Billionaires, Bifurcation, and a Stock Photo That Refuses to Die

October 07, 2025

Aloha !

Welcome to this month’s Hawaiʻi Hotel Hui Insider.

First up, congrats to our issue sponsor Castle Resorts & Hotels, who take over management of the Waikīkī Circle Hotel on November 1. It’s the property’s first new operator in 30 years. See what happens when you sponsor the newsletter? 😉

Quick housekeeping before we dive in: we’re switching our email domain. Future issues will now come from [email protected] and [email protected], so if you want to actually see the newsletter (not fish it out of spam), please whitelist both. Curious how? We’ve got a quick how-to here.

Now, onto the fun stuff...

In this issue: a billionaire buys the land under his own hotel, Outrigger and Springboard swap execs, we have a new word of the week (bifurcation), and the HTA Conference delivers data, discussions, and our favorite stock model.

Know someone in Hawaiʻi hospitality who should be reading this? Forward it their way, sharing is caring (and helps us grow the Hui).

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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 😄

Billionaires Land Club

A fund tied to Michael Dell just dropped $400 million to buy the land under the Four Seasons Hualālai on the Big Island. He already owned the hotel, but the land was held by the Kamehameha Schools (KS) Trust.

We’ve been talking about leaseholds lately, and this one’s a standout. It’s pretty rare for KS to sell land, because while a sale gives you a one-time profit, holding on generates steady income in perpetuity. 

For Dell, the math is easy. He now owns the property outright, which makes any future sale much cleaner and surely a lot more lucrative.

Just as a reminder: Larry Ellison bought 98% of Lānaʻi, including two of the three hotels, for $300 million back in 2012. He later picked up Hotel Lānaʻi, so he now owns all the hotels on the island (along with the Island). That is just pocket change for Larry, who recently had a one-day stock gain of $100 billion.

So yeah, Dell paid more for the land under one resort than Ellison did for an entire island.

Put that on your Monopoly board.

Let’s say Eliisons’ and Dells’ are unlikely to be like the Robinson family of Niihau (see entertainment section).

If you are interested in a deeper analysis of the investment, my friends at Powell & Aucello explain it in detail here.

Castle Joins the Circle

This month’s issue sponsor, Castle Resorts & Hotels, is also making headlines.

Starting Nov. 1, Castle will take over management of the Waikīkī Circle Hotel. It's the property's first new operator in over 30 years. It becomes Castle’s 18th property. The hotel was previously managed by Aqua-Aston.

I really liked this quote from Castle CEO Matt Bailey:

“The Circle has always stood out for its shape, but not always its presence. Castle plans to change that, honoring its 1960s legacy and keeping it family-owned and locally run. A refreshing angle in a market where ‘heritage’ is often little more than brochure copy.”

Congrats to Castle, will be interesting to see what they do with it.

Trading Places

Outrigger just hired Jason Pirock as VP of Global Brand Marketing, effective September 1. If the name sounds familiar, it’s because he was previously the Head of Marketing & Brand at Springboard Hospitality, who manage 13 properties here in Hawaiʻi (and many elsewhere).

In talking with Jason, the big driver behind the move was the chance to help shape Outrigger into a truly iconic global brand, and it doesn’t hurt that he gets to move to paradise. Aloha and Welcome, Jason!

AI is changing search. Are guests finding you?
-Featured Partner-

Most hotel websites were built for people, not machines. But that’s changing; guests won’t “search,” they’ll ask AI.

And if your content isn’t structured and human-friendly, you’re invisible.

three&six builds brand, web, and content ecosystems designed for discovery, by guests and machines.

Built for humans. Structured for AI.

Outrigger Owner KSL Refis, But Still No Exit

KSL Capital Partners just closed a $480 million refinancing deal on two of its Hawaiʻi properties: Outrigger Reef Waikiki Beach Resort and Sheraton Kauaʻi Coconut Beach Resort. Both are owned by KSL, but only the Reef is part of the Outrigger portfolio.

KSL used most of the proceeds to pay off existing loans and pulled out nearly $148 million in equity, while maintaining full ownership. Private equity rarely wants to tie up its own capital longer than necessary. If they can refinance, pay off old loans, and pull out equity while keeping control, they’ll do it. Debt becomes a tool for liquidity, in other words, more cash to buy more stuff.

