Who’s Spending $100M, Who’s Selling Dirt, and Who Marked Us as Spam? - September 2025 Issue 1

September 02, 2025

Aloha !

Welcome to the latest from the Hawaiʻi Hotel Hui Insider! This month, we’re kicking off our new twice-a-month format. Look for fresh issues on the first and third Tuesday of each month.

This issue, we’ve got stalled vacation rental crackdowns, a century-old Waikīkī land lease that just sold for $215 million (yes, just the land), a “direct booking” startup with a middleman, and a new Green Fee council now figuring out how to spend $100 million a year.

But first, let’s talk SPAM, and not the canned kind your Aunty puts in fried rice. But the email kine.

Did you know the term SPAM used for junk mail is an actual acronym? It comes from a law called the Controlling the Assault of Non-Solicited Pornography and Marketing Act of 2003 (CAN-SPAM Act), and the acronym SPAM was a nod to this Monty Python skit. 

Why do I mention this amusing and somewhat random tidbit? Well, I received a few notes from people that they have to dig this newsletter out of their spam folder. If you're finding this in your spam folder, here is a link to directions to ensure that you get your HHHI fix, especially now that we are going twice a month! 

Now we can get back to the only kind of Spam we actually like. Unless you’re like me, team Portuguese sausage (no hate mail please).

As always, if you’ve been enjoying these issues, we’d be grateful if you passed them along to a colleague or friend. More voices make for a stronger hui!

And for those who haven’t subscribed yet, we welcome you to subscribe to the Hui below!

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 Ground Beneath Waikīkī Just Shifted (Literally)

After more than 100 years of holding the land beneath the Hyatt Regency Waikīkī, the Steiner family has sold their six parcels to Texas-based Montgomery Street Partners for $215 million. That’s right, this wasn’t the hotel, just the dirt under it, making this Waikīkī’s largest land sale in years.

Facade of the Hyatt Regency Waikīkī

For those unfamiliar: in Hawaiʻi, some of the most valuable land, especially in Waikīkī and urban Honolulu, is owned by large trusts like Kamehameha Schools, Queen Emma, Lili‘uokalani Trust, or by longtime family landholders like the Steiners. They lease out the land, and others build on it, and while the building often changes hands, the land under it usually doesn’t.

This setup isn’t just for hotels. Plenty of residential buildings and shopping centers sit on leased land, too. Owners control the structure, but not the land beneath it.

When the lease ends, if you can’t strike a new deal, you’re basically out of luck. Unless, of course, you can figure out how to move a building. 

Who Are the Steiners? (I had no idea, so I found out)

The Steiner family’s Hawaiʻi roots begin with James Steiner, who arrived from Bohemia (current day Czech Republic) in 1882 and rose from waiter to landowner. By the early 1900s, he had picked up prime parcels in downtown Honolulu and Waikīkī, including the land beneath what would become the Biltmore Hotel, which was demolished in 1974, then redeveloped into the Hyatt Regency Waikīkī. According to PBN, they also own the land below the AC Hotel in downtown Honolulu. 

As discussed in previous issues, hotels can sometimes be a tangle of owners and operators: one group can own the building, another manages the property, and another owns the flag. And sometimes the land itself belongs to yet another party, adding one more layer to the puzzle. I am exhausted just writing that!

Maui Delays, Honolulu Stalls - It’s a Staycation for Vacation Rental Regulation

As discussed previously, Bill 9, which would phase out thousands of short-term vacation rentals in Maui’s apartment-zoned areas, has cleared committee but still needs a full council vote.

The current proposal gives West Maui until the end of 2028 and the rest of the island until 2030. Hotel and resort-zoned properties are untouched for now, but expect lawsuits, amendments, and plenty more debate before anything is final.

Honolulu 90-Day STR Rule: Hurry Up and Wait

Honolulu’s much-discussed 90-day minimum rental rule, set to start next month, is still on hold. A federal court ruled in early 2024 that the city can’t enforce it until it creates a clear system for managing rentals that were legally operating before the new rule (“non-conforming uses”). That system isn’t ready yet, and as of now, I haven’t seen any timeline for when it will be. In the meantime, the city is still enforcing the old 30-day minimum rental period for most properties.

That lack of clarity and enforcement hasn’t gone unnoticed. This quote from Rob Robinson, President of Springboard Hospitality, during the HTA Oʻahu Virtual Community meeting (as reported by the Star-Advertiser), really shines a light on the issue:

[Efforts should be turned] toward vacation rental regulation and tax collection. We’ve passed a bunch of rules and we haven’t enforced them, and our governments — local and state — haven’t been able to really help in a meaningful way. We often get attacked in the hotel industry, but the reality is we were just as happy when we had 5 million visitors — the extra 5 million are not staying in our hotels; they are staying elsewhere.”

