The $4 Trillion Handoff: What AI Agents Should Never Do With Your Money

AI agents are about to take over the money decisions most of us neglect, and the fight over who controls them has already started. More than $1 trillion a year in financial services revenue is about to be up for grabs. By 2035, that figure could reach $4 trillion. That’s the projection from a new model by Joseph Chalom , CEO of the Ethereum treasury company SharpLink , and it describes a shift most people haven’t noticed yet. Millions of everyday money decisions are moving from people to software: where your cash sits, when your loans get refinanced, what gets sold for a tax loss, and what gets borrowed against. Every bank, broker, payments network and crypto platform wants to own the agent that makes those calls for you. Chalom counts Visa, Mastercard, Stripe, Coinbase and Robinhood among the firms already competing, with JPMorgan and BlackRock watching closely. Whoever wins, Chalom writes, “decides which products the agent may recommend and which fund your idle cash could get swept into.” The prize is your inattention. Subscribe now A $180 Billion Blind Spot By Chalom’s estimate, American households keep roughly $15 trillion in checking, savings and short-term deposits, and miss out on at least $180 billion a year in interest. YEs, you read that right…$15 TRILLION in cash or cash equivalents. With interest rates rising this makes a lot of intuitive sense. Why bother making risky plays with your cash when it can earn up to ~4% in some savings instruments. The FDIC’s national average for interest checking was 0.07% this month, and savings averaged 0.37%. A government money market fund, which holds short-term Treasury debt and pays close to current rates, yielded 3.63% the same week. Ironically however, folks can earn higher yields using stablecoins with standard rates at exchanges hovering above 4%. One move separates $7 from $363. Money market funds aren’t FDIC-insured, which is the trade-off to understand before switching. Nobody chooses to earn $7 on $10,000. It happens because a CD matures and sweeps back into checking, and life gets busy. An agent doesn’t get busy. “An agent does not forget,” Chalom writes, and for this kind of mistake, memory is the cure. I’d let an agent fix that tomorrow. The same agent that sweeps your cash, though, is being built to do a lot more. The $19 Billion Day Chalom’s model goes further down the list. He describes agents that lend out your tokenized stocks for extra income, pledge them as collateral, and borrow against them so you can “access liquidity without selling.” Borrowing against an asset means a lender holds it as collateral. If the price falls far enough, the lender sells it automatically to get repaid, which is called a liquidation. You don’t get a vote, and you don’t get the asset back. On October 10, 2025, more than $19 billion of leveraged crypto positions were liquidated in 24 hours, the largest single-day event on record, according to CoinDesk research. The systems that did it worked exactly as designed, which is the uncomfortable part. Each of those positions had been set up so that one bad day couldn’t be undone. I’ve watched a small version of this on my own screen. Earlier this year I built a paper-trading bot to accumulate a crypto position on a schedule. It never got tired, never got bored, and followed its rules to the letter. In a 30-day replay it lost 0.6%, while holding the same asset and doing nothing gained 1.15%. My own replay, paper trading only. A small sample, but a clean illustration of attention without judgment. The rules were the weak point, and more attention only meant the bot acted on them more often. This is problematic for accounts that pay fees on transactions and a case for just buying and holding in some cases. As Buffett once said: “hyperactivity is the pickpocket of enterprise”. Every Money Decision is a Door Jeff Bezos has the best language I know for the difference. In his 2015 letter to Amazon shareholders, he split

Kalshi's Trading Volume Is Real. That's the Problem.

A quant flagged it, the Wall Street Journal confirmed it, the CFTC is looking. Kalshi's own rebuttal says the volume is bought. I use Kalshi. Not heavily, and not for income, but I've kept an account since it launched because it offers markets you can't find anywhere else, and I like poking at new financial plumbing to see how it works. It’s also been a wonderful sandbox for building with AI. Back in April, I was able to successfully use their API to pull pricing details that I was able to arbitrage during the March Madness basketball tournament this year. Fun times! Walk past a restaurant with a line out the door at seven o’clock and you’ll assume the food is good. That’s the point of the line. It’s the cheapest advertisement a restaurant can buy, and it’s cheap because it can be bought: pay a dozen people to stand on the sidewalk and the neighborhood fills in behind. Trading venues have a line out the door too. It’s called volume, and this week the line at Kalshi’s crypto counter got a second look from a quant, then the Journal, then the CFTC….that’s never a good sign. Share What Happend? It started September 19th with a quant posting as Beni, whose thread opened “Kalshi fakes their crypto volume and I can prove it.” His exhibit was the ETH perpetual: about $539 million of volume in a day against roughly $3.1 million of open interest, the value of positions still open at day’s end. The ratio says $174 changed hands for every $1 anyone chose to keep. His follow-up found one trade size, right around $5,500, making up roughly half of ETH perp notional over four days. On Tuesday the Wall Street Journal ran its own analysis of Kalshi’s public data and found the same fingerprint at scale citing roughly $5 billion of near-identical trades, and a CFTC review. Accounts of the article add that the pattern runs to nearly a million trades since August and more than a third of recent activity in the market. A review is not a finding, and nothing public shows who was trading. Still, when a large share of a market arrives in one lot size, the simplest explanation is a program, and the question is who’s running it and why. Figures as posted by Beni on X, September 20. Kalshi disputes the framing. Sources: CoinDesk, crypto.news. Kalshi answered Tuesday with a full post, and it’s worth reading. The short version: the trades were real, both sides wanted them, and the pattern is a liquidity program working as designed. Wash trading is banned in the rulebook, self-trades are blocked by the matching engine, pre-arranged trades are surveilled, and the company says it’s seen no evidence of either. On the narrow question of whether a rule was broken, Kalshi’s account is credible, and the CFTC will decide whether it’s complete. The wider question is what it admitted along the way. Kalshi’s Answer is the Interesting Part Here’s the mechanism, in Kalshi’s own framing. The exchange pays market makers a flat monthly fee to keep fixed-size orders, say $5,000 a side, resting inside a tight spread most of every hour. Separately, firms that clear their own trades are on a fee holiday: every perps fee comes back as a rebate at month end. Put the two together and you get a predictable scene. The paid maker has to keep quoting after the price moves, and faster, fee-free takers pick him off every time. By Kalshi’s own reading of the critic’s data, the takers walked away with about $98,000. Reconstructed from the worked example in Kalshi’s September 22 post. The firm names in the post are fictional; the mechanics aren’t. Kalshi presents this as proof of real economic activity, and it’s right. It’s also volume that exists because the exchange pays for it. The maker is on the book because Kalshi writes him a check. The takers are there because Kalshi waived their fees. Remove either subsidy and the $5,500 lots stop printing. The post also answers the complaint that a three-cent contract counts as a dollar of volume, and fairly: a three-cent YES

Stock Tokens Just Got a 5-Year Hall Pass. You’re Not Bullish Enough.

Real shares of U.S. companies can now trade on blockchains with a time limit and a chaperone, and paired with August's safe harbor for founders, it's clear who the new rules were written for. Whew…what a week it’s been for digital assets: Tuesday: the Senate blocked the Clarity Act. Wednesday: Circle switched on its own blockchain, with BlackRock, Visa and Mastercard among the validators. Thursday: the SEC quit waiting for Congress and said real shares of U.S. companies can trade on blockchains. The SEC calls it the Innovation Exemption . I’d call it a hall pass. You remember the deal. You’re allowed out of class, but only to one place, only for so long, and the teacher can take it back. Nobody confuses a hall pass with graduation, but it’s still the first time you’ve been allowed in the hallway. Stock tokens got that deal this week: five years, a short list of places to go, and a regulator watching the clock. Share First, What Exactly is a “Stock Token” A stock token is a share of a public company that lives on a blockchain. Done right, it’s the same share with the same vote and the same dividend, except it sits in your wallet, trades at 3 a.m. on a Sunday, and settles in seconds. Done the other way, it’s a side bet. Most “tokenized stocks” sold offshore track a stock’s price without giving you the stock. Robinhood’s Stock Tokens work that way. They’re debt issued out of Jersey, they carry no shareholder rights, and Americans can’t buy them. Thursday’s order picks a side. Only tokens carrying the same rights as the real share qualify, and synthetics are out. It does two things, each for 5 years. Trading venues can match buyers and sellers of these tokens without registering as a stock exchange, and the firms funding those venues’ trading pools don’t have to register as dealers. The pools are automated market makers, the same formula-driven pots of two assets that power most crypto trading. Until Thursday, running one for Apple shares made you an unregistered exchange. The venue in the middle gets the relief. Everything around it is the price of that relief. Source: SEC Release No. 34-106402. What’s Written on the Hall Pass Real ownership only. Votes and dividends included; the venue has to verify it. The company can veto. 30 days to object before a 3rd party tokenizes its stock. Size limits. Caps on how many tickers and volume each venue can handle. Halts travel together. When the stock stops on its home exchange, the token stops too. Open code, guest list at the door. The contracts are public on a public chain, but the venue decides who trades. Getting the pass is the easy part. A venue posts a public notice, tells the SEC, and waits 30 days. There’s no application and no approval queue, which puts the first possible opening around October 17. I’ve structured more than $250 million of Reg D private placements, and the pattern from exempt offerings holds here. When compliance drops from a multi-year registration to a notice and a checklist, the first people through the door are small. The Other Half: Safe Harbor for Crypto-Based Founders This order has a sibling. In August the SEC proposed Regulation Crypto Assets, which I covered in August . It lets a startup raise up to $5 million without registering, opens bigger lanes at $20 million and $75 million, and gives a team a way to certify its work is finished so the token stops being treated as a security. One rule covers how a new token gets born. The other covers how an old-fashioned share gets to trade like one. The catch is timing, because the stock token order is live today while the founder rules are still a proposal sitting in a comment period. The last row is where the big names sit. Kraken’s Ink has been live since December 2024. Robinhood Chain opened July 1. Coinbase started listing stocks on Base in August. Circle’s Arc went live Wednesday, one day before the order. Green dots are companies building rails, gold dots are the SEC writin

