Doug Fleener
Coach / Author
Doug Fleener is the author of Start With What If: Weekly Questions to Spark Immediate, Practical Change and Growth for Everyday Life.
After rebuilding his life from addiction and the collapse of his family business, Doug went on to become Director of Retail for Bose Corporation and later a CEO. The same principle that helped him turn his life around now shapes how he helps individuals and leaders create clarity, take action, and grow — at home, at work, and under pressure.
Doug's work is practical, grounded, and immediately usable. It shows that change and growth are not complicated — they begin the moment you ask a better question.
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June 19, 2026
Transform Your Life with ‘What If?’ | From Rock Bottom to Clarity
Doug Fleener on Sobriety, Self-Trust, and the “What If” Rule: Pause, Question, Go On Real Men Feel, Andy Grant talks with Doug Fleener, author of Start with What If, about how asking better questions can spark practical change. Doug shares how addiction and bankrupting his family business led to a pivotal interruption—“What if today you just went today without drink or drug?”—launching nearly four decades of sobriety. They discuss why men often wait for “rock bottom,” how shame thrives in isolat...
Guest: Doug Fleener