Jeff Ross Says the AI Financing Boom Echoes 2008, and Bitcoin Would Get Sold First if It Unwinds

Jeff Ross, founder of Vailshire Capital Management and a former board certified radiologist, joined the show after a two year break from social media to lay out his macro view of Bitcoin. His argument: the four year cycle framework most Bitcoiners grew up on is losing relevance, and the bigger risk sitting ahead is a financing structure in the AI sector that looks a lot like the run up to 2008.

A NEW ERA, NOT A FOUR-YEAR CYCLE

Ross has argued for several years that Bitcoin now trades as a macro asset rather than on a fixed four year rhythm. He said the current price sits right around the 200 week moving average, a level that in past cycles has marked a bottom or the region of one. He said his TradingView chart put that average at $63,997, against a live Bitcoin price of $63,986 at the time of the interview.

"This is just a great area to be accumulating and it has been."

THE THREE-BURNER THEORY

Ross explained his framework for what drives Bitcoin's price using an analogy of three burners under a pot: liquidity, the US manufacturing business cycle, and leverage. He said 2025's disappointing cycle top happened because liquidity was rising but the manufacturing PMI never broke into expansion, so the leverage-driven blow off that normally follows never showed up. He said the silver lining is that a smaller run up means less excess leverage has to get flushed out in the current downturn.

WHY THE AI FINANCING BOOM WORRIES HIM

Ross drew a direct line between the current AI infrastructure buildout and the mortgage backed securities boom of the mid 2000s. He described a sequence where chipmakers and hyperscalers have burned through free cash flow, raised equity, then moved to bond markets and private credit lenders to keep funding data center buildouts, with those loans now being packaged into rated tranches. He said if a link in that chain fails to pay, Bitcoin would likely be sold too in the initial panic, since it is one of the most liquid assets available around the clock and gets caught up in margin calls regardless of an investor's conviction. He pointed to what happened to Bitcoin during the March 2020 crash, when it dropped roughly 50 percent before recovering faster than other assets, as his template for how a similar shock could play out this time.

"Bitcoin, sound money, hard assets in general do really well in these time periods."

THE YEN INTERVENTION AND THE BIG PRINT THAT HASN'T ARRIVED

Ross also addressed the recent coordinated action to support the Japanese yen. The Financial Times reported that the Federal Reserve Bank of New York sold euros to buy yen on behalf of the US Treasury Department, an intervention that marked the first American yen intervention in 15 years. Treasury Secretary Scott Bessent has since pushed for the Fed's FIMA Repo Facility to be expanded so Japan can raise dollars using Treasuries as collateral rather than selling them outright, a facility that allows foreign central banks to borrow against Treasuries for short periods instead of selling them and pressuring US yields. Ross read the move as an indirect form of yield curve control, aimed at keeping Japan buying US assets without forcing a Treasury selloff that would push American borrowing costs higher.

On the long anticipated "big print," Ross said it has not happened yet and will likely be triggered by a specific event, most likely a failure somewhere in the AI financing chain, rather than arrive as a scheduled policy shift.

THE TAKEAWAY

Ross's framework does not promise a smooth ride. He expects Bitcoin to sell off hard alongside everything else if the AI financing structure cracks, and he expects that same selloff to be the trigger for the fiscal and monetary response that eventually sends money back into scarce assets. For him, the specific unresolved question is not whether that response comes, but which event in the AI credit chain breaks first and forces the government's hand.

This story comes from the Simply Bitcoin Live show. Watch the full episode.