2025 Italy Retreat: Meeting the Moment
September 24 - 28, 2025
La Guardia | Giglio Island, Italy
This retreat is currently sold-out, get in touch with lara@founderspledge.com to be added to the waitlist.
We stand on shifting ground. Institutions we once relied on are faltering, governments are stepping back from global responsibilities, and urgent challenges are being met with deadlock or indifference. But when systems fail, it’s our opportunity to meet the moment.
In uncertainty, there is agency. The choices we make now – how we invest, collaborate, and innovate – will shape the future. It’s up to us to build the networks, foster the solutions, and drive the change that institutions can’t or won’t. This is not just a challenge; it’s a call to action.
This summer, we’re inviting you to join us on Giglio Island off the coast of Tuscany, Italy, to ask: in a time of instability, what does it mean to step up? How can we, as leaders and philanthropists, take meaningful action where governments and institutions fall short?
Over five days, we’ll learn about some of the most pressing problems of our time before focusing on our unique ability to foster solutions. Through expert-led sessions, candid discussions, and practical workshops, we’ll explore bold, high-impact interventions across philanthropy, policy, and entrepreneurship — from tackling state failure and misinformation to funding resilience, innovation and action.
When we refuse to wait for others to act and take responsibility for driving change, we can see what’s truly possible.
Our retreats are as much about deepening our impact as they are about forging meaningful connections. You’ll be joined by a community of about 40 peers – Founders Pledge members and their partners – who share your drive to act. Beyond thought-provoking conversations, there will be time to recharge at the stunning La Guardia Hotel, explore ancient vineyards, hike coastal trails, and sail crystal-clear waters.
And Giglio is no ordinary destination. A small, rugged island off the Tuscan coast, it has a history of resilience and collective action. It’s an island that embodies self-sufficiency, adaptation, and courage—the very qualities we need to meet today’s global challenges. We welcome and encourage the attendance of partners and those closest to your giving.
It’s time to meet the moment. We can’t wait to see you in Italy!
What You’ll Gain
Through immersive discussions, expert-led sessions, and time spent connecting with the Founders Pledge community, you will:
- Connect with a community of action-oriented leaders – Forge deep relationships with fellow entrepreneurs and philanthropists who share your drive to step up where institutions fall short.
- Clarify your role in driving change – Identify where your unique skills, resources, and influence can make the greatest impact in an era of uncertainty.
- Move from analysis to action – Go beyond diagnosing problems to identifying tangible, high-impact interventions in philanthropy, policy, and entrepreneurship.
- Strengthen your philanthropic approach – Refine how you give, invest, and engage in systemic change, ensuring your efforts are both meaningful and effective.
- Recharge and reflect – Amidst stimulating conversations, enjoy time to explore Giglio’s rugged coastline and clear waters, while taking in the island’s inspiring history of resilience.
You’ll leave with renewed clarity, a refined strategy for your impact, and a network of peers ready to take on the challenges of our time—together.
Speakers & Session Leaders
Rutger Bregman
Historian and Author
Rutger Bregman (born April 26, 1988) is a Dutch historian, author, and co-founder of The School for Moral Ambition. His books Utopia for Realists (2017) and Humankind: A Hopeful History (2020) have been translated into 46 languages and sold over 2 million copies worldwide.
The Guardian described him as “the Dutch wunderkind of new ideas,” while TED named him one of “Europe’s most prominent young thinkers.” His TED Talk, Poverty Isn’t a Lack of Character; It’s a Lack of Cash, was selected by TED curator Chris Anderson as one of the top ten talks of 2017.
In 2024, Rutger co-founded The School for Moral Ambition, a non-profit inspired by his latest book, Moral Ambition. The organization helps ambitious people tackle the world’s most pressing problems. On May 6, 2025, the English edition of Moral Ambition: How to Stop Wasting Your Talent and Start Making a Difference will be released, followed by translations in over 20 languages.
Photo by Maartje ter Horst
Caitlin Tulloch
Senior Director for Research, Learning, and Product - GiveDirectly
Caitlin Tulloch is a recognized expert in cost-effectiveness analysis and evidence-based policy, with a proven track record in leading research and shaping program strategies in humanitarian and development sectors.
She is the Senior Director for Research, Learning, and Product at GiveDirectly, a non-profit that sends cash transfers directly to people living in poverty. Previously, she was the Deputy Office Director and Team Lead for Evidence Use at USAID's Office of the Chief Economist, where she led efforts to integrate rigorous cost-effectiveness evidence into program design, influencing over $1 billion in commitments. Amidst the collapse of USAID, she and several colleagues led an independent effort to mobilize tens of millions in private funding to support the most cost-effectively life-saving projects affected by USAID cuts.
Before entering government, Caitlin spent eight years at the International Rescue Committee, spearheading the development of organization-wide strategies for using cost-effectiveness evidence and managed a large-scale consortium of analyses. She holds an MPA from Princeton University and a BA in Economics from the University of Chicago.
Jason Rezaian
Director of Press Freedom Initiatives - Washington Post
Jason Rezaian is a journalist, author, and one of the world’s most compelling voices on press freedom and resilience in the face of authoritarian suppression. As The Washington Post’s Tehran bureau chief from 2012 to 2016, he reported on life inside Iran during a period of intense political and social transformation. His commitment to truth came at a profound personal cost—in 2014, he was unjustly imprisoned by Iranian authorities and held for 544 days in Tehran’s Evin Prison on baseless charges of espionage.
Last Year's Retreat
Last year’s retreat took place in the Agafay Desert, 40 minutes south of Marrakesh. We gathered a top group of like-minded entrepreneurs from a range of industries & geographies. Check out the video below for a glimpse of the time we shared.
Our retreats are attended by the Founders of the following companies:
