The Way of St. Frances
171 Kilometers | 19 Cities | 21 days
4 PILGRIMS
Rediscovering an ancient faith
from Florence to Assisi and on to Rome.
1 QUESTION
What does a medieval monk have to say to our anxious age of AI?
Hear the story
About The Book
Shadowing Saint Francis is the memoir of a pilgimage that explores the meaning of faith in an age of algorithms and anxiety.
Follow the author and his three German friends along ancient paths from the beauty of Florence through Umbria to Assisi, then on to Rome to see the Pope—ending among 70,000 people gathered to hear Bruce Springsteen at the ancient Circus Maximus.
Through the journey, it becomes clear that St. Francis’ approach to power, his love of the unlovable, and his view of nature as a sacred gift offer a coherent, relational reframing of faith for our technological age.
Join the Journey.
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Share the Jubilee.
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About The Author
Jonathan Bentley is a writer, technology entrepreneur, and lifelong student of theology. For thirty years, he built digital infrastructure for the financial services industry, founding a fintech company that he led through cloud transformation before its successful sale.
Over that time, he served as a local church elder, worship musician, and teacher—thoughtfully navigating his own faith alongside the technology shaping modern life.
Nearing seventy, he set out to re-examine faith with fresh eyes. The pilgrimage that followed—recounted in Shadowing Saint Francis—combines a technologist’s perspective with a pilgrim’s search for a grounded, relational way of being. It also laid the foundation for his broader work exploring the intersection of Franciscan wisdom and emerging intelligence.
Jonathan lives on the edge of Umstead Forest in Raleigh, North Carolina, with Judy, his wife of nearly fifty years, and within minutes of most of his six grandchildren.