Bruce Fenton is a longtime Bitcoin advocate since 2012, securities professional, and one of the early pioneers of tokenized securities. He is the founder and CEO of Chainstone Labs and founder of Atlantic Financial. 

Alongside Overstock founder Patrick Byrne, Bruce was involved in some of the earliest efforts to bring securities and financial-market infrastructure onto blockchain rails. In 2018, he tokenized equity in his own company, Chainstone Labs, on the Ravencoin blockchain—years before tokenization became one of Wall Street’s biggest narratives.

In this episode, Bruce breaks down naked short selling, the plumbing behind traditional securities markets, and why he believes much of the problem is ultimately a ledger problem. We dive into questions such as: Who actually owns the stocks sitting in your brokerage account? How can shares be lent and rehypothecated? What role do brokers, clearing firms, DTCC, and Cede & Co. play in determining who owns what? And could blockchain replace an opaque system of claims and intermediaries with a transparent ledger showing exactly where an asset is and who owns it?

We unpack what “tokenized stocks” actually means—and the important distinction between a token that simply gives you exposure to a stock’s price and a security issued natively onchain, where the token itself represents the actual share and the ownership rights that come with it.

Bruce discusses how tokenization could allow smaller businesses to tokenize ownership and have their stock traded globally without needing to be listed on a traditional exchange like the NYSE, as well as what a future without KYC could look like. Finally, we get into Wall Street’s embrace of tokenization, the SEC’s evolving approach to tokenized securities, and one of the biggest questions surrounding the future of this technology: who ultimately controls these new financial rails?

I sat down with the lovely and beautiful Bonnie Freeman, wife of Ian Freeman, a longtime libertarian activist and host of Free Talk Live. Ian was one of the very first voices to introduce Bitcoin to a radio audience.

Free Talk Live began discussing Bitcoin all the way back in 2010, and Ian's mission was to get Bitcoin into more people's hands. He sold Bitcoin directly to customers, operated Bitcoin vending machines, and went into local businesses helping onboard them to Bitcoin—giving them tablets and helping them set up point-of-sale systems. He used his time to actually help people use Bitcoin.

He was also fiercely outspoken against the government and became a major advocate for Bitcoin, financial privacy, and individual freedom.

On March 16, 2021, their home was violently raided by federal agents. Bonnie takes us inside that morning, describing armed agents, armored vehicles, a drone, and a flashbang used during the raid.

We break down what Ian was actually accused and convicted of and how the government and media painted him out to be a fraudster.

Prosecutors claimed Ian's operation processed more than $10 million connected to romance scams and internet fraud, said his business “catered to fraudsters,” and publicly called him an “internet fraudster.”

But the romance-scam allegations are much more nuanced than the headlines. Ian was not convicted of committing the underlying romance fraud. Investigators never produced communications showing Ian and the actual romance scammers agreeing to defraud victims.

Ian also had his own customer-screening procedures. He asked customers why they were buying Bitcoin and tried to identify potential scams. According to his defense, some victims actually concealed the true purpose of their transactions because Ian may have stopped them if they admitted they were sending the money to an online romantic interest. Ian also had a business incentive to prevent customers from being scammed because his reputation depended on satisfied customers.

So we examine one of the biggest questions surrounding his conspiracy conviction: How can you establish that Ian knowingly joined a conspiracy if you haven't demonstrated an agreement between Ian and the people actually committing the scams?

Testimony from scam victims was also presented to the jury, and Ian's defense argues that it emotionally tied him to the scammers even though he wasn't the person committing the underlying romance fraud.

Ian ultimately received an eight-year federal prison sentence.

And at the center of our conversation is a much bigger question: Was this simply the prosecution of financial crimes the government believed he committed, or did his influence on Bitcoin adoption and his outspoken opposition to government power put a target on his back? And was this really an attempt to silence an influential Bitcoin advocate and send a message to an industry that threatened the traditional financial system?

Bonnie shares why she believes Ian's name was smeared, what prison has taken from their lives, and why she believes his case belongs in the broader conversation about the war on crypto.

Key Points:

Jim argues the war is about much more than the U.S. and Iran. In his view, Iran is only the visible front of a broader conflict between U.S. nationalism and the City of London, with the Strait of Hormuz becoming a key battleground because of its importance to global oil flows.

