
Strategic Conversations for Leaders
Who Want More Than Noise
Where Leadership, Faith, Culture & Legacy Intersect

Strategic Conversations for Leaders
Who Want More Than Noise
Where Leadership, Faith, Culture & Legacy Intersect

Private Conversations for Thoughtful Leaders
Wisdom. Perspective. Conversation.
A private monthly mastermind hosted by
Gordon Pennington and Don Gleason,
featuring curated conversations
on leadership, faith, culture,
legacy, courage, and the future.

Gordon Riddle Pennington III brings a rare and fascinating life story to the table. A native of Michigan, Gordon’s life experiences have moved through some of the most fascinating and influential rooms in modern culture, business, media, education, and faith. His professional journey has included Wall Street, international branding, major corporate advisory work, media, classical education, and faith-based cultural thought leadership.
He is widely recognized for his work as a former Director of Marketing for Tommy Hilfiger during one of the brand’s defining growth eras. He later founded and led Burning Media Group, advising organizations, institutions, and leaders on communications, culture, technology, media, and influence. He is a founder of charity: water, the most successful grassroots nonprofit start-up of the 21st-century.
Gordon’s story is not merely a résumé. It is the story of a man who has seen the machinery of modern culture from the inside: fashion, media, celebrity, marketing, technology, global brands, influence, and has emerged with a deeper perspective on the key question: What forms a life worth living?
There is also a generational and cinematic facet to Gordon’s story. His father, now 101 and living in Miami, comes from an old money family in Cleveland, Ohio, who invested with John D Rockefeller in the Gilded Era and had homes in the United States and Europe by the turn of the 20th century and afforded Gordon's grandfather, Gordon Riddle Pennington a private school education in Switzerland before World War I where upon he served the United States Army command in France as a bilingual artillery captain and expert rider cavalry officer. He returned from World War I to Detroit, where he became one of the leading automotive engineers and innovators in the burgeoning world of automotive design and manufacturing in an era when Detroit was the fastest-growing and wealthiest industrial city in the world.
His son, Gordon Riddle Pennington Jr, grew up in Bloomfield Hills, Michigan, and was conscripted into the US Army Air Force at age 18. He graduated from the University of Michigan and was later connected to the extraordinary world of Formula racing, Enzo Ferrari, and international motorsport in the late 1950s and early 1960s. That family thread stretches from Michigan to Modena, Majorca to Mumbai, from Montego Bay to Miami, from American reinvention to European racing history, from ambition to legacy.
Gordon Riddle Pennington III has traveled to 63 nations and has spoken and lectured extensively as he brings generational stories, behind-the-scenes insights, unique survival tales, and, more importantly, timely perspective.

Don Gleason brings a different but complementary life journey. Don’s career has moved through hospitality, entertainment, entrepreneurship, consulting, education, and executive leadership. He served as Director of International Marketing and Sales at Disney, working across global markets including London, Frankfurt, Hong Kong, Tokyo, São Paulo, Toronto, and Buenos Aires. He later served as President of Universal Studios Vacations, with senior responsibility for growth, sales, operations, and profitability.
For decades, Don has advised companies, entrepreneurs, and leaders across industries, combining the practical discipline of business growth with the human side of leadership, faith, resilience, and calling. He understands the boardroom, the classroom, the startup table, and the personal cost of building something meaningful.
Together, Don and Gordon bring two lives of uncommon experience: Entertainment and Technology, Disney and Ferrari, Wall Street and Universal, global branding and personal faith, media and meaning, leadership and legacy. A combination of vision and values, difficult to find.
This Mastermind is for people who sense that the world is moving fast, but wisdom is still slow, personal, and relational. It is for people who want to think more clearly, live more faithfully, lead more wisely, and meet people whose lives are worth knowing.
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