Most private equity holds last 5 to 7 years; KSL is already at year 8+ into it’s acquistion of Outigger. For now, they’re holding (re-financing) and still investing in upgrading the properties.

Notes from The HTA Conference

From left to right: Jason Gamel, Hannah Smith, Raul Mamani, Dan Wacksman

I had the chance to attend the HTA Annual Conference on September 22nd and 23rd, and was honored to moderate a panel on “The Evolving Landscape of Lodging in Hawaiʻi.” It was a packed two days of updates, data, and discussions. A Few Quick Hits from the HTA Conference (and my panel):

  • Hotel Growth? Blink and You’ll Miss It. 

    • Since 2006, Hawaiʻi has added… wait for it… just 60 new hotel rooms. We’re now at roughly 43,236 rooms statewide (for scale, Vegas has over 150,000 rooms).

  • Vacation Rentals: The Real Growth Story

    • Since 2006 legal vacation rentals jumped 839%, from around 2,400 to 17,531. And that’s definitely understated, as only legal units are counted in the DBEDT numbers.

    Convention Center: More than Just a Leaky Roof

    • Repairs include $114 million to fix leaks and another $48.8 million for visible upgrades, restrooms, A/V systems, and fresh paint, among other improvements. More Details Here.

    • The current forecast? Reopening in 2028. While I was excited by the plan outlined by Convention Center GM Teri Orton, I am a bit skeptical of the timeline, as construction, in general, and government-led construction projects are not known for being on time. 

  • Water, Water Everywhere, But Not a Drop to Irrigate

    • Ran into several Maui friends at the conference, and let’s just say, losing the Sentry golf tournament hit hard. The financial loss is one thing (~$50 million). The reputational damage? Even worse. Future tournaments are in doubt, and visitors are left wondering if Maui’s ready for tourists.

  • The Ubiquitous Stock Photo Star Lives On 

    • Years ago, while deep in marketing, I kept seeing the same face in ads for hotels, airlines, banks, you name it. I dubbed her the “ubiquitous Asian lady” because she was the Asian model in nearly every ad I saw. Turns out, she’s Rebecca Givens, a hapa Canadian model and the world’s most-used stock photo star. This 2016 article tells the story. Once you see her, you’ll spot her everywhere. Sure enough, she popped up at last week’s HTA conference on at least three occasions.  Still smiling. Some things change (HTA Drama, AI, OTAs, enshittification)… but some stock photos are forever.

Hotel Performance

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

From Enshittification to Bifurcation

In the last issue, we talked about enshittification, a term Rafat Ali has used to describe what happens when businesses slowly degrade when they shift from serving users to extracting profits. At first, they serve the customer, then shareholders, and eventually, everyone’s experience suffers. Hotels aren’t immune; loyalty programs, resort fees, and shrinking service levels are all symptoms of the same slide.

At the HTA conference, STR tossed another word into the mix: bifurcation. That’s the industry’s way of describing a split market, high-income travelers still spending big, while everyone else is pulling back. Luxury is holding strong while budget and select-service are under pressure.

And it’s not just consultants saying it. Marriott’s CEO flagged the same bifurcation trend at a recent investor event.

So now we’ve got names for two forces shaping the hotel landscape: enshittification (the slow decline of value) and bifurcation (travelers splitting into haves and have-nots). Both of these phenomena are on display in this now-viral TikTok video taking to task a Waikiki resort. Can you name the resort? Do you agree with here take? Are you enshitfying your guests experience?

AHICE Aloha: Big Voices, Bigger Conversations
-Featured Partner-

Over 50 hotel leaders from Hawaiʻi and beyond will take the stage at this year’s AHICE Aloha, including execs from Outrigger, Marriott, Wyndham, Springboard, Colliers, HVS, and more.

Expect sharp takes on development, operations, investment, and tech—plus a front-row seat to the issues shaping our industry.

We’ll be there. Will you? See the events section below for an opportunity to get some free tickets!

