A few years ago, I had finally internalized one brutal truth about entrepreneurship:
Trying to do everything yourself is a recipe for failure.
My early days were a classic entrepreneurial trap. I thought I could handle it all - wearing every hat, managing every detail, leveraging offshore VAs to stretch myself as far as possible without hiring expensive 100x talent.
My first company was constrained by my biggest limitation: myself.
The hardest lesson? My business could only grow as far as I could personally carry it.
Looking back, it was destined to remain a small operation - a lifestyle business that would never truly move the needle in the hospitality industry.
When I started Onera and Oasi, everything changed.
I realized success isn't about working harder. It's about finding the right people and giving them room to excel.
Take my journey with my cofounder at Oasi - a story that might surprise you.
Years ago, he was my boss. And yes, he fired me while I was getting sober. Honestly? The firing was completely justified. I wasn't in a place to be a reliable team member.
Fast forward a few years, and he saw something in what I'd built with Onera. Our conversations about doing something together again grew more serious. As Oasi's vision took shape, it became increasingly clear that we needed each other.
At first, the idea of giving up significant equity was terrifying. He wanted more than just a small piece - he wanted a substantial stake that reflected his belief in our potential. But he didn't want to be CEO again. He wanted to be the product genius.
The more we talked, the more it became a no-brainer. His obsession with content was unlike anything I'd seen. He sees marketing differently - not just as a function, but as an art form.
Giving up control was scary. But watching him work? Totally worth it.
He's transformed our entire approach. Most of our viral formats come directly from his mind. Plus, he’s brought in incredible talent along with him.
With my GC on the construction side, Banks, it was a similar story.
He proved himself repeatedly on the development of Onera Wimberley and the expansion of Onera Fredericksburg. When he asked to be a true partner in Baya, I had to take a hard look in the mirror.
But I realized something crucial: I'm not building this without him.
The playbook for scaling isn't complicated, but it's counterintuitive:
Hire slowly. Be patient. Look for A-players who complement your skills.
Be willing to give up equity for force-multiplier talent. The right partners are worth it.
This year, we've been ruthless about maintaining quality on our team. We trimmed the fat, keeping only our best people. Every new hire goes through multiple interviews and tests. We start most people on a contract basis, knowing many won't cut it.
The result? A team where everyone is motivated. Where the sum becomes greater than its individual parts.
And here's the real magic: we're no longer constrained by my individual limitations.
With this team, we're now positioned to do something truly transformative. We're not just another marketing agency - we're reimagining how hotels connect with modern travelers. The hospitality industry is ripe for change, and now we have the collective firepower to make a real impact.
What was impossible at my first company is now our everyday reality. We can take on larger clients, bring innovative strategies to market, and genuinely move the needle for hotels struggling to adapt to a new era of travel.
All because I didn’t try and wear every hat this time around.
My biggest lesson? People are everything.
Arm your best people with incredible support. Create an environment where A-players want to stay. Be willing to compensate them not just fairly, but generously.
Because at the end of the day, your business is only as good as the people building it.
Ready to have a team of experts running your marketing and revenue strategy?
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, and pricing strategy.
If you want to boost revenue and drive more direct bookings, we'd love to help.
Fill out an inquiry here and let’s explore how we can work together.
See you guys 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
🎥 Check Out My Podcast Episode on the Action Academy about Making Millions Through Direct Bookings
Ben Wolff
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