MicroStrategy

company on 11 shows · 34 statements across 13 episodes · said 122 times in 35 episodes since 2013

My First Million 76 TBPN 13 All-In 10 the MAD Podcast 8 20VC 6 Capital Allocators 4 Big Technology 2 the Startup Ideas Podcast 1 WTF is with Nikhil Kamath 1 Top Founders 1 More or Less

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My First Million 76TBPN 13All-In 10the MAD Podcast 820VC 6Capital Allocators 4Big Technology 2Top Founders 12 more shows

2026 4 mentions in 2 episodes 2 per episode
2025 14 mentions in 9 episodes 2 per episode
2024 54 mentions in 12 episodes 5 per episode
2021 43 mentions in 5 episodes 9 per episode
2018 1 mention in 1 episode
2017 1 mention in 1 episode
2016 2 mentions in 2 episodes 1 per episode
2015 1 mention in 1 episode
2014 1 mention in 1 episode
2013 1 mention in 1 episode

every mention on every show, scene by scene, with the transcript →

34 statements about MicroStrategy, every show

TBPN Assertion Supported
Coogan: MicroStrategy stock dropped 50% following a controversial published statement
“Obviously, people are dunking on this because the stock has traded down 50% since this was published.”
John Coogan Nov 15, 2025 ▶ 11:48 Blue Origin Lands Rocket, Valve Drops Steam Machine, Cantor Group Surges | Diet TBPN
20VC Opinion
Green: MicroStrategy's strategy of issuing debt for crypto is a house of cards
“The idea, like, from what I understand, microstrategy is effectively issuing debt to buy, to go in the market and buy more To go to buy more like crypto and they just keep doing it. But if that reverses, eventually got paid on the debt. I don't know. It just s…”
Mitchell Green Mar 26, 2025 ▶ 1:13:53 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Sam Lessin: MicroStrategy is a hack for fund managers to buy Bitcoin
“The reason that MicroStrategy stock exists, right, is because there's a lot of fund managers Right. Who would love to invest in Bitcoin, but it's just too fucking painful that for them to deal with it with their funds. And so micro strategy is just this hack f…”
Sam Lessin Jan 31, 2025 ▶ 35:33 #84: China's DeepSeek Shakes the Tech World · More or Less Podcast
ALL-IN Opinion
Calacanis: Borrowing billions to corner Bitcoin is antithetical to Bitcoin's purpose
“Financial strategy of taking out billions of dollars in loans and then trying to corner the market and be the largest shareholder of Bitcoin, which is antithetical to the concept of Bitcoin, somebody cornering the market, also taking out loans and something th…”
Jason Calacanis Jan 20, 2025 ▶ 49:03 All-In Inauguration Day Livestream with the Besties from Washington, DC!
ALL-IN Opinion
Calacanis asserts MicroStrategy's valuation multiple over its Bitcoin holdings is unsustainable
“Then I looked at micro strategies and that made no sense to me that they were trading at two, three, four times The book value of their Bitcoin. And I think that's not sustainable.”
Jason Calacanis Jan 4, 2025 ▶ 44:11 2025 Predictions: Tech, Business, Media, Politics!
ALL-IN Opinion
Chamath: Saylor turned MicroStrategy into a massively levered long Bitcoin play
“He's really running their Bitcoin position, and he's created this massively levered long Bitcoin play. He's borrowing money at essentially zero. It's his returns are bananas right now.”
Chamath Palihapitiya Dec 25, 2024 ▶ 47:30 The All-In Holiday Spectacular
ALL-IN Assertion Partly supported
Baker: MicroStrategy's core business generates only $400M in annual revenue
“But the, but his, the underlying business that, you know, pays the interest expense on the debt only does four hundred million dollars a year in revenue, and it's, you know, high gross margin revenue.”
Gavin Baker Dec 7, 2024 ▶ 42:13 New SEC Chair, Bitcoin, xAI Supercomputer, UnitedHealth CEO murder, with Gavin Baker & Joe Lonsdale
MY FIRST MILLION Assertion Supported
MicroStrategy stock surged 2,600% over five years, vastly outperforming Nvidia.
“And it is, so it's up in the last five years by 2600%. Okay, so it's shot up. It's if you compare it to even Nvidia stock this year, it's outperformed Nvidia, which is pretty insane.”
Shaan Puri Dec 5, 2024 ▶ 27:05 3 Stories of Crazy Geniuses: Fenn’s Treasure, Michael Saylor’s Infinite Money Glitch + more
MY FIRST MILLION Assertion Partly supported
MicroStrategy’s core software business is declining 10% annually and is functionally irrelevant.
“The actual software business is declining 10% a year, and is something like a couple hundred million in revenue and under a hundred million of net income. So it is a rounding error. It is not, it is no longer relevant to the stock price.”
