Why earn points when you could earn equity? Coinbase, JPMorgan, BofA, Mercury, Revolut, Starbucks, etc. should just give customers tiny amounts of stock. Spend $1,000 → get $1 of equity. Instead of earning some bullshit points program nobody understands, you slowly become an owner of the business you use. Imagine using Starbucks for 20 years and realizing you own $5,000 of Starbucks stock. Technically this seems trivial now. The alignment + customer lock-in would be insane. Surprised someone hasn’t cracked this yet.

Dude tells me Kuwait is going through massive capital market reforms. So naturally I spend the evening looking at the Kuwait Stock Exchange and discover a collection of weird little investment companies, property companies and family-controlled holding companies trading for tens of millions of dollars. Some below book. Some on single-digit earnings. Almost nobody on Western Twitter seems to care. I started trying to figure out which one to buy. Now I’m wondering if I should just buy the whole fucking basket.

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Investors constantly confuse risk with uncertainty. “It could take five years” becomes “it will take five years.” “We don’t know what’s there” becomes “there’s nothing there.” That confusion is where a lot of the money is made. I don’t mind uncertainty. I want to be overpaid for it. Underwrite the setup, not the prediction.

Looking for recommendations for a sharp, responsive boutique accounting firm that understands Delaware LLCs, partnership returns/K-1s, distressed investments and crypto. Our entities are generally single-investor SPVs formed to acquire an asset or claim and hold it through a bankruptcy or restructuring, sometimes for 5–10 years. Many are nearly dormant in the interim; others eventually produce substantial recoveries. We understand that a genuinely large or complex entity costs more. What we cannot justify is paying institutional-level annual fees for a tiny SPV simply because the underlying asset is tied up in a foreign bankruptcy or involves crypto. We had an excellent firm in Savannah that understood the difference and scaled its fees accordingly. It was acquired by Baker Tilly, and the service since then has been atrocious. We are looking for a technically capable, highly responsive firm that values a long-term relationship across a portfolio of entities—and applies some common sense to pricing. Serious recommendations welcome.

The technical founders/AI-native VCs have earned their victory lap. AI is huge, it’s real, and it’s going to get much bigger. But bull markets always leave little tells. When the winners start dunking on the “boomers” and declaring everyone who didn’t get it an idiot... start paying attention.

This is very measured, and it's great to see. Michael took an even more thoughtful and disciplined approach than I had suggested. This is a win for Bitcoin, a win for the common shareholders, and a win for the preferred holders. If Bitcoin can remain around $60,000 while Strategy sells up to $1.25 billion of BTC, it would be a huge validation of the Strategy model as a Bitcoin treasury company. It would also strengthen the investment case for the other Digital Asset Treasury (DAT) companies. Congratulations to Michael and the entire team. Well done.

Jeremy Grantham: The Drapes Don't Match the Curtains. I watched Jeremy Grantham on Diary of a CEO and CNBC. Joe Kernen pushed back on a lot of it, but one thing Jeremy said caught my attention. He mentioned that he's given 90-95% of his wealth to the Grantham Foundation. So I thought, "Alright... let's see how Jeremy Grantham actually invests Jeremy Grantham's money." I pulled the Foundation's 990. This is where the story gets interesting. The Foundation has about $782 million in assets. Roughly: $536M in venture funds and private companies $115M in public equities $78M cash $32M other investments $20M receivables This isn't some sleepy index portfolio. It's a complicated institutional portfolio built around active manager selection, private markets and frontier technology. The venture managers alone are basically a who's who of elite VC: Thrive, Lux (five different funds), Founders Fund, Flagship, Foundation Capital, FirstMark, Lakestar, Formation8, Arch, Atlas, Threshold (DFJ), Greycroft, Lowercarbon, Technology Impact, Eclipse, The Engine, Owl, Susa, Accomplice, Rincon... and a lot more. These aren't vanilla managers. They're some of the best investors in AI, software, robotics, biotech, climate tech, semiconductors, defense tech and frontier technology anywhere in the world. Most people couldn't get an allocation if they tried. Several of them also have meaningful exposure to SpaceX or the broader space economy, which is pretty funny considering how dismissive Jeremy was of SpaceX in the interview. Then there are the direct investments: Fervo Energy. Zap Energy. QuantumScape. Oxide Computer. Via Separations. Lilac Solutions. Radiant. GreenLight Biosciences. InventWood. Carbon Ridge. Again... this doesn't exactly scream "hide under the bed." Even the public equity portfolio isn't exactly boring: Recursion Pharmaceuticals (AI drug discovery) Oscar Health Instacart Evolv Technologies ACV Auctions Sana Biotechnology Riskified Now compare that to the message he's selling: "Sell US tech." "Don't own US stocks." "AI is the biggest bubble in history." "SpaceX is a BS story." "Just buy index funds." Here's my issue. There is absolutely nothing wrong with the way he's investing. Honestly, I think it's a very thoughtful institutional portfolio and I'd happily own a lot of these managers myself. But the portfolio doesn't match the sales pitch. His own money isn't sitting in index funds or hiding in cash waiting for the apocalypse. It's invested with some of the best venture capital firms in the world whose entire job is finding the next generation of technology winners. That's a very different message than the one he's selling on TV. Top-down he's a permabear. Bottom-up he's paying elite venture investors to own frontier technology. Those two stories don't really line up.