Green Fee Gets Its Brain Trust

As mentioned in past issues of HHHI, the Green Fee passed earlier this year, adding a 0.75% hike to the Transient Accommodations Tax (TAT) starting January 1st, 2026. Now, Governor Green has named a 10-member Green Fee Advisory Council to help decide how the projected $100 million per year will be spent. It’s classic government: create a massive fund to solve a problem, then forget to define the actual solution. What could go wrong?

Chaired by Climate Hawaiʻi’s Jeff Mikulina, the council includes voices from policy, science, community, and tourism. Since hotel guests will be footing most of the bill, it’s good to see at least one hotelier on the council: Outrigger CEO Jeff Wagoner, a seasoned hotel executive with a strong community lens.

It’ll be interesting to see how the money actually gets allocated. Hard not to be reminded that the TAT was originally earmarked specifically for tourism-related efforts… until it got sucked into the general fund. Will the Green Fee follow the same path?

How One Wailea Resort Found $1M in Revenue - Without Adding a Single Room
-Sponsored-

A 5-star property on one of the most beautiful stretches of beach in Wailea had doubts about welcoming day guests. 

Before joining ResortPass in 2020, they had understandable concerns, among them: pool crowding and a potential hit to the guest experience. So they dipped a cautious toe in, offering just two cabanas with highly limited inventory.

Despite the hesitation, they pulled in $385,000 in sales that first year.

By 2023, they leaned in. The property offered up to 12 day passes per day (based on occupancy), doubled the cabana inventory, and began renting daybeds, welcoming up to 30 day guests daily. The result? Gross sales climbed to $892,000.

Now in 2025, this property is on track to hit its first million-dollar year. They recently added an Adult Spa Pass that drove $7,600 in sales in just 3 weeks. 

All while maintaining a serene, high-end guest experience. No drop in satisfaction. In fact, they ranked high in Condé Nast Traveler’s 2024 Readers’ Choice Awards.

This shows that luxury properties can attract day guests and generate substantial revenue, while still upholding a standard of excellence for their overnight guests.

So if you want to potentially drop a cool million to your bottom line without compromising the guest experience, and at no additional cost, it might be time to take a second look at your pool deck.

A Politician with A Rationale Idea?

I liked this quote on LinkedIn from Senator Wakai: “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).” 

Curious to hear what the Hui thinks. 

Do you agree or disagree with this?

Login or Subscribe to participate in polls.

When the Airlines Call You Back

Photo courtesy of Alaska Airlines

It still surprises me that so many people are reading HHHI, and I occasionally get contacted by readers and leadership at companies to clarify (and sometimes correct) information.

I love this for two reasons: one, it shows people are actually reading and paying attention; and two, I’ve always wanted this newsletter to be a conversation, not a monologue, and the Hui a community.

This week, I was glad to speak with Daniel Chun, Alaska/Hawaiian’s MD for Hawai‘i Public Affairs & Sales, about our recent piece on the Hawaiian–Alaska merger. He wanted to add some color to recent changes:

  • While 787s shifted to Seattle (enabling one-stop Europe-Hawai‘i routes), all A330s remain Hawai‘i-based, with Pualani on the tail, the HA brand onboard, and major interior upgrades coming.

  • The combined network opens up 100+ new North America destinations for travelers from Hawai‘i.

  • Despite some non-union reductions, 600+ new frontline roles in Hawai‘i are being added; pilots, flight attendants, airport agents, and maintenance techs.

  • New regional leadership team includes a CEO and many from Hawaiian Airlines, reinforcing commitment to a strong Hawai‘i HQ.

  • An upgraded website and mobile app are launching this spring to enhance the HA guest experience.

  • Alaska/Hawaiian is deeply invested in Hawai‘i and has, in fact, created an advisory board to help ensure this.

I appreciated the conversation and his candor. Their current intentions seem genuine, yet with any merger, the real test will come through actions over time. We’re hopeful, but also keeping a close eye.

Hotel Performance

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

DirectBooker: “Direct” Bookings… Via Someone Else

Apparently, the new way to break free from OTA dependence is to hire ex-Google and ex-Tripadvisor execs… to become your new middleman. DirectBooker, backed by former Tripadvisor CEO Steve Kaufer and ex-Google Travel head Richard Holden, wants to pump your hotel data straight into ChatGPT and Gemini so travelers can “book direct”, just not direct.

The pitch is that they’ll beat the OTAs at their own game by giving LLMs richer info and better prices. The reality? You’re still paying someone in the middle, only now it’s a startup with no product, no hotel partners, and a “pre-seed” war chest to burn. Sure, OTAs are expensive, but swapping one tollbooth for another isn’t exactly the revolution.

