In this episode of 5 to 50: Financial Strategies for Growing Companies, Jeff Rudner sits down with Brandon Spear, CEO of TreviPay, whose three-decade career spans four continents and multiple successful exits. Brandon shares his journey from co-founding South Africa's first commercial internet service provider in the early 1990s to leading TreviPay through its recent private equity carve-out. He offers candid insights on navigating the 2008 financial crisis, turning around struggling businesses through customer-centric approaches, and preparing companies for strategic acquisitions. Brandon also discusses the future of B2B payments, the role of AI in creating competitive moats, and why building trust is the most undervalued leadership skill. Whether you're a founder preparing for an exit or scaling through uncertainty, this episode is packed with battle-tested wisdom from someone who's been there multiple times.