My eleven-year-old is obsessed with football, the round-ball kind, and something tells me he’s interested in the business of the sport.
On a walk the other morning, the topic of borrowing money came up.
I was explaining how interest works when he asked whether football clubs borrow from the bank to buy players from other teams. I told him I thought so, and we got onto how clubs make money in the first place. He worked out ticket sales on his own, and somewhere in that conversation I remembered what I was obsessed with at his age.
I was baseball-card mad in the 1980s, and the part I loved was the back of the card. Every card had the same little grid of numbers, and I’d scour them to work out who was actually good: batting average, home runs and RBIs for the hitters, wins, ERA and strikeouts for the pitchers.
What the cards couldn’t tell you was how a great shortstop stacked up against a great starting pitcher, because there was no common number for that.
That job belonged to the scouts, the old-school baseball people who spent the season at ballparks, and the winters at leagues in other countries, just watching players play. Most scouts were mostly right most of the time, and things worked just fine for over a hundred years. Statistical analysis was a thing, but scouts ruled the day.
Meanwhile, Bill James was writing about baseball in a way most front offices ignored, and the sabermetrics he started eventually grew into WAR, wins above replacement. It’s one figure for how many wins a player adds over the kind of replacement a team could pick up for next to nothing, and once you have it you can put a shortstop and a pitcher on the same scale. If wins put bums on seats, you can work out what a player is worth to the bottom line, and what to pay him.
It took a long time to land. Billy Beane’s Oakland A’s were leaning on numbers like on-base percentage by 2002, the Moneyball season, and that winter the Red Sox hired a 28-year-old Theo Epstein as general manager and brought Bill James in as an advisor. In 2004, my beloved Boston Red Sox won the World Series for the first time in 86 years. Theo was almost as much of a hero to me as David ‘Big Papi’ Ortiz, and when I saw Theo late-night shopping at Star Market in Boston’s Back Bay, I nearly fell over. Even then, WAR didn’t become a number everyone used until the late 2000s.
I still wonder what would have happened if Bill James had walked into a front office twenty years earlier, right in the middle of my baseball-card years. With a Theo Epstein to look up to alongside Jim Rice, I might have ended up in the business of baseball, since lord knows I could never hit the damn ball.
I’ve thought about that more than once since September, because four conversations on the show kept coming back to the same problem from different angles.
The box
On episode 324, Justin Swart, Partner at BITKRAFT Ventures, picked up a line from Aleks Larsen at Blockchain Capital and built the whole conversation around it: “tokens will do to finance what the shipping container did to trade and logistics.”
The story behind it comes from Marc Levinson’s The Box. Malcom McLean was a North Carolina trucker who got fed up watching longshoremen unload ships one crate at a time, and the steel box he pushed into service ended up rebuilding world trade.
The part that gets skipped in most retellings is how long the box took to win. Competing sizes and fittings sat side by side for years, and the standard only stuck once McLean released Sea-Land’s patents royalty-free to the International Organization for Standardization so every port, crane and truck could build to one spec.
So I asked Justin the obvious follow-up. Robinhood’s stock tokens are debt securities with no ownership claim, and Coinbase, Kraken and Superstate each run a different structure over the same names. If every issuer builds its own version of the container, is that still containerization, or did we just move the fragmentation problem onchain?
His answer went back to the shipping history, where the standards were fought over for years before regulators pushed the industry to converge. Baseball had the same problem before WAR, with every scout carrying his own read on a player and no common number to settle the argument.
Five wrappers, one stock
Steve Whyman spent 20 years running fixed income books at Bear Stearns, ABN AMRO and BlackRock before running digital assets and tokenization at Fidelity International. On episode 325 he told me what pulled him onchain was the chance to put every instrument on the same settlement rail, and what frustrates him is how the industry has used it.
Tokenization has been built issuance-first. Five issuers can wrap the same underlying stock five different ways, and those wrappers don’t net against each other because they’re different legal instruments, some carrying rights and some carrying none. Steve’s view is that everybody should be doing this the same but better, and what we’ve mostly done is add layers.
