Inside the Curious Builder Boot Camp: Costa Rica 2026 Entrepreneur Retreat

There are a lot of conferences, business retreats, networking events, business workshops, and educational summits in our industry. While those all have their place, the Curious Builder Boot Camp was never meant to be one of them.

Boot Camp came out of something much simpler: the realization that entrepreneurship (and building in particular) can be a lonely road.

Over the years, the Curious Builder Podcast showed me that just talking honestly about the struggles and uncertainty of running a business created a sense of solidarity. That, in turn, sparked better ideas, deeper relationships, and healthier perspectives.

Boot Camp became a natural extension of that.

At first, it was just an excuse to bring people together in a place I loved. But it quickly grew into something much bigger: a true entrepreneur retreat designed to help builders and business owners reset, reconnect, and return home with more clarity.

Who Boot Camp Is For

At its core, Boot Camp is an immersive reset. It’s a place to unplug from the constant noise of emails, job sites, schedules, and responsibilities. We step away from the day-to-day so we can actually check back in with ourselves, our businesses, and each other.

We spend our days outside. We move our bodies. We have real, honest conversations. And when it’s over, most people leave feeling refocused and reenergized.

Boot Camp is for builders, entrepreneurs, and anyone leading a high-stress, high-output life.

When I look at the people who are thriving in business and in life, they all share similar rhythms. They wake up early. They exercise. They read. They reflect. They create space to think.

Boot Camp doesn't teach those ideas in a classroom session. We actually living them, together, for a few days. When you experience those rhythms in community, something shifts.

Learn more about the past bootcamp here!

Why Costa Rica Was So Special

This year’s Boot Camp took us to Costa Rica! We stayed at a villa where everyone lived under the same roof. There were shared rooms, family-style dinners, and long evenings together on the rooftop.

It felt a little like summer camp for adults.

Those shared spaces created a level of intimacy that’s hard to replicate anywhere else. We’d sit together at sunset, talking about everything from business ideas and struggles to family life to our biggest fears and most meaningful memories. Those conversations were some of the most memorable parts of the trip.

Movement, Nature, and a Little Adventure

Nature is always at the core of Boot Camp. Whether we’re in the mountains or on the coast, being outside has a way of clearing your head.

Every morning started with movement. We worked out together, pushed each other, and then carried that energy into the day. We also mixed in physical team competitions and outdoor adventures.

One day we were surfing. Another day we were canyoneering. There was whitewater rafting, hiking, and plenty of time in the sun.

Some of my favorite moments were just watching grown adults laugh like kids. On the rafting trip with Brad Leavitt, it felt like we were a bunch of puppies at a dog park: pure energy, zero pretense, just enjoying the experience together.

Food That Fuels the Experience

One thing we don’t overlook at Boot Camp is food. You can’t show up physically or mentally if you feel terrible.

Costa Rica made that part easy. The food was fresh and delicious. Tons of fruit, eggs, and meals prepared by great chefs. It was simple and nourishing: exactly what you need for long, active days.

What I Took Away

Every Boot Camp leaves me with something different. This one was a reminder to slow down, be present, and laugh more.

Our jobs are intense. There’s always another project, problem, or decision waiting for us. But at the end of the day, we’re all human in need of connection. And those conversations, the laughter, and the shared experiences make everything else worth it.

Boot Camp 2027

We’re still finalizing the details for 2027, but the general idea is to rotate environments ith mountains one year and beach the next.

Right now, we’re exploring options in places like Colorado, Montana, Mexico, or Puerto Rico. Different settings, same mission: get outside, move, connect, and come back better than you left.

If this sounds like something you need, you’re probably right.

Step away long enough to gain the perspective you can’t find in the middle of your normal routine.

If you’d like to be part of the next Curious Builder Boot Camp, join the interest list and be the first to hear when 2027 details go live!