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.Episode Chapters:00:00 Intro: Meet Brandon Spear, CEO & Serial Entrepreneur02:00 Early Risks & The Birth of the Internet in South Africa06:00 Turning Around Quadrant Through Customer Feedback12:00 Navigating the 2008 Financial Crisis: Cutting Fat vs. Muscle17:00 Preparing for Exit: Selling to Ariba in 201121:00 Joining TreviPay: 11 Years of Growth and Evolution25:00 Choosing the Right Private Equity Partner27:00 The Future of B2B Payments: AI, Digitization & Stable Coins36:00 Building Leadership Teams: Timing Executive Hires Right43:00 Rapid Fire: Career Lessons, Books & Leadership SkillsEpisode Resources:Jeff Rudner on LinkedIn: https://bit.ly/3DEGINHBrandon Spear on LinkedIn: https://www.linkedin.com/in/brandon-spear-171a112/ TreviPay Website: https://trevipay.comTreviPay on LinkedIn: https://linkedin.com/company/trevipayProseer Website: https://proseer.co/Book a Consultation Contact Us: https://proseer.co/contact/Download Our eBook Transforming Accounting Solutions: https://proseer.co/rules-ebook/Book Mentioned:The Innovator's Dilemma by Clayton M. Christensen - Available on Amazon: https://amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780Previous guests include: Sabrina Valle and Jessica Quon, co-founders of the Jam Stand and Mighty Picnic, Tom Hunt, Founder and CEO of Fame, Kenny Dettman, Founder and CEO of TaxNow, Rick Zullo, founder and managing partner of Equal Ventures, Adam Schwartz, founder and CEO of Parable and former co-founder of TeePublic.Check out our three most downloaded episodes:Scaling Smarter: Adam Schwartz on Data, AI, and Entrepreneurial GrowthThe Exit Playbook: Johan Hoernell’s Secrets to Scaling and SellingPivot & Prosper: Scaling a CPG Brand the Smart Way with Sabrina Valle and Jessica Quon