Shaan Puri Dec 5, 2024 ▶ 27:32 3 Stories of Crazy Geniuses: Fenn’s Treasure, Michael Saylor’s Infinite Money Glitch + more
MY FIRST MILLION Assertion Supported
MicroStrategy holds nearly 400,000 Bitcoin and has outperformed the entire S&P 500.
“They've basically acquired almost 400,000 Bitcoin. they've outperformed every company in the S&P 500. And last week alone, it saw one hundred and thirty six billion dollars of trading volume.”
Shaan Puri Dec 5, 2024 ▶ 37:54 3 Stories of Crazy Geniuses: Fenn’s Treasure, Michael Saylor’s Infinite Money Glitch + more
Michael Saylor intentionally detached MicroStrategy from its software fundamentals into a meme.
“So he's basically created, he's Intentionally turned him, turned MicroStrategy into a meme stock. Meaning, he's detached it from the underlying business in the way that GameStop did.”
Shaan Puri Dec 5, 2024 ▶ 38:09 3 Stories of Crazy Geniuses: Fenn’s Treasure, Michael Saylor’s Infinite Money Glitch + more
MY FIRST MILLION Assertion Supported
MicroStrategy trades at a massive 2.5x multiple of its underlying Bitcoin NAV.
“MicroStrategy stock, which today trades at like a two and a half times Multiple of NAV. You know, NAV is the net asset values, like the underlying asset that it holds, right? It owns thirty-three billion dollars of Bitcoin. So the question is, why is it an eig…”
Shaan Puri Dec 5, 2024 ▶ 41:35 3 Stories of Crazy Geniuses: Fenn’s Treasure, Michael Saylor’s Infinite Money Glitch + more
MY FIRST MILLION Assertion Supported
MicroStrategy currently owns approximately 1% of the entire global Bitcoin float.
“He owns about one percent of the Bitcoin float today, and he's trying to get, you know, two percent, basically.”
Shaan Puri Dec 5, 2024 ▶ 43:08 3 Stories of Crazy Geniuses: Fenn’s Treasure, Michael Saylor’s Infinite Money Glitch + more
MicroStrategy's debt-fueled Bitcoin acquisition strategy is not a risk-free free lunch.
“There is no strategy that is risk-free. There is no free lunch. And I think that right now, the entire narrative is about how this is a free lunch, how this is a free money glitch, and I don't believe that.”
Shaan Puri Dec 5, 2024 ▶ 44:01 3 Stories of Crazy Geniuses: Fenn’s Treasure, Michael Saylor’s Infinite Money Glitch + more
Sam Parr refuses to invest personal funds in MicroStrategy's Bitcoin strategy.
“I wouldn't, I, with my own money, I wouldn't touch any of this. Yeah. Yeah. That's what I would say right now. I have no proof other than it just, it doesn't feel good.”
Sam Parr Dec 5, 2024 ▶ 48:25 3 Stories of Crazy Geniuses: Fenn’s Treasure, Michael Saylor’s Infinite Money Glitch + more
TBPN Assertion Supported
MicroStrategy's Stock Returned to Its All-Time High in November 2024
“MicroStrategy is back to their all-time high as of, like, last week.”
Jordi Hays Nov 23, 2024 ▶ 1:14:18 FACT CHECKERS vs. tech article (ep14)
TBPN Opinion
MicroStrategy Is Essentially a Bitcoin ETF Trading at 3x Book Value
“It is basically a Bitcoin ETF that trades at a three X to book value.”
Jordi Hays Nov 23, 2024 ▶ 1:14:28 FACT CHECKERS vs. tech article (ep14)
MY FIRST MILLION Assertion Supported
Pompliano: MicroStrategy was first non-crypto public company converting balance sheet to Bitcoin
“And so he was the first public company that wasn't like a crypto miner or something like that to go and say, I'm going to put like 85% of my balance sheet into Bitcoin.”
Anthony Pompliano Mar 27, 2024 ▶ 8:07 The Man Who Owns 1% Of ALL Bitcoin
MY FIRST MILLION Assertion Supported
Pompliano: MicroStrategy owns over 210,000 Bitcoin, exceeding 1% of total supply
“And he went from owning zero Bitcoin in July of 2020 to today he has more than 210,000 Bitcoin, which is more than one percent of the Bitcoin network.”
Anthony Pompliano Mar 27, 2024 ▶ 8:49 The Man Who Owns 1% Of ALL Bitcoin
MY FIRST MILLION Assertion Supported
Puri: MicroStrategy holds $15B in Bitcoin, up 97% on $7.3B invested
“So he currently has 14.96 billion Dollars of Bitcoin in MicroStrategy, and it's up 97% all time. So he's put in 7.3 billion, and now it's sitting on fifteen billion of assets.”
Shaan Puri Mar 27, 2024 ▶ 10:42 The Man Who Owns 1% Of ALL Bitcoin
MY FIRST MILLION Assertion Supported
Puri: MicroStrategy's stock remained flat from 2007 to 2020
“The stock was basically flat from 2007 to 20 20 before he started making his bet. And that's a long time, right? That's 2007 to 20 20. That's a 13 year period.”
Shaan Puri Mar 27, 2024 ▶ 11:30 The Man Who Owns 1% Of ALL Bitcoin
Sorkin: MicroStrategy has turned into a leveraged Bitcoin fund
