Early Uber Investor Calacanis Warns Bitcoin May Never Reach $250,000, Saying Saylor 'Broke the Game'
Key Takeaways
- •Jason Calacanis contends that Michael Saylor's attempt to corner the Bitcoin market through Strategy has damaged the cryptocurrency's chances of reaching $250,000 or even $1 million per coin.
- •Anthony Scaramucci remains bullish on Bitcoin, predicting the next halving will tighten supply and lift the price back above $100,000, although he expects the recovery to grind slowly.
- •Strategy began buying Bitcoin as its primary treasury reserve asset in 2020 and has financed further purchases through convertible bonds, preferred stock offerings, and at-the-market share sales.
- •Calacanis has previously described Strategy as the most convoluted way to buy Bitcoin ever invented and questioned whether the asset can continue attracting new investors.
- •Bitwise CEO Hunter Horsley directly rejected Calacanis's assessment, underscoring the industry divide over whether Saylor's accumulation model strengthens or undermines Bitcoin.

Bitcoin may struggle to reach $250,000 — let alone $1 million — because billionaire Michael Saylor has fundamentally altered the cryptocurrency market through Strategy's aggressive accumulation and financial engineering, according to early Uber investor Jason Calacanis.
"Will it ever hit $1 million? Heck, will it even hit $250,000?" Calacanis wrote on X on Wednesday. "I think Saylor broke the game of bitcoin by trying to corner the market and doing all kinds of funky financial engineering around it."
Calacanis was responding to Anthony Scaramucci, founder of investment firm SkyBridge Capital, who remains bullish on Bitcoin despite describing the current market environment as a bear market. Speaking to CNBC's Andrew Ross Sorkin at the Wyoming Blockchain Symposium, Scaramucci said Bitcoin has been unusually resilient during its latest downturn.
"I think as the halving cycle comes in again and we cut the supply of coins again, it will tighten prices," he said, referring to the process built into Bitcoin's code that halves the rate of new coin issuance roughly every four years. "And I think you'll see the thing move back up over 100,000. But it's going to grind for a while."
"The most convoluted way to buy Bitcoin"
Calacanis has been a long-time critic of Strategy, the software company turned Bitcoin accumulator formerly known as MicroStrategy that has amassed one of the largest Bitcoin holdings in the world. The firm, where Saylor serves as executive chairman, began buying Bitcoin as its primary treasury reserve asset in 2020 and has since funded further purchases through convertible bonds, preferred stock offerings and at-the-market share sales — the financing mechanisms at the heart of Calacanis's complaint. Earlier this month, he described Strategy as "the most convoluted way to buy Bitcoin ever invented," arguing that investors who want Bitcoin exposure should simply buy Bitcoin itself.
"My analysis has been consistent: MicroStrategy is the most convoluted way to buy Bitcoin ever invented, and investors should just buy Bitcoin if they want Bitcoin," Calacanis wrote on Aug. 7.
He also questioned whether Bitcoin can continue attracting enough new investors.
"Bitcoin requires a growing community of believers... at least for the price to go up," Calacanis wrote in another post on Aug. 7. "For the last couple of years, people looking for appreciation and speculation seem to have found more interesting bets. Do you think Bitcoin will get to $1M a coin? If so, when?"
In Calacanis's view, Saylor's attempt to accumulate an enormous portion of Bitcoin with the help of increasingly sophisticated financing mechanisms could ultimately undermine the very asset he is betting on.
Not everyone agrees. Bitwise CEO Hunter Horsley directly rejected Calacanis's assessment on Wednesday, writing in response: "I think you're wrong." Bitwise is the asset manager behind a US spot Bitcoin exchange-traded fund, and the exchange underscored the ongoing divide over whether Saylor's accumulation model strengthens Bitcoin's market or, as Calacanis argues, undermines it.
Source: CryptoNewsNet