Know where you're going.Know that you're getting there.
The Annual Planning Retreat brings nine founders to Joshua Tree, December 17–20, to build a complete plan for the year and a system for keeping it on track.
Reserve your seatFounding cohortRegistration closes November 15
You set goals in January, but you're fighting fires by February.
The business runs on your memory and your energy. Your team works hard, but if you asked them to name this year's priorities, you're not sure what they'd say. You squeeze in "deep work" when you can spare half an hour, but there's no continuity, and nothing sticks.
You don't need more ideas. You need a direction everyone can name, the few moves that matter most right now, and a weekly way to tell whether it's working.
The less time you think you have for clarity, the more you need it.
A different kind of planning
The Annual Planning Retreat is a time to reset before the new year: a time to work on your business, not in it. Most founders know they should. Few ever hold the space for it.
A small group of founders spends two full days building their plans together – talking, challenging each other, and thinking clearly away from the noise.
There are no keynotes and no tactical training. The two days go to strategy and the system that carries it, built for how small, scrappy teams actually work.
What you leave with
Your Why and Vision.
Where the business is going, and why it matters to you.
Your 1-year targets.
A small number of results that define a good year, and a clear list of what you're not doing.
Your Q1 priorities.
The few things that have to happen this quarter, each with one owner.
Your scorecard.
The signals that show whether it's working, including the ones you control, and what you'll do if they slip.
Your accountability map.
Who owns what this year, including any role changes you've decided on.
Your plan for bringing it home.
How you'll share it with your team to get their buy-in.
Most importantly, you leave with a way to choose your next moves every quarter. The plan keeps up with the business, so agility is built in.
How it works
1. Before you arrive.
Guided prep: a look back at what worked and what didn't last year, and a sense of your purpose and vision. You'll arrive with your thinking underway, and time together goes to the conversations that only happen in person.
2. Two days together.
You'll work through your Why on a walk in the desert with another founder, sharpen your Vision in small groups, make the hard choices about the year, and turn them into Q1 priorities and a scorecard. Before you leave, you'll rehearse sharing it with your team, with peers playing the people back home.
3. Ninety days after.
The same cohort stays together, accountable to the plans you built side by side. You'll check in each month, with scorecards shared in Integritty so progress is visible.
Why a small group
The people in the room aren't in your business, so they have no reason to flatter you or protect the way things have always been done. They ask the hard questions your team can't, and they offer an outsider's perspective to challenge the habits you've quietly built.
Over two days they become your borrowed leadership team, and for the next 90 days they hold you to what you said you'd do.
This group is accountable to one shared thing: the plans everyone built together.
The setting
Three nights at a private venue in Joshua Tree, a serene location to tap into your best work. Every meal is prepared by Da-Chen Huang, who has led teams in Michelin three-star kitchens around the world and now builds hospitality and wellness businesses. Between sessions: a guided desert hike, sauna and cold plunge, and mindful moments.
Everything is handled, from your transfer from Palm Springs to the last cup of coffee, so your attention stays on your business and the people around you.
Your business can't be at its best if you aren't. The setting is part of the work.
Your host
Josh Greenberg
I spent four years as the COO of a fully remote startup, joining as its first full-time hire and growing the company to a team of 35. I ran EOS there as both implementer and integrator: installing the systems and meeting rhythms, owning the follow-through, and helping shape the vision.
I've been in the trenches of how small teams work — and more importantly, how they don't. I've seen goals too vague to measure, or pointed away from the bigger picture. I've seen good goals missed because we let pebbles crowd out our rocks. I've seen us praise hard work that didn't move the needle, while we neglected the work that would have. And I've been too busy fighting fires to fix the clarity, systems, and culture that kept starting them.
We had a phrase for those quarters: "red, but it wasn't our fault." Every miss came with a reason, and the reason let us off the hook. Most founders I respect have their own version of that phrase.
Good strategy fails in the gap between the plan and the execution. Closing that gap is my work now: I advise founders one-to-one, I host retreats like this one, and I build software that helps teams set and follow their plans.
This is the most brilliant piece of advice I've received in a long time.
Who it's for
- Founders who value strategic thinking and clear direction, but struggle to make it hold up all year.
- Operators of scrappy teams whose systems are still taking shape.
- Leaders who enjoy planning around one table with a few peers who'll challenge them, then hold them to what they said they'd do.
- Pairs who share the load of setting direction and following through: a founder and their second-in-command, or partners who own a business together.
It's probably not for you if you're looking for a conference, a large network, or tactical training in a specific function. It's also not the right fit if you want answers handed to you, or if your business is in a crisis that needs help this week.
Founding cohort
This is the first Annual Planning Retreat. Founding members get:
- The founding rate, kept for future runs of this retreat.
- First access to future events.
- A say in what we build next.
| Seat | Founding rate (USD) |
|---|---|
| Individual | $5,000 |
| Leadership pair (two people from the same business, sharing a room) | $8,000 |
| Private room | On request, limited availability, supplementary charge applies |
Includes three nights, all meals and drinks, transfers from Palm Springs, the full program, 90 days of follow-through, and 12 months of Integritty for your team.
Plan next year before it starts.
Mid-December gives you clarity before January's rush, and you're home in plenty of time for the holidays.
Our guarantee
You leave with your complete plan: your Why and Vision, your 1-year targets, your Q1 priorities, your scorecard, your accountability map and your plan for implementing it with your team. If you don't, we keep working together one-to-one until you do, at no extra cost.
FAQ
What does a day look like?
Each day will flow between deep work, full-group discussions, breakout groups, and restorative activities. Shared meals are less structured, allowing time to deepen our relationships with insightful conversations. Day one centers on your Why and Vision; day two turns them into your year, your quarter and your weekly numbers.
How much prep is there?
A couple of hours over the weeks before the retreat, guided step by step.
I've never used a planning framework. Is that a problem?
No. In fact, that may be why you're here. The method is introduced in plain language. If you've used EOS or similar before, you'll go deeper with what you already know.
Can I bring my business partner or second-in-command?
Yes. Leadership pairs share a room at the pair rate. You'll work in different small groups for some sessions, then come back together to build your plan.
Can I have a private room?
Private rooms are limited and available on request, with a supplementary charge. Choose your room preference in the intake form and we'll confirm availability with you directly.
What should I plan for travel?
Fly into Palm Springs (PSP), arriving in the afternoon or evening on December 17. We'll take you from there. Departures are on the morning of December 20. Let us know if you're driving, and we'll share directions to the property.
What if I need to cancel?
Registrations are non-refundable and non-transferable. If you cancel, your fee becomes credit toward a future event, if we're able to resell your seat. Full details are in our Terms.
Will there be photos or video?
We may photograph and film parts of the retreat for promotional use, but never the content of confidential discussions. Details are in our Terms.
Is this a tax-deductible business expense?
We'll invoice it as a business development retreat. Check with your tax advisor to see how you can deduct it.
What happens after the 90 days?
You keep running your plan with Integritty, our software built to keep you on track. Founding members get first access to future retreats and to ongoing support for those who want it.
Reserve your seat
Nine seats. Registration closes November 15. Start with a short intake survey, then complete payment.
Trouble with the form, or prefer to talk first? Contact us.