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At what #Bitcoin price does #MicroStrategy actually face risk? Is this a genius long-term capital structure or a massive balance-sheet gamble heading into 2028? Michael Saylor At this point, we’re all wondering… did you strategically disable the “Sell” button? Analysis by Emre İşlek

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TraderLex

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90,688 views • 6 months ago •via X (Twitter)

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6 months ago Michael Saylor told Grant Cardone that Strategy’s balance sheet could withstand a -90% drawdown in Bitcoin’s price before being collateralized. Price of Bitcoin at the time = $95,000. He said the company can tolerate the price going to $10,000. Michael Saylor famously said if the price of Bitcoin was to go to a $1 tomorrow, the company would just buy all the Bitcoin. Bitcoin is currently down over 35% since this interview and sits around $60,000. Credit: Grant Cardone
1:11

6 months ago Michael Saylor told Grant Cardone that Strategy’s balance sheet could withstand a -90% drawdown in Bitcoin’s price before being collateralized. Price of Bitcoin at the time = $95,000. He said the company can tolerate the price going to $10,000. Michael Saylor famously said if the price of Bitcoin was to go to a $1 tomorrow, the company would just buy all the Bitcoin. Bitcoin is currently down over 35% since this interview and sits around $60,000. Credit: Grant Cardone

The ₿itcoin Therapist

42,539 views • 2 months ago

A lot of the criticism aimed at Michael Saylor is about short-term dilution to Bitcoin per share. His answer: sometimes that’s the right long-term move because every decision is a balance between chasing growth and managing risk. Here’s how he explains it in full:
24:22

A lot of the criticism aimed at Michael Saylor is about short-term dilution to Bitcoin per share. His answer: sometimes that’s the right long-term move because every decision is a balance between chasing growth and managing risk. Here’s how he explains it in full:

Natalie Brunell ⚡️

30,623 views • 2 months ago

💥 BREAKING: Jim Cramer just said it out loud: Michael Saylor will fight the shorts “by any means necessary.” This isn’t satire. This is balance sheet warfare. Saylor isn’t just holding Bitcoin he’s defending it. - MicroStrategy holds ~214,400 BTC - Avg entry: ~$35K - Unrealized gains: ~$12B - Still buying, even at ~$93K This isn’t a trade anymore. It’s a public company using debt, equity, and conviction to absorb supply and pressure shorts. When a player with billions, no sell button, and infinite patience steps in the game changes. This isn’t Saylor vs shorts. It’s conviction vs disbelief.
0:46

💥 BREAKING: Jim Cramer just said it out loud: Michael Saylor will fight the shorts “by any means necessary.” This isn’t satire. This is balance sheet warfare. Saylor isn’t just holding Bitcoin he’s defending it. - MicroStrategy holds ~214,400 BTC - Avg entry: ~$35K - Unrealized gains: ~$12B - Still buying, even at ~$93K This isn’t a trade anymore. It’s a public company using debt, equity, and conviction to absorb supply and pressure shorts. When a player with billions, no sell button, and infinite patience steps in the game changes. This isn’t Saylor vs shorts. It’s conviction vs disbelief.

Crypto Tice

281,792 views • 8 months ago

“There was never any talk of the risk.” Peter Schiff is just lying at this point. The risk of $STRC was always obvious: it is preferred equity issued by a Bitcoin Treasury Company. Saylor said it clearly: if Bitcoin goes down long term or forever, that is the risk. And what are we seeing now? Bitcoin under pressure. Liquidity rotated into AI and IPOs. Maximum fear. STRC down. That is not some hidden scandal. That is risk premium repricing. Strategy does not magically control STRC’s market price. They can adjust the dividend rate, but the market prices the risk of Bitcoin and Strategy’s ability to keep paying dividends. And when Bitcoin starts going up again, what do you think happens? The same risk premium reprices in the other direction. If you buy preferred equity in a Bitcoin company, you are making one core assumption: Bitcoin goes up over the long term. That was never hidden.
0:42

