Grant Cardone bets Jason Calacanis $1M that Bitcoin hits a new high within 2 years — Calacanis calls it 'free money'

His advice to investors: “Just sell and shift from Bitcoin to Super Intelligence because one provides little to no value, and the other provides unlimited upside for humanity.”

A two-year timeframe

That’s when real estate mogul Grant Cardone chimed in. He wants Calacanis to put $1 million where his mouth is. If Bitcoin breaks its previous all-time high of $126,210.50 “on or before October 28, 2028, 12PM PST,” Cardone wins the $1 million. Otherwise, Cardone has to send Calacanis the cash.

So far, Calacanis has only replied, “So much free money!”and asked Cardone if there’s an “escrow or platform that can actually lock this in?” There aren’t any details yet on whether this bet is official.

This isn’t the only $1 million bet Calacanis has been challenged with since making his bold Bitcoin predictions. The investor and well-known Bitcoiner Fred Krueger also offered Calacanis $1 million, but wasn’t as bold as Cardone. Instead of a two-year timeframe, Krueger says Bitcoin must hit its all-time high before Oct. 28, 2036.

Palihapitiya puts extra pressure on Bitcoin’s bull case

Another “All-In Podcast” star, Chamath Palihapitiya, recently made headlines with his bearish Bitcoin predictions. But unlike Calacanis, Palihapitiya doesn’t just think Bitcoin is headed back to its previous lows — he thinks its days are numbered.

On an episode of “Moonshots” with Peter Diamandis, Palihapitiya talked about why he believes the upside in crypto is “capped,” including hacks from AI and data leaks tied to personal identities. As Palihapitiya put it, “I think crypto’s a bit lost in the woods here.”

When asked whether “Bitcoin is cooked,” Palihapitiya said, “I just think it’s capped, and I think eventually it gets hacked and then it goes to zero.”

That’s a complete reversal from Palihapitiya’s prior stance on the crypto industry. In 2017, Palihapitiya was one of the most prominent proponents of the crypto boom, even claiming on CNBC that Bitcoin could reach $1 million in two decades.

Palihapitiya admitted on “Moonshots” that he seeded all of his Bitcoin investments to Digital Currency Group (DCG). Today, he only has indirect exposure to crypto through DCG shares.

Bitcoin still has plenty of believers

Even though Bitcoin hasn’t outperformed equities year-to-date, it has bounced significantly in 2026, from a July low near $57,500 to a September peak of over $86,500. Many diehard Bitcoiners argue this is just the start of a bull run.

One of the biggest Bitcoin believers, Michael Saylor, explained to Calacanis on X why BTC still has room to run. As Saylor argued, “AI creates abundance. Bitcoin enforces scarcity. One expands humanity’s ability to create value. The other lets us preserve and transfer it across time and space. Digital Intelligence and Digital Capital are complementary, Jason. The world needs both.”

Currently, Saylor’s company, Strategy, holds over 848,500 Bitcoin, with three large purchases so far in October.