Top Bitcoin Holder: He Asked AI to Build Something That NEVER Existed, Here's What Happened!

Michael 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. 00:00:00 Intro 00:02:47 Why Michael's Background Matters for Everything That Follows 00:03:45 Why Bitcoin Is So Powerful Compared With Traditional Money 00:05:02 How Digital Money Actually Works Behind the Scenes 00:07:37 What Cash Really Is—and Why Most People Misunderstand It 00:10:29 Why Buying a House May Not Be the Wealth Strategy You Think 00:14:17 Why Stocks Still Matter in a Changing Financial World 00:15:26 Gold vs. Bitcoin vs. Stocks: Which Asset Wins? 00:17:41 How AI Could Transform the Economy Faster Than Expected 00:21:34 Is the Age of Abundance Closer Than We Think? 00:27:08 What Happens If AI Replaces Millions of Jobs? 00:29:48 Subscribe for More Conversations Like This 00:32:09 How AI Helped Generate $16 Billion in Value 00:37:50 Can AI Really Help You Find Your Next Billion-Dollar Business? 00:41:29 What Happens Next in the AI Revolution 00:46:57 Ads 00:48:24 What Will Be the Real Moat in an AI-Driven World? 00:56:15 Can Anyone Still Stand Out in the Age of AI-Generated Content? 01:12:55 Why Long-Term Thinking Creates an Unfair Business Advantage 01:18:21 Michael's Best Advice for Anyone Entering Adulthood 01:24:32 Michael's Bitcoin Accumulation Strategy Explained 01:31:34 Who Shouldn't Invest in Bitcoin—and Why 01:34:24 What’s One Thing You Believe That People Don’t Follow Michael: X: https://link.thediaryofaceo.com/bk3BNX Instagram: https://link.thediaryofaceo.com/HYkhXCE Website: https://link.thediaryofaceo.com/EfE3G6S Free education: https://link.thediaryofaceo.com/HDTRXYT The Diary Of A CEO: ◼Join DOAC circle here - https://doaccircle.com/ ◼Buy The Diary Of A CEO book here - https://link.thediaryofaceo.com/BWjLTZK ◼The 1% Diary is back - limited time only: https://thediary.com/products/one-percent-diary ◼The Diary Of A CEO Conversation Cards (Second Edition): https://thediary.com/products/the-conversation-cards-2nd-edition ◼Get email updates - https://link.thediaryofaceo.com/5IB1H6E ◼Follow Steven - https://link.thediaryofaceo.com/AGU9QP4 Sponsors: Cometeer - https://cometeer.com/DOAC use code DOAC for $20 off Pipedrive - https://pipedrive.com/CEO

Michael SaylorguestSteven Bartletthost

Aug 6, 20261h 39mWatch on YouTube ↗

EPISODE INFO

Released: August 6, 2026
Duration: 1h 39m
Channel: The Diary of a CEO
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Michael 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. 00:00:00 Intro 00:02:47 Why Michael's Background Matters for Everything That Follows 00:03:45 Why Bitcoin Is So Powerful Compared With Traditional Money 00:05:02 How Digital Money Actually Works Behind the Scenes 00:07:37 What Cash Really Is—and Why Most People Misunderstand It 00:10:29 Why Buying a House May Not Be the Wealth Strategy You Think 00:14:17 Why Stocks Still Matter in a Changing Financial World 00:15:26 Gold vs. Bitcoin vs. Stocks: Which Asset Wins? 00:17:41 How AI Could Transform the Economy Faster Than Expected 00:21:34 Is the Age of Abundance Closer Than We Think? 00:27:08 What Happens If AI Replaces Millions of Jobs? 00:29:48 Subscribe for More Conversations Like This 00:32:09 How AI Helped Generate $16 Billion in Value 00:37:50 Can AI Really Help You Find Your Next Billion-Dollar Business? 00:41:29 What Happens Next in the AI Revolution 00:46:57 Ads 00:48:24 What Will Be the Real Moat in an AI-Driven World? 00:56:15 Can Anyone Still Stand Out in the Age of AI-Generated Content? 01:12:55 Why Long-Term Thinking Creates an Unfair Business Advantage 01:18:21 Michael's Best Advice for Anyone Entering Adulthood 01:24:32 Michael's Bitcoin Accumulation Strategy Explained 01:31:34 Who Shouldn't Invest in Bitcoin—and Why 01:34:24 What’s One Thing You Believe That People Don’t Follow Michael: X: https://link.thediaryofaceo.com/bk3BNX Instagram: https://link.thediaryofaceo.com/HYkhXCE Website: https://link.thediaryofaceo.com/EfE3G6S Free education: https://link.thediaryofaceo.com/HDTRXYT The Diary Of A CEO: ◼Join DOAC circle here - https://doaccircle.com/ ◼Buy The Diary Of A CEO book here - https://link.thediaryofaceo.com/BWjLTZK ◼The 1% Diary is back - limited time only: https://thediary.com/products/one-percent-diary ◼The Diary Of A CEO Conversation Cards (Second Edition): https://thediary.com/products/the-conversation-cards-2nd-edition ◼Get email updates - https://link.thediaryofaceo.com/5IB1H6E ◼Follow Steven - https://link.thediaryofaceo.com/AGU9QP4 Sponsors: Cometeer - https://cometeer.com/DOAC use code DOAC for $20 off Pipedrive - https://pipedrive.com/CEO

SPEAKERS

Michael Saylor
guest
Executive chairman of MicroStrategy and prominent Bitcoin advocate known for leading large corporate Bitcoin purchases.
Steven Bartlett
host
Entrepreneur and host of The Diary of a CEO, known for interviewing high-profile business and cultural figures.

EPISODE SUMMARY

In this episode of The Diary of a CEO, featuring Michael Saylor and Steven Bartlett, Top Bitcoin Holder: He Asked AI to Build Something That NEVER Existed, Here's What Happened! explores michael Saylor on Bitcoin, AI arbitrage, and building durable wealth Saylor frames Bitcoin as “digital empowerment,” emphasizing permissionless ownership and transferability versus cash and bank-dependent fiat money.

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