The Only Place You'll See Me Live in 2026.

You don't have an information problem. You have an environment problem.

Five days · Six coaches · All-inclusive · Flights included

Reserve Your Spot

Talk It Through First

September 14–24, 2026 · Cancun, Mexico · All-Inclusive

Limited spots · Registration closes August 25th.

You're drifting.

You might not call it that. You might call it planning. Building. Figuring things out.

But if you're honest — really honest — you've been in roughly the same place for a while now.

The ideas are there.

The ambition is there.

The plans are sitting in a notes app somewhere.

Nothing is moving.

Not because you're lazy. You're probably one of the most capable people in any room you walk into.

The problem isn't you.

It's the environment.

Same surroundings. Same conversations. Same version of yourself waking up every day doing the same things and wondering why nothing changes.

You keep consuming. Courses. Podcasts. Books. Frameworks. At some point, preparation became the thing you do instead of the thing you're preparing for.

Drift doesn't feel dangerous. That's why smart people stay stuck in it for years.

You don't notice it while it's happening. You notice it when another year is gone.

More information isn't going to solve this. Neither is more discipline.

Sometimes you need to get completely out of your normal environment before you stop telling yourself the same shit every day.

That's what this retreat is.

The Moment I Knew

I run my entire business online. By design. I built it that way. I teach it that way.

So when I tell you there's one event on my 2026 calendar — one — that should tell you something.

Last year I went to Cancun as a coach for this retreat. It's run by Billie Olds — kick-ass serial entrepreneur, basically my little sister at this point (even my mom says so), and one of the few people I trust completely when it comes to this stuff.

I expected it to be solid. It was more than that.

Here's the moment.

One of our guys strapped into a raft at the top of a 135-foot waterslide. Pitch darkness. Seventy-five seconds before you hit the wave at the bottom.

Somewhere in the middle of that thing he realized something.

Velocity.

He either creates it or destroys it. Every day.

And he'd been destroying it for a year. Every "safe" decision. Every "I'll wait until I'm ready." Every excuse dressed up to sound responsible. Brakes. All of them.

He came out of the water talking differently. Faster. More certain. For about 75 seconds he quit bullshitting himself.

That same trip, someone found his entire mission over hibachi dinner. Not in a session. Over steak and shrimp. I was sitting right there. Right question at the right time. A month later he raised his prices 50%. Nobody was surprised.

A guy who'd been "thinking about" leaving his corporate job for three years made the decision on day four. He took a remote role first. Then moved abroad. Now he's building his first business.

One woman got home and finally launched the podcast she'd been talking herself out of for months. Started talking into a microphone instead of sitting around overthinking everything.

You get people out of the same environment long enough and weird things start happening fast.

Environment always wins.

How It Actually Works

From the outside this probably looks like a nice trip with some coaching. It's not.

There's a reason the biggest shifts happen on waterslides and at dinner tables instead of in classrooms.

Here's what happens.

You show up guarded. Everybody does. Still half in your normal life. Sizing people up. Keeping it professional.

Then the first night gets weird fast. Karaoke. Ridiculous gifts nobody asked for. Icebreakers that make no sense until suddenly they do.

Which matters more than it sounds.

By the second night nobody's trying to sound impressive anymore.

Then the days start stacking. You're moving through caves together. Zip lining over cenotes at night. Somebody comes back from the cenotes quieter than before.

By day two people stop trying so hard to sound put together. The real stuff starts coming out.

After that, people stop dodging the real conversations. Somebody says the thing you've been avoiding and suddenly there it is.

By day four somebody's barefoot in the lobby booking a flight. Somebody else is finally raising their prices. Somebody's pacing near the pool rehearsing a text they're finally about to send.

You leave and things are different. Not because someone gave you a framework. Because after five days there, going back to the old patterns feels weird.

What the Five Days

Feel Like

Imagine this.

You wake up in a beachfront resort on the Caribbean. Ocean wind at breakfast.

Everything handled. Flights. Transfers. Meals. Drinks. Tips. You didn't plan anything. You just showed up.

Breakfast at 8. Somehow half the table is still there at 10. A conversation about someone's pricing turns into Kristy saying something that lands like a brick. By the time the plates are cleared someone's restructured their whole offer.

Mid-morning, Billie runs a session. Every conversation somehow circles back to the same thing: are you actually gonna do this or what?

After lunch someone suggests archery. A friendly competition turns into a conversation about risk tolerance and decision speed. Nobody planned it.

