Why Bitcoin at $1M Is Just the Beginning and How David Bailey Got Donald Trump Into Bitcoin

In this episode of When Shift Happens, I sit down with David Bailey, Chairman of Bitcoin Magazine, the man behind the world’s largest Bitcoin conference, and CEO of KindlyMD, to discuss the inside story of how he helped shift Donald Trump from a Bitcoin sceptic to an unlikely advocate. 

Over the course of four months, Bailey and a small circle of allies built the case that Bitcoin was not just a financial technology, but an “America First” policy. The campaign culminated in a pivotal Trump Tower meeting that Bailey says “changed everything.” What followed was a feedback loop that unlocked trillions in potential industry value and may have altered the trajectory of Bitcoin’s political legitimacy in the United States.

But Bailey’s story is much bigger than one high-profile pitch. Over the past 13 years, he’s gone from a Tennessee farm town to becoming one of the most influential operators in Bitcoin. Along the way, he’s lost fortunes, built them back, and developed a thesis that Bitcoin is not only here to stay, but that $1 million per coin is merely the floor.

Early Lessons in Money and Markets

Bailey’s fascination with money started long before Bitcoin. As a teenager, he was already experimenting with the idea of value, from playfully counterfeiting bills for his family to watching his parents run a small business. High school investing brought him early luck: turning $7,000 into nearly $200,000 by betting on Apple and Google. But when the 2008 financial crisis wiped out those gains, he learned the hard truth that “if you’re watching CNBC, you’re probably the exit liquidity.”

That loss set him on a path toward Austrian economics, Ron Paul, and Peter Schiff, ideas that primed him to see Bitcoin as more than a scam. Still, his first reaction to the Silk Road headlines was scepticism. “Why would anyone trade a commodity for fake Ponzi money?” he recalls. But after two months of research, he couldn’t explain why it wouldn’t work. By 2010, he was all in.

Bitcoin Only — After Losing Everything

Bailey admits his journey hasn’t been a straight line. In the ICO boom of 2016–17, his company invested in nearly everything, amassing hundreds of millions on paper, only to lose it all in the crash. That pain forced him to rethink his convictions. “If I’m going to go bankrupt,” he told himself, “at least let it be on something I believe in.” By late 2018, Bailey and his partners divested from every altcoin and doubled down exclusively on Bitcoin.

That decision, ridiculed at the time, became the turning point. His firm BTC Inc., and later UTXO Management evolved into top-performing Bitcoin-focused investment vehicles. Rather than chase fads, Bailey pioneered the concept of Bitcoin treasury companies, backing firms like Japan’s Metaplanet and the UK’s Smarter Web. The returns were staggering: a $1 million “fun” investment in Metaplanet ballooned into billions in market value.

Journey to Trump Tower

These treasury plays weren’t just about profit; they also solved structural barriers to adoption. Many investors wanted Bitcoin exposure in familiar wrappers: equities, ETFs, or retirement accounts. “If you want to sell someone Bitcoin,” Bailey explains, “you’ve got to put it in a form they can actually buy.”

That same pragmatic logic guided his most audacious campaign: orange-pilling Donald Trump. What began as a casual idea over drinks in Puerto Rico turned into a months-long back-and-forth with Trump’s inner circle, facilitated by unlikely connections like Paul Manafort. Eventually, Bailey’s team sketched out a Bitcoin platform framed as “America First.”

By April 2024, they were sitting across from Trump in Trump Tower. Bailey remembers the moment clearly: “We pitched him. He said, ‘Okay, I’m in. Now you have to deliver.’” Deliver they did, rallying industry support and ultimately securing Trump’s appearance at the Bitcoin Conference that summer. The crowd’s electric response sealed the deal. Trump walked away, declaring, “These are my people. I love Bitcoin, Bitcoin loves me.”

The $1 Million Floor

For Bailey, the political breakthrough reinforces a much bigger thesis: Bitcoin’s inevitability as the world’s reserve asset. He frames its value in stark terms: “Bitcoin is gold, but better.” Unlike gold, it’s scarce, portable, divisible, and instantly auditable. On a relative basis, that means Bitcoin’s fair value is already north of $1.2 million per coin, making $1 million not a ceiling, but a floor.

Asked about the upside, Bailey doesn’t hedge: “$50 million Bitcoin is plausible. $100 million Bitcoin is plausible.” The real challenge, he notes, is not whether Bitcoin works, but how society adapts to an asset so powerful it could distort GDP measurements and reshape the global financial system.

Beyond the Four-Year Cycle

For years, Bitcoin’s rhythm has been defined by four-year boom-and-bust cycles. Bailey believes that era is over. The arrival of institutional adoption, from hedge funds, insurers, pensions, to sovereigns, creates a steady bid that makes deep bear markets unlikely. “It’s going to be faux pas not to have some exposure to Bitcoin,” he argues, pointing to the way capital allocation incentives force institutions to follow their peers.

Instead of sharp crashes, Bailey envisions Bitcoin slowly synchronising the world’s financial heartbeat. As it becomes embedded in credit ratings, government bonds, and even religious frameworks (“I’d make the case Bitcoin is halal,” he quips), the cycles of the past give way to structural integration.

Dream Bigger

Perhaps the most striking theme of Bailey’s conversation is scale. From high school stocks to multi-billion-dollar treasury plays, from ICO wipeouts to pitching the President, his career reflects a willingness to think beyond conventional limits. “Bitcoin is the biggest idea to happen in a very long time,” he says. “If it’s really going to be the reserve asset of the world, then pitching the next U.S. president isn’t crazy, it’s necessary.”

For Bailey, the lesson is simple: dream bigger. Whether that means government-issued “bitbonds,” integrating Bitcoin into mortgage credit ratings, or making it the money of AI and space, the design space is unlimited. “People rally around ideas,” he concludes. “If you can paint a vision, even if it’s very ambitious, you can make it happen.”

Final Thoughts

David Bailey’s story is a reminder that Bitcoin isn’t just a technology. It’s a cultural, political, and financial force reshaping the world in real time. 

“Fifteen years of Bitcoin did this,” Bailey insists. “All of us did this. It’s more fun to be part of history than to watch it passively.”

👉If you enjoyed reading the summary, head over to When Shift Happens on YouTube or your favorite podcast platform to access the full convo.