From Simi Valley to Silicon Valley: A Story of Hard Work, Serendi

To succeed in business and in life, you must be focused and committed. But it also takes serendipity and a certain amount of alchemy.

Stephen Gillett went from part-time technology specialist at an Office Depot to one of the youngest CIOs of a Fortune 500 company by keeping himself fully present and open to all possibilities. In From Simi Valley to Silicon Valley, he shares his remarkable journey and the valuable lessons he learned while working with Bill Gates, Starbucks’ Howard Schultz, and a host of other influential innovators.

Serendipity is more than being in the right place at the right time. It’s about being flexible enough to allow unexpected things to enter and transform your life. Stephen’s inspiring personal story of extraordinary achievement will light the path for others who are willing to keep their minds open, stay true to their values, and embrace their own contradictions.

Stephen Gillett is a tech executive, entrepreneur, and business leader who worked his way up from minimum-wage retail jobs to become one of the youngest Fortune 500 Chief Information Officers in history. Over the past two decades, he's led massive digital transformations, navigated high-stakes corporate acquisitions, and helped steer major international brands through periods of intense change.

A former Division I football player and lifelong gamer, Stephen learned early on that the strategy, teamwork, and sharp problem-solving built during long gaming sessions translate surprisingly well to the corporate boardroom. He brings that same down-to-earth mindset to his writing and speaking, sharing honest lessons on modern leadership, career resilience, and staying adaptable when life throws a curveball. Through every career twist and turn, Stephen remains centered as a family man, grounding his work in the love and steady support of his wife and kids.