“There was never any talk of the risk.” Peter Schiff is just lying at this point. The risk of $STRC was always obvious: it is preferred equity issued by a Bitcoin Treasury Company. Saylor said it clearly: if Bitcoin goes down long term or forever, that is the risk. And what are we seeing now? Bitcoin under pressure. Liquidity rotated into AI and IPOs. Maximum fear. STRC down. That is not some hidden scandal. That is risk premium repricing. Strategy does not magically control STRC’s market price. They can adjust the dividend rate, but the market prices the risk of Bitcoin and Strategy’s ability to keep paying dividends. And when Bitcoin starts going up again, what do you think happens? The same risk premium reprices in the other direction. If you buy preferred equity in a Bitcoin company, you are making one core assumption: Bitcoin goes up over the long term. That was never hidden.

Alex 👽

21,172 views • 1 month ago

“Never sell your Bitcoin” was never meant as: “Never make intelligent financial decisions.” When Michael Saylor talks about potentially selling BTC from the $MSTR balance sheet, he’s talking about strategic capital allocation designed to maximize long-term Bitcoin ownership. That’s very different from: “I sold my Bitcoin to buy a sports car.” Before selling Bitcoin, always ask yourself: Will this thing I’m buying still matter in 10 years? 20 years? 100 years? Because Bitcoin probably will. As Saylor said: "You don’t sell Cyber Manhattan for a horse and buggy."
1:46

“Never sell your Bitcoin” was never meant as: “Never make intelligent financial decisions.” When Michael Saylor talks about potentially selling BTC from the $MSTR balance sheet, he’s talking about strategic capital allocation designed to maximize long-term Bitcoin ownership. That’s very different from: “I sold my Bitcoin to buy a sports car.” Before selling Bitcoin, always ask yourself: Will this thing I’m buying still matter in 10 years? 20 years? 100 years? Because Bitcoin probably will. As Saylor said: "You don’t sell Cyber Manhattan for a horse and buggy."

Alex 👽

97,024 views • 2 months ago

Bitcoin is Suffering From Capital Rotation Michael Saylor (Michael Saylor) notes that capital markets have deployed approximately $400B into the AI sector over the last six months, triggering a massive liquidity rotation away from digital assets. Market data and institutional filings confirm roughly $4B in outflows from $BTC ETFs since May 14, placing significant downward pressure on the $BTC price action. He added, "This is a capital rotation, not a Bitcoin impairment." What do you think?
0:30

Bitcoin is Suffering From Capital Rotation Michael Saylor (Michael Saylor) notes that capital markets have deployed approximately $400B into the AI sector over the last six months, triggering a massive liquidity rotation away from digital assets. Market data and institutional filings confirm roughly $4B in outflows from $BTC ETFs since May 14, placing significant downward pressure on the $BTC price action. He added, "This is a capital rotation, not a Bitcoin impairment." What do you think?

BSCN

10,628 views • 2 months ago

I sat down with Strive CEO Matt Cole to discuss digital credit, $ASST, and $SATA. Matt Cole breaks down the mechanics, the dividend structures, what the risks are, Michael Saylor's decision to sell bitcoin, and why a thriving ecosystem of digital credit issuers is better for bitcoin long-term. YouTube: Apple: Spotify: TIMESTAMPS: 0:00 - Intro 0:41 - What is digital credit & what problem does it solve? 5:17 - How the carry trade works 8:48 - Daily dividends & dividend structure 10:52 - Downside risk & balance sheet protection 16:18 - The strongest critique of digital credit 19:32 - Michael Saylor selling bitcoin 27:03 - Bitcoin price action vs. bullish headlines 31:32 - Where is digital credit taking capital from? 36:44 - Banks, Jamie Dimon & systemic risk 38:52 - Strive vs. Strategy 42:38 - Too much bitcoin held by public companies? 48:33 - Strive's mission & the road ahead
52:17

