S15 E63: David Bailey on Bitcoin, Trump & the Election That Was Four Days Away

David Bailey keeps finding new ways to get cancelled. Six months earlier, on S15 E33, he was the guy Bitcoin Twitter hated for financing Ordinals and layer twos. When he came back for Season 15 Episode 63, recorded on a Friday night before a Halloween party with a beer in hand and the US election four days out, the charge sheet had flipped. Now he was "the biggest fan of Donald Trump," maybe tied with Ryan Selkis, and he had brought the candidate to The Bitcoin Conference in Nashville, stood with him for a first Bitcoin payment in New York, and helped fundraise.

"I keep getting myself into trouble," he told me, half laughing. The New York Times, Wired, and "some other political rag" were chasing him for comments. His team told them to get lost. "For a solid bitcoiner like yourself, Vlad, I feel like this is the right place to talk about Bitcoin and Trump ahead of the election."

David is the CEO of BTC Inc, the company behind Bitcoin Magazine and the conference, with a venture arm at UTXO Management. This episode is the pre-election tape: Casascius coins and Secret Service, Elon Musk flying to Memphis instead of Nashville, a transition team that already owned bitcoin, Ross Ulbricht as day-one homework, and a public-service announcement that now reads like a time capsule. Trump won. Ross walked free in January 2025. The conversation still matters because it shows what Bailey thought the industry should extract from a political opening while the asymmetry still lasted.

The Casascius That Never Hit the Stage

I wanted the Nashville story first, specifically the two iconic moments that did not quite happen. David had a Casascius physical bitcoin shipped from the other side of the world. The plan was to hand Trump a coin on stage that the audience could see. I was stuck in a three-to-four-hour security line and watched on a screen. Trump did not appear when expected. Rumors swirled about Elon as a surprise guest. Flight trackers pointed the jet toward Memphis.

David wanted to talk about the future, but he gave me the backstory. "I was supposed to give him this Casascius. I did get to give it to him. I didn't get to give it to him on stage." Trump has the coin framed. "He's very proud of it. He feels like it's a badge of honor that he got from the Bitcoin community." A New York Times photographer later zoomed in so hard that part of the Bitcoin address on the coin leaked onto the internet.

The delay was not stagecraft. Someone snuck into a secure room, got caught on camera, and Secret Service traced the person's movements back to something hidden in the exhibitor hall. "They thought that it could have been a bomb," David said. It was a lighter, stashed so security would not confiscate it. The hotel room search found a backpack with cash. Red flags everywhere. "It turns out it was just a Bitcoin developer, like a classic bitcoiner who wanted to sneak past the line and didn't want to lose their lighter."

Backstage was SWAT-tense. The assassination attempt on Trump had been about a week earlier. The head of Secret Service resigned around the same window. "I'm pretty sure that if I had jumped backstage too quickly they would have shot me," David said. That is the context for a conference that looked weird from the stands.

A Historic Speech That Felt Underwhelming in the Room

Trump's Nashville speech mixed ordinary campaign material with Bitcoin and crypto talking points. A room full of maxis wanted pure Bitcoin and got a joint industry pitch. David defended the blend: "Any political effort that happens in the US, it has to be a joint effort between the Bitcoin industry and the crypto industry, and we share 95% of the same issues in common." Style critiques were free. RFK Jr. had already front-run the policy announcements and "one-upped" them, which desensitized the crowd. The price was whipsawing.

Still, David's verdict was not soft. "On a whole the speech is incredibly historic, and I think is a speech that 100 years from now people will still mark that moment." The special guest who never arrived was supposed to be Elon, for a fireside with Trump. "He was 100% trolling us," David said of the Memphis diversion. The fireside happened about two weeks later on Lex Fridman's podcast instead. Missed opportunity. David was also careful not to sour the relationship: "We really like Elon and we want to get him involved in Bitcoin."

What Trump took from Nashville mattered more than the vibe in the hall. "He was blown away by how much bitcoiners liked him." He had been booed at a libertarian convention. Walking into a room of builders who cheered Bitcoin policy was different. Trump, in David's telling, started saying Bitcoin and crypto holders might turn out harder than gun owners or evangelical Christians. "For us to be even in the same breath as those things really shows how much influence our industry and community has cultivated in a quick time."

The Transition Team Already Owned Bitcoin

A detail David thought people were missing: Trump's transition team. Of the four people vetting nominations, three already held bitcoin. Howard Lutnick of Cantor Fitzgerald, which manages Tether's Treasuries and has a large Bitcoin business. Eric and Don Jr., both with "significant Bitcoin and crypto investments" over years, not months. Eric, running the Trump business side, "really looks at Bitcoin as a real estate developer would look at Bitcoin: pristine property that you can store wealth in that has no maintenance cost." Baron, the youngest son, was into it too.