Mastermind playbook for MicroStrategy: I think Saylor pushed the financial engineering too far. Maybe it ultimately works, maybe it doesn't. But I think it's fair to say the original MicroStrategy playbook is effectively over. Ironically, I think he's now setting up what could become one of the best distressed trades of the next cycle. If this plays out the way I think it will, the preferred stack could eventually trade at 30%+ yields as unpaid dividends accrue and claims begin to compound. That's when things get interesting. Here's how I think the sequence unfolds: • mNAV goes solidly negative. • Saylor stops issuing common stock. • Saylor suspends preferred dividends. • He waits, hoping Bitcoin bails him out. • June 2028 becomes judgment day - not because the converts mature (they don't until 2029), but because the put rights become exercisable, potentially forcing a refinancing or triggering a default. Advanced distressed discussion: Assuming these instruments are treated as securities, there's an interesting bankruptcy wrinkle. If they become unsecured claims, post-petition interest generally stops accruing, and claim amounts are determined under the Bankruptcy Code. That creates a strong incentive for convert holders to organize quickly and push for a pre-packaged or pre-arranged restructuring. One bonus: this isn't technically a single-asset real estate case, so there may be enough runway for management to extend the process another 90-120 days after a filing. That could push a restructuring into late 2028. Bottom line: Next 1-6 months: I think the common, preferreds, and especially the converts remain expensive. The common is probably the cleanest short simply because of its liquidity and the number of dilution paths - additional equity issuance, preferred dividend overhang, or satisfying convert obligations with stock or cash. Next 6-18 months: If the common and preferreds ultimately get wiped or heavily impaired, the distressed debt could become one of the most attractive convex risk/reward opportunities heading into the next Bitcoin cycle. But what do I know? I only do this for a living.

I like Nic and generally agree with a lot of his work, but I think he's using the wrong framework here. This isn't a CCC bond. It's a distressed special situations security. I've spent the better part of two decades in distressed credit and roughly the last 12 years buying distressed crypto. I've competed with or worked alongside many of the largest distressed investors. When I ask myself who the marginal buyer of STRC is today, it isn't a traditional high-yield fund. It's an opportunistic credit fund. Those funds don't wake up looking for 15% returns. They generally need 30%+ IRRs before they commit capital to something this uncertain. Today you can buy: • Government refund claims targeting 10-15% IRRs. • Distressed crypto claims with recoveries denominated in dollars and often substantial collateral protection for 20-25%+ IRRs. STRC is riskier than both. You're subordinated. There are essentially no meaningful lender protections. The dividend is non-cumulative. The collateral is one volatile asset. There is negative convexity. And unlike a traditional distressed loan, you don't control the collateral or have meaningful enforcement rights. This isn't lending against Bitcoin. It's taking directional Bitcoin exposure through a structurally weak preferred security. There's an important distinction people miss. Common shareholders have a fiduciary relationship with management. Creditors don't. Management's job is to obtain the cheapest possible financing for shareholders - not to create an attractive security for creditors. To Strategy's credit, they did exactly that. They issued extraordinarily issuer-friendly paper because the market let them. Good for them! But once that paper leaves the hands of income-oriented crypto investors, who is the next buyer? That's the question. I think it's an opportunistic distressed investor. And that buyer isn't showing up for a 15-20% required return. They're looking for something closer to a 30%+ IRR. At an 11.5% coupon, that implies a price of roughly $38.33 (11.5 ÷ 30%), versus about $76.67 for a 15% yield and $57.50 for a 20% yield. Maybe 30% isn't exactly the right number. Maybe it's 35%. Maybe it's 40%. But I think anchoring this off CCC spreads misses who the actual marginal buyer is.

I'd bet dollars to donuts that Kalshi and Polymarket eventually end up being donuts in a lot of VC portfolios. I'm not against prediction markets. I actually think they're fascinating. But let's not pretend they were invented yesterday. Prediction markets have been around for decades. People have experimented with them for elections, weather derivatives, corporate forecasting, and all sorts of other applications. The problem is taking an interesting forecasting tool, pouring hundreds of millions of venture dollars into it, and then applying the Silicon Valley "growth at all costs" playbook. That playbook works when you're building something with massive social utility. Uber connected riders and drivers. Airbnb unlocked housing inventory. You can argue they bent or even broke rules, but there was an obvious public benefit that justified the debate. What's the public benefit of turning every human event into something people can gamble on? How many dildos get thrown onto a WNBA court. Whether a war escalates. Whether a politician resigns. Whether a government contract gets awarded. Sports. Celebrity gossip. Every random event in life slowly becoming a ticker symbol. The more I look at these businesses, the less they look like forecasting tools and the more they look like consumer gambling products wrapped in the language of markets, information, and democratization. And because they're venture-backed, they don't just need customers. They need hypergrowth. That means aggressive marketing, regulatory arbitrage, influencer campaigns, and constantly finding new users to keep the flywheel spinning. Philip Tetlock and the superforecasters have spent years studying forecasting. The results are genuinely interesting. But forecasting tournaments never became a mass-market consumer product because most people don't actually want to forecast. They want to gamble.

Breaking: In today’s AMA, Charles offered what may be the most specific explanation yet for the fate of the 1,096 BTC (approx 70m USD today) held by the Isle of Man Foundation: that the BTC was used back in 2016/2017 to satisfy demands related to Michael Parsons and the original audit process. If that’s the explanation, then the next step is simple: publish the invoices, agreements, approvals, and payment records. The question was never whether audits cost money. The question was where 1,096 BTC went, who received it, and why. And if Foundation assets were used to resolve disputes involving Michael Parsons, it raises another obvious question: how did IOHK ultimately end up controlling roughly 95% of the BTC raised and receiving billions of ADA, while the Foundation received only a fraction of the economics? The AMA may have answered one question. It created several more. Discord, Governance, and Community Management via @YouTube