Ep.39 - Andy Rafal - Investor Turned Operator

In this episode, I sit down with Andy Rafal, CEO of OLI—a 50+ year-old chemical engineering software company operating at the intersection of AI and the physical world.Andy and I have known each other for over 20 years, going back to our early days in New York City. This conversation covers his journey from hedge fund investing at Tiger to becoming an operator and CEO—and the lessons learned along the way.We talk about career transitions, decision-making under uncertainty, and what it really means to build something over the long term.We also dig into how AI is reshaping industries—especially those rooted in the physical world—and why the biggest opportunities may lie in bridging the gap between software and real-world systems.Episode Timestamps00:00 - Intro + what we cover02:20 - Andy’s early career path: Cornell, law school, and following curiosity07:15 - Why he turned down law for Tiger22:43 - Lessons from Tiger: wins, losses, and what actually matters28:06 - Why curiosity and lifelong learning are career superpowers30:22 - The transition from investor → operator — and the difference between analyzing a business vs. building one37:58 - How COVID reshaped leadership, culture, and strategy38:26 - Building teams, culture, and long-term thinking41:01 - Taking over a 50+ year-old company founded by his father41:31 - The challenge of modernizing a legacy business44:23 - How AI is impacting engineering, chemistry, and real-world systems48:29 - The risk of AI “getting things wrong with confidence”49:46 - Writing publicly, learning in public, and finding a voice as a CEOKey TakeawaysCareer paths are rarely linear—following curiosity often leads to better outcomes than rigid planningInvesting teaches you how businesses work—but operating teaches you how hard it is to build oneNot every decision needs to be perfect—but you need to update your thinking as new information comes inThe biggest opportunities often sit at the intersection of old systems + new technologyAI will transform industries—but human judgment and real-world context still matter deeplyTaking time to think (and not rushing into the next thing) can be one of the most valuable decisions you makeConnect with Andy on LinkedIn: https://www.linkedin.com/in/andy-rafal/Follow Andy on Substack: https://arafal.substack.com/If you enjoy conversations like this, I write a weekly newsletter called Intentional Wisdom where I share:Notes on health, performance, and longevityCareer insights and lessons from conversations like thisTools and ideas I’m experimenting withYou can subscribe here: https://gregcampion.substack.com/