What if Strategy’s bitcoin strategy is just the beginning? In this episode, we sit down with Tad Smith, former CEO of Sotheby’s and Madison Square Garden, to explore why bitcoin is resonating with a generation priced out of the system. Tad explains how liquidity drives asset markets, how bitcoin is quietly demonetizing art and education, and why he believes consolidation is coming for bitcoin treasury companies. We discuss Michael Saylor’s latest innovations like Stretch, what makes a credible mNAV premium, and why bitcoin may be transforming into the foundation for a new financial system. Tad also shares his personal investing framework, what he would do if he were running Semler Scientific, and how his generation failed the next one.Timestamps:00:00 - Intro01:00 - How Tad thinks about macro cycles and investing03:22 - Why liquidity is the key macro signal05:20 - When Tad takes profits and how he does it06:30 - Where he parks cash short term and why07:42 - Why gold is useful—but only short term08:10 - Are we near the end of the current bitcoin bull market?10:07 - Why Tad thinks we may be in the final minutes of this cycle11:20 - Long-term vs short-term bitcoin investment mindset12:34 - Could bitcoin ever crash like 2022 again?13:05 - Black swans and the evolution of bitcoin’s investor base14:37 - What happens to money market funds if rates are cut?16:11 - Interest rates and bitcoin-linked preferred stocks17:17 - Why Tad prefers common shares over preferreds18:35 - Stretch, bitcoin, and the birth of a stablecoin?20:19 - Is MicroStrategy becoming the new JP Morgan?22:09 - Why bitcoin resonates with younger generations25:22 - How money printing punishes the working class28:26 - The case for a new monetary system32:35 - Why bitcoin treasury companies are booming34:35 - What Tad would prioritize at Semler Scientific35:46 - Would Sotheby’s or MSG have adopted bitcoin?39:20 - Why every investment must outperform bitcoin’s hurdle rate41:09 - The future of bitcoin treasury companies42:53 - Why consolidation is inevitable44:09 - How Tad thinks about MNAV premiums47:41 - Is bitcoin demonetizing art and education?50:45 - Tad sold his wine collection for bitcoin51:18 - Final thoughts and closing remarks