Grand Cayman · May 2027
An invitation to Generous Giving to bring a JOG to the Cayman Islands during Rise, several days anchored on the Emancipation Day holiday. The room is already flying in. We would like you to have a table in it.
Every year on the first Monday in May the Cayman Islands close for Emancipation Day, marking the reading of the proclamation at Fort George in George Town. What happened here after it was read is what makes the day worth building a week around.
Across most of the British Caribbean, emancipation arrived with an apprenticeship period attached, years of labour still owed before freedom was actually handed over. Cayman had none of it. Freedom came immediately and without condition, and no part of it was withheld or paid down in instalments.
You do not teach giving as a portion measured out. You teach a whole life handed over. Cayman closes the country once a year for that same idea.
So the week carries its theme before anyone writes a line of programming. Generous Giving has been having this conversation since four friends started it in the late 1990s, and it lands differently in a country that has a national holiday for freedom given in full. Rise sits inside that holiday. Generosity is the natural conversation of the week rather than a track we bolted onto it.
Rise is several days in Grand Cayman anchored on the Emancipation Day holiday in May 2027, built for up to 4,000 flown-in VIPs from major faith-forward organizations whose combined audience reach runs into the millions. Music carries the week. Ministries, broadcasters, foundations, studios and universities bring their people, and the main stage is the reason everyone is on the same island at the same time.
Rise is not built on ticket sales. Sponsoring organizations fly their donors and their leadership in, and what happens in the smaller rooms off the main stage is the reason those organizations commit. A JOG belongs in one of those rooms.
A JOG needs eight to sixteen people who will sit down together, put their guard down about money, and stay in the room long enough for the conversation to get somewhere honest.
Hosts give themselves six to eight weeks to fill those seats and still lose good people to a calendar. Getting the right guests in one place on the same day is most of the work. Getting them to actually stop working once they arrive is the rest of it, and that second part is the one that quietly decides whether the retreat lands.
At Rise, both are handled before you send a single invitation. Your guests flew in. The week is already cleared, the phones are down by the second morning, and nobody is watching the clock to beat traffic home.
Ministry and foundation principals, broadcast and media leadership, university advancement teams, artists, and the donors those organizations flew in themselves.
Warm water, a long table, no commute and no next meeting. People arrive at a JOG guarded. Here they arrive three days into a week that has already loosened them up.
Generous Giving brings the materials and the trained facilitator, which is the part only you can do. Rise carries the room, the meals, the invitations and the logistics.
Facilitator training starts with having sat through a Journey first, so every seat in that room is a possible host somewhere else. You would be running a JOG for people whose whole working life is convening rooms, and most of them go home to a donor base, a congregation, a board, or a broadcast audience with reach of its own.
Journeys already run in more than sixty countries and thirty languages. Rise is a short path into the next set of them, and the organizations sitting at the table are the ones who can open those doors in a single email.
Rise is international by design. The people flying in are not all American, and the week puts your material in front of leaders who would take a Journey home to places you are not yet working.
Every guest at the Rise table is a candidate for facilitator training and a candidate to host the next one. One room in May seeds a year of Journeys elsewhere.
The JOG itself stays closed and confidential. Anything captured for your library happens outside that room, on the main stage or in interviews you approve.
Three formats, all of which Rise can host inside the week. Pick what you want out of it and the page will draft a brief you can take into your next team meeting.
1. Format
2. Who you want at the table
3. Where it sits in the week
14 seats · one long table
Rise is a week where organizations activate donors, and we would rather say that plainly than dress it up for you. Which is exactly why the JOG has to be walled off from the rest of it.
No appeal and no pledge card. Nothing that follows anyone home afterward, and no sponsor buying its way into those seats because it likes who is sitting in them. The room runs the way it runs anywhere else you host one, and Generous Giving owns what happens inside it.
We will write that into the partnership agreement rather than ask you to take it on a handshake. You hold the guest list, the confidentiality and the facilitation. Rise holds the invitation, the logistics and the line at the door.
Rise is not auctioning a category. We would be glad to have more generosity and stewardship organizations in the room over the years, and the week is better with them in it.
What is on the table now is the first seat. Generous Giving sets the standard the others get measured against, and the Journey becomes the format everyone else ends up working around.
Hosted, staffed and paid for by Rise, in a setting chosen with your facilitator, with meals and the guest list handled on our side.
Named across the week in the generosity and stewardship category, on stage and in everything that carries the partner roster.
At the partner rate, so your own board, hosts and key givers fly in with you rather than watching the week from a distance.
A main stage moment and interview capture outside the JOG room, cut for your channels and cleared by you before anything runs.
The position carries a rights fee and a seat block with a deposit at signature. Numbers go in front of you in the working session rather than on a web page. No seats are given away at Rise, and that is the reason a week of this size can pay for itself without ticket revenue and without government money inside it.
A little over an hour in the air from Florida, with direct service from Miami, Tampa, Atlanta, Dallas, New York and Toronto.
English is the language, the currency is stable, the water in May is warm enough that nobody needs convincing, and the islands carry one of the lowest crime rates in the region. Cayman is a British Overseas Territory whose constitution names Christian values and the protection of the family in its opening pages, which is not a small consideration when you are choosing where to hold a conversation like this one.
One point of contact who can speak for Generous Giving without routing every question through a committee.
Emancipation week, May 2027, pencilled in, so the format conversation has something real to sit against.
Tell us who would run the room and we will build the guest list around the way that person works.
One working session where the format, the seat block and the numbers all sit on the same page.
The organizations we are working with build their spring donor calendars in the fall, which means agreements have to be signed in the autumn of 2026 for a May 2027 week to work properly. That is the only piece of urgency in this, and it is a scheduling one.
Sixty minutes with your team and ours. Format, seat block, protections and numbers.
One page, non-binding. It says we are building this together and stops either side having the same conversation twice.
The founding position, the seat block, the no-ask protections and the confidentiality terms, all in writing.
The JOG window is fixed inside the week and the guest list is built with the organizations flying those people in.
Several days in Grand Cayman anchored on Emancipation Day, with your table in the middle of it.
The Global Gathering of Faith, Music, and Purpose
Rise Cayman is a music festival held over several days in Grand Cayman, anchored on the Emancipation Day holiday in May 2027. The main stage is the reason everyone is on the same island at the same time. Artists, ministries, broadcasters, foundations, studios and universities bring their people, and up to 4,000 flown-in VIPs arrive from major faith-forward organizations whose combined audience reach runs into the millions.
The festival is Caymanian owned and led, produced with Echo Concerts out of Nashville and Williams Productions in Grand Cayman. It runs on sponsorship and donor support rather than ticket sales, which is what lets partner organizations use the week to fly their own people in.
www.RiseCayman.com
Emancipation week · May 2027 · Grand Cayman
The Tide Is Rising.
The room is already flying in. We would like Generous Giving to have a table in it.