Notes on Young Michael Saylor

I dive into evolution of Michael Saylor alongside his company, MicroStrategy, illustrating Saylor's rise from humble beginnings, the establishment of MicroStrategy driven by his tech foresight, and the challenges he faced post an accounting scandal in 2000. I consider Saylor as a visionary who deftly navigates through adversities, embraces innovations like Bitcoin, displays skin in the game, and always a willingness to risk it all.

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"I can't hedge [against the probability of future problems]. I'm going to go to extremes. I have $50,000 in the bank, $7 [million] to $8 million in the company. Either we're going to make it big or lose it all,"
“The lessons are that people are capable of accomplishing great things if they set their mind to it and that we should not allow ourselves to be hijacked by a small goal or a pedestrian thought”
"The first few million is important. You can buy a nice house. The rest gives you credibility to approach people to ask them for things. When you're worth a certain amount, you get the attention of everyone in the room."
..your anti-technology tendencies are exactly what the establishment wants, because every financial provider is taking advantage of you, every medical provider is taking advantage of you, every standard vendor is taking advantage of you in the current status quo"
"I'd rather lose $100 million and take my shot at greatness than sell out and become a millionaire." - Michael Saylor
Michael Saylor


Andrew Flattery, CFP®

Andy Flattery is a CERTIFIED FINANCIAL PLANNER™ and Owner of Simple Wealth Planning. He serves young and affluent families that are working to lower their time preference and achieve financial sovereignty. Flattery is the host of The Reformed Financial Advisor Podcast, where he relates stories in Kansas City history to pivotal themes in personal finance. When he’s not helping individuals build wealth, you can catch him playing rec sports, reading Austrian economists, and spending time with his wife and three children.