No Solana investment
For years, Calacanis had insisted that he had never owned Solana and questioned the blockchain's real-world utility.
In late 2024, the prominent venture capitalist said he had "never owned $SOL." He claimed that no one had been able to explain meaningful applications for the network beyond speculation.
He reiterated that position several times through early 2025, stressing that he owned only Bitcoin while distancing himself from both Solana and XRP.
Calacanis has recently become much more positive on Solana. In recent interviews and posts, he has argued that entrepreneurs are building on "$TAO, $SOL, etc." and that Solana is producing real products.
Still, he has not publicly disclosed any investment in the token or direct ties to Solana Labs via his launch venture firm.
Long-running criticism of Strategy
Even though Calacanis is a longtime Bitcoin holder, he has been a very harsh critic of Strategy co-founder Michael Saylor.
Earlier this year, the investor argued that Bitcoin has a "Strategy problem." He is convinced that Saylor's company has become too dominant within the ecosystem and is distorting the market narrative.
He has repeatedly urged investors to buy Bitcoin directly instead of purchasing Strategy shares. The firm's financing model creates unnecessary risks, according to Calacanis.
In previous remarks, Calacanis said he would "never touch" Strategy stock even if it suffered a steep decline. He claims that there should be no taxpayer-funded bailout if the company were ever to run into financial trouble.