I spoke with Dan Rupp, founder and CIO of Parkway Capital, about what it means to leave a respected institution, launch a fund in the teeth of an Asian bear market, and build an investment business from scratch. Dan launched Parkway in 2024, when sentiment in Hong Kong and across much of Asia was still deeply depressed, but he was unusually confident that the opportunity set was improving. That made this a good moment to explore not just his investment views, but how starting Parkway has sharpened his thinking about the craft and business of investing. We discuss what Dan wanted to build at Parkway that he could not build at Overlook, why a smaller size opens up parts of the market that larger firms cannot easily access, and how his process has evolved now that it is live and supported by a growing team. He explains how Parkway narrows a huge Asian universe into an actionable set of ideas, how tools, scorecards and AI fit into the workflow, and why human judgment still matters most when assessing management, correlation, risk and portfolio fit. We also talk about the business side of running a fund: marketing, time allocation, culture, delegation, and the challenge of being fully responsible for both investment results and the firm itself. Dan reflects on lessons carried over from Richard Lawrence and Overlook, especially the importance of serving LPs well through alignment, fee discipline, fund-size limits and a focus on capital-weighted returns rather than asset gathering for its own sake. The conversation closes on a more personal note, with Dan reflecting on energy, longevity and the example set by his mother, who is still selling real estate at nearly ninety. As always, this conversation is for general discussion only, not investment advice.
