August 6, 2026
137,695
6,489
1,622
5.89%
Every word spoken in this episode is indexed. Type any phrase to jump straight to the moment it was said.
Type any word or phrase that may have been spoken. Click a result to seek the player to that exact moment.
Try a name, a topic, or a quoted line
Episode Timeline
Every episode in order around the one you’re watching — click any card and the page flips straight to it.
1:39:55Now PlayingMichael made $15 billion last year using ChatGPT, by building something that has never existed in the history of the world. He argues that the dollar has lost 7% of its value every year for a century, that the safe options; your savings, your bonds, your house are quietly making you poorer, and that the people who get ahead now will be the ones who know what questions to ask AI.
Michael Saylor is the founder and Executive Chairman of Strategy, formerly MicroStrategy, the first publicly traded company to adopt Bitcoin as its primary treasury asset. He holds dual degrees from MIT in aerospace engineering and the history of science, is a named inventor on more than 48 patents, founded Alarm.com and Angel.com, and wrote The Mobile Wave. His company now holds 847,000 Bitcoin, more than anyone on Earth except Satoshi. He is one of the most divisive figures in finance, and one of the very few who has been proven right so far.
He explains:
◼ Why he says you shouldn't buy a house, and the tax nobody factors in when they do
◼ How he used ChatGPT to design a financial instrument that had never existed in the history of the world, and made $15 billion
◼ Why the dollar loses 7% of its value every year, and what that quietly does to your savings
◼ Where he thinks Elon is wrong about the age of abundance, and why money will still matter when the robots arrive
◼ What happened when the market decided his company's $55 billion of assets were worth nothing
The views expressed are those of the guest, and this conversation is intended for general informational purposes only. This podcast and its associated materials should not be used as a substitute for professional medical, legal, or financial advice.
Follow Michael:
Free education
The Diary Of A CEO:
◼Join DOAC circle here
◼Buy The Diary Of A CEO book here
◼The 1% Diary is back limited time only
◼The Diary Of A CEO Conversation Cards (Second Edition)
◼Get email updates
◼Follow Steven
Sponsors:
Cometeer use code DOAC for $20 off
Sentinel Indexing in Progress
Metadata and chapters are available. Claim extraction for this episode is pending.
All video content is delivered via YouTube embedded players in accordance with the YouTube Terms of Service. Sentinel provides research tools that promote discovery and accountability across political media.