3 June 2026
Today’s episode runs through Iran sanctions, stablecoin rails, George Santos allegedly betting against his own public appearance, Schwab’s slow move toward advisor Bitcoin access, Washington’s 401(k) fight, and Microsoft’s increasingly creepy vision for AI at work. And, boy is it creepy.
The U.S. Treasury just sanctioned Iran’s biggest crypto exchange, Nobitex, along with other Iranian exchanges and individuals tied to the country’s digital asset infrastructure. The more interesting part is just how close this thing sits inside the Iranian power structure. When an exchange is tied into sanctioned institutions and leadership circles, you can see why OFAC took this very seriously. Sanction the company, sure. But sanction the founders and executives too, because that is where the real pressure starts.
The problem is that nobody really knows what is happening with Iran right now with any clarity. Early on, the information came like a fire hose. Now it feels like the whole thing has slowed to a trickle. You can flip between NPR, CNBC, Fox, social media, and whatever else you want, and still walk away feeling like you have less understanding than when you started. Governments are sanctioning crypto exchanges, freezing assets, talking about regime money, and hinting at broader warfare around payments, and the average person is left trying to piece together reality from rumor. Fog of idiocy only now with a ticker symbol.
George Santos is back on deck, because apparently we are not allowed to have normal scandals anymore. Santos reportedly told the public he planned to attend Trump’s State of the Union address, while allegedly betting on Kalshi that he would not attend. Then he did not attend. Then he posted that watching from an airport TV “was not part of the plan.” Clever trade? No. That is a clown car pulling into a regulatory checkpoint. Kalshi reportedly flagged the activity and referred the matter to the CFTC and DOJ, and multiple outlets have reported federal scrutiny around the alleged trades.
But there's a catch: prediction markets are running directly into a problem the old rulebook never really anticipated: what happens when the person betting can influence the outcome? This is not really “inside information” in the traditional sense. It is trading on your own conduct and that's a different beast. And frankly, if the platforms are the ones catching this faster than the regulators, that tells you something. Maybe prediction markets are not lawless. Maybe the platforms understand the risk better than the people writing the press releases. Yeah . . . right.
Meanwhile, Charles Schwab is moving toward spot Bitcoin access for advisors by mid-2027. Schwab already announced spot crypto trading for retail clients through Schwab Crypto, with custody through Charles Schwab Premier Bank. But the advisor channel is different. A retail customer clicking a button is one thing. A registered investment advisor buying spot Bitcoin inside a client wealth-management account is another. That requires custody, compliance, account integration, and all the plumbing that makes traditional finance move slowly while pretending it is being responsible. It's much slower of a roll-out than I anticipated.
And of course, Washington found a way to turn Bitcoin in 401(k)s into another Trump fight. Sanders and Warren are pushing back against rules that could make it easier for retirement plans to offer Bitcoin and other alternative assets, but the real energy is not retirement policy. The real energy is the ethics angle: Trump’s family is deep in crypto, therefore every crypto opening becomes another way to accuse him of profiting from workers and retirees. Are there legitimate questions there? Sure. The Trump family’s crypto entanglements are not exactly subtle. But pretending this is only about protecting retirees is a stretch. Such is politics.
DING DING DING DING! Microsoft has announced our savior for the hostile work environment. Scout, WorkIQ, agentic AI, background coordination, email, calendars, files, meetings, and collaboration pattern recognition are all part of the new roll out in Microsoft 365. All of it sounds helpful right up until you remember that “helpful” at the enterprise level usually means “management can measure it.” Microsoft says Scout is part of its new AI push at work, and reporting from Build 2026 describes it as an agent that can operate across workplace tools like Teams and other Microsoft services. But once a system can map who talks to whom, how often, about what, and through which files, the obvious next question is not “how productive can this make us?” It is “who gets to use that map against whom?” Self-employment may be a slog, but every time one of these tools ships, the monastery and the Amish start looking a little more competitive.
Circle P Vendor of the Day
Sagebrush Corporate Solutions
Everywhere you look, there’s another gatekeeper.
Banks want more paperwork. Platforms want more data. The compliance machine wants to know everything about everybody.
But Bitcoiners already understand the point: ownership matters. Privacy matters. Structure matters.
That’s why I want to tell you about Sagebrush Corporate Solutions in Cheyenne, Wyoming.
Sagebrush helps Bitcoiners form and maintain Wyoming companies without turning the process into a giant mess. LLCs, corporations, nonprofits, DAOs, registered agent service, remote online notarization, apostille facilitation, templated formation documents, compliance reminders, the whole thing.
And they are not some national filing factory pretending to know Wyoming. They are based in Cheyenne. They do one thing well: Wyoming business formation.
Wyoming has no state income tax, low annual fees, strong privacy protections, and a legal framework that actually recognizes digital assets. For people building, saving, mining, or operating in Bitcoin, that makes sense.
Sagebrush also accepts Bitcoin through their own BTCPay Server. On-chain or Lightning. No bank account required for payment. No middleman wedged into the middle of it.
Registered agent service is $125 a year, and they offer full-service formation packages if you want them to handle the moving parts.
Go to https://www.sagebrushcs.com/ and use promo code BitcoinAnd for 10% off when you pay in Bitcoin.
Sagebrush Corporate Solutions.
Privacy isn’t a perk. It’s the plan.
Member discussion: