Interwoven Episode 21- From Compressor Rooms to Culture Change: Jeff Dewing’s Unlikely Path to Founding
FULL EPISODE SUMMARY
Before he was a founder, Jeff Dewing spent long nights as a refrigeration engineer, fixing urgent breakdowns and thinking on his feet. His early years were full of practical challenges, but the real turning point came not from technical problems, but from office frustrations: opaque decisions, lack of transparency, and a moment when his own initiative—building early business software at personal cost—went unrewarded. When the business owners refused even to reimburse him for a desperately needed computer, it was the final nudge: “If they’re ever gonna be that stupid, then I’m leaving to start my own business.”
What followed was a decade of fast growth, unchecked confidence, and eventual crisis. Rapid early success taught Jeff Dewing little about what really underpinned a sustainable business—until, in his words, “the success... papered over the cracks.” A foray into running a football club brought new energy but, as his first company faltered in his absence, he was forced to face the reality that skill in one area does not guarantee success across the board. Eight years working within other organisations honed his understanding, exposed him to broken industry cultures, and led to clarity: business could—and should—be done differently.
Founding Cloud FM, Jeff Dewing built on the full spectrum of his past—technical grit, a taste for risk, and above all, lessons from his mistakes. He centred transparency, trust, and autonomy, learning that culture comes before numbers and that the hardest choices often open the door to lasting change. For anyone contemplating a bold shift, his journey is a testament to both uncertainty and possibility: entrepreneurs are not finished products, but people learning, failing, picking themselves up and building anew.