I sat down with Strive CEO Matt Cole to discuss digital credit, $ASST, and $SATA. Matt Cole breaks down the mechanics, the dividend structures, what the risks are, Michael Saylor's decision to sell bitcoin, and why a thriving ecosystem of digital credit issuers is better for bitcoin long-term. YouTube: Apple: Spotify: TIMESTAMPS: 0:00 - Intro 0:41 - What is digital credit & what problem does it solve? 5:17 - How the carry trade works 8:48 - Daily dividends & dividend structure 10:52 - Downside risk & balance sheet protection 16:18 - The strongest critique of digital credit 19:32 - Michael Saylor selling bitcoin 27:03 - Bitcoin price action vs. bullish headlines 31:32 - Where is digital credit taking capital from? 36:44 - Banks, Jamie Dimon & systemic risk 38:52 - Strive vs. Strategy 42:38 - Too much bitcoin held by public companies? 48:33 - Strive's mission & the road ahead

Anthony Pompliano 🌪

308,426 views • 2 months ago

"Michael Saylor has invented our fantasy" - Yves Choueifaty on The State of Bitcoin Markets. He covers: - The “dream” trade: borrow from big banks against Bitcoin, pay interest, never repay principal - How Saylor has built this model at scale via MicroStrategy - Why buying MSTR effectively plugs investors into that structure - How leverage can compound Bitcoin exposure like a “rocket on a rocket”
3:41

"Michael Saylor has invented our fantasy" - Yves Choueifaty on The State of Bitcoin Markets. He covers: - The “dream” trade: borrow from big banks against Bitcoin, pay interest, never repay principal - How Saylor has built this model at scale via MicroStrategy - Why buying MSTR effectively plugs investors into that structure - How leverage can compound Bitcoin exposure like a “rocket on a rocket”

Roxom

133,414 views • 5 months ago

People are overthinking the 32 BTC sale. “Why sell?” “Why not just buy less next week?” “Is this bearish?” Michael Michael Saylor already explained the logic: • If Bitcoin can’t be sold, critics say it has no value. • If it has no value, the balance sheet value is zero. • If the balance sheet value is zero, credit rating agencies ignore it. • So you sell a tiny appreciated portion to prove Bitcoin is liquid, valuable, and real.
2:28

People are overthinking the 32 BTC sale. “Why sell?” “Why not just buy less next week?” “Is this bearish?” Michael Michael Saylor already explained the logic: • If Bitcoin can’t be sold, critics say it has no value. • If it has no value, the balance sheet value is zero. • If the balance sheet value is zero, credit rating agencies ignore it. • So you sell a tiny appreciated portion to prove Bitcoin is liquid, valuable, and real.

Alex 👽

1,231,739 views • 2 months ago

Michael Saylor Explains Why He May Sell Bitcoin Strategy founder Michael Saylor Michael Saylor said in a May 9 interview with Bonnie Blockchain that if the company needs to sell a small amount of Bitcoin, it would be to realize capital gains and pay STRC credit dividends. He compared the model to real estate development: raising capital through credit instruments, buying an asset, and later monetizing it through a sale or refinancing after it appreciates. Responding to Peter Schiff's "Ponzi scheme" criticism, Saylor said the more accurate principle is to "never be a net seller of Bitcoin." At this stage, even if Strategy sells 1 Bitcoin, it would buy 10 to 20 at the same time.
3:25

Michael Saylor Explains Why He May Sell Bitcoin Strategy founder Michael Saylor Michael Saylor said in a May 9 interview with Bonnie Blockchain that if the company needs to sell a small amount of Bitcoin, it would be to realize capital gains and pay STRC credit dividends. He compared the model to real estate development: raising capital through credit instruments, buying an asset, and later monetizing it through a sale or refinancing after it appreciates. Responding to Peter Schiff's "Ponzi scheme" criticism, Saylor said the more accurate principle is to "never be a net seller of Bitcoin." At this stage, even if Strategy sells 1 Bitcoin, it would buy 10 to 20 at the same time.

