The Book

“Rob, there’s a book in there somewhere.”

In more than a decade of writing the Weekend Briefing, I heard that gentle nudge from many of my heroes in our profession.

So I set out to find that book. It took a while, but I did. Winning: The Five Truths of Fundraising brings together the best of the Weekend Briefing with the most important fundraising lessons I’ve learned in the last four decades.

Available now in print, eBook and audiobook on

“I just wept my way through the story of The Prom in ‘Winning.’ This book is inspiring me in ways that I must have needed. A drink of fresh water – and I didn’t even know I was thirsty.”

—Jane McCracken, Sr. Director of Development and Campaign, Family Service, Billings, MT

“This book is a must-read for any fundraising professional– whether just starting in the field or seasoned veteran. All nonprofit professionals can learn from this book. Most importantly, Rob gets to the heart of reminding us why we do this noble work.”

—Joel Cencius, CFRE, Chief Development Officer, St. Joan Antida High School, Milwaukee, WI

“Rob Cummings’ “Winning” boils our work in philanthropy down to its essential elements. Our profession, at its best, is still about spending time in the right way; developing relationships, listening, and saying thank you really well. Rob understands this and, through stories, brings to life the lessons that will help development officers at any stage of their career.”

—Jonathan E. Bridge, Assistant Head of School for Advancement, University School, Hunting Valley, OH

“I started receiving The Weekend Briefing just as I transitioned into fundraising. Rob was my first mentor and he didn’t even know it. “Winning truly incorporates all that is great about Rob’s approach to fundraising. Anyone who works in development should embrace his Five Truths. Practice the Five Truths and the donor will win, your organization will win and you, the gift officer, will win.”

—Allison Nickle Egidi, Associate Vice President for Development, University of Virginia