Late afternoon. The pool. Humid air. Cold drink. A coach floating two feet away. Nobody's even sitting normally anymore. Somebody's sketching out a new offer on a napkin while somebody else is finally admitting what they already know they need to do. Nobody's really "off" anymore.

Dinner. Different restaurant. The person next to you built a SaaS company from nothing. The one across from you just quit her job to go full-time. First time in a long time you don't have to explain why you want this life.

After dinner. Wet sandals from the pool. Tired laughter. Somebody still pacing around the lobby working through something. Barefoot. Still holding the same drink from an hour ago. Somebody says they're heading to bed. Twenty minutes later they're still standing there talking.

Loud karaoke downstairs. Half the group still at the bar at 1am. Somebody grabs a drink and six people end up by the pool again. People are sunburned and exhausted and nobody's checking what day it is anymore.

That's one day. You get five.

The Underwater Museum

New for 2026

Underwater sculpture museum. Beginner-safe, nobody drowns,

I'm figuring out the snorkel the same time you are. It's genuinely

one of the strangest things I've ever heard of and we're doing it.

Xplor Fuego

Xplor Fuego after dark. Zip lines, underground rivers, amphibious vehicles

through caves, and a dinner buffet at the end. I still wish I'd done the ziplines!

Everything else.

Sunrise on the beach. Archery after lunch. Karaoke way too late. You think you're heading upstairs for ten minutes and somehow end up in another conversation until 1am. You lose track of where conversations started. Breakfast somehow turns into the pool. The pool somehow turns into dinner. Dinner somehow turns into karaoke at midnight.

“I didn't realize how heavy it was until

I put it down for a week.”

2025 Retreat Attendee

The Tribe

Something surprised me last year.

By day three, people were saving seats for each other at breakfast.

Not because anyone told them to. Because by day three the group moved like a tribe. People staying behind after dinner because someone was working through something. People checking in on each other the next morning. Somebody says they're grabbing a drink and five people come with them without planning it.

Every entrepreneur I know is isolated. Your friends don't get it. Your family thinks you should get a "real job." Eventually you stop trying to explain it.

You're making decisions alone, carrying uncertainty alone, doing things nobody around you really understands.

Then you spend five days around people who actually get it and realize how tired you were of carrying all of this by yourself.

"Damn. I thought I was crazy for thinking that."

Three other people at the table just nodded.

People from last year still talk constantly. Group chats. Random check-ins. Business partnerships. Calls that start with "quick question" and turn into two hours. Some people from last year still talk almost every day.

Environment always wins.

Who You Spend the
Five Days With

Every coach. All five days. Breakfast, excursions, dinner, the conversations that run past midnight.

Caleb Jones — Me.

If you want real time with me this year — meals, coaching, late nights, all of it — this is the only place. Only live event on my 2026 calendar. Been doing this for over 15 years without needing an office, a boss, or permission. This is the only live thing I'm doing in 2026.

Business Auntie Billie

BOSS Cooperative · Retreat Architect

Billie runs BOSS Cooperative, works alongside me inside the 90 Day Business Builder, and somehow gets ambitious people to stop acting guarded around each other faster than anyone I've ever seen. A lot of them are probably making more money because she bullied them into charging what they were worth. The whole feel of this retreat comes from her. Not just the logistics. The energy.

Matthew Samp

30+ Years Direct Response Marketing

Runs his firm from a hotel he owns on the Brazilian coast. If your marketing is burning cash, Matt will tell you exactly why before you finish your second sentence. Thirty years of not sugarcoating anything.

Yan Guerif

Makes sales stop feeling weird. Twenty years building systems that feel like actual conversations instead of scripts and pressure tactics. If you're overcomplicating sales, Yan will spot it fast.

Kristy Lake

Gets underneath the thing that's been quietly keeping you stuck. Most people walk in skeptical. Then around day two people start realizing maybe the business wasn't actually the thing screwing them up.

Peter Young

25+ Years FAANG + Startups

Figures out what's actually broken and gets everything pointed the same direction. If you're chasing a distraction wearing a costume, he'll call it before you waste another month.

The Question You're

Really Asking

You're not wondering if this is good. You've read this far.

You're wondering whether now is the right time. Whether you're "ready."

“I can't take five days.”

Five days isn't the risk. Staying exactly where you are for another year is the risk.

“I don't have a business yet.”

People come at every stage. Day-one idea. Side hustle. Established company that hit a wall. Last year, one of the biggest shifts happened for someone who hadn't launched anything yet.