FROM IDEA TO EXECUTION

Some ideas change your life. Most never leave your head.

Five days. Six coaches. One immersive business learning adventure designed to explore what stands between having an idea and actually doing something about it.

All-Inclusive · Flights Included

September 16–20, 2026 · Cancun, Mexico

This happens once a year. Registration closes August 25th.

Let's start with something uncomfortable.

You probably already know what your next move is.

Not every move. Just the next one.

The business you've been thinking about.

The offer you've been meaning to launch.

The project you've been circling for months.

The conversation you've been avoiding.

The decision you've been postponing until you feel more certain.

You know the one.

Most people assume they need more information before they're ready to take that step.

Maybe one more course.

One more book.

One more podcast.

One more month to think about it.

But after years of working with entrepreneurs, I've noticed something interesting.

The people who come to this event rarely need more information.

They've already done the reading.

Taken the courses.

Listened to the experts.

Collected enough advice to fill an entire bookshelf.

And yet the idea is still sitting there.

Waiting.

At some point, preparing became the thing you do instead of the thing you're preparing for.

The trap is that it doesn't feel like a trap while you're in it. It feels responsible. Productive. Like you're making progress.

Then one day you realize another year has passed and the idea is still exactly where you left it.

That's why From Idea to Execution exists.

Not because you need another conference.

Not because you need another framework.

And definitely not because you need five days of people talking at you from a stage.

This experience was built around a question I've been fascinated by for years:

Why do some ideas become reality while others remain ideas?

Not as a thought experiment.

As something worth exploring in real life.

Because every year I watch people arrive carrying ideas they've been thinking about for months, sometimes years, and leave with something much more valuable than motivation.

They leave with momentum.

And momentum changes things.

The breakthroughs almost never happen where you'd expect.

After three years of running this event, that's the thing that still surprises me most.

When we first created it, I assumed the biggest shifts would happen during coaching sessions.

Sometimes they do.

Just as often, they show up in the middle of something that looks nothing like business.

Last year we spent a day at Chichén Itzá, a thousand-year-old Mayan city a couple of hours from Cancun. You spend the day surrounded by structures that have survived for centuries, and it's difficult not to think about what lasts, what changes, and what patterns people repeat generation after generation without ever questioning them.

On the bus ride back, someone started singing.

Within a few minutes nearly the whole bus had joined in. People from different countries.

Different generations. Different backgrounds. Somehow knowing many of the same songs.

A few days later one of the men on the trip told me he couldn't stop thinking about that bus ride.

Earlier that day he'd been looking at patterns that had survived centuries. That evening he'd been singing songs that had survived decades. Somewhere between those two experiences, he noticed a pattern in himself that had been running for years.

Every time he got close to making a certain move in his business, the same hesitation appeared.

The same explanation.

The same reason to wait.

He'd been telling himself that story for so long he'd stopped hearing it.

What changed things wasn't noticing the pattern.

What changed things was being surrounded by people who could see it too.

People who asked questions he'd never thought to ask.

People who challenged assumptions he'd stopped questioning.

People who had already done the thing he was afraid to do.

He didn't leave that bus with everything solved.

He left able to finally see the thing clearly.

And you can't change a thing you've never been able to see.

The adventures aren't a break from the learning. They're how it lands.

Most business lessons are taught in conference rooms.

We prefer to make them memorable.

One participant learned more about feedback loops and measurement while holding a bow and arrow than from hours of reading about KPIs. Miss. Adjust. Miss again, but closer. Adjust again. Then hit the target.

Suddenly feedback wasn't theoretical anymore.

It was obvious.

Another participant found herself standing at the edge of a cenote, a crystal-clear natural swimming hole formed over thousands of years. The hesitation before grabbing the rope swing sounded remarkably similar to the hesitation she'd been feeling around a decision in her business.

Different situation.

Same voice.

Same story.

This year we'll head to Xplor Fuego, an after-dark adventure park filled with underground caves, jungle trails, rivers, and experiences I'd rather not spoil in advance.

We'll explore the underwater museum off the coast of Cancun, where hundreds of sculptures rest beneath the ocean's surface and familiar questions somehow start looking different.

We'll spend time in places designed to wake you up, challenge your assumptions, and make it harder to keep thinking the same thoughts you've been thinking at home.

Because that's the thing about perspective.

Once it changes, action becomes much easier.

This isn't five days of people talking at you.

Most business events are built around a stage.

A speaker talks.

You take notes.

Maybe you get thirty seconds to ask a question.

Then everyone shuffles off to an awkward networking mixer where nobody really knows how to start a conversation.

This is the exact opposite of that.

The value isn't on a stage.

The value is in the immersion.

It's the conversation that starts over breakfast and somehow continues three days later.