Wu Blockchain

12,629 views • 2 months ago

Welcome back to The Bitcoin Treasuries Podcast. Today's guest is Michael Mescher, CEO of Gammon Capital. Michael and I discuss derivatives, institutional capital, balance sheet protection, and the future of Bitcoin treasury management. Here's my conversation with Michael Mescher. 0:00 - Intro 0:40 – Michael’s path from derivatives to Bitcoin treasury strategy 3:18 – What a 50% collateral haircut really means for a Bitcoin treasury company 11:15 – The coming $10 billion "Put Wall" and why 2027 matters 13:21 – Why Bitcoin treasury companies are paying too much for capital 15:02 – Using derivatives as balance sheet protection - not speculation 16:55 – Building a Bitcoin treasury playbook for bear and sideways markets 19:05 – What Michael Saylor gets right about financial engineering 22:15 – What separates the strongest Bitcoin treasury companies from the rest 24:42 – Why the market still hasn't built a better Bitcoin credit facility 26:54 – How Bitcoin treasury companies can unlock institutional capital 29:04 – Managing asset-liability mismatches on a Bitcoin balance sheet 32:38 – Capital efficient hedging strategies for downside protection 34:46 – How to sell a hedging strategy to a long-only Bitcoin executive 37:17 – What a strategic engagement with Gammon Capital looks like 38:18 - Where to find Michael Mescher and Gammon Capital
38:38

Welcome back to The Bitcoin Treasuries Podcast. Today's guest is Michael Mescher, CEO of Gammon Capital. Michael and I discuss derivatives, institutional capital, balance sheet protection, and the future of Bitcoin treasury management. Here's my conversation with Michael Mescher. 0:00 - Intro 0:40 – Michael’s path from derivatives to Bitcoin treasury strategy 3:18 – What a 50% collateral haircut really means for a Bitcoin treasury company 11:15 – The coming $10 billion "Put Wall" and why 2027 matters 13:21 – Why Bitcoin treasury companies are paying too much for capital 15:02 – Using derivatives as balance sheet protection - not speculation 16:55 – Building a Bitcoin treasury playbook for bear and sideways markets 19:05 – What Michael Saylor gets right about financial engineering 22:15 – What separates the strongest Bitcoin treasury companies from the rest 24:42 – Why the market still hasn't built a better Bitcoin credit facility 26:54 – How Bitcoin treasury companies can unlock institutional capital 29:04 – Managing asset-liability mismatches on a Bitcoin balance sheet 32:38 – Capital efficient hedging strategies for downside protection 34:46 – How to sell a hedging strategy to a long-only Bitcoin executive 37:17 – What a strategic engagement with Gammon Capital looks like 38:18 - Where to find Michael Mescher and Gammon Capital

Tim Kotzman

21,481 views • 1 month ago

Meet Hero. This is genius. Simple point your phone at things you need to sell, it will classify and figure out a recommended price Built by Joshua Voydik Links below
0:27

Meet Hero. This is genius. Simple point your phone at things you need to sell, it will classify and figure out a recommended price Built by Joshua Voydik Links below

Linus ✦ Ekenstam

285,177 views • 2 years ago

Is Saylor selling Bitcoin low only to buy it back higher with STRC? "Clearly selling Bitcoin is not a problem, and the fact that he's not buying is seemingly not a problem for the market either. But the thing I'm wondering now, and this remains open ended, is now that he's selling Bitcoin to buy STRC, what happens when STRC inevitably gets back to a hundred bucks and the old machine of using STRC to buy Bitcoin kicks back into motion?" "Are they actually going to be selling STRC to buy Bitcoin back at a higher price? Are we selling the lows on Bitcoin after buying the highs, only to buy that Bitcoin back higher with the very same instrument he's buying back? I'd say Michael Saylor here is in a bit of a pickle" "Having this not be the main narrative for crypto at the moment is really good news. Michael Saylor spent years turning dollars into Bitcoin. Now he's discovered there's a reverse button, and I don't love it"
0:59

Is Saylor selling Bitcoin low only to buy it back higher with STRC? "Clearly selling Bitcoin is not a problem, and the fact that he's not buying is seemingly not a problem for the market either. But the thing I'm wondering now, and this remains open ended, is now that he's selling Bitcoin to buy STRC, what happens when STRC inevitably gets back to a hundred bucks and the old machine of using STRC to buy Bitcoin kicks back into motion?" "Are they actually going to be selling STRC to buy Bitcoin back at a higher price? Are we selling the lows on Bitcoin after buying the highs, only to buy that Bitcoin back higher with the very same instrument he's buying back? I'd say Michael Saylor here is in a bit of a pickle" "Having this not be the main narrative for crypto at the moment is really good news. Michael Saylor spent years turning dollars into Bitcoin. Now he's discovered there's a reverse button, and I don't love it"

