In this episode, I sit down with the brilliant and very grounded Jenny Stilwell, a woman who has spent her life helping businesses move from surviving to scaling. Jenny has led companies through complexity, run her own advisory firm, and written the book The 7 Percent Club, which reveals why only a small number of businesses ever grow past two million in revenue.
What I love about Jenny is how honest she is about the messy middle of leadership. She talks about that awkward moment when you step up for the first time and suddenly discover you have no reference point for the role you have just taken on. She shares how founders often choke their own growth by holding onto everything, and how letting go is more like a dance of trust and release than a single decision.
We go deep into the traps that stop businesses from scaling. Complexity that creeps up quietly. Early team members who suddenly find themselves drowning under bigger titles. Capability gaps. Shiny object syndrome. And the hard truth that you cannot grow if you are still operating like the scrappy startup you once were.
Jenny also breaks down why knowing your numbers is not optional. It is the backbone of every decision you make. Margin, ratios, revenue per employee, wage to sales, client insights, operational indicators. She brings it all alive in that way only Jenny can. Practical, plain speaking, and instantly usable.
And of course, she answers our Future Fit Leadership questions. Adaptability. Strategic thinking. Emotional intelligence. And a powerful reminder that AI is shifting the ground under our feet faster than many leaders realise.
This is a conversation packed with clarity, humanity, and a few reassuring laughs about the things we all struggle with. If you are leading a business, scaling a team, or trying to find your footing in a world full of moving parts, you will love Jenny’s wisdom.
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