Is Michael Saylor’s Bitcoin Strategy Genius or Reckless?

[SeriouslyGiveaway]

Peter Schiff disagrees with Saylor’s view of Bitcoin as “digital gold.” He argues that Bitcoin is extremely volatile and cannot serve as a hedge against inflation.

If it is about inflation, Bitcoin is less inflation than gold and if we need a thing that has total supply and future supply is not high inflation like fiat currency, nearly deflation or deflation, it's Bitcoin, not Gold.

Controlled supply.
Equivalent Network Time.

Bitcoin has yet deflation but it has come nearly to its phase of very small and almost no inflation already and new demand on Bitcoin increases much more than future Bitcoin supply from next Bitcoin blocks.

[cryptomaniac_xxx]

At what point does a conviction play become reckless? And will Saylor ultimately be proven right or wrong in the near future?

Looking forward to hearing different views.

There will be always two side of the story here, as a visionary, his supporters will tell us him as brilliant and sort of visionary. Because just like the rest of us here, Bitcoin is a hedge against inflation, store of value and obviously a investment to make money for us in the future as a profits.

On the other hand, there are more people who criticized him for being the the picture of Bitcoin now. They say that Saylor is leveraging loans or debt against Bitcoin's inherent volatility.

So I guess there is no right or wrong answer whether he is a genius or reckless. For us, it will depend on our strategy, whether we want to follow Saylor's strategy of keep on buying.

[Bbluez]

Most people for sure will say reckless only if Bitcoin goes to 0 or goes dump hard and they can't sustain it anymore.
What I don't agree with Saylor is their company's stock, which most of the time now is mostly correlated with Bitcoin price action, so let's say if you want to invest in their stock, why not just buy Bitcoin instead?

MSTR has more advantages, you can read more on it.

[OgNasty]

I think the moment that Saylor started issuing preferred shares that earn dividends, he became wildly reckless and forced us all into his financial death spiral.  He's been managing to keep it together so far as investors are just bailing and letting new investors pick up shares at a discount to NAV with the hopes of recovery.

The death spiral financial vehicle he has created is bad enough, but doing it with preferred offerings screwed his shareholders over so hard...  It is hard to imagine a future that Strategy isn't tied up in litigation.  I'm far less bullish on BTC until Strategy goes bankrupt and think Bitcoin is much weaker as a potential global reserve currency if it doesn't.

[Ahli38]

His strategy represents a maximum-conviction play. Some see it as visionary, while others view it as reckless.

The real question is:
At what point does a conviction play become reckless? And will Saylor ultimately be proven right or wrong in the near future?

Michael Saylor started buying Bitcoin several years ago. He has complete conviction to Bitcoin in the long term. His strategy has proven to be correct so far and even if he is wrong he has stopped buying Bitcoin. But Saylor continues to buy Bitcoin. Earlier this year he was reported to have purchased Bitcoin again. MicroStrategy's position in Bitcoin holdings remains the top leader among other public companies. I personally believe that Michael Saylor will still prove the validity of his conviction and even prove the critics wrong who label him as reckless. In the end they will consider his strategy genius.

[wickedgoodtrader]

He's 100% wreckless and it's going to end in a very bad way for MSTR and BTC, and here is why.

He publicly tells everyone he's going to buy $40 billion or so in BTC. So everyone loads up as they should and front runs him causing him to pay inflated prices. He has an inflated stock price because uneducated people fall for his sales pitch and buy MSTR for 2x the price they could have just bought BTC. He is able to use their money to buy the BTC. He then even takes out 8 billion in loans to buy BTC. He doesn't stop there. He sees those avenues are about to dry up so he issues "preferred" shares that require the price of BTC to increase by 10%+ annually. He buys at a rate of over twice the annual mining issuance, pumping the price from $30k to $125k. He just keeps smash buying billions weekly. He even cheers on the rest of the world to do the same and has them borrow money also to create more "bitcoin treasuries".  And that brings us to here.

All the smart money who front ran him saw his avenues drying up so they dumped as they should. Now he has massive interest payments and debt coming due AND NO WAY TO RAISE MORE MONEY. Yes, he raise a couple years worth of dividend payments in cash, but he's not including the 8 billion in debt that come due also. He created a massive pump, and will be a forced seller in a just under 2 years. Forced sellers are what cause 90% draw downs. Nobody in their right mind is going to HODL with the largest buyer in history, who caused the pump, becoming a seller.

