My 2025 wins, what didn't work, and contrarian bets for 2026

January 6th, 2026

Read time: ~7 minutes

Welcome to our weekly chats navigating the future of hospitality!

Hospitality is changing faster than we have ever seen. Each week, I share insights and strategies to help you navigate the future of hospitality marketing, revenue management and the demands of the Modern Traveler.

Let’s craft the future of this industry together.

2025 was all about execution.

For years I’ve talked about starting a podcast. Finally launched This Week in Hospitality.

For years I knew I should focus on my personal Instagram brand. Finally committed – grew from 3K to 40K followers in 8 months.

For years I wanted to build another hotel brand. Finally assembled the team and founded Baya. Raised all the equity for our first location in South Florida’s Redlands and finalized the full capitalization plan.

The biggest lesson from 2025: just do the thing you keep putting off.

Here’s the full breakdown of what worked, what didn’t, and where I’m placing my bets for 2026.

What Worked in 2025

This Week in Hospitality

Launched the podcast with Zach Busekrus, Scott Eddy, and Edwin Kramer. Something I’ve been thinking about for years but never pulled the trigger on.

Turns out the format works. Breaking down the biggest hospitality stories each week with people who understand every facet of the business.

Instagram growth

Finally focused on short-form video for my personal brand on Instagram after years of knowing I should.

3K to 40K followers in 8 months. Found a content format with consistent engagement and regular virality that resonates with our target audience – making me and Oasi more visible to ideal hotel clients.

Baya

Brought the team together to found Baya in early 2025.

Raised all equity and finalized a full capitalization plan of both debt and equity to fully finance Baya location one in the Redlands. Started building out a roadmap for locations 2 through 15.

This wouldn’t have happened without leveraging my personal brand to assemble a best-in-class team, raise capital, and find the right opportunities.

Onera Wimberley

Climbing closer to stabilization. October was our best month to date at $326,000 in revenue compared to $196,000 last year – 66% growth year-over-year.

Period-over-period growth in the last six months has been strong:

ADR climbed from $433 to $460
Occupancy grew from 60% to 76%
GOP increased from 49% to 60%

Group sales went from $18K in the first half of the year to $108K in the second half.

Onera Fredericksburg expansion

Opened on time and on budget with some of our most unique and ambitious designs yet.

The Monolith unit with its 40-foot cantilever wrapped in floor-to-ceiling glass is my personal favorite design we’ve ever done.

Oasi pivot

This is the one that required the most discipline.

We stopped chasing revenue and started being ruthless about only partnering with the best hotels in the world.

Earlier in the year, we brought on clients just to get revenue in the door. We had to unwind some of those short-sighted decisions.

Now we’re uncompromising about our ideal client profile – hotels we can work with across both marketing and revenue management.

We expanded from a social media and content agency to fully outsourced CMO and CRO services. Built out our creative content team. Expanded our proven content formats from 1 to 5.

What Industry Trends Validated Our Approach

Three things I’ve been betting on for years kept accelerating in 2025.

Outdoor hospitality isn’t a fad. A lot of people think the outdoor trend was manufactured by Covid and would fade. For those doing it right – unique, authentic, experiential outdoor hospitality – it’s just getting started.

Farm hospitality and agritourism. Properties like Blackberry Farm, Southall, Babylonstoren, and The Newt are crushing it as well as ranch properties like Brush Creek, Ranch at Rock Creek, and Paws Up. This category is having a moment, and the data backs it up.

Health and wellness travel. Wellness is flowing into everything from corporate offsites to leisure stays. Properties treating this as core product are winning.

The 2026 Roadmap

Oasi: Building out and refining a B2B funnel for our ideal client profile – the best hotels in the world.

Baya: Executing on location 1 with a goal of finishing construction by year end. The project completion estimate is Q1 2027, but Q4 2026 is the reach goal. Building out the roadmap for our next 10-15 locations.

Instagram: Growing from 40K to 100K followers.

Onera: Stabilizing and refinancing both Wimberley and the Fredericksburg expansion.

Three Big Bets for 2026

I’m betting big on three trends that most people are sleeping on.

1. Farm Hospitality Goes Mainstream

For those who know, farm hospitality is already the hottest trend in luxury travel.

2026 is when it hits center stage.

The global agritourism market is growing at 12% annually. Properties earning Michelin Keys and James Beard awards. Guests paying premium rates to harvest vegetables for dinner and understand exactly where their food comes from.

But here’s what’s going to happen: big brands will try to hop on the trend by slapping gardens and farm-to-table menus onto big box hotels. They’ll miss the mark entirely.

