February 10, 2022

Michael Saylor’s Killer Interview

GM, This is the Milk Road. We help you get a little smarter about crypto every day.

In Today's Email:

  • 🛥️ Michael Saylor's Killer Interview

  • 💨 Quick Hits

Michael Saylor's Killer Interview

If you don’t know who Michael Saylor, he is: 

  • A rocket scientist

  • A billionaire

  • CEO of Microstrategy 

  • Domain collector (Hope.com, Voice.com, Alarm.com, Michael.com etc.) 

  • One of the biggest bitcoin bulls on earth

Most of you know him, because his company owns $5.5B of Bitcoin on it’s corporate treasury. That’s more than any company on the planet (Tesla is next, $1.9B, and Square (now known as Block, $353M). I use CryptoTreasuries to keep track of this list. 

He also bought ~17,723 bitcoin when it was priced at ~$9k, so he personally holds ~$700M of bitcoin himself. 

I’ve seen about 50+ of his interviews, read his book from a decade ago, and even hosted him on my podcast

TBH – he’s usually pretty repetitive. Bitcoin is the best. It’s a bank in cyberspace. yada yada.

But the best interview I’ve seen him do was on UpOnly last week. 

It was 2 hours long, so let me share my notes with you.

Here’s my favorite 5 points from the episode:

#1 Diversifying is selling your winners to buy more losers

“If you look at most industries, you get one clear winner, one guy that treads water, and a shit ton of losers.” 

Ecommerce → Amazon clear winner ($1.6T+ company), #2 is Walmart is 5x smaller

Phones → Apple, clear winner ($2.88T), the #2 player Samsung is 7x smaller

Social Networks → Facebook, clear winner (~$650B), #2 player Snap is 10x smaller


When you bet on a winner, diversifying is likely to be a case of you selling the winner to buy the loser.

#2 He wasn't brave, he was desperate

He didn’t say this exactly, but he did open up about the tough position he was in. 

Microstrategy’s business was going nowhere. The stock price was flat for nearly 10 years before they bought Bitcoin.

During the interview, he admits that the company was stuck. They had $500M of cash, but nowhere to invest it. They tried hiring engineers, but didn’t grow faster. 

They tried marketing on Facebook, and conferences, but didn’t grow faster. 

Investors basically wanted them to just distribute the cash, which would only drive their stock price down. 

Saylor: “It felt like I was rowing a boat against the wind. And the wind was blowing harder than I could row”.

Bitcoin became the strategy (and story) that he could tell the market for what to do. 

#3 Inflation is real

He told a couple stories about his first hand experiences with inflation.

Microstrategy had a company in Argentina and lost millions of dollars because he was forced to keep money in the Argentinian peso which was inflating like crazy (going to zero soon). 

He tried brainstorming ways to get out of the peso (“can we use it to buy a yacht, float it to the US, and sell it here?”), but couldn't figure anything out.

#4 Most businesses are getting crushed, and don't even realize it yet

You own a hair salon. Your business not only survived the pandemic, but grew 10% this year! 

But wait, your biz earns dollars…and if true inflation is ~10% a year…then your company isn’t really growing. You’re working harder, but staying in the same place. 

Many businesses owners are so in the weeds, they lose sight of the dollars diminishing purchasing power. 

“It’s like a poker game. If I give you pocket Aces, you have a valuable hand. But if I take out a gun, point it at your head and say ‘gimme all your chips’, well, your aces aren’t really worth much anymore.”

#5 Bitcoin vs. Other Cryptocurrencies

Bitcoin has 4 major advantages that Saylor mentions: 

  1. Biggest brand & history

  2. It’s simple. It’s digital gold. Most other tokens are very complicated, which prevents adoption.

  3. It is classified as property, not a security. Saylor thinks every proof of stake coin is a security. As a public company CEO, he can never endorse a security. But he can talk about property he owns. That’s why he never says “buy Microstrategy stock” but can freely say “buy Bitcoin” 

  4. Bitcoin is “one day away”. There are 10,000 large institutions, or sovereign wealth funds that could wake up tomorrow and decide to buy Bitcoin.

Overall – great interview by Cobie and Ledger at UpOnly. They got Saylor off his script, and he shared some gold nuggets.

Quick Hits

Luna just signed a $40M deal to sponsor the Washington Nationals (I gave my luna bull & bear case here)

AssangeDAO raised $55M and won the NFT auction for $53M! (we covered their idea on monday)

And more:

– Shaan “ain’t nothing micro about my strategy” Puri

P.S. check out this twitter thread we made compiling the best memes about the Bitfinex robbery

What'd you think of today's email?