His biggest mistake was pumping the price against himself and taking on debt to buy. Yes bitcoin may do 10% annually, but not if you intentionally pump the price 400% against yourself and blow half your load at the absolute top and then run out of money and then have to become a seller.

[TastyChillySauce00]

Genius or not depends on the outcome of his investment. If he could create the biggest profit from just holding bitcoin till the end then he's genius, if he got liquidated and need to unwind some holding, people will think he's reckless.
From my point of view though, he's kinda reckless with his convertible bond to keep buying at pretty high price. Don't get me wrong buying bitcoin at high price for long term holding is fine, but it's only a problem if you need to unwind it when prices dumped to certain threshold.

[Webutxo]

His strategy represents a maximum-conviction play. Some see it as visionary, while others view it as reckless.

The real question is:
At what point does a conviction play become reckless? And will Saylor ultimately be proven right or wrong in the near future?

Looking forward to hearing different views.

Michael is a believer of Bitcoin and that's it. If you decide to be different, people will think you are abnormal but the moment they start seeing positive aspect of your beliefs, they try to be with you. The people that started Bitcoin were not much, many people didn't like them because they thought Bitcoin wasn't a thing that time but today, it's one of the biggest assets in the world. Those people that hold are worth millions and they are still holding.

The money Saylor is investing in Bitcoin started not today, it's way back back 10 years ago or so and he has been doing that until he went full mode with the company. This was when Bitcoin price was small but today it's bigger and yet we still doubt his decision. By the time Bitcoin hit a million then we are going to appreciate his effort for going full Bitcoin.

[DeeppRockk]

His strategy represents a maximum-conviction play. Some see it as visionary, while others view it as reckless.

The real question is:
At what point does a conviction play become reckless? And will Saylor ultimately be proven right or wrong in the near future?

Looking forward to hearing different views.

Michael is a believer of Bitcoin and that's it. If you decide to be different, people will think you are abnormal but the moment they start seeing positive aspect of your beliefs, they try to be with you. The people that started Bitcoin were not much, many people didn't like them because they thought Bitcoin wasn't a thing that time but today, it's one of the biggest assets in the world. Those people that hold are worth millions and they are still holding.

The money Saylor is investing in Bitcoin started not today, it's way back back 10 years ago or so and he has been doing that until he went full mode with the company. This was when Bitcoin price was small but today it's bigger and yet we still doubt his decision. By the time Bitcoin hit a million then we are going to appreciate his effort for going full Bitcoin.

nah i feel that but at the same time saylors whole thing was never about being "different" for the sake of it-he saw btc as the best inflation hedge out there and went all in. not sure if thats genius or just really confident betting also the gold comparison gets old fast but his move did force a lot of people to actually look at btc as an asset class instead of just some tech experiment

[Franctoshi]

Michael Saylor’s strategy has been one of the most talked-about in the cryptocurrency space. His approach is basically to “buy all the Bitcoin sellers are willing to sell” and commit to holding long term. No hedging. No trading. Just conviction.

Peter Schiff disagrees with Saylor’s view of Bitcoin as “digital gold.” He argues that Bitcoin is extremely volatile and cannot serve as a hedge against inflation.

Saylor’s strategy cannot easily be copied by retail investors or small companies. We can agree that they do not have the same advantages, as Saylor has access to capital markets and the authority of a founder-CEO. When small companies or retail investors attempt to play the same conviction game, it can easily appear more like gambling than long-term investing.

His strategy represents a maximum-conviction play. Some see it as visionary, while others view it as reckless.

The real question is:
At what point does a conviction play become reckless? And will Saylor ultimately be proven right or wrong in the near future?

Looking forward to hearing different views.

Even without no one telling you, and if you understand mathematics, and the law of demand and supply, Vs the worlds population
Against the (21M Bitcoin) limited supply, you will definitely get to understand what Michael Saylor is doing by his continued accumulation of Bitcoin with MicroStrategy. Saylor started his Bitcoin DCA strategy way earlier than other major institutional investors like BlackRock and the rest of them, either when Bitcoin was around $15k or $30k, and since then time has been proving him right, and what would you do in a situation where a strategy is working for you? Other than to continue or even increase or double down on your purchases.  

[macson]

It wasn't a genius or reckless strategy, he simply believed in Bitcoin's potential when others doubted it. He just did what he believed was the right strategy for his company to store assets with better long-term value.