The Wolf Of All Streets

36,187 views • 7 days ago

Arthur Hayes: Don't Expect Michael Saylor to Protect Your BTC Wallet BitMEX founder Arthur Hayes Arthur Hayes said in a May 13 interview with The Wolf of All Streets that investors need to understand Michael Saylor's role: he is protecting his own company, not the Bitcoin held by ordinary investors. Hayes said Saylor is a genius in corporate finance, and MicroStrategy's ability to launch related products and derivatives comes from its unique balance sheet and market relationships. He added that this does not mean Saylor is doing anything wrong; rather, he will do what best serves the company's shareholders.
1:01

Arthur Hayes: Don't Expect Michael Saylor to Protect Your BTC Wallet BitMEX founder Arthur Hayes Arthur Hayes said in a May 13 interview with The Wolf of All Streets that investors need to understand Michael Saylor's role: he is protecting his own company, not the Bitcoin held by ordinary investors. Hayes said Saylor is a genius in corporate finance, and MicroStrategy's ability to launch related products and derivatives comes from its unique balance sheet and market relationships. He added that this does not mean Saylor is doing anything wrong; rather, he will do what best serves the company's shareholders.

Wu Blockchain

16,755 views • 2 months ago

THE BITCOIN DISCOUNT SAYLOR WARNED YOU ABOUT IS HERE This one’s from a while back, but it aged perfectly. $BTC price dips like this are exactly what he was talking about. He said you can wait until it’s “easy and risk-free”… and pay $10 million per #Bitcoin. Or buy when it’s messy -- at a 99% discount. This is the phase most people miss. 🤯
1:14

THE BITCOIN DISCOUNT SAYLOR WARNED YOU ABOUT IS HERE This one’s from a while back, but it aged perfectly. $BTC price dips like this are exactly what he was talking about. He said you can wait until it’s “easy and risk-free”… and pay $10 million per #Bitcoin. Or buy when it’s messy -- at a 99% discount. This is the phase most people miss. 🤯

CryptosRus

214,630 views • 9 months ago

Michael Saylor: We Sold Bitcoin to Prove It Wouldn't Crash the Market Strategy founder Michael Saylor Michael Saylor said in an August 6 interview with The Diary Of A CEO that the market believed Strategy could not sell Bitcoin because doing so might cause BTC to crash, leaving the company trapped in a "doom loop" of repeatedly selling equity to pay dividends. To break that narrative, Strategy sold Bitcoin when BTC was trading at around $59,000 to $60,000, and the price instead moved higher. Saylor said the company's break-even point is about 3.2%, meaning that if Bitcoin appreciates by that amount, Strategy can sell part of its BTC to pay dividends without continuing to sell equity.
2:23

Michael Saylor: We Sold Bitcoin to Prove It Wouldn't Crash the Market Strategy founder Michael Saylor Michael Saylor said in an August 6 interview with The Diary Of A CEO that the market believed Strategy could not sell Bitcoin because doing so might cause BTC to crash, leaving the company trapped in a "doom loop" of repeatedly selling equity to pay dividends. To break that narrative, Strategy sold Bitcoin when BTC was trading at around $59,000 to $60,000, and the price instead moved higher. Saylor said the company's break-even point is about 3.2%, meaning that if Bitcoin appreciates by that amount, Strategy can sell part of its BTC to pay dividends without continuing to sell equity.