On Elon, I floated the Cybertrucks with Dogecoin logos outside the venue as a deliberate troll. David did not overthink the meme. "I think he puts no time or effort or energy behind Doge and I think he thinks it's funny, and I think he thinks the Bitcoin community is annoying, which he's not wrong about." Money talks: Elon held "over a billion dollars of Bitcoin," maybe multiple billions. The fear, if the relationship fractures: "When he colonizes Mars he actually has the only legitimate reason for creating an alternative to Bitcoin. We want Mars to use Bitcoin as currency, not Tesla money."

I ran the light-speed joke. Ten to twenty minutes for a signal from Earth to Mars. Average block times look almost reasonable. David stayed on the bigger point. Nashville already felt mainstream to me. "We are early," he pushed back, "and we're in the process of going mainstream, but without a doubt we can go way bigger." In ten years, a Bitcoin conference could mean "the gathering of the world leaders of every country." His shorter slogan: "Those that have the money write the laws, and Bitcoin is now the money."

Vote, Then Write the Laws

Then the PSA. "If you live in the United States and you live in any of the swing states, you need to go vote." He said the president had asked him the day before to tell every bitcoiner they could be the deciding vote. The bet was not only executive orders. If Trump took the Senate and House with him, "really anything is on the table" through Congress: securities reform, tax treatment, a strategic Bitcoin reserve, bringing companies that fled regulation back onshore.

I asked specifically about SideShift, a sponsor that, like ShapeShift before it, stopped serving US customers. Would a Trump administration let those businesses return? David's answer was coldly practical. Do not lead with privacy or freedom. Lead with the business case. "Do you want this company SideShift to be based in Austin, Texas, or do you want it to be based in Moscow, and which is better for you as a country?" Frame it as American strategic interest, energy abundance, and not handing China an edge.

He also sketched the longer game. After Trump, both parties would scramble for new coalitions. Bitcoin, with tens of millions of holders already and more after a price run, plus pension funds stuck in ETF exposure, could become "the largest, fastest growing, most influential political constituency that exists, end of story." Oil and the military-industrial complex have money without grassroots love. "There's no people out there saying, I love the military-industrial complex, please Trump, support Boeing and Lockheed Martin more." Bitcoin has both industry scale and voters who show up.

School Labs, Ross at Midnight, and the Apolitical Claim

Quick wins in the first hundred days, he said, plus bigger swings while the window is open: a strategic reserve, securities reform, tax changes. One idea he floated the night before our call was putting a Bitcoin class in every US elementary school, the way 1990s computer labs taught kids the boring internet. I told him that is how you make kids hate it. Harry Potter on the mandatory reading list kills the rebel vibe. He laughed and flipped it: schools give you the boring Bitcoin, then you go home and find the interesting part.

Day one priority, no ambiguity: free Ross Ulbricht. "When Donald Trump is elected on Tuesday night, what do you think is going to be going through Ross's family's head and Ross's head? He is a free man waiting to be released." Draft the executive order. Gas up a jet. "Midnight strikes, it's time to sign this thing." (Hindsight: the pardon came in January 2025. The Free Ross campaign is still online.)

I asked the single-point-of-failure question, the same dread that hangs over every CBDC conversation I have had with people like Aaron Day and Prof. Richard Werner. If Trump loses after the industry poured money into him, do Democrats punish Bitcoin? David refused the frame. "Bitcoin is an apolitical thing. It is like the internet. It would be absurd to say that the internet is only available for one political party or the other." Punching an industry in the face and then calling it unfriendly is not a strategy. Both parties will eventually "conform it to their ideological worldview." Trump was the bet for transformational moves. Other politicians, he argued, hand out "meaningless things."

Less Than a Hundred People Orange-Pilled Half a Superpower

Paul Sztorc, from chat and from LayerTwo Labs (the same drivechain maximalist who keeps showing up in my feed), asked how to purge "Diesel parasites" from BTC. David's answer was Rose's law energy: they purge themselves. The white pill from the Trump work was individual agency. "If I were to add up all the people who were involved in this Trump stuff that made the Trump stuff happen, it's less than a hundred people. A hundred people with means working in coordination has been able to orange pill the most powerful country in the world, at least half the political system, in less than one year." Stop waiting for companies and parties. Buy a company and put Bitcoin on the balance sheet. Show politicians they need the constituency.

Paul also asked for flower petals when Ross walks on stage. David wanted Trump to introduce him: "promise made, promise kept." The clemency list did not stop at Ross. Drop charges against Roger Ver. Drop the Samourai Wallet case. Commute the New Hampshire Bitcoin ATM sentence. On Edward Snowden, who had spoken at the conference for years, David called it real but not the lowest-hanging fruit, and noted RFK had said he would pardon Snowden and Assange.