He invested consistently and didn't chase short-term profits, and steadily built up his Bitcoin portfolio. And that's a conviction you rarely find, one that stems from his understanding of Bitcoin's long-term potential.

[Cryptomultiplier]

Michael Saylor’s strategy has been one of the most talked-about in the cryptocurrency space. His approach is basically to “buy all the Bitcoin sellers are willing to sell” and commit to holding long term. No hedging. No trading. Just conviction.

Peter Schiff disagrees with Saylor’s view of Bitcoin as “digital gold.” He argues that Bitcoin is extremely volatile and cannot serve as a hedge against inflation.

Saylor’s strategy cannot easily be copied by retail investors or small companies. We can agree that they do not have the same advantages, as Saylor has access to capital markets and the authority of a founder-CEO. When small companies or retail investors attempt to play the same conviction game, it can easily appear more like gambling than long-term investing.

His strategy represents a maximum-conviction play. Some see it as visionary, while others view it as reckless.

The real question is:
At what point does a conviction play become reckless? And will Saylor ultimately be proven right or wrong in the near future?

Looking forward to hearing different views.

Michael Saylor's holding strategy is top notch and he is doing what done investors are scared to do and that's putting his faith in Bitcoin until it hits the $250k mark, or perhaps he has a time frame where he holds all this BTC and then sell to make some good returns.

I don't think he is reckless because he has built a massive cash cushion and that's about 3% of the total amount of BTC in circulation or to be mined.
He is doing what he is doing based on conviction and deep research and I respect that and he may be mathematically correct in the possible future, if all things be equal and BTC does not dip further without rising.

[wickedgoodtrader]

Let's not forget how many times he has flip flopped or lied about the companies plans.

First it was they wouldn't ATM shares when mNAV was 2.5 or below. As soon as 2.5 hit he changed that and said they will dilute as they please and the stock tanked and has been tanking since.

2nd, he has always said NEVER SELL YOUR BITCOIN and he many times stated they would never sell bitcoin. That is until a couple months ago. Now they are saying they will sell if they need to but acting like they will never need to, which they most definitely will. Then also stating that the amount they will have to sell would not make the price drop, just like he has said his ATM sales don't drop the price of MSTR.

The guy is a liar and even if he was right about bitcoin, his company has done terrible against bitcoin itself. He has obvious paid shills all over the internet touting his products. I don't see it working out for anybody who has to lie like he has and have other people lying for him.

[nakamura12]

The real question is:
At what point does a conviction play become reckless? And will Saylor ultimately be proven right or wrong in the near future?

I've seen those headlines before that Saylor was skeptic about Bitcoin. People need to look at what he's changed his heart towards that thought about Bitcoin.

Now, his company has got the most bitcoin's ever in holdings. And there is no need for him to prove himself right or wrong because it's already shown that bitcoin has saved his company.

So, there's nothing to prove anymore. And it will only be reckless if he comes back to being skeptic again while holding a lot of Bitcoins which is a public data now.

I don't think that he will be skeptic again since as you have said that it save his company while holding lots of bitcoin and as for the charts I think it will that he won't be skeptic again since it shows good chart provided that it has surpassed many ATH during those times. If bitcoin didn't save his company as you have said then I don't think he would be holding lots of bitcoins now if it really that's the case and would have just say the same things as before.

[serjent05]

The real question is:
At what point does a conviction play become reckless? And will Saylor ultimately be proven right or wrong in the near future?

Looking forward to hearing different views.

Conviction becomes reckless if the person is blinded by it.  For example, in a scenario where one conviction gives him a negative result and keeps on aligning himself on that conviction, then that one can be said a reckless one.  If we think of it, Saylor's conviction seems good because Bitcoin had been uptrending since the day he committed himself to investing in Bitcoin.  It will only become reckless if he saw that Bitcoin is crashing and is doomed and will not be able to recover  and still stick to his plan of accumulating Bitcoin.

But I do not think Saylor is stupid like that, he will eventually jump ship or sell his holdings the moment he sees the sign of the Bitcoin market's irrecoverable downtrend.

[PrivacyG]

If Bitcoin was an 100 year old Asset, I would say this is a genius strategy.  But considering Bitcoin has only existed for under two decades, I tend to believe it is a rather reckless one.  If things work out the same way they have so far and Bitcoin surprises all the haters with another crazy Bull Run, it will turn out to be genius to all the people at the time.  But for now, no thing is guaranteed and the amounts he is throwing at Bitcoin are in my opinion actually reckless.