The cost shows up in what he calls the wings of finance. Everyone fixates on the shiny tokenized equity at the core, while the real prize sits out at the wings in financing and collateral: moving the same collateral across five locations, and going from just-in-case financing to just-in-time. That only works if the collateral is in a box every venue accepts. Five wrappers that don’t net are five scouting reports on the same player, each fine on its own and impossible to add together.
The people who own the ports
In the last week of October two stories landed together:
Nearly half the companies on the OKX-ICE tokenized stock list opted out, JPMorgan among them (it’s now 55 of the 63), and DTCC switched on its tokenization service on Canton with JPMorgan among the banks signed up.
With traditional finance finally moving onto blockchain rails, I’ve long assumed one likely outcome was TradFi eventually merging into decentralized finance, or DeFi. Those two stories made me less sure.
So, I put it to Ben Biondi, co-founder and CEO of Folks Finance and a Techstars mentor, on episode 329.
Ben has been in DeFi for seven years and was more sympathetic to the issuers than I expected. His read is that part of TradFi does want DeFi’s reach, the 24/7 trading and global access, but can’t take on the risk of its stock trading permissionlessly to anyone.
Canton and DTCC, as he put it, are big institutions using decentralized infrastructure for operations that meet their own standards. He thinks that’s a good thing, and he was clear it isn’t DeFi.
His name for it is one I know well: onchain finance.
So the standard is being decided right now by the people who already own the ports. WAR went the same way, since the numbers only became standard once Theo Epstein and the other front offices decided to use them.
Who’s loading it
Episode 328 with Alejandro Gutierrez of Superteam Ireland counted the different boxes. I ran through six ways to tokenize a share in play today, from DTCC and Nasdaq putting the same share in a new format, through issuer-sponsored shares like Galaxy’s on Superstate and custodial one-to-one tokens, to notes and certificates, synthetic wrappers and equity perps.
We compared it to stablecoins six or seven years ago, before that market consolidated, and Alejandro suspects it will take a regulator rather than a Terra-style collapse to force the same thing here. That’s where Justin landed too.
Then Alejandro pointed to Solana data showing more than 60% of tokenized stock trading happening outside US market hours. My view is that human traders are filling those hours for now, but those hours will become the playing field for agents rebalancing onchain portfolios around the clock.
Steve had already put the harder question on 325: can an agent legally settle a trade when a smart contract can’t own a security and a human still has to press the button? If agents do become the heaviest users of these rails, they’ll be the ones with the least patience for six versions of the same share, in the same way a front office’s analytics platform would get cranky about six versions of a scouting report.
The founder in the gap
If you’re wondering what kind of founder it takes to cut through the noise and make any of this work at scale, go back to episode 323 with Andrea Miele, co-founder and CEO of Beezie (Note: I backed Beezie through Techstars in 2024).
Beezie works with a different kind of asset. It takes a physical collectible, vaults it with Brinks, puts a digital twin onchain and lets people buy, sell and swap it, with an instant buyback smart contract waiting if you’d rather have the cash than the collectible.
The collectibles they started with as their go-to-market wedge? Yep, trading cards.
Strip out the collectibles and it’s the same fight as everything above: asking a market to trust a new settlement rail and a new pool of liquidity, and to let an asset sitting in a vault do things it never could in a shoebox.
Every piece of that draws detractors, and Andrea met a lot of them. Some of the best-known funds in the space passed on her more than once, and I remember telling her in 2024 not to get worried until the no’s hit 100. She kept building, found her lead investor, and in both of her fundraising rounds since then, she ended up turning away capital that wasn’t the right fit.
Allard Luchsinger gave me the phrase unstoppable founder on episode 296. Andrea is who I think of when I hear it. The boxes in finance will get standardized eventually, by regulators or by the incumbents or by both, and the founders I want to back are the ones still building on the day it happens.
Bill James spent the best part of 25 years writing for fans before a front office brought him in, and Andrea has that same stubborn patience.
My guess is the incumbents will be the ones who make a common standard for tokenized assets stick, the same way the front offