₿ Is Michael Saylor Still Right About Bitcoin?

In today’s newsletter I ask if Michael Saylor is still right about Bitcoin, Ben Affleck has sold his AI filmmaking startup InterPositive to Netflix, The Department of Justice just caved and settled with LiveNation for a measly $280 million dollars, OpenAI’s Head of Robotics and Consumer Hardware Caitlin Kalinowski resignedafter OpenAI signed a deal with the Department of War, Anthropic has just filed a lawsuit against the Trump administration, following the Department of War's decision to designate Anthropic as a supply chain risk, Intercontinental Exchange (ICE) just announced an investment in the cryptocurrency exchange OKX, New York Federal Reserve President John Williams recently said that the burden of current tariffs have fallen "overwhelmingly" on American businesses and consumers (Duh!), and the Miami Dolphins just release of their Quarterback Tua Tagovailoa but still owe him $54 million dollars this year.

Let’s get into it!

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₿ Is Michael Saylor Still Right About Bitcoin?

On May 1, 2025, Michael Saylor made a bet that Bitcoin would reach $1 million dollars per coin by 2030. At the time Bitcoin was trading around $94,808 dollars. Earlier that year, President Donald Trump had taken office, and with his crypto friend administration Bitcoin had already rallied 60% off its lows set during the anti-cryptocurrency Biden administration era. Bitcoin hit a record high of $126,272 dollars on October 6, 2025. Since then Bitcoin has fallen from its high to around $69,160 dollars per Bitcoin today. With Bitcoin down 45% it’s fair to ask the question: Is Michael Saylor still right about Bitcoin? The answer is complicated. Let's get into it.

Michael Saylor has been predicting the price of Bitcoin for years, but those predictions haven’t come true….yet. Since his prediction that Bitcoin will eventually reach $1 million dollars per coin Bitcoin has rallied and sold off. That’s not entirely unprecedented, and crypto winter is nothing new. In fact, it’s cyclical. But this time feels different. The sell off didn’t follow a cycle. It resulted from large institutions selling off their Bitcoin holdings when the price began to fall, triggering margin calls on the capital they leveraged to expand their Bitcoin holdings. That led to more selling, before Bitcoin leveled out around its current $68,000-$70,000 range.

Before Michael Saylor went all in on Bitcoin he ran a company called MicroStrategy that sold enterprise software to big companies, and specialized in business intelligence (BI), analytics tools, and mobile software. Then Michael Saylor caught the Bitcoin bug, and on February 5, 2025 he changed the company’s name to just Strategy, and began buying Bitcoin. Today Michael Saylor’s company Strategy holds 738,731 Bitcoin in their treasury, and they’re still buying. Strategy paid at an average price of $75,862 dollars per coin over the last year as they’ve raised various rounds of capital. To date Strategy has spent $56.04 billion dollars buying Bitcoin. At the current market price of $69,160 dollars the total value of these holdings is approximately $51.09 billion dollars. I’m no financial analyst, but that means Michael Saylor’s Strategy is looking at a paper loss of about $4.95 billion dollars on their Bitcoin investments. But

Michael Saylor’s not done buying. Just this week Strategy bought another 17,994 bitcoin for $1.3 billion dollars for an average price of $72,246 dollars per coin, which I should point out is above the current price of Bitcoin at $69,160 dollars. So again, Strategy’s Bitcoin purchases and holdings are in the red.

Remember when I mentioned that the price of Bitcoin has historically moved in cycles ever since it was first created over 17 years ago in 2009. The market has gone through many periods where the price reached a new all-time high, only to be followed by a drop of 50 percent or more. Those times are often referred to as crypto winter, and we’ve been here before. Unfortunately crypto winters usually last a while, and can lead some investors to lose faith in Bitcoin and other cryptocurrencies. But not Michael Saylor. He doubles down, and he maintains his resolve that Bitcoin represents the future of money.

Every time cryptocurrencies fall, critics say that Bitcoin is a failure and all the naysayers jump on board in their criticism of an asset class they don’t understand and usually don’t even own. But when Bitcoin rallies back and makes new all-time highs all you hear are crickets from those same analysts, and bold leaders like Michael Saylor are interviewed and portrayed in countless interviews as being visionaries. Both of these groups can’t be right all the time, but neither are they completely wrong.

The current fall of Bitcoin from its high of $126,272 dollars fits within these historical cycles of volatility that have defined the asset since its inception. Supporters of Michael Saylor argue that this is just another temporary phase, and that the price will eventually move toward his predictions of more than $1 million dollars per Bitcoin someday after 2030; a target that continues to be moved further out to avoid being wrong. They argue that because there will only ever be 21 million Bitcoins coins in existence it will lead to scarcity, and that the price can only go up from here. While the finite number of Bitcoin is factually correct, prices can and have gone anywhere but straight up.

