedIn post, where he said, “HTA is expected to grow the tourism sector and, at the same time, keep inconsiderate tourists out. I believe HTA should focus on marketing and have stewardship under another agency (Dept Consumer Affairs, or Office of Planning).”  

The results: 73% of you agreed with the sentiment, while 27% disagreed. 

One reader had a very strong opinion, and I am paraphrasing it a bit due to space limitations: 

“Wakai is right… Destination management isn’t their core competency, and they haven’t proven they can do it. DLNR may be a mess, but it’s their lane. HTA should be supporting, not substituting.

Also, let’s be real, the dedicated funding isn’t coming back. We’ve got an underfunded, unstable org with no mandate. Who’s going to take that CEO job at less than a good hotel GM’s salary? You want someone who can drive serious ROI for the state? Then pay them like they can. Just ask June Jones.”

Editor’s Note: June Jones made $800K coaching UH football. The current coach makes $700K, for a mediocre team (please, no hate mail) that loses money. Meanwhile, the HTA CEO leads a small agency tasked with influencing an industry responsible for ~$20 billion in annual spending and the associated jobs and taxes that come with that.

Got thoughts of your own? Sharp opinions? Personal vendettas? Just want to argue with a fellow reader anonymously? Send your take to [email protected], and maybe you’ll make it into next month’s inbox therapy session.

About Us

Hawaiʻi Hotel Hui was started by hotel industry veteran Dan Wacksman, the CEO of Sassato, a Hawaiʻi-based consultancy that combines deep local expertise with a global perspective to help hotels and travel businesses overcome challenges and thrive. With a team of seasoned industry professionals who call Hawaiʻi home, Sassato offers an intimate understanding of the market, culture, and key players, paired with decades of experience in technology, marketing, revenue management, operations, finance, and overall strategy.

While Hawaiʻi is our backyard, our global footprint enables us to bring best practices from around the world. At Sassato, we don’t just consult, we deliver results with a no-nonsense approach to getting sh*t done.

Recent engagements include brand transitions, system selection and implementation (e.g., website, booking engine, PMS, CRS, CMS, CDP, F&B), feasibility studies, competitive analysis, strategic planning, training, meeting facilitation, and audits in marketing, distribution, and technology. If you need help, we’ll either assist you directly or connect you with the right experts. Our ultimate goal is to be a trusted partner and resource for Hawai‘i hotels.