Michael Saylor: Bitcoin is the Best Property in the World

In this episode of UpOnly, Cobie & Ledger talk to Michael Saylor, CEO of MicroStrategy, and one of the biggest advocates for Bitcoin in the world.

Audio Version


Show Partner

This episode is presented by FTX. Trade on an awesome mobile interface fee-free, and still get all the great portfolio tracking features you know and love: https://uponly.tv/ftx

Show Notes

Bitcoin Journey

– First tweeted about Bitcoin in 2013, was sceptical

– Would comment on early tech, very unknown at the time

– Would tweet about Bitcoin and people find his old tweets

– Learned about Bitcoin through poker and online gambling



– Diversifying is selling the winners to buy the losers

– Amazon wins

– Walmart kinda treads water

– and 15,000 companies lose

– It’s nearly impossible to beat a digital monopoly

Banking Experience

– Lost $1M in a bank rug

– Lost $1M in an Argentina rug as well

– Banks wouldn’t let him move his money around

– He got crushed by Argentina inflation

– Kept getting smoked – “can we buy a yacht, float it to the US, then sell it here?”

– Couldn’t do that, eventually gave up

Current Bitcoin Experience

– Then had $1B company with $500M cash on balance sheet

– Knew it was gonna get inflated away

– Saylor: “It’s like losing half your body – like amputating your left arm and left leg”

– Now has like $5B worth of Bitcoin

– If you’re on main street you had the worst year of your life

– If you’re on Wall Street you had the best year of your life

– First Bitcoin buy in August was defensive

– Bought first amount at like $11k BTC ($250M buy)

– Then got $600M loan at 1% interest…and just bought Bitcoin lmao

– Saylor: “All time high is just the all time high to date”

Business and Bitcoin

– Cobie: “Given the cyclical nature of crypto, I’ve seen life ruining bear markets and pre up only euphoria bull markets. Will you keep buying bitcoin forever?”

– Saylor: “Yeah” LMAO

– Devaluing currency is crushing basically every small business

– Saylor: “It’s like you’re rowing 7 knots, but the current is moving against you at 7 knots”

– Michael Sailor! *credit to CryptoCred*

– Saylor: “It is true that if I deal you double aces, you have an advantage in the poker game. But if I put a gun to your head, you don’t have that advantage anymore!” think he’s saying zoom out, think bigger lol

– More war/ poker/ boating analogies

Bitcoin vs Other Cryptos

– The others are very complicated, there’s likely a crypto economy in the future

– Bitcoin is not like them it is simple

– Once a sovereign wealth fund owns $5B of it, then its OK for big companies to own $5B of it, and there’s a domino effect

– One regulator could wake up tomorrow and put out a press release that doubles the market

– There are 10,000 big institutions that can start to pour in and that tips everyone in

– Saylor: “If you’re Apple, you can take your market cap up $2 trillion. Do you want $2 trillion???”

– The real Bitcoin bond – borrow $1B at 1% interest and buy Bitcoin

Countries Buying Bitcoin

– Cobie: “So El Salvador did it and now there are rumors of Honduras doing it – I do think the second person to follow is a strong form of leadership”

– Ledger: “Your top job as a large holder of Bitcoin is to convince others to buy Bitcoin to increase the network effects”

Bitcoin Maximalism

– Ledger: basically asked if there is any chance Saylor buys anything besides Bitcoin?

– Satoshi disappeared, price was a penny, there’s no pre-mine, its PoW, there’s no yield

– Basically, it’s pure

– Saylor: “Every proof of stake coin is a security”

– If you are a person of any fame, you cannot endorse a security

– However, you can endorse property

– “Saylor Coin, Saylor Moon Coin, Son of Shiba Moon Coin”

– China could create China Coin (only legal to mine in China)

– There is risk in property, but its heavy and sound

– You want property to be heavy and durable

Crypto Future

– The first decade of crypto was off shore, entrepreneurial

– The second will be on shore, institutional

– We are in the middle, and will be there for 3-5 years

– Cobie (summarizing): “you buy Bitcoin because you know what Bitcoin will be in 50 years”

– Other coins not so much

Life Advice

– Saylor: “Stay in your lane”

– You start trying to express a nuanced opinion and next thing you know your debating a nobel prize winner in that field

– There are black swan tail risks that can crush everything so can’t worry about them much

– If you think there’s a 95% chance Bitcoin goes to 0 then alright put 5% of your money in

– Misc. good quotes:

– “Bitcoin could be a $100 trillion asset without L2s without Lightning Network or anything”

– “The block of granite under Manhattan doesn’t move. It still has value”

Do you own Bitcoin as well personally?

– Yes, Michael Saylor owns 17,732 BTC


– “Focus.”

– “Just because you can acquire a thing doesn’t mean you can maintain a thing, and just because you can maintain a thing doesn’t mean you can enjoy a thing” referring mostly to a boat

– “The hardest thing is to compete forever, profitably”

Notes by Kevin and Luke

Music by GiovanniPickle