Learning, Leading and Letting Go with Dean Matthews

In this episode, Chris sits down with Dean Matthews, founder of SaaS platform OnTheClock, to unpack what failure really looks like across a 20-year journey of bootstrapping, building, and staying focused.Dean shares how failing fast became a competitive advantage, why chasing shiny objects nearly derailed him early on, and the hard lessons that come from spreading yourself too thin. From walking away from side projects, to learning when to say no, to making decisions with incomplete information and real financial consequences, this is an honest conversation about discipline, delegation, and learning in public.It’s a grounded look at anti-failure in practice. Not dramatic blow-ups or overnight wins, but the quiet decisions that compound over time and turn setbacks into momentum.