Pivot, Plan, and Persevere: Navigating Uncertainty with Philip Chao – Part 2

Navigating Uncertainty and Building Resilience with Philip Chao (Part 2)

In this second installment of our conversation with Philip Chao, Chief Investment Officer of Experiential Wealth, we continue to unpack what it takes to lead a business through uncertain times. Philip brings decades of experience—and his signature straight-talking style—to the table, sharing hard-won insights on navigating risk, seizing opportunities, and staying true to your long-term goals.

We dive into the importance of liquidity—why it’s critical to have ample reserves when the unexpected happens—and how business leaders can position themselves to capitalize on new opportunities even in the most challenging climates. Philip’s advice is both practical and philosophical: it’s about keeping your feet on the ground while still reaching for the stars.

Chelsea and Philip discuss the power of a well-crafted business plan, not just as a document, but as a process that forces you to challenge your assumptions and refine your goals. From building the confidence to pivot when necessary, to understanding that resilience is about both grit and humility, this episode is a masterclass in long-term thinking.

We also explore the importance of having an outside perspective—someone who can challenge your decisions and ask the tough questions that help you grow. Whether it’s making that next hire, expanding your business, or deciding to hold steady, Philip’s insights remind us that just because we were successful yesterday doesn’t guarantee success tomorrow.

If you’ve ever felt the weight of leading a team through uncertainty or struggled with knowing when to push forward or pivot, this episode is for you. Tune in to learn how to navigate the business rollercoaster with confidence, clarity, and a healthy dose of curiosity.

Curiously Stuck Podcast

Welcome to Curiously Stuck

Every founder, executive, and creative leader has been there—that pivotal moment where you don’t know the next move, but you know something has to change. Curiously Stuck is a podcast for those moments. Hosted by Chelsea Rae Stuck, brand strategist and founder of Craeve & Co., this series dives into the honest, often messy stories behind leadership pivots, unexpected challenges, and the curiosity that drives reinvention.