Jim believes Europe will break before the United States. With Brent crude above $100 and Europe heavily dependent on imported energy, he argues the energy shock could accelerate industrial decline, political instability and ultimately the disintegration of the European Union, with Germany particularly vulnerable because of its energy-dependent manufacturing base.

 A 5% 10-year Treasury yield is Jim’s major danger line. He predicts that crossing it could trigger a stock-market correction, a major decline in residential real estate and a wave of foreclosures. With more than $10 trillion in Treasuries maturing this year, he believes the pressure could become far larger than 2008 once combined with an unwind of the yen carry trade.

Jim believes the U.S. is being pushed toward outright debt monetization because there simply aren’t enough natural buyers for all the debt. His argument is straightforward: when Treasuries mature or foreign holders sell and no replacement buyer appears, the government will ultimately print money to absorb the debt. He calls monetization of U.S. government debt potentially “one of the biggest stories of the century.”

Jim believes BRICS nations and other foreign holders have a growing incentive to dump U.S. Treasuries. He argues countries increasingly view Treasuries as vulnerable to sanctions, asset freezes and confiscation, while major financial institutions are also selling as bond prices fall. In his view, central banks converting Treasuries into gold is part of the same move away from sovereign debt.

The yen carry trade is one of Jim’s biggest systemic risks. He rejects public estimates that put the trade in the hundreds of billions and says he believes it is at least $4 trillion. As the yen strengthens and institutions face losses on both their Treasury holdings and yen-funded borrowing, he expects a multi-trillion-dollar rush to sell Treasuries that could become the bond crisis.

Jim believes XRP could become a neutral global settlement asset as confidence in government debt deteriorates. He argues that countries doing bilateral trade will increasingly want something other than another nation’s depreciating sovereign debt, and he sees tokenized stocks, bonds and potentially derivatives creating a much larger settlement role for XRP.

Jim remains extremely bullish on precious metals, particularly silver. He believes Shanghai’s move toward physical metal weakens the influence of COMEX and the LBMA, while military demand, solar, EVs and other industrial uses are creating a silver deficit that will continue to worsen. He even raises the possibility that Wall Street banks could eventually require a bailout over massive silver short positions, and predicts silver can trade above $100 on a sustained basis next year.

In this episode of Free The Money, I sit down with Jack Gamble host of Nobody Special Finance to break down what he believes to be the “biggest misallocation of capital in history,” following the biggest monetary expansion in history.

Jack explains the circular financing behind the AI boom and why he believes OpenAI and Anthropic’s massive spending is supporting the entire bubble, despite both companies losing tens of billions of dollars. We also discuss NVIDIA, CoreWeave, private credit increasingly financing the AI data-center buildout, and the debt being sold to people’s Pensions, 401Ks and IRAs. Jack refers to this as “one giant crowded trade that everybody is in, whether they realize it or not.”

We get into the parallels with 2008, attempts to turn future GPU compute revenue into asset-backed securities, problems Jack sees developing in private equity and life insurance, and the warning signs surrounding a potential OpenAI IPO.

Finally, Jack argues that “the real economy is doing very poorly, even though speculative asset bubbles are inflating more and more,” and explains how the enormous borrowing needs of the AI buildout are beginning to compete with the U.S. government for capital, putting upward pressure on interest rates.

Tyler Spalding is President of the Acronym Foundation and the former Co-Founder & CEO of Flexa, a digital payments network. He has been mining, coding and building in crypto since 2011 and has more than 20 years of experience across technology, payments and aerospace, including engineering work on U.S. Air Force and NASA programs. His work in crypto and Web3 has spanned a number of projects, including Anvil and Digital Spenders Club, with a longstanding focus on advancing real-world digital asset adoption.

In this episode, Tyler shares his perspective on what it will actually take for digital assets to become usable money and why privacy is essential for adoption at scale. For the first time publicly, Tyler discusses his longtime support for Zano, what he believes the project has gotten right, and why its approach to privacy and security has positioned it ahead of the curve in preparing for emerging AI threats.

We also discuss stablecoins, private digital dollars, Zano’s Hard Fork 6, cross-chain interoperability & Zcash. Tyler makes the case for Proof of Stake over Proof of Work, including the security risks he sees in PoW networks, and we explore the bigger challenge of moving crypto from something people simply hold to something they can privately and securely spend in the real world.