How we built a viral content system in 5 days

December 9th, 2025

Read time: ~ 6 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.

A quick note before we jump in...

Limited time offer to support Onera Wimberley and get immediate monthly cash returns.

We are raising $4 million in private debt for Onera Wimberley at 11%-12%%+ annual yields for up to 24 months from accredited investors

Our private debt offering will close on December 19th. We have $2 million committed so far and expect to be fully subscribed by next week.

Opening just one year ago, Onera Wimberley has already achieved market-leading ADR and occupancy. Revenue is still trending upward and we expect to stabilize in 2026.

We may also be open to simultaneous equity investments from our private debt partners. This represents a nice balance of short-term monthly cashflow via private debt, and bigger upside long-term via equity.

Interested in this Onera Wimberley offering? Join our webinar on December 10th at 5pm Central [register here] or reach out directly to discuss the opportunity.

Now, back to today's topic:

Viral content systems...

I'm not a big face time guy.

I used to hate the expectation of showing face at the client sites when I was working in corporate at McKinsey. The assumption that presence equals productivity.

My motto has always been: if you produce, you can and should have all the flexibility in the world.

That philosophy has shaped how I've built every company from the start. I've relied heavily on overseas talent – it opens up a broader pool of exceptional people and allows me to pay competitive wages relative to cost of living in regions where world-class talent often goes overlooked.

Remote collaboration has always been my default. And it's worked incredibly well for three years.

But…

After 3 years of not seeing my co-founder and much of our Lisbon team in person, I finally made the trip.

5 days. That's all it took to be reminded just how valuable in-person time can be.

I still believe in remote. The flexibility, the global talent pool, the ability to build lean and efficient – all of that remains true. But I'd love to make it back to Lisbon quarterly with how productive we were and how much momentum we created.

Reality is, with 2 kids under the age of four at home, quarterly isn't realistic. But a couple times a year? Non-negotiable.

Here's what made it so worthwhile.

The Breakthrough That Made The Flight Worth It

In my first 10 minutes sitting down with my co-founder after I arrived, I was able to download his brain on something we had talked about on the phone for months:

Viral hooks.

We'd been discussing this on calls for months. Trading ideas. Sharing frameworks. Getting close but never quite landing on something elegant enough to scale across our entire team.

In person, something clicked and what followed after 10 mins was the most elegant system for generating viral hooks that anyone on our team had seen before.

I'm still not sure why face-to-face made such a difference. Maybe it's the bandwidth – body language, real-time feedback, the ability to sketch concepts and iterate together. Maybe it's just the focus that comes from being in the same room without the distractions of home.

Over the next few days, our team got together to teach each other everything we knew about hooks.

We called it Hook University.

Not just theory – we were building a system. Something repeatable. Something we could train others on.

Here’s the breakdown of what we came up with.

The 3-Part Framework That Changes Everything

Every viral hook – regardless of platform, industry, or content type – answers three fundamental questions:

1. Desire – What’s the goal or payoff the audience wants?

2. Challenge – What’s the obstacle standing in their way?

3. Payoff – What’s the resolution or solution you’re offering?

The elegance is in the simplicity. But there’s one critical nuance that separates good hooks from viral ones.

Your hook should only provide a partial payoff – just enough to signal that you have the solution while leaving the details behind the engagement. The payoff needs to relate back to both the desire and the challenge, creating a bridge that makes people want to cross it.

This is what creates the curiosity gap.

I’ve heard countless creators talk about “creating curiosity” or “signaling value before delivering it.” But nothing has been quite as simple and actionable as this three-part system.

The beauty is in its flexibility. You don’t need to follow the 1-2-3 order. You can lead with challenge, tease the payoff, then reveal the desire. Or show the desire visually while stating the challenge in text. The components can be implied, reordered, or mixed across formats.

Let me show you how this works in practice.

Example 1: Wellness Resort Content

Imagine you’re promoting a wellness resort with a sleep optimization program.

Desire: Better sleep and real restoration
Challenge: Been to doctors, tried many supposed sleep hacks, no clue what to try next.
Payoff (partial): “Here’s what 3 days at a sleep resort did to my Oura ring scores”

The hook signals a measurable transformation (Oura scores changed) but doesn’t reveal how it happened. That gap – between knowing something worked and understanding the mechanism – is what drives engagement.

