
Interwoven Episode 21 - Doing the Opposite: How Bold Choices Built Cloud FM
FULL EPISODE SUMMARY When Jeff Dewing began his career as a young refrigeration engineer, the idea of entrepreneurship was far from his mind. The world he entered was hands-on and technical, with little access to the inner workings of the businesses he served. Yet, it was precisely this outsider’s perspective—and the challenges of fixing “impossible” problems, often alone and against the odds—that quietly set the stage for his future. Frustrated by the lack of transparency and resistant management, Jeff Dewing began experimenting: teaching himself computing at home, building software in his spare time, and slowly uncovering the invisible mechanics of business. But recognition didn’t come easily. When his innovation was dismissed by his employers, the frustration pushed him into action—he left to start his own company, despite the financial strain and the need to bluff through unfamiliar territory. “As an entrepreneur, you bite off more than you can chew, and then you learn very fast how to chew it,” he reflects. Early success brought not expertise, but hidden cracks—complacency, boredom, and a loss of purpose that would eventually upend his business and sense of security. Only after experiencing major business failure did Jeff Dewing realise the difference between chasing wealth and solving real problems. His eventual return to entrepreneurship was shaped by new skills, clearer priorities, and a measured willingness to do the opposite of industry convention, even if it risked ridicule, resistance, or financial insecurity. For listeners considering a fresh start or wrestling with uncertainty, Jeff Dewing’s story offers candid proof that identity and expertise are always a work in progress. The founder’s path is less about bold visions and more about reflection, adaptation, and the courage to challenge what “everyone” does—again and again—until your own version of success becomes possible. KEY THEMES Reinventing through adversity The risk and honesty of change Learning across roles and industries Defining success beyond wealth LISTENER TAKEAWAY This conversation reminds us that growth comes not from certainty, but from experimenting, adapting and having the courage to challenge our own assumptions—especially when the alternative is simply following the herd. awake.WeAreTheWeave.co.uk Jeff Dewing