Wu Blockchain

22,843 views • 8 days ago

I’ve been a Balance Sheet Volatility manager my entire career (12+ years). Below is my presentation at Risk World yesterday. Focused on explaining the similarities of insurance balance sheet risk management to Bitcoin balance sheet risk management. The primary difference: Bitcoin data is more observable, easily accessible, and calculable in real time. This is a feature, not a bug. And btw, there were only about 12 people in the seats, and 2 were my own colleagues. 0:21–0:46 Background in reinsurance and risk 0:46–1:13 How this work changed his perspective on risk 1:13–1:37 Bitcoin as digital capital 1:57–2:42 Insurance, reinsurance, and volatility reduction 6:54–8:08 Turning Bitcoin volatility into a credit instrument 13:50–15:38 Risk modeling, experience rating, and Monte Carlo analysis 17:21–20:06 Monetary debasement and digital credit 20:06–24:22 Digital credit vs. catastrophe bonds
24:27

I’ve been a Balance Sheet Volatility manager my entire career (12+ years). Below is my presentation at Risk World yesterday. Focused on explaining the similarities of insurance balance sheet risk management to Bitcoin balance sheet risk management. The primary difference: Bitcoin data is more observable, easily accessible, and calculable in real time. This is a feature, not a bug. And btw, there were only about 12 people in the seats, and 2 were my own colleagues. 0:21–0:46 Background in reinsurance and risk 0:46–1:13 How this work changed his perspective on risk 1:13–1:37 Bitcoin as digital capital 1:57–2:42 Insurance, reinsurance, and volatility reduction 6:54–8:08 Turning Bitcoin volatility into a credit instrument 13:50–15:38 Risk modeling, experience rating, and Monte Carlo analysis 17:21–20:06 Monetary debasement and digital credit 20:06–24:22 Digital credit vs. catastrophe bonds

Jeff Walton

20,094 views • 3 months ago

"What is the point of Bitcoin at this point?" 📉🤔 Nick O’Neill doesn't hold back on the state of the market. It’s not acting as a store of value, it’s completely un-correlating from tech stocks while they rip, and the Michael Saylor/MicroStrategy catalyst is flipping negative. If the tech is slow and the OG narrative is shifting, what's the actual thesis for holding?
1:54

"What is the point of Bitcoin at this point?" 📉🤔 Nick O’Neill doesn't hold back on the state of the market. It’s not acting as a store of value, it’s completely un-correlating from tech stocks while they rip, and the Michael Saylor/MicroStrategy catalyst is flipping negative. If the tech is slow and the OG narrative is shifting, what's the actual thesis for holding?

HENRY

98,388 views • 2 months ago

Michael Michael Saylor lays out Strategy: You buy Bitcoin with a variable rate perpetual preferred stock,” creating “what is in essence a nearly risk free swap.” Are you really overpaying at “8% or 9%” if you’re using that capital to buy an asset that keeps appreciating? “There’s only $30 million of Bitcoin available for sale every day and we’re buying all of it.” “What’s the best way to predict the future? It’s to determine the future." “If we basically buy $100 billion of Bitcoin, it’s probably not going up to 0%." ⚡
2:14

Michael Michael Saylor lays out Strategy: You buy Bitcoin with a variable rate perpetual preferred stock,” creating “what is in essence a nearly risk free swap.” Are you really overpaying at “8% or 9%” if you’re using that capital to buy an asset that keeps appreciating? “There’s only $30 million of Bitcoin available for sale every day and we’re buying all of it.” “What’s the best way to predict the future? It’s to determine the future." “If we basically buy $100 billion of Bitcoin, it’s probably not going up to 0%." ⚡

Bankless

11,866 views • 4 months ago

IPO, IPO, IPO… yeah, it’s a big word at eToro right now! But what does it actually mean? Depends who you ask 👀 Here’s how our team defined it. Drop your own definition in the comments ⬇️ #eToroIPO #NasdaqListed ⚠️ This shall not constitute an offer, or the solicitation of an offer, to buy or sell these securities. Your capital is at risk.
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IPO, IPO, IPO… yeah, it’s a big word at eToro right now! But what does it actually mean? Depends who you ask 👀 Here’s how our team defined it. Drop your own definition in the comments ⬇️ #eToroIPO #NasdaqListed ⚠️ This shall not constitute an offer, or the solicitation of an offer, to buy or sell these securities. Your capital is at risk.

eToro

1,726,184 views • 1 year ago