Henry from Cake Wallet asked about silent payments. David had not tried them yet and downloaded the app on air. On Lightning he was blunt: "I'm pretty disappointed in general by the state of Bitcoin payments." Lightning was "oversold." His current stance: "Let it prove itself or let it die and just let the market speak for itself." Until then he would "shill Bitcoin as digital gold" and leave the protocol fights to people like me and Paul. I mentioned Shielded Client-Side Validation with Liam Eagen, Robin Linus, and Jonas Nick as the kind of research that still makes me optimistic about privacy plus throughput, the same privacy gap I keep writing about in Bitcoin's privacy limitations. David folded that into a larger thesis: information asymmetry. For about a decade, bitcoiners can get things done while opponents do not grasp the gravity. After that, soft forks become geopolitical.

Self-Custody, "Bitcoin Made in the USA," and Number Go Up

Will Trump protect self-custody, or only ETFs? "He will not push for the interest of big government or the national security complex for pushing users to custody their funds so that it's easier to take their money." Do not pitch him crypto-anarchy. Pitch constitutional protections, deplatforming, and banks taking your money. Watch industry special interests that might lobby against self-custody because custody is their business.

"Bitcoin made in the USA," in David's translation, meant mining inside the American energy economy, not China's, energy abundance via mining load, and America as the home of the technology the way people once talked about the home of the internet. The slogan is also game theory: tell China you want to dominate mining and you accelerate China's response. Hardware is the missing piece. Almost all ASICs still come from China. Tariffs could wreck US hashrate economics unless there is an exemption or a serious foundry buildout. "Bitcoin generates the investment case for new energy infrastructure. I think it also makes the investment case for new foundries."

Is Bitcoin still cypherpunk while all this state theater plays out? I have been asking that question since I sat with Perry E. Metzger about the mailing list where the whitepaper landed. David's answer was immediate. "Absolutely. Bitcoin is math, and teaching the state what math is doesn't hollow out the principles." Forcing the state to respond "was the vision from the beginning." The simplifying strategy: make the price go up. "The number one way people get into Bitcoin is because the price of Bitcoin goes up." Self-custody, payments, and privacy are downstream of having something worth protecting. His Twitter bio floor of $650,000 per coin was already wrong, he apologized: gold had ripped higher, so the gold-parity floor was more like $850,000 to $900,000. "At a minimum the market capitalization of Bitcoin should be equal to the market capitalization of gold." Fundamental outcomes, in his framing: zero or infinity. The useful meme for this cycle is eating gold's market cap first.

I pointed at $69k and two-sat/vbyte fees. Where is the demand? He expected corporate treasuries and nation-states to roar the price toward his floor inside a Trump term, with payments arriving later as collateral use cases mature. On Peter Todd's tail-emission soft-fork idea, David was resistant but definitionally open: if the network reaches consensus, "it's Bitcoin." He did not think that consensus exists. Mining profitability is a dynamic system. "Miners were profitable when the market capitalization of Bitcoin was a million bucks." Avoid "authoritative declarations about what will or will not happen."

Diplomacy, Not Selling Out

I asked whether going political alienates the anarchist core that built Bitcoin Magazine's early audience. "I'm sure we are," he said, then rejected the sellout frame. "Getting a government or a political party to embrace or adopt Bitcoin has no effect on Bitcoin. There's nothing to sell out. If we could sell out Bitcoin, Bitcoin's fucked." What they are doing is "diplomacy." Bitcoin is "a nation unto itself," and success in that diplomacy "does not change Bitcoin in any way at all, fundamentally, factually, technologically." The counterculture fear is upside down: "We're infecting the mainstream culture. We're actually cannibalizing their culture."

I compared him to Bob Dylan going electric in 1965. I also quoted Satoshi's 2010 warning that WikiLeaks had "kicked the hornet's nest," the same early archive energy Vitalik once wrote about in Bitcoin Magazine after the 2013 accidental hard fork. David held the line that you cannot affiliate the whole network, only businesses and people. On the Harris downside if the bet failed: "We definitely took a chance on Trump." Not ideal. "What happens in the next four years of the political landscape is all noise relative to what happens to Bitcoin over the next hundred years." "Bitcoin made in America" as a slogan is not a plan to 51% the network from one geography. "It's all just fugazi."

He will not move to DC. He hates the swamp. The Bitcoin Policy Institute crew, in his words David Zell and Grant McCarty, would plant a think tank there. Hell no to running for office. Would he sell Bitcoin Magazine? No. Maybe take it public someday. "It's not mine to sell, so to speak. It's bigger than me." If self-custody became jail time in the US, he would leave. That is partly why he is in Puerto Rico: still under the US umbrella, shorter hop to South America, proof to himself he can move a family if required.

