We open Season 1 of Winning the Away Game with two guests who know what it means to be tested far from home.
Bryan Habana is a Rugby World Cup winner, Springbok legend and Toulon star who has had to rebuild his identity after retirement.
Orrin Klopper is the CEO of NetSurIT, a global MSP that has survived multiple crises, acquisitions and a full reinvention of its business model in recent years.
In this conversation we explore how both of them learned to win long after the final whistle.
In this episode we cover:
The day a 13-year-old Bryan watched the 1995 Rugby World Cup final at Ellis Park and realised rugby could unite a country – and change his life.
How King Edward VII School created a sense of brotherhood and belonging for both Bryan and Orrin, even when they weren’t the stars or prefects.
Why Orrin went from being expelled from schools to selling hot dogs, VHS tapes, second-hand shoes and eventually technology services.
The early NetSurIT years: bootstrapping, Microsoft partnerships, and the first US acquisition that nearly broke everything.
Bryan’s move from the Bulls and Stormers to Toulon: French club politics, media pressure, injuries and learning to live in a totally different culture.
The brutal personal chapter in New York where Orrin’s marriage imploded, the NYPD were looking for him after false allegations, and he had to rebuild his own sense of reality through deep self-work.
How COVID, the loss of major clients and an uncertain future forced NetSurIT to cut costs aggressively, rethink its core and launch a new “Innovate” offering in AI, automation and digital transformation.
Bryan’s lowest moment: realising a knee injury had quietly ended his career, announcing his retirement, and breaking down at home as he opened the door and heard his son laugh.
The five transferable traits Bryan believes every successful person needs: discipline, sacrifice, hard work, resilience and perseverance – regardless of industry.
Why he says rugby was never his full identity, and how “unlearning to learn” is the key to his next chapter as an entrepreneur with Paymenow.
How fatherhood shifted Orrin’s decision-making, made him more decisive, and paradoxically helped the business grow faster.
What legacy looks like for both men over the next decade: purpose-driven businesses, stronger families and using their stories to help others win their own “away games”.
Guests
Bryan Habana – World Cup–winning Springbok, former Toulon wing, entrepreneur and co-founder of Paymenow.
Orrin Klopper – CEO and founder of NetSurIT, a global managed services provider with operations in South Africa and the US.
About the show
Winning the Away Game is hosted by Justinus Adriaanse and Flip van der Merwe. We bring together stories from rugby and business to explore what it really takes to succeed when you’re far from your comfort zone.
Winning The Away Game is produced by Jonathan Warncke