Key Takeaways
- Grant Cardone offered Jason Calacanis a $1 million bet that Bitcoin will hit $126,210.50 by Oct. 28, 2028.
- Calacanis predicts Bitcoin will revisit $57,000 within a year and never reach another record high.
- Fred Krueger and Terence Michael offered separate challenges, bringing the proposed wagers to $3 million.
Real estate investor Grant Cardone has challenged venture capitalist Jason Calacanis to a $1 million wager that Bitcoin will reach $126,210.50 within two years, pushing back against the podcast host’s prediction that the cryptocurrency will never set another record.
Cardone offered to place the money with an independent third party. The challenge follows Calacanis’s call for investors to sell Bitcoin and redirect their capital toward artificial intelligence.
However, the public exchange has yet to produce a confirmed, funded agreement.
Cardone Sets a Two-Year Deadline
“Jason, I’ll bet you $1,000,000 it will break its ATH,” Cardone wrote, quoting Calacanis’s declaration that Bitcoin would never surpass its previous peak.
His proposed winning condition is specific: Bitcoin must hit or exceed $126,210.50 on or before Oct. 28, 2028, at “12PM PST.”
Cardone said the wager would settle immediately if Bitcoin reached that threshold. Otherwise, settlement would occur when the deadline expired.
He also offered two payment arrangements: trust Calacanis to pay the losing side’s obligation, or have both participants deposit their stakes with an independent escrow provider.
The distinction between the headline prediction and the actual terms matters. Cardone’s proposal requires Bitcoin to touch the specified price before the deadline; it does not require the cryptocurrency to remain above that level or to finish 2028 at that level.
Calacanis subsequently asked about an escrow service that could lock up the money, according to BlockTempo’s reporting on the exchange. The outlet reported no formal acceptance or announced escrow arrangement.
Without those steps, the challenge remains a public offer.
Calacanis Favors AI as Bitcoin Struggles
Calacanis, an early Uber investor and All-In podcast co-host, triggered the dispute with an Oct. 27 post arguing that Bitcoin faced another difficult year.
He predicted a return to $57,000 within 12 months and pointed to withdrawals from Bitcoin exchange-traded funds as evidence of weakening demand.
Those funds lost approximately $774 million across the preceding Thursday and Friday, before attracting $110 million on Monday.
That rebound complicates any suggestion that flows move consistently in one direction.
Calacanis’s broader argument centers on competition for investor capital. He believes artificial intelligence offers more productive opportunities than Bitcoin’s store-of-value proposition.
His position does not amount to rejecting every cryptocurrency. CoinDesk also reported that he remains invested in TAO, the token associated with the decentralized AI network Bittensor.
Bitcoin traded around $80,847 when Cardone tweeted his challenge. From that reference price, reaching the proposed threshold would require approximately a 56% gain.
That calculation illustrates the scale of Cardone’s bullish position without establishing how likely the outcome is.
More Million-Dollar Offers Join the Dispute
Cardone is not the only investor challenging Calacanis.
Bitcoin investor Fred Krueger offered a separate $1 million wager allowing Bitcoin until Oct. 28, 2036, to exceed its previous high. Producer and Bitcoin educator Terence Michael also offered $1 million under Cardone’s proposed terms, bringing the publicly discussed challenges to $3 million.
Cardone’s enthusiasm also aligns with his company’s investment strategy.
Cardone Capital markets funds combine multifamily property with Bitcoin exposure. Its website describes using rental cash flow to purchase additional Bitcoin, linking income-producing real estate with potential cryptocurrency appreciation.
Those projected benefits remain investment assumptions rather than guaranteed returns.
For now, the outstanding question is whether either investor will turn the online disagreement into an agreed and funded wager.
The information provided in this article is for informational purposes only. It is not intended to be, nor should it be construed as, financial advice. We do not make any warranties regarding the completeness, reliability, or accuracy of this information. All investments involve risk, and past performance does not guarantee future results. We recommend consulting a financial advisor before making any investment decisions.
Giuseppe Ciccomascolo began his career as an investigative journalist in Italy, where he contributed to both local and national newspapers, focusing on various financial sectors.
Upon relocating to London, he worked as an analyst for Fitch's CapitalStructure and later as a Senior Reporter for Alliance News. In 2017, Giuseppe transitioned to covering cryptocurrency-related news, producing documentaries and articles on Bitcoin and other emerging digital currencies. He also played a pivotal role in establishing the academy for a cryptocurrency exchange website. Crypto remained his primary area of interest throughout his tenure as a writer for ThirdFloor.
