The Crooked Monkey 2026 Retreat Is On — and It’s Bigger Than Ever

 

The Crooked Monkey 2026 retreat is officially happening — and this year, it lands differently. Eight new team members are joining us for the first time, some of them still in the middle of onboarding. The group chat is already buzzing. Someone has started a countdown. And at least one team is deep in Snack Wars prep mode. More on that in a second.  

 

What the Retreat Actually Is

For those new to our world: once a year, the entire Crooked Monkey team gets together in person. We’re a fully remote, international crew — the US, Venezuela, Argentina, Brazil, Israel, Colombia, Chile, the Philippines — so this is the one moment when the Google Meet grid becomes a real room. And we take it seriously. Not in a buttoned-up, agenda-every-hour kind of way. Seriously as in: we plan for months, we obsess over the details, and we show up ready to make the kind of memories that carry us through the rest of the year. Meet the team behind all of this — including the eight new Monkeys who are about to experience their first one.

 

 

The Retreat Starts Before the Retreat

Here’s something that tells you everything about how Crooked Monkey operates: the retreat doesn’t begin when the first flight lands. It begins weeks earlier — with planning, anticipation, and a level of production that, frankly, most companies reserve for client deliverables.

Behind the scenes, a dedicated retreat team takes over: flights, hotel, activities, meals, transfers — every logistical detail handled so the only thing everyone else has to do is show up. And then there’s the design team, working on the retreat theme and aesthetic. That part stays under wraps until Micha (our CEO) reveals it on day one, so we’re not going anywhere near that here.

This year, we built a full branded microsite for the preps. Not a shared Google Doc, not a PDF with flight info. An actual site, with an itinerary, packing list, flight and transfer details, weather tips, and a WhatsApp group — all wrapped in a design that’s unmistakably us. Because if we’re going to do something, we’re going to do it right.

Oh, and the swag? That’s being handled too. Quietly, carefully, and with the same obsession we bring to every client order. It’s one of the best parts of the retreat — and it doesn’t happen by accident.

The preparation is part of the experience. And for the new team members joining this year, it’s also their first taste of what working at Crooked Monkey actually feels like.

 

 

A Local Host, a New Retreat Location, a Familiar Feeling

We almost always choose the retreat destination based on one simple principle: does one of our own call this place home? This year, the answer points straight to Córdoba, Argentina — and to the one Monkey on our team who grew up there and knows it like the back of his hand.

Córdoba is one of Argentina’s most beautiful provinces — colonial architecture in the city, stunning sierras just outside it, a food scene that earns its own reputation, and a warmth that feels immediately like home. It’s the kind of place that surprises you. And having a local host changes everything — it’s the difference between being tourists and being guests. The hidden spots, the real restaurants, the stories behind the streets: that’s what you get when one of your own is leading the way.

And yes — there will be mate. There will be fernet. Not because we couldn’t have them anywhere else, but because drinking them here, in Córdoba, with him pouring, just hits differently. Some things are better in context.

 

 

How It Kicks Off: The Opening Talk

Every retreat starts the same way. Micha — our founder and CEO — gathers the team and opens with a talk. Not a corporate presentation. Something more personal than that. He reflects on the year behind us, shares what he’s learned, and sets the tone for the days ahead. It’s part keynote, part life lesson, part love letter to the company he’s been building for over 20 years. It’s also the moment when the retreat theme gets revealed — so we’re not spoiling that here. What we can say is that it always lands, it always sets the energy for the whole week, and it always reminds everyone why we chose to build something together.

 

The Traditions That Make It Ours

After the opening, the retreat unfolds through a set of traditions we’ve built — and refined — over the years. None of them came from a team-building manual. All of them came from us.

• Snack Wars. What started as a casual “bring something from your country” moment has evolved into one of the most anticipated events of the year. Each team — grouped by country or region — prepares a full cultural presentation: traditional music, history, fun facts, costumes, and of course, a spread of food and drinks that represents where they come from. It’s a competition in the most joyful sense.  The winner is always up for debate. The experience never is.
• Monkey Talks. Think of these as our in-house version of a TEDx talk — except the slides always include at least one meme. Team members share frameworks, ideas, and lessons that go well beyond the day-to-day. Not just work tips, but ways of thinking you carry with you long after the retreat ends. The conversations these talks spark don’t stop when the presentation does — they keep going by the pool, over dinner, on the last night when nobody wants to call it.
• The Swag Drop. We’ve never believed in the saying “the shoemaker’s son goes barefoot.” If we obsess over every detail of a corporate gifting order for a client, we do the same for ourselves. Every retreat, we unveil a curated set of swag designed around the retreat theme — premium quality, thoughtful details, and hours of internal debate behind every piece.
• The Surprise Activity. Every retreat includes one big activity that nobody sees coming until the reveal. We love the drama of it. We’re just not saying what it is. We’re not talking about a generic team-building exercise. We’re talking about the kind of thing that gets people genuinely excited, laughing before it even starts, and talking about it for months after.
• The Unscheduled Moments. These are, honestly, the best part. The brainstorming that breaks out over breakfast with no agenda and somehow produces the best ideas of the quarter. The guitar that appears from nowhere on night two. The pool conversation that goes deeper than anyone planned. The spontaneous High School Musical performance that happened last year and still lives rent-free in everyone’s memory. You can’t put these on a calendar. You just create the conditions — and get out of the way.

 

New Monkeys, Big Welcome

Back to those new team members. There’s no faster way to go from “new hire” to “one of us” than sharing a Snack Wars table, hearing Micha’s opening talk in person, and surviving the surprise activity together. Remote onboarding works — we’ve built the systems, the documentation, the culture — but this is something else entirely. By the end of this retreat, they’ll have inside jokes, opinions about last year’s swag, and at least one story they’ll be telling for years. That’s always been the whole point. As someone once said, our culture doesn’t live in a handbook: it lives in us. And moments like these are exactly how it gets passed on.

Stay tuned. We’ll be sharing more as the retreat unfolds. Follow us on LinkedIn and Instagram so you don’t miss a thing.

 This is the team that will handle your next merch order, your corporate gifts, your swag program. Real people, real care, real results. If you want us on your next project — let’s talk.