Jason Calacanis, an angel investor, advises individuals to invest in Bitcoin directly rather than following the corporate strategy advocated by Michael Saylor. He cautions that MicroStrategy’s bold approach to accumulating Bitcoin may heighten risks, misrepresent the company’s true valuation, and tarnish Bitcoin’s overall market image.
Calacanis asserts that owning Bitcoin outright provides investors with greater control and mitigates the volatility associated with a single corporation’s large cryptocurrency holdings.
Calacanis Critiques MicroStrategy’s Strategy
The Silicon Valley entrepreneur and early supporter of Uber has encouraged investors to steer clear of MicroStrategy—now known as “Strategy”—despite its substantial Bitcoin assets. He argues for direct ownership of Bitcoin instead of depending on a public entity’s exposure to it in order to sidestep unnecessary corporate risks.
Repeatedly expressing doubt about Michael Saylor’s aggressive acquisition tactics, Calacanis believes that shares in Strategy should be valued lower than their net asset value due to their business model being heavily reliant on fluctuations in Bitcoin prices. This reliance introduces volatility that does not accurately represent the company’s fundamental operations, according to him.
My top financial advice remains: buy bitcoin if you want exposure; avoid $mstr at all costs — it’s complicated and layered which leads you to lose control.
..: but remember not to take financial guidance from a podcaster/angel… pic.twitter.com/pOAFDQXvyY
— @jason (@Jason) September 12, 2025
Doubts About Market Reputation
The investor further argues that Saylor’s prominent purchases of Bitcoin might harm its reputation despite being praised by some crypto supporters. Calacanis warns that concentrating such significant amounts within one corporation could skew market behavior and foster narratives around centralized power—contradicting the decentralized principles underpinning Bitcoin.
Since 2020, MicroStrategy has poured billions into acquiring Bitcoins, establishing itself as the largest publicly traded holder of this cryptocurrency. While this tactic has garnered interest from both institutional investors and retail markets alike, it also leaves the company vulnerable during volatile market conditions. Critics like Calacanis argue that its stock price is now more reflective of fluctuations in Bitcoin rather than its core software business operations—putting shareholders at risk.
Calacanis stresses that those interested in digital assets should completely bypass corporate middlemen. “If you want access to bitcoin, just buy bitcoin,” he stated emphatically while highlighting how direct ownership empowers investors by allowing them better management over their own risk without having faith placed in corporate governance or management decisions.
This article originally appeared on BeInCrypto under the title “Don’t Buy DAT Stock; Buy Bitcoin: Investor Warns.”