Brad Willson
Founder, Rolling Start
I help ambitious leaders scale their business without losing their sanity. Using the Scaling Up framework, I've helped companies achieve 2x cash flow, 3x profitability, and 10x valuation.
What Brad's clients achieve
Is Brad right for you?
- A growth-stage business hitting scaling barriers — revenue is there but execution is messy
- A founder or leadership team wanting to reduce management time by up to 80%
- Ready to implement structured rhythms around People, Strategy, Execution, and Cash
- Based in Australia, South Africa, or open to remote coaching globally
- ICT, digital services, and technology companies — Brad scaled his own IT business across three countries
- Cash flow optimization using the Cash Flow Story and Power of One tools
- Leadership teams that want a coach who's been in the CEO seat — lived experience, not theory
- Companies ready for the full Scaling Up implementation, not just a workshop
About Brad
"I believe the best coaching relationships are collaborative partnerships built on trust and fit. I don't just tell you what to do — I walk alongside you, challenge your thinking, and celebrate your wins. Because scaling a business should be exciting, not exhausting."
Before I coached, I built. I was a shareholder and director of an IT company for over 10 years, scaling it across three countries (Australia, South Africa, and the UK). I experienced first-hand the chaos of growth without systems — the 80-hour weeks, the cash flow rollercoaster, the leadership team that couldn't align.
That experience is what makes my coaching different. I'm not teaching theory — I'm sharing battle-tested lessons from the trenches. When I discovered the Scaling Up framework, it transformed my own business. Now I help other ambitious leaders implement the same systems: the One-Page Strategic Plan, the Rockefeller Habits, and the Four Decisions framework.
My clients typically see dramatic improvements in cash flow, profitability, and — perhaps most importantly — quality of life. Because what's the point of building a successful business if it runs you into the ground?
Real results from Brad's coaching
Challenge
Early-revenue startup needed a reliable, sustainable growth path to move beyond founder-led sales.
Outcome
Established long-term coaching partnership focused on sustainable scaling with structured quarterly rhythms.
Challenge
10-year-old business needed cash flow clarity across multiple divisions and service lines.
Outcome
Deep analysis using Cash Flow Story revealed hidden performance patterns and freed up working capital.
Challenge
Leadership team spread across regions needed aligned strategic direction and execution cadence.
Outcome
Facilitated high-impact strategy sessions that unified the leadership team around key priorities.
What Clients Say
Brad showed us resources we could use, explained things concisely, and gave us practical takeaways we could action immediately. His experience running his own company makes a real difference.
Andrew Stead
CEO, onebasehealth.com
Brad's advice and analysis on our cash flow has been invaluable. He challenged our assumptions and helped us see opportunities we were missing. Highly recommended for any business serious about scaling.
Craig Cairns
Co-founder & Director, Tilt Commercial
Brad's facilitation had a tremendous impact on our leadership team — insightful, inclusive, and focused on outcomes that matter. He kept us accountable without being prescriptive.
Deyasha Sukdeo
Managing Director, Global Access
How Brad Works With You
- Scaling Up CoachingFull implementation of the Scaling Up framework across the Four Decisions: People, Strategy, Execution, and Cash.
- Workshops & FacilitationIn-person and remote workshops for strategic planning, quarterly reviews, and team alignment sessions.
- Cash & Performance AdvisoryDeep dives into cash flow patterns, financial strategy, and performance optimization using proven Scaling Up tools.
Scaling Up Coaching
Full implementation of the Scaling Up framework across the Four Decisions: People, Strategy, Execution, and Cash.
Workshops & Facilitation
In-person and remote workshops for strategic planning, quarterly reviews, and team alignment sessions.
Cash & Performance Advisory
Deep dives into cash flow patterns, financial strategy, and performance optimization using proven Scaling Up tools.