The Ascent

Duane Jackson talks old lags, Lords and the long-game

The Ascent

Show Notes

Guy talks to Duane Jackson, founder of KashFlow, Supdate and Staffology. After a turbulent childhood - separated from his mum at the age of 11 and growing up in care - Duane left school with no qualifications. In between IT contracting and looking for some fast cash, he became involved in his friend's drug trafficking business, but in 1999 at Atlanta airport, he was caught with over 6,000 ecstasy tablets and was handed a five-year prison sentence. On release, he set up as a web developer with support from The Prince’s Trust, but finding that accounting products such as Sage and QuickBooks didn't meet his needs, he developed a web-based application, initially for his own use; that software became Kashflow, and within 10 years, Duane had sold the company for an undisclosed sum, thought to be in the tens of millions of pounds. Duane’s story is one of adversity, resilience and redemption, with many personal and professional triumphs, including the full-circle achievement of becoming a patron of The Prince’s Trust.

More from The Ascent

Oct 8, 2025

Tom Whicher is the founder of DrDoctor, a platform reshaping outpatient care across the NHS. In this episode, Tom shares how he turned a simple insight into a digital health solution used by millions, the reality of scaling behaviour-change tech, and what it takes to build products - and teams - that stick. A must-listen for anyone interested in purposeful innovation.

Oct 1, 2025

James Whiting is the Chief Executive of Doughty Street Chambers and a leader whose career has spanned law, global advocacy, and human rights. From frontline legal work to senior roles at Friends of the Earth and Malaria No More UK, James has consistently led with purpose. In this episode, he shares how to shape strategy in complex environments, build high-trust teams, and stay values-driven in moments that matter. A rich conversation with a truly principled and visionary leader.

Sep 23, 2025

Saskia Clark MBE is a three-time Olympian, Olympic gold and silver medallist, and one of Britain’s most decorated sailors. In this episode, she shares what it takes to stay resilient at the elite level, how to build strong partnerships under pressure, and the power of being deliberate in pursuit of success. From unshakable mindsets to smart decision-making, Saskia’s journey is packed with insights for anyone aiming to win - in sport, work, or life.

Sep 16, 2025

Adie Shariff is a performance psychologist with over 25 years of experience helping teams and individuals operate at their best when it matters most. From elite sport to business and the military, his approach is grounded, practical, and built on proven frameworks. In this episode, Adie unpacks the five core mindsets of performance, how to align teams through structure and accountability, and how to make change stick. A must-listen for anyone serious about elevating performance.

Sep 10, 2025

David Hopley OBE brings three decades of elite military leadership to the table - from commanding the UK Special Forces to mentoring leaders in business and sport. In this episode, he shares battle-tested insights on trust, decision-making under pressure, and the difference between managing and truly leading. Whether you're building a team, navigating challenge, or striving for high performance, David’s philosophy of creating meaningful step changes will leave you inspired.

See all episodes →