Dugout Dinners #9: ‘Failing Upwards’ with Felix Riley bought to you by The Peer Space

We like to think of ourselves as rational decision-makers, but the truth is, fear quietly controls much of what we do – and don’t do – every day. We fear failure, ridicule, starting over, even success itself. Fear disguises itself as caution, pragmatism, or “being realistic,” and it keeps us locked in the familiar, choosing comfort over growth. In business and in life, that fear leads to missed opportunities, small thinking, and regret.

This talk is about recognising that fear – not avoiding it, not pretending it’s not there – but understanding it, naming it, and then using it.

Because fear, properly harnessed, can be rocket fuel. It tells us exactly where the next breakthrough lies. Behind the door we’re scared to open is the thing we most need to do. It won’t be easy – the path will zig-zag, setbacks are guaranteed, and it will feel deeply uncomfortable. But no success story exists without someone facing their fear and doing it anyway.

About Felix Riley

Felix Riley began his career as a comedy writer before transitioning to finance in The City. There, he launched his own company, which he later sold to an NYSE-listed American brokerage. He stayed with the firm as a Managing Director and joined its Global Executive Board. His work has since spanned sectors and continents – from negotiating mining deals with President Banda in Zambia to turning around struggling UK businesses.

He is also the author of two thrillers published by Penguin. For over a decade, Felix has worked as a Business Strategist, helping organizations take more creative approaches to problem-solving and growth. One client at a major consultancy calls him “the consultant to the consultants,” aptly summarizing his impact.

His diverse client base includes global law firms, management consultancies, charities, hospitals, private banks, accelerators, enterprise-level IT companies, CO2 reduction enterprises, e-commerce platforms, domiciliary care providers, agricultural consultants, and various start-ups.

Felix combines business acumen, creative insight, and exceptional problem-solving abilities. He helps both entrepreneurs and senior executives unlock fresh thinking and drive meaningful, transformative change.

Tickets £65 (includes a 3-course meal and welcome drink)

*Event might include photography and videography, if you are not keen on being filmed or photographed, please let our team know.