Ace in the Hole: Prince Hotels Goes Lifestyle

Seibu Prince Hotels is buying Ace Hotels (and its in-house creative arm) for about $90 million. The Prince brand feels a bit dated, and adding Ace gives them the lifestyle edge they’ve been missing. It also helps diversify their portfolio, important if they’re serious about their 250 hotels by 2035 growth plan. The deal adds nine properties (eight open, one in development), taking Prince’s total to about 95 hotels worldwide.

Seibu Prince currently has two properties in Hawai‘i: Prince Waikiki and the Westin Hapuna Beach. Maybe an Ace will be next? 

Minority Report or Big Bang Theory?

OK, I’m a gadget nerd, and quite possibly just a nerd. So when a friend showed up wearing Meta’s Ray-Ban smart glasses, I did what any reasonable person with a credit card and weak self-control does: I bought a pair immediately.

I mostly use them to take pictures without pulling out my phone, listen to music, and ask the AI random questions. The real-time translation feature is slick too, though the language options are still pretty limited.

Of course, days later, Meta dropped the Hypernova: their new $800 smart glasses with actual displays and a neural wristband for gesture control. Basically, Ray-Bans with a heads-up display and jazz hands. Think Minority Report, but instead of Tom Cruise, think Sheldon from The Big Bang Theory.

I’m enjoying the Ray-Bans, though I’m slightly self-conscious about looking like a glasshole. And honestly, I think I’m giving off more Sheldon than tech visionary.

Industry Events

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

three&six will be in Hawaiʻi Oct 26–31, visiting partners on Oʻahu, Maui, and Hawaiʻi Island. If you’re exploring new digital support, curious about 2026 trends, or want to see how your property shows up in AI search, let’s start with a quick pre-meeting. From there, we’re happy to stop by or host a pau hana with your team.

Win a Free Ticket to AHICE Aloha
-Vendor Pop-Up-

Want to attend the 2025 AHICE Aloha Conference on November 7th, 2025 at Prince Waikiki - for free?

We’ve got a limited stash of comp tickets, and here’s how to grab one:

  1. Repost any HHH story on LinkedIn

  2. Shout out Hawaiʻi Hotel Hui in your caption

  3. Send a screenshot of your post to [email protected]

First-come, first-served, while supplies last.

You’ll join hotel leaders and execs from across Hawaiʻi and around the world for a full day of panels, keynotes, and big industry conversations.

*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].

I recently watched Kuleana: Niʻihau, and it totally pulled me in.

As alluded to in our billionaire update, Niʻihau and Lānaʻi are the only two privately owned Hawaiian islands (still don’t really get that). This short doc gives a rare peek into daily life on Niʻihau. Watch it here.

Parts are in English, but a good chunk is in ʻōlelo Hawaiʻi, not staged, not translated, just everyday talk. Hearing it used so naturally was one of the coolest parts, along with seeing the island and everyday life. If someone has to own an island (which I think is very strange), I’d rather it be someone like the Robinson family than a tech billionaire who looks like an evil villain from a Marvel movie.

I’m always grateful when people take the time to write in, whether it’s praise, critique, or unsolicited policy reform. Below are a few standouts from this month’s inbox. As always, I don’t necessarily agree with these takes… but I’m glad we’re talking about them.

Praise from the Peanut Gallery

  • “Even though I’m not in the hotel business, I read every word. Fascinating insider stuff.”

  • “Always love getting the inside scoop, especially that TikTok OTA bit. Social media is changing how families plan Hawaiʻi trips.”

  • “Luxury is here to stay. People who can afford great service will keep paying for it.”

  • “Love seeing a woman CEO take the reins 🙌🏽.” [Re: Hawaiian Airlines]

  • “Congrats to Castle Resorts on the sponsorship, well deserved.”

HTA: Hype Team or Hall Monitor?

  • “HTA keeps trying to be two things at once, cheerleader and cop. You can’t say ‘Visit Hawaiʻi!’ and then scold people for how they visit.”

  • “Split the job: HTA does marketing. Give stewardship to another agency, Planning or Consumer Affairs, maybe.”

  • “It is possible for one org to market and manage tourism if you hire the right leader and keep politics out of it.”

Want to weigh in? Agree? Disagree? Hit reply or email [email protected], and you might end up here next time, anonymously, of course.

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 and other acronyms), 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.