The Mustard Seed Bitcoin Podcast

What happens when a Wall Street quant abandons the fiat casino to chase the hardest money on earth? We unpack Matt McDonagh’s journey from machine-read value screens to an AI-driven venture thesis, tracing how warped price signals, momentum trading, and excess money printing pushed him toward bitcoin’s decentralized rails and a future where technological abundance meets absolute scarcity.Timestamps:00:00 - Intro00:55 - Investment banker beginnings02:15 - Building a machine-read hedge fund04:10 - First brush with bitcoin at Princeton Club06:45 - Hedge fund collapses, tech pivots09:30 - Counting missed satoshis and opportunity cost11:12 - Ai and bitcoin: dueling singularities17:45 - Peering around the technological corner22:07 - Centralization versus decentralization26:21 - Fiat distortions and the asset owner advantage30:17 - Real estate as a leaky store of value35:14 - Technology deflation meets absolute scarcity39:56 - Robots, bio-ceramics, and cheaper housing46:06 - Suppressed tech, electrification, and AI parallels49:15 - Infinite abundance paired with bitcoin scarcity50:52 - Satoshi theories: AI or state project?52:34 - Closing thoughts and thanks

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

Bitcoin is eating the financial system. In this episode, Michael lays out the blueprint for bitcoin treasury companies and explains why preferred equity is the key to unlocking trillions in passive capital. We explore how MicroStrategy’s strategy could be copied, why bitcoin should outperform the S&P 500 long term, and how capital markets are being reshaped around digital scarcity. Michael also breaks down how to weaponize BTC-backed credit to protect NAV, force short squeezes, and magnetize index fund flows.TIMESTAMPS:0:00 – Intro1:00 – First priority as director of bitcoin strategy3:11 – Should bitcoin companies copy MSTR’s preferreds?5:02 – Structuring credit: BTC ratings from 2 to 106:25 – Long-term CAGR for bitcoin vs S&P 5008:28 – Why bitcoin has fewer risks than stocks10:36 – The global index with no counterparty risk15:14 – Is bitcoin a global productivity index?16:56 – Will MSTR join the S&P 500?18:14 – Why Vanguard owns MSTR19:23 – Unlocking passive capital for bitcoin21:14 – Why BTC companies magnetize capital23:24 – Mag 7 adoption playbook: fast vs slow25:47 – Most CEOs don’t want the money27:15 – Who should adopt bitcoin—and who won’t29:20 – Why MSTR is going all-in on preferreds31:21 – Preferreds are better than convertibles32:32 – Will BTC companies still trade above NAV in bear markets?34:09 – Why 2022 was a crypto-catalyzed bear market35:14 – Difference between 1.1x and 100x leverage37:07 – How to defend BTC NAV with credit instruments39:14 – How to create a bitcoin short squeeze41:20 – Why shorts don’t have the courage43:20 – The future of BTC-backed credit and equity45:04 – A new theory of bitcoin corporate finance49:30 – Copy MSTR: it’s good for everyone50:26 – Harvard’s outdated bitcoin case study52:16 – Why the smartest firms are making bad moves54:16 – Why academics ignore strategy’s success55:15 – How the world could look in four years57:09 – Final thoughts and wrap-up

Hello everyone! I’m excited to relaunch my podcast under a new name:

The Mustard Seed—a bitcoin and contrarian long-term thinking podcast.

My first real job out of graduate school was in technology consulting at Ernst & Young. After gaining a little experience there, I made the decision to jump full-time into bitcoin. One of the most valuable things I did early on was host a bitcoin podcast. It allowed me to learn directly from some of the most intelligent minds in the space and build lasting relationships.

The podcast is my way of staying connected to the most thoughtful people in bitcoin. It helps me better understand how capital is flowing into bitcoin and how the smartest leaders are positioning themselves as bitcoin continues to reshape global capital markets.

In my role as Director of Bitcoin Strategy at Semler Scientific, my top priorities are strategic execution of bitcoin acquisitions and generating stockholder value. These conversations sharpen my thinking, surface new ideas, and help educate a broader audience about both bitcoin and Semler Scientific.

I believe we’re still incredibly early in global bitcoin adoption. I think thoughtful dialogue and deeper understanding can help accelerate hyperbitcoinization, and this podcast is one way I plan to contribute. The first episode is coming soon, and it will be with Michael Saylor. If you have specific questions you’d like me to ask, let me know.

Please subscribe if you enjoy my work.