Duane Jackson: How I Came to Appreciate Big Companies

When Duane sold KashFlow, his first business, he exited early from his earnout after suggesting he might set up a workforce union – he wasn’t keen on working in a large organisation…

Two successful company exits later and following the acquisition of his third business, he’s been with the acquirer for over three years. What changed? It wasn’t the acquirer – in both cases Iris Software – one of the UK’s largest private software companies. Duane discusses how his views on entrepreneurship, starting and selling companies has evolved over time and appreciating different perspectives has been a central part of his growth as an entrepreneur. He also shares some of the things that have made his companies such irresistible targets for acquirers.

Duane Jackson

Founder, KashFlow & Staffology

Duane is an entrepreneur with a bio that includes the words, ‘which culminated in my arrest at Atlanta Airport with 6,500 ecstacy tablets‘, He became an entrepreneur after the subsequent, almost inevitable, prison sentence because he was left with no alternative given the ‘large black hole in my CV’.

He set up a web design business with the help of a grant from The Prince’s Trust a UK based organisation to help give people a second chance. His realisation that accounting programmes sucked was the inspiration for KashFlow, a SaaS based simple web accounting package for small business. He sold KashFlow in 2013 and has subsequently created and sold two more SaaS companies, most recently Staffology.

If you’re interested in the early story and how he applied his marketing brilliance to growing KashFlow, you should watch this conversation from BoS Europe 2015.

You should also read his book, Four Thousand Days: My Journey From Prison To Business Success.