And while DirectBooker tries to wedge itself between hotels and guests, Airbnb is quietly muscling in from the other side. CEO Brian Chesky says the company is “going significantly more aggressively into hotels,” courting independents and filling gaps in high-demand markets. You might remember they acquired HotelTonight in 2019; now it looks like they actually plan to use it. Between AI intermediaries and Airbnb’s renewed hotel push, “direct” bookings may soon need their own air quotes.

Check out DirectBooker.com.

ADA Demand Letters: Pay Up or Lawyer Up

When I was head of digital for a hotel company, I got more than my share of ADA demand letters, basically legal shake-downs claiming our website wasn’t ADA compliant and asking for a quick payout to make it go away. Fortunately, we knew we were in compliance and had lawyers ready to push back.

Many hotels just cut a check to make nuisance cases go away, exactly what the attorneys in this cottage industry are banking on. But as Zarco Hotels proved, if you’re in the right and willing to fight, you can win… and even send the bill back to the sender.

Zarco didn’t just beat the claim; they were awarded over $142K in legal fees. The court called it what it was: a money grab.

The lesson? If your website’s in compliance, don’t panic. Document everything, get legal eyes on it, and think twice before writing that check. Not every demand letter deserves one.

Is Google Chrome the next Netscape?

If you’re as old as me, you remember when Netscape ruled the web, until Microsoft buried it with Internet Explorer (which has since been rebranded as Edge), which was then slowly eaten alive by Chrome. It’s been a while since anyone seriously challenged the browser status quo… until now.

Between Comet (from the folks at Perplexity) and ChatGPT with browsing enabled, we’re not just talking about new browsers; we’re talking about replacements for the whole concept of browsing. These tools don’t just help you find links. They summarize, compare, cite, and even interact with websites for you. Ask ChatGPT to find the best hotel in Wailea next weekend, and it doesn’t send you to ten OTA tabs; it just tells you.

Comet pushes this further with its built-in assistant that reads articles, manages tabs, and automates tasks inside the browser itself. It's light, private, and yes, still buggy. But the direction is clear: the old browser is starting to feel like the PDF of the internet, technically useful, but a bit stale.

I’ve been playing with Comet (got an early invite), and it's impressive. The built-in assistant is genuinely useful, and the ability to summarize pages, manage tabs, and even take simple actions feels like a peek at what web browsing should be. It’s less about search and more about delegation, and that’s a big shift.

For hoteliers, marketers, and anyone who relies on search to drive bookings, this is not a passing trend. It is the future. AI is reshaping how people search and what they see. If your hotel isn’t built into the new conversation, it risks disappearing from view altogether.

If you are interested in trying Comet, you can check it out here: https://www.perplexity.ai/comet.

I’m grateful (and frankly shocked 😅) that people are actually reading, and especially thankful when you take the time to write in. 

This month’s feedback covered everything from ResortPass love to culinary redemption arcs. 

Here’s what’s come through the inbox lately: the praise, the pushback, and the occasional poetic rage. As always, all anonymous, all appreciated.

Praise

  • “I look forward to your newsletter every month (and LinkedIn updates). Random note, but Eleven Madison Park just ended their vegan-only run and is back to an all-inclusive (meat-friendly) menu.”

    • Editor Note: Now  I need to start saving so I can go to EMP again!

  • “Such great info, Dan – and love your personal touches to the stories.  Keep it up!”

  • “Keep it up!  …  this information keeps me in the loop and in the know. I will continue to share the goodness by passing it on to help you grow.”

  • “I love your newsletter! I’ve been sitting here reading the entire thing. I’m a big fan of ResortPass and have used it with my family on the Big Island. I’m going to forward this to all of the internal team, so I think you should be getting a few more subscribers.”

  • “Thank you for another enjoyable and informative Hawaiʻi Hotel Hui Insider.   First time for me to hear the phrase vibe coding.”

Strong Opinions (Not Mine)

  • “Awesome congratulations for my Braddah Lanai Tabura — no better selection to represent Hawaiʻi and Hawaiians … imua e nā pōkiʻi brah… 🎉💪👌”

  • “Having been a customer with Hawaiian for 15 years and flying to Hawaiʻi at least twice a year gives me concerns. Flights from non-major hubs to Hawaiʻi and inter-island connections + cost have changed dramatically.”

  • “It’ll go just like any other local company bought out by mainland corporations. No Aloha at all!!! I’m already seeing the trends and hearing the complaints!!”

On Hospitality

  •  ‘It became clear that while we had built something meaningful, we had also unintentionally kept people out. This is the opposite of what we believe hospitality to be.’” Daniel Humm (Chef Eleven Madison Park).

    • Editor’s Note: For those who missed it, that quote came when Eleven Madison Park reversed their vegan-only menu. The message? If your version of hospitality isn’t welcoming everyone, it’s probably not hospitality. 

Industry Events

*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; just send the job link to [email protected].

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/ownership/management 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.