Schiff likes the traditional way and some times he does have a point.  As much as I like it, Bitcoin still has to prove itself in my opinion in the face of many negative economical events, wars et cetera.  Gold has proved itself many times over and over again.  Until Bitcoin does too, it will still pose a large risk of the unknown.

At the end of the day, Bitcoin versus Gold has been a very long never ending debate.  In this situation, I believe two things matter a lot.  Bitcoin is easily movable while Gold is not.  At the same time, Gold exists even when the grid is down while Bitcoin only exists as long as you can use the Blockchain.  Considering there have been many wars starting in the last years that can always turn into a much feared larger scale war and many Economies seem to be in a rapid fall, what do you choose?  The digital Asset that lets you move faster or the physical Asset?

Now returning to the Saylor strategy.  If a large scale war happens in the next months or years, it takes one general panic where people run for the physical Assets such as Gold that may cause a Bitcoin crash for a while.  This does not mean Bitcoin dies or becomes useless.  It however can be brutal for strategies of people like Saylor.  I trust that Bitcoin will do good in the longer term no matter what happens today or tomorrow.  But I can not lie to myself and say that it is 100 percent going to repeat its own history over and over again for ever or that there may not be a time when people will sell off Bitcoin and cause a significant crash putting some of the Bitcoin businesses in danger.

[Mrbluntzy]

Sailor's strategy is not reckless, considering that others are not following his strategy or do not like his strategy doesn't mean his strategy is reckless, when someone believes or feel so confident about their strategy, in their head, their own strategy invalidates any other strategy that is not theirs. So, it's okay for anyone to feel that his strategy is not good or it's reckless, but let's not forget that Microstrategy started buying Bitcoin since 2020 till 2025 and will still be buying more this year and continuously. Considering that Microstrategy already have thousands of Bitcoin that they bought at a low price and are still holding it, they are in profit unless Bitcoin price falls below it's price 5 years ago.

[PrivacyG]

Sailor's strategy is not reckless, considering that others are not following his strategy or do not like his strategy doesn't mean his strategy is reckless, when someone believes or feel so confident about their strategy, in their head, their own strategy invalidates any other strategy that is not theirs. So, it's okay for anyone to feel that his strategy is not good or it's reckless, but let's not forget that Microstrategy started buying Bitcoin since 2020 till 2025 and will still be buying more this year and continuously. Considering that Microstrategy already have thousands of Bitcoin that they bought at a low price and are still holding it, they are in profit unless Bitcoin price falls below it's price 5 years ago.

But this is exactly what 'reckless' is.  Cambridge dictionary explains it this way,

'RECKLESS definition: 1. doing something dangerous and not worrying about the risks and the possible results'

Bitcoin dropping to a point that puts his business and strategy under danger is a possibility.  He does not worry about it or the level of danger throwing this many Billions of Dollars at Bitcoin involves.  Is this not being reckless?

[wickedgoodtrader]

Sailor's strategy is not reckless, considering that others are not following his strategy or do not like his strategy doesn't mean his strategy is reckless, when someone believes or feel so confident about their strategy, in their head, their own strategy invalidates any other strategy that is not theirs. So, it's okay for anyone to feel that his strategy is not good or it's reckless, but let's not forget that Microstrategy started buying Bitcoin since 2020 till 2025 and will still be buying more this year and continuously. Considering that Microstrategy already have thousands of Bitcoin that they bought at a low price and are still holding it, they are in profit unless Bitcoin price falls below it's price 5 years ago.

His average price is $75,000. Not the best return considering he started buying 5 years ago. He blew his load borrowing money and smash buying as much as 20k BTC/week at the top in the $110-$120k range. He literally was trying to pump the price himself. Which he did. He's desperately trying to keep BTC from falling below that number.

[bubilas]

Michael Saylor's Bitcoin buying strategy is quite ingenious, as it partially replicates the patterns of the DCA strategy, which allows you to buy Bitcoin over a certain period of time. Ultimately, it appears to have been purchased at some absolute average price.
Currently, Michael Saylor's Bitcoin purchases average $75,000, which is already significantly lower than the current Bitcoin-to-dollar market price. This means he can confidently say he's profitable, and you can even calculate this profit based on the current Bitcoin price and the average purchase price I mentioned above, $75,000.