Example 2: Hotel Marketing Strategy

Or let’s say you’re teaching hotels how to reduce OTA dependence.

Desire: More direct bookings, less reliance on third parties
Challenge: Can’t break through with existing marketing efforts
Payoff (partial): “The one content strategy that got us to 80% direct bookings”

You’ve proven the result is achievable. You’ve acknowledged why it’s hard.

But the actual strategy?

That requires them to engage with your content.

This framework works because it mirrors how humans naturally process decisions. We want something. Something’s stopping us. We’re looking for a bridge between the two.

When your hook explicitly addresses all three, you’re creating relevance.

From Framework to System

Over the course of Hook University, we generated hundreds of specific hooks and proven formats across every industry we work in – hospitality, wellness, real estate, e-commerce.

But we didn't stop at examples.

We took the entire framework – the three-part system, all the hooks we'd created, all the structural variations – and uploaded it to a custom GPT.

The results were shockingly good.

This isn't just another AI tool that spits out generic suggestions. It's trained on our specific framework and thousands of high-performing hooks. It understands the nuance of partial payoffs. It knows how to sequence desire, challenge, and resolution for maximum impact. It can adapt across industries, platforms, and content types while maintaining the core elegance of the system.

Right now, it's purely for internal use at Oasi. We're using it to scale our content production while maintaining quality across every client we work with.

But we're considering offering the full hook framework breakdown and access to the generator on a subscription basis.

If that interests you, hit reply and let me know. We’re gauging demand before we build out the full offering.

Beyond Hooks

The hook framework alone would have justified the trip.

But when you get your entire team in a room for 5 days, you tackle more than one problem.

We spent focused time on the strategic questions that are hard to resolve over Zoom calls:

Business focus and priorities – We mapped out exactly what we're doubling down on for the next 12 months and, just as importantly, what we're saying no to. Clarity on what not to do is often more valuable than adding to the roadmap.

Top priority hires – We identified the specific roles we need to scale Oasi effectively. Not just "we need more people" but exact skill sets, reporting structures, and how each hire compounds our ability to serve clients.

Financial goals – We set our 3-year targets for Oasi's growth. Ambitious but grounded in what we know we can execute.

Oh, and because my co-founder Jesse is a biomechanics savant, he spent an hour dissecting my golf swing and gave me specific feedback I can actually practice when I get home. That alone might have been worth the flight.

I'm already planning my next trip back – likely with my family this time – for mid-2026.

Between now and then, we have a lot of work to do.

Why Do Hooks Even Matter?

The hook framework isn't about chasing viral moments or racking up vanity metrics like impressions and followers…

It's about understanding how the Modern Traveler actually discovers and evaluates hotels in 2025.

They're not starting on Google. They're not comparing properties on OTAs. They're scrolling through content – Instagram, TikTok, LinkedIn, newsletters – and making split-second decisions about what deserves their attention.

If your hook doesn't stop the scroll, you simply don't exist.

But here's what most hotels get catastrophically wrong:

They lead with features instead of desire.

They describe the property instead of the transformation it enables.

They answer questions no one is asking.

“Luxury beachfront resort with world-class amenities” tells me nothing about whether this place solves my problem.

But “Here’s how we helped a burned-out executive sleep for 10 hours straight for the first time in 5 years”? That’s a hook. That’s desire (rest), challenge (chronic exhaustion), and payoff (measurable transformation) in a single sentence.

The Desire → Challenge → Payoff framework forces you to think like your guest instead of like a hotelier.

What do they actually want? What’s preventing them from getting it? How does your property bridge that gap?

When you nail that structure consistently across every piece of content, something remarkable happens. Your engagement increases. Your audience grows. Your direct bookings follow. Not because you’re gaming algorithms, but because you’re creating genuine relevance.

This is the shift we help hotels make at Oasi.

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 a content system that actually drives bookings instead of just likes, 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

P.S. If you’re interested in getting access to the full hook framework breakdown and our custom GPT hook generator (trained on thousands of high-performing hooks across every industry), hit reply and let me know. We’re gauging demand before we build out the full offering.

🎥 Check Out Our Latest Podcast Episode On “This Week In Hospitality”

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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