The properties that win are the ones that build the hotel around the farm. Where the agricultural operation comes first and everything else flows from that.

Those properties are already winning. And the gap will widen in 2026.

2. Content Becomes Core Strategy

More hotels will finally wake up to how far behind the industry is on social media and content marketing.

Full-time in-house content teams will become the gold standard.

Not a social media coordinator who also handles email and event planning. Actual dedicated teams – videographers, editors, creative strategists, producers.

Content will become the primary pillar that all hotel marketing and revenue strategy revolves around.

I also think Instagram rolls out their version of TikTok Go in 2026. I just hope they give hotels the ability to drive bookings direct instead of partnering exclusively with big OTAs.

Either way, this pushes hotels to take content even more seriously.

3. Equity Capital Flows Again

By mid-2026, equity capital is going to be flowing like we haven’t seen since 2022.

Interest rates coming down means more hotel projects pencil. Investors are looking for yield. Less volatility and more optimism about the economy.

My first project in 2021 was the easiest raise I’ve ever done – $1 million in equity in less than two weeks. Rates were at zero and everyone was chasing yield.

2023 through early 2025 tough for raising equity into ground-up hotels with interest rates at all-time highs.

The past six months while raising for Baya, I saw equity investors coming back to the table. The momentum feels like it’s building as rates drop further.

My Contrarian Take for 2026

Many hotel and travel industry experts are calling for flat or declining growth year-over-year.

Last year I thought many of these same experts were overly optimistic in their growth projections. They kept revising estimates downward as the year went on.

With interest rates coming down, new and exciting hotel projects getting funded and opening, inflation stabilizing, and some renewed optimism overall – I see 2026 as a rebound year for travel and hospitality after a slow 2025.

Here’s why.

Travel is a life priority for Millennials and Gen Z, not a luxury. These generations are moving into their peak earning years. Travel and unique experiences are core priorities for them in ways they weren’t for prior generations.

Revenge travel is coming again. Many people skipped or shortened trips in 2025 due to the economy, inflation, and uncertainty. Those travelers will want a little more in 2026 to make up for what they missed in 2025.

Unique experiences beat big box hotels. Not only are leisure travelers choosing boutique and experiential stays, but so are groups – corporate offsites, social events, retreats. The undifferentiated big box hotel model is losing ground.

Hotel supply has been constrained. High interest rates and build costs kept new supply limited. As rates come down and projects pencil again, you’ll see more unique properties opening that drive demand.

What to Watch in 2026

A few specific things I’m tracking:

Health and wellness accelerates. Non-toxic everything becomes table stakes. Sauna and cold plunge go from luxury amenity to expected. Self-serve wellness circuits start popping up everywhere. Sleep health becomes a core differentiator – smart beds, circadian lighting, sleep wellness programs. Hotel gyms finally move beyond being a box-ticking afterthought.

AI SEO becomes critical. Every executive and owner cares about their hotels are showing up in ChatGPT search. Properties that figure this out early will have a massive advantage.

Short-term rentals struggle. Regulatory pressure everywhere. Even Airbnb is welcoming hotels now, which feels like throwing up the white flag. Too many people chasing the same amenity-rich STR strategy in too few markets where it actually works.

Mid-tier hotels get squeezed harder. People don’t want to pay 50% more for a mediocre product. They’ll pay 5-10x for a world-class experience or 50% less for a budget option and spend more at their destination. The middle is getting hollowed out.

What This Means for 2026

The biggest opportunities in 2026 are for operators who commit fully to what they’re building.

Farm hospitality properties that build the hotel around the farm, not the other way around.

Hotels that treat content as core infrastructure, not a nice-to-have.

Properties that understand wellness as foundational to the experience, not a spa add-on.

Developers who move fast as equity capital becomes available again.

The operators who’ve been waiting for the market to turn – this is your window.

At Oasi, we help hotels position themselves for exactly these shifts.

We act as your outsourced Chief Marketing Officer and Chief Revenue Officer, giving you executive-level leadership backed by a full team of specialists in content, social media, ads, email, SEO, pricing & distribution strategy.

If you’re ready to build for 2026, we’d love to help.

Fill out an inquiry here and let’s explore how we can work together.

See you next week.

— Ben Wolff

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🎥 Check Out My Podcast with Steve Turk Diving into The Story Behind Baya, Our New Tropical Landscape Resort

🎥 Check Out My Episode on The Bigger Pockets STR Podcast on Redefining Luxury Hotels and Outperforming Traditional Hotel Models