I keep on going back to the idea that it's really difficult to do nothing.
Bogle figured it out. We are wired to trade. We can't stand still. We keep on second guessing ourselves.
But in Bitcoin, like Stocks, the big money is in waiting.
E172: @Saylor: Why Hard Work Won't Make You Rich
Michael Saylor is the chairman of @Strategy - the world's largest corporate holder of Bitcoin with over 840,000 BTC and $65+ billion deployed. He bought his first Bitcoin in 2020 when the Fed cut rates to zero hasn't stopped since.
With WSH, I always want to go much deeper than the current narrative and that’s exactly what we did here. We gradually moved past the surface and into the things that really shaped Michael. We talked about his childhood, growing up in a military family, buying domain names in the 1990s and flipping them for tens of millions, losing $6 billion of his net worth in a single day during the dot-com bubble, his great Apple bet in 2012, why working hard won't make you rich, why you should mortgage your house but probably not sell your kidney to buy BTC, why "THERE IS NO SECOND BEST", and a lot more. The conversation lasted more than two hours, much longer than originally planned, and it was just amazing. I hope you enjoy it as much as I did.
Timestamps:
00:00 - Intro
03:05 - Explain what you do to an Uber driver
05:35 - Advice for Rick, the struggling Uber driver
07:07 - Who is Michael Saylor?
11:02 - Sponsors @Trezor & @Bitwise
11:48 - Kevin's Business Intelligence Company
13:14 - Michael's childhood and chip on the shoulder
17:56 - Has Michael conquered the world yet?
19:49 - Just because you can, doesn't mean you should
28:23 - Sponsors @KASTxyz & @sumsub
30:02 - Low time preference and scarcity
43:50 - Buying and flipping domain names for tens of millions
55:11 - Bitcoin is a lifeboat
1:01:31 - Should you mortage your house to buy Bitcoin?
1:09:50 - The great $60B in Bitcoin bet: risks
1:15:32 - Sponsors @JupiterExchange , @ethena
1:16:16 - Sell the kidney if you must but keep the Bitcoin
1:20:14 - What's the endgame for Strategy?
1:28:16 - Where does Bitcoin price end?
1:29:36 - Where would Bitcoin price be without Michael Saylor?
1:31:06 - What is STRC?
1:35:34 - Should my mom put her life savings in STRC?
1:37:12 - How do you always invent new ways to buy more Bitcoin?
1:49:19 - From God to Madman every 6 months: handling insane volatility
1:51:49 - How Michael lost $6 Billion of his net worth in one single day in 2000 and then watched MSTR go down another 99%
1:59:09 - Why Michael doesn't have children
1:59:44 - Why working hard is the worst advice you can get
2:07:37 - Why THERE IS NO SECOND BEST, there is only one crypto asset
2:15:03 - Thanking Michael from the whole crypto industry
Economics is pretty simple.
Private property.
Free trades between people.
No state should try to make the market efficient, the market is efficient by design.
And that’s it.
Strategy has acquired 24,869 BTC for ~$2.01 billion at ~$80,985 per bitcoin and has achieved BTC Yield of 12.6% YTD 2026. As of 5/17/2026, we hodl 843,738 $BTC acquired for ~$63.87 billion at ~$75,700 per bitcoin. $MSTR $STRC https://t.co/y1zvePEuym
Strive just took this one step further by going daily payments on $SATA. This is what the future of digital credit looks like.
Well done @Strive@ColeMacro !
Der CLARITY Act hat soeben es mit 15 zu 9 Stimmen durch den Bankenausschuss des Senats geschafft. 🇺🇸🔥
Das war eine zentrale Hürde – als nächstes steht die Abstimmung im Senat an, die erfolgreich sein muss, bevor das Krypto-Markstrukturgesetz verabschiedet werden kann. 👀
Today we announce our new identity.
Strive. The Daily Dividend Company.
Beginning June 16, $SATA dividends will be paid each and every Business Day. No more waiting.
This marks a major step forward in aligning dividend paying securities with the speed of modern markets. We are extremely proud to be the first company to bring daily dividends to our investors.
In addition, we are now DEBT FREE. Zero debt, completely clean balance sheet with amplification provided solely by $SATA.
Just over eight months ago, we held zero Bitcoin. Today, we hold 15,009 BTC and are unlocking major innovations across the equity markets for the benefit of our shareholders.
This is just the beginning.
Strive for Excellence.
Hal Finney (@halfin) wäre heute 70 Jahre alt geworden. 🎂
Der inzwischen leider verstorbene Cypherpunk war der Empfänger der ersten Bitcoin-Transaktion – und laut einer neuen Recherche vielleicht sogar auch Satoshi Nakamoto. 👀
Ruhe in Frieden! 🕊️🕯️
⬇️
https://t.co/Iw13pbkcX7