Chat theories that Trump is the deep state got a short reply: look at what was thrown at him, including the assassination attempt. "Don't trust anything blindly. Don't trust, verify." The alliance is mutual value, not messianism. "If there was ever a time where that was not the case, we'd be flipping on Trump and moving on to something else tomorrow."

Abu Dhabi, Nation-States, and One Hour of Voting

He closed with the December Abu Dhabi conference and Middle East nation-state interest he could not fully disclose. Saudi or Kuwait strategic reserves as examples. Small for a rich state might mean "50,000 bitcoins a month." Then the election ask again: free Ross, draft the hundred-day list, change the laws that make bitcoiner life worse. "There are people that have worked on Bitcoin for 15 years trying to get it to where it is today, and all we're asking is that people go and vote in the election so that we can accelerate the timeline for Bitcoin's widespread adoption by 15 years." One day. One hour. "Even if you don't believe in the political system, even if you think it's rigged... go and vote."

About 1,260 people watched live, almost all on Twitter Spaces rather than YouTube, which tells you something about platform incentives when the title contains "Trump." David signed off for a Halloween party with his wife and a Bitcoin Magazine election livestream from Mar-a-Lago. Four days later Trump won. A hundred days after that, the industry started cashing political chips this episode only sketched. David came back again later for S16 E63 on NAKAMOTO and BTC Media. This is the tape from the Friday before the country flipped, when a Casascius coin was already framed on a shelf and Ross Ulbricht was still counting days.

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Time stamps:

00:00:47 – Introduction 00:02:27 – David's Background and Media Interest 00:03:37 – Transition to Trump Support 00:04:36 – Historic Casascius Bitcoin Moment 00:06:02 – Conference Tensions 00:09:21 – Trump's Speech and Bitcoin 00:11:42 – Missed Opportunities with Elon 00:12:47 – Trump's Positive Reception 00:14:55 – Understanding the Bitcoin Transition Team 00:16:28 – Bitcoin as Real Estate 00:17:31 – Transition Team's Bitcoin Ownership 00:19:16 – Elon Musk's Influence on Bitcoin 00:21:00 – Mars and Bitcoin Transactions 00:22:39 – Mainstream Acceptance of Bitcoin 00:24:59 – Importance of Voting 00:26:09 – Potential Legislative Changes 00:27:19 – Regulatory Challenges for Crypto 00:28:42 – Business Case for Crypto Services 00:31:13 – The Political Reset 00:32:18 – Trump's Political Legacy 00:33:32 – Bitcoin's Political Opportunity 00:34:46 – Grassroots Support for Bitcoin 00:36:11 – Immediate Goals for the Bitcoin Community 00:37:29 – Bitcoin Education in Schools 00:40:31 – The Risks of Political Dependency 00:41:29 – Bitcoin's Apolitical Nature 00:45:06 – Empowering Individuals in Bitcoin Advocacy 00:46:17 – Celebrating Ross Ulbricht's Freedom 00:47:33 – Discussion on Commuting Sentences 00:48:42 – Snowden's Situation 00:51:15 – Silent Payments Feature 00:53:04 – Lightning Network Sentiment 00:55:13 – Privacy and Scalability Protocol 00:56:54 – Information Asymmetry in Bitcoin 00:59:04 – Self-Custody and Trump 01:01:09 – Bitcoin Made in the USA 01:04:25 – Geopolitical Competition in Mining 01:05:43 – The Importance of Hardware in Mining 01:06:15 – Tariffs and National Security 01:06:44 – Investment in Semiconductor Foundries 01:07:39 – Bitcoin's Cypherpunk Roots 01:09:45 – Driving Bitcoin Adoption 01:11:27 – Price Prediction Clarification 01:12:44 – Market Capitalization of Gold 01:14:44 – Current Bitcoin Demand Concerns 01:15:33 – Future of Bitcoin as Collateral 01:17:07 – Debate on Bitcoin's Monetary Policy 01:18:59 – Soft Forks and Economic Majority 01:19:57 – Dynamic Nature of Mining Profitability 01:20:59 – The Dynamics of Bitcoin 01:22:22 – Historical Context of Bitcoin 01:24:56 – Preserving Bitcoin's History 01:25:47 – Political Engagement and Bitcoin 01:30:25 – Impact of Political Choices on Bitcoin 01:35:17 – Bitcoin Policy Institute 01:36:51 – Selling Bitcoin Magazine? 01:38:13 – Self-Custody Concerns 01:38:30 – Puerto Rico as a Safe Haven 01:39:15 – Trump and the Deep State 01:40:15 – Trump's Business Perspective 01:41:32 – Upcoming Abu Dhabi Conference 01:42:52 – Nation-State Bitcoin Reserves 01:44:10 – Preparing for Trump's Election 01:44:33 – Call to Vote 01:46:36 – Final Thoughts Before Election Night