It's the coffee break that turns into an impromptu coaching session because somebody asks a fascinating question and half the group gathers around to explore it.

It's sitting down at dinner beside someone from another country and discovering they're wrestling with the exact same challenge you are.

It's having direct access to coaches throughout the week instead of hoping you'll get sixty seconds of their attention before they disappear backstage.

You travel together.

Eat together.

Learn together.

Celebrate together.

By the end of the week you'll know what people are building, what they're excited about, and probably a few stories they'll still be telling years from now.

Some of those people will still be in your life next year.

The kind you text when you're about to do something scary and need someone who understands what you're trying to build.

Those moments are difficult to create in a room full of spectators.

They're much easier to create when everyone is part of the experience.

That's why we keep it intentionally small.

This is the only event all six coaches do together.

Billie. Caleb. Matt. Kristy. Peter. Yan.

Six entrepreneurs.

Six different perspectives.

Six people who have built location-independent businesses and lives.

This is the only event where all of us come together in one place.

Every year we clear our calendars for it.

Not because Cancun is beautiful, although it is.

Not because the resort is incredible, although it is.

Because this event creates moments that simply don't happen anywhere else.

Ask any of the coaches what their favorite event of the year is.

You'll hear the same answer.

This one.

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!

Yes, you'll do real business work.

This isn't five days of vague inspiration in a beautiful location.

We'll talk about offers.

Marketing.

Sales.

Visibility.

Pricing.

Systems.

Decision-making.

Execution.

We'll look closely at why smart people avoid the very actions that would move their businesses forward.

We'll explore what makes a plan actually usable once you're home.

We'll examine the stories, assumptions, habits, and patterns that quietly influence decisions without announcing themselves.

The difference is that none of it is separated from the experience.

You won't spend five days collecting notes and hoping something changes when you get home.

You'll be learning, testing, questioning, applying, adjusting, and refining in real time.

Because the gap between idea and execution is rarely just tactical.

Sometimes it's something you've been carrying around for years without realizing it.

Some parts of the experience stay secret on purpose.

You'll know where you're staying.

You'll know the major excursions.

You'll know your coaches.

You'll know what's included.

What you won't know are all the moments you'll still be talking about a year later.

Neither do we.

Those reveal themselves when the right people gather in the right environment.

Part of moving from idea to execution is learning to step into the unknown without needing to control every detail first.

Some things are better experienced than explained.

Celebration is part of the work.

Ambitious people have a habit of accomplishing something and immediately moving on to the next thing.

The next goal.

The next project.

The next responsibility.

This week makes room for something many business events forget.

Celebration.

Great food.

Meaningful conversations.

Adventure.

Laughter.

The simple pleasure of looking around and realizing you've built a life that allows you to be here.

Not because celebration is separate from the work.

Because enjoying what you've built is part of the work.

“I didn't realize how heavy it was until

I put it down for a week.”

2025 Retreat Attendee

A year from now.

A year from now you'll still have ideas.

The only question is whether they'll still be ideas.

Or whether you'll be living one of them.

You can spend another year in the same environment, having the same conversations, waiting to feel ready.

Or you can spend five days somewhere designed to help you see differently, think differently, and act differently, surrounded by people doing the same hard thing you are.

One of those changes what happens next.

You already know what the other one does.

This happens once in 2026.

Registration closes August 25th.

And then we'll do it all again next year with a completely different group of people, creating a completely different set of stories.

Who You Spend the
Five Days With

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

Business Auntie Billie

BOSS Cooperative · Retreat Architect

Billie runs BOSS Cooperative, works alongside Caleb 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.

Caleb Jones

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.

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.

“What if I'm the least experienced person there?”

Then you're in the right environment.

“I'm not sure I'm ready.”

That's the drift talking.

Drift always sounds reasonable while it's happening.

Ready is what you become during the five days. Not before them.

Everything Included

Remove friction so all your energy goes toward movement, connection, and action.

  • Flights from select cities

  • 5 nights beachfront all-inclusive resort

  • Underwater Museum snorkeling

  • All excursion transportation

  • 4+ hours daily coach access

  • Resort pools, beach, restaurants, entertainment

  • Airport transfers both ways

  • All meals, drinks, and gratuities

  • Xplor Fuego + dinner buffet

  • Daily coaching sessions

  • Full coach access — all day, every day

$4,997 · All-inclusive · Flights included

Structured business education event — almost certainly tax deductible.  Talk to your tax professional.

FROM IDEA TO EXECUTION

September 16–20, 2026

Cancun, Mexico

All-Inclusive · Flights Included

Investment: $4,997

Registration closes August 25th.

— Billie Olds, Your Business Auntie

You already know what staying feels like.

© 2026 BOSS Cooperative LLC · From Idea to Execution: Cancun Business Immersion