Harley Bassman, managing partner at Simplify Asset Management and widely known as the “Convexity Maven,” joins Monetary Matters to break down the hidden risks shaping today’s markets. He explains why inflation is likely to remain structurally higher, why massive fiscal deficits matter more than Fed policy, and how passive flows continue to support equities despite growing cracks underneath. The conversation dives deep into bonds, mortgage-backed securities, credit risk, gold as an alternative currency, and why convexity is the key concept investors consistently underestimate. Bassman also outlines practical portfolio hedges designed to perform when markets move to extremes, offering a rare, long-horizon framework for navigating uncertainty in 2026 and beyond. Read Harley’s 2026 Stocking Stuffers here: https://www.convexitymaven.com Follow Harley Bassman on Twitter: https://x.com/ConvexityMaven Follow Jack Farley on Twitter: https://x.com/JackFarley96 Follow Max Wiethe on Twitter: https://x.com/maxwiethe Follow Monetary Matters on: Apple Podcast https://rb.gy/s5qfyh Spotify https://rb.gy/x56dx5 YouTube https://rb.gy/dpwxez Timestamps: 00:00 Introduction to Financial Crises and Convexity 00:30 Meet the Convexity Maven: Harley Bassman 01:08 Macro View: Inflation and Economic Drivers 01:48 Demographics and Spending Trends 03:24 Immigration and GDP Growth 04:21 Fiscal Policy and Inflation 05:36 Bond Market Predictions 13:27 Equity Markets and Passive Flows 17:31 Mortgage-Backed Securities: A Safe Bet? 23:51 Leveraged Trades and Interest Rate Hedges 32:09 Comparing Long Duration Investments 33:50 Understanding Positive Carry in Options 40:36 Private Credit and High Quality BDCs 48:48 Investing in Big Oil and MLPs 55:03 Gold as an Alternative Currency 01:00:12 Portfolio Construction and Sizing 01:01:50 Conclusion and Future Episodes