STRC: The Most Hated Rally in Crypto

You could’ve bought $1 bills for 70 cents this summer. Almost nobody did, and the reason has more to do with Strategy’s playbook than with Bitcoin. You could’ve bought dollar bills for 70 cents this summer. Almost nobody did, and the reason has more to do with Strategy’s playbook than with Bitcoin.

Talking Tokenization on Stage at Boston Blockchain Week

The SEC opened the week, vaults came up again, and I spent my panel making the case that AI makes advisors better at their jobs. Tokenization has moved from pitch decks to plumbing, and the regulators are in the room while it gets built. That was my takeaway from three days at Boston Blockchain Week. It’s always good to be back in my old stomping grounds. Boston University is my alma mater, or as we like to call it, the “Harvard of Boston.” The event ran September 8 through 10 in Quincy Center, just south of the city, and this was its fifth year. The theme was “The Digital Infrastructure Stack,” and the program stuck to it: settlement, tokenization, security, and capital formation. Going in, the organizers said the questions had shifted from what blockchain is to how you integrate it, stay compliant, and run it at scale. After three days, I’d say that held up. Subscribe now The SEC Set the Tone The week started strong with Taylor Lindman. He joined the SEC in February as chief counsel for its crypto task force after more than 5 years in senior legal roles at Chainlink Labs. The Task Force is the group inside the SEC working to write clear rules for digital assets, and it was set up in January 2025 to move the agency away from its earlier enforcement-first approach. [ADD: one or two specific points from Lindman’s Boston remarks] Lindman’s public comments this year keep returning to a point every investor buying tokenized products should hold onto. A recap of his June conversation at a Katten symposium listed the idea that tokenization leaves the underlying nature of a security unchanged as one of the practical takeaways. Ultimately, a tokenized fund share is still a fund share, with the same protections and obligations attached. The timing added weight. The SEC published its Regulation Crypto Assets proposal on August 18, three weeks before the conference, and I covered what it means for individual investors here. My inclination is that there isn’t consensus about whether CLARITY will pass and the SEC is now working to remove restrictions related to how projects can now fund raise under these new proposed safe harbor rules. When walls come down, money tends to flow in. Time will tell. On Stage: Tokenizing Real-World Assets “Real-world assets” means things that exist off the blockchain, like Treasury bills, real estate, private credit, or fund shares, represented as tokens you can hold and transfer onchain. I shared the stage with Chris Russell, CTO at tZERO . tZERO describes itself as one of only two original special purpose broker-dealers, with years of experience holding tokenized assets directly onchain. We talked about where tokenization stands today and where each of us sees it heading. Also joining us was Mohsin Masud, Founder and CEO of AKRU . He characterizes the organization as the Tokenization Operating System (TOS) for institutional finance: end-to-end infrastructure to issue, onboard, administer, service, and trade tokenized securities on one platform, built on an institutional-grade ledger. I wrapped up the panel by making an important point that I want people to take away: Just because an asset is tokenized does NOT mean that it’s worthy of investment. Investors still need to to considerable diligence on all fronts before we elevate their status based on technology alone. Vaults, Again Back in March at the Digital Asset Summit in New York, I kept hearing the word “vaults” in conversations that had nothing to do with each other. Six months later in Boston, they were still one of the biggest topics in the building. A quick refresher: a vault is a smart contract, meaning a program running on a blockchain. It takes deposits and puts them to work in a predefined strategy, like lending stablecoins or holding tokenized Treasuries. You receive shares representing your slice of the pool. Vaults get complicated because management happens at three separate layers. First, there’s the asset sitting ins