“Michael Saylor at MicroStrategy. He's now effectively raising money from public investors in taking out loans. This is like a, his company's turned into a leveraged, basically a leveraged Bitcoin fund is effectively what it is.”
Andrew Ross Sorkin Jun 16, 2021 ▶ 24:31 Andrew Ross Sorkin on Meme Stocks, Bitcoin, SPACs, and Elon Musk
Saylor: MicroStrategy bought $2.2B in Bitcoin and holds over $5B
“No we bought 2.2000000000 worth of Bitcoin. We own about five, a bit more than five billion, depending upon the day.”
Michael Saylor Mar 17, 2021 ▶ 1:41 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
Saylor: MicroStrategy's Two Strategies Are Selling Software and Holding Bitcoin
“The business has two strategies, and the first strategy is we sell business intelligence software to our customers, and the second strategy is we acquire and hold Bitcoin. That is the business.”
Michael Saylor Mar 17, 2021 ▶ 22:10 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
MY FIRST MILLION Assertion Supported
Saylor: MicroStrategy Raised $650M in Convertible Debt at 75 bps
“Then we did a convertible debt offering for six hundred fifty million dollars of debt at 75 basis points.”
Michael Saylor Mar 17, 2021 ▶ 23:24 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
MY FIRST MILLION Assertion Supported
Saylor: MicroStrategy Issued $1B Convertible Offering at 0% Interest
“And then we did a billion dollar debt offering. And we did that billion dollar convert offering at zero percent interest.”
Michael Saylor Mar 17, 2021 ▶ 23:39 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
Saylor: MicroStrategy offered $250M Dutch auction buyback before buying Bitcoin
“So we offered to buy back two hundred fifty million dollars worth of the stock in this Dutch auction. So if you disagree with the decision to buy Bitcoin, you can sell the stock back at a profit. Our stock was one 20. We offered to buy the stock back at up to …”
Michael Saylor Mar 17, 2021 ▶ 32:50 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
MY FIRST MILLION Prediction Open · timeframe Mar 2041
Saylor: MicroStrategy's Bitcoin will generate more value than software operations over 20 years
“The investment income for sure.”
Michael Saylor Mar 17, 2021 ▶ 34:16 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
Saylor: Companies should convert cash, debt, and equity into Bitcoin
“So the big idea here is you want to fix any company, sweep all the cash flows into Bitcoin, convert the treasury into Bitcoin. Borrow against your future cash flows in dollars. Convert that into Bitcoin. Finance all your fixed assets in dollars. Convert that i…”
Michael Saylor Mar 17, 2021 ▶ 42:20 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
MY FIRST MILLION Assertion Supported
Saylor: MicroStrategy's 2,000-person core software business generates $75M annually
“Well, all 2000 people doing a 100,000 things right perfectly for the entire year competing against Microsoft that has more money than God, they can generate seventy five million a year.”
Michael Saylor Mar 17, 2021 ▶ 47:05 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
MY FIRST MILLION Assertion Not checkable as stated
Saylor: MicroStrategy's Bitcoin Strategy Greatly Improved Recruiting and Retention
“It's been great for retention, and it's been great for recruiting. We can get, we get people, first of all, the company's brand has been amped up by a factor of a thousand. I mean, a lot more people know us now.”
Michael Saylor Mar 17, 2021 ▶ 1:00:17 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
Saylor: MicroStrategy's Bitcoin Cost Basis Is $24,000 With Permanent Capital
“Well, we have permanent capital, so it doesn't make a difference to us, right? Like right now, for example, we have a three billion dollar investment gain. So if you cut Bitcoin in half, we would still have an investment gain, right? I mean, our basis is 24,00…”
Michael Saylor Mar 17, 2021 ▶ 1:05:48 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
MY FIRST MILLION Assertion Supported
Shaan Puri: MicroStrategy holds $5B in Bitcoin against a $7B market cap
“They own five billion dollars of Bitcoin. The company's worth seven billion dollars”
Shaan Puri Mar 17, 2021 ▶ 1:20:13 MFM #161: Why Michael Saylor Believes Bitcoin is Hope
20VC Assertion Partly supported
MicroStrategy lost 72% of its $30B market cap in a single day
“We went public, had a thirty billion market cap valuation, And then lost 72% in one day.”
Christian Hernandez Mar 9, 2016 ▶ 2:14 20VC: Christian Hernandez on The Importance of Mobile and The Relationship Between Growth vs Revenue

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