Michael Saylor isn’t the only self proclaimed Bitcoin expert to predict the price will someday reach seven or even eight figures. Cathie Wood, who runs the firm ARK Invest, predicted on April 24, 2025 that Bitcoin could reach $2.4 million dollars by the end of 2030. She’s since updated that number to $3.8 million dollars per Bitcoin, based on institutional adoption and the introduction of new financial products like Bitcoin ETFs. Cathie Wood’s logic is based on her belief that as more companies and institutions add Bitcoin to their balance sheets as a reserve against inflation, the price of Bitcoin will go up, because of….you know….good old supply and demand.

Several prominent figures in the finance and tech industries have publicly predicted that Bitcoin will eventually be worth more than $1 million dollars, including Arthur Hayes, co-founder of BitMEX and the current CIO of Maelstrom. Jack Dorsey, the co-founder of Twitter and current founder and CEO of Block, believes Bitcoin will reach $1 million dollars based on its collaborative ecosystem as the primary driver of its value. Balaji Srinivasan, who was the CTO of Coinbase, and Brian Armstrong, co-founder and current CEO of Coinbase, both believe Bitcoin will be worth more than $1 million dollars.

Robert Kiyosaki, the author of the popular book “Rich Dad Poor Dad”, believes Bitcoin will someday be worth more than $1 million dollars per Bitcoin based on his belief that the current financial system is collapsing, corrupt, and that there is a "carefully orchestrated reset" designed to favor the elite by destroying the value of the U.S. dollar through relentless printing. He argues that savers are losers, urging people to exit fiat currency and invest in real assets like gold, silver, and Bitcoin.

Since Michael Saylor made his first prediction that Bitcoin would be worth more than $1 million dollars by 2030, he’s gone on to make a much more aggressive prediction that Bitcoin could reach $13 million dollars over the next two decades, or by 2045, and that Bitcoin would become a global reserve asset.

With Bitcoin off its high of $126,272 dollars set back in October 2025, down some 45% from its peak, it’s fair to ask if Michael Saylor’s prediction that Bitcoin will be worth more than $1 million dollars per Bitcoin by 2030, or within the next decade, is still realistic. The answer to that question is complicated, to say the least, but if the cyclical nature of Bitcoin is any indication, we haven’t seen the last of the boom-and-bust cycle of Bitcoin.

Quick Hits

🎬 Business

Ben Affleck has sold his AI filmmaking startup InterPositive to Netflix after the streaming giant withdrew their $83 billion dollar bid to acquire Warner Bros. Discovery. No one even knew Ben Affleck had started an AI company in his spare time, or that he’d been running it since 2022. The terms of the deal haven’t been released, but AI companies are cheap to acquire these days, so I’m guessing Ben Affleck just made out even better than he does as a leading actor in his movies. All of Ben Affleck’s 16 person team will join Netflix, and Ben Affleck will serve as a senior advisor at Netflix alongside his business partner, and my favorite actor, Matt Damon. InterPositive uses AI to assist with post-production tasks. Instead of generating content from text prompts, like other AI generative tools, InterPositive trains their AI on real filmmaking footage from the film’s shoots to help edit in post-production. InterPositive’s proprietary tools help to reduce production costs that often range from 15-50% of a film’s budget.

AI startup founder - now that’s not something I ever thought I hear in the same sentence as Ben Affleck. 

🎫 Entertainment

The Department of Justice just caved and settled with LiveNation for a measly $280 million dollars, which is nothing compared to the $25.2 billion that LiveNation made in 2025, or only 1.11% of their 2025 revenue! Artists and consumers have been complaining about LiveNation’s monopoly of concerts and pricing for years, and sued the company to try and force the sale of TicketMaster. With the DOJ caving into special interests, we can all expect higher ticket prices and less competition. Thanks a lot, DOJ!

🤖 Tech

OpenAI just lost their Head of Robotics and Consumer Hardware (now that’s a title). Caitlin Kalinowski resigned from the position after OpenAI signed a deal with the Department of War, after Anthropic lost their contract because they wouldn’t agree to to allow the U.S. government to use their AI software for domestic surveillance of American citizens, or for the military to  enable AI to decide on the use of lethal weapons.

Those seem like pretty good safeguards to have in place, but apparently OpenAI didn’t agree. So Caitlin Kalinowski resigned. At least someone still has values.

🪖 AI

Anthropic has just filed a lawsuit against the Trump administration, following the Department of War's decision to designate Anthropic as a supply chain risk. This follows an argument with Secretary Pete Hegseth and the canceling of Anthropic’s $200 million dollar contract. This classification effectively bars Anthropic from any federal contracts, and prevents any businesses that are currently doing business with the federal government from doing business with Anthropic. Seems a little harsh if you ask me.

This all stems from Anthropic's decision to not allow the Department of War to remove Claude’s safeguards against mass domestic surveillance, and allow for the autonomous use of lethal weapons. Those seem like pretty good safeguards to have.

By designating Anthropic as a supply chain risk, which is usually reserved for foreign companies that have been deemed to provide support to foreign countries, the federal government is attempting to blacklist a privately held U.S. government who wouldn’t roll over and give the current administration what it wants, regardless of legality. Congratulations to Anthropic for standing up for what’s right and just.

Right after the Department of War canceled Anthropic’s $200 million dollar contract, they immediately awarded that same contract to Sam Altman’s OpenAI, which apparently isn’t as concerned about the U.S. government using their AI software for domestic surveillance of American citizens, or of the military enabling AI to decide on the use of lethal weapons.

Hello America? Shouldn’t we have a discussion about the use of AI by the federal government? I’m pretty sure we still have a constitution, and nowhere in that document does it mention throwing out American’s liberties in favor of using AI for unlawful purposes.

🪙 Crypto

The parent company of the NYSE, otherwise known as Intercontinental Exchange (ICE), just announced an investment in the cryptocurrency exchange OKX at a valuation of $25 billion dollars. No details of how much ICE invested, but it was enough for them to purchase a minority stake in OKX. The deal will allow ICE to license pricing data from the 120 million accounts on the OKX platform to develop regulated futures contracts that will trade on the NYSE. Back in October 2025 ICE invested $2 billion dollars in the prediction market Polymarket at a $9 billion dollar valuation. I predict this won’t be the last investment Intercontinental Exchange makes in new markets.

📉 Economics

New York Federal Reserve President John Williams recently said that the burden of current tariffs have fallen "overwhelmingly" on American businesses and consumers. Speaking at a conference in Washington, D.C., John Williams cited a New York Fed analysis that said  approximately 90% of the added costs from tariffs have been passed on to domestic producers and consumers, which directly contradicts President Donald Trump’s claims that foreign countries would pay the tariffs. That’s simply not how tariffs work, and the American people are smarter than that. One of my idols, Kai Ryssdal who’s the host of Marketplace, constantly explains that tariffs are essentially taxes on American businesses and consumers who pay those costs, and not foreign nations.

The New York Federal Reserve estimated that tariffs have contributed between 0.5-0.75 percentage points to the current U.S. inflation rate, which currently sits at roughly 3%; above the Federal Reserve’s 2% targeted rate for inflation. John Williams said he expects the impact of tariffs on the rising rate of inflation to be transitory, and for the Federal Reserve’s inflation rate target to be reached by 2027. Yea, I’m not as hopeful about hitting that rate by 2027, so we’ll just have to wait and see.

The New York Federal Reserve’s report also mentioned the tension between their research and Kevin Hassett, the Director of President Donald Trump’s National Economic Council, who has criticized the New York Federal Reserve’s report as the "worst paper" he’d seen from the institution. If you ask me, the New York Federal Reserve is crushing it, and should just keep on doing what’s right for the American people in these difficult and trying economic times.

🏈 Sports

The Miami Dolphins’ General Manager Jon Eric Sullivan announced the release of their Quarterback Tua Tagovailoa, which will result in a record $99.2 million dollars in dead cap space for the Dolphins, which is the worst kind of NFL record to make. The Miami Dolphins will split that cost over two years, with a $67.4 million dollar hit in 2026 and $31.8 million dollars in 2027, which goes against how much room they have available to spend on their players for both of those years. The Miami Dolphins are still on the hook to pay Tua Tagovailoa the $54 million dollars in guaranteed salary they owe him, that is unless someone picks him off in free agency.

The odds of the injury and concussion prone Tua Tagovailoa landing a starting Quarterback position with any of the other 31 NFL seems was about 50/50, but only hours after the Miami Dolphins released him Tua Tagovailoa reportedly agreed to a one-year, $1.3 million deal with the Atlanta Falcons where he’ll compete for the starting Quarterback position, while he still gets paid by the Miami Dolphins the difference between what the Falcons are paying him and the $54 million dollars he’s guaranteed in salary for the year. Nice deal if you can get it!

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The Business Behind The News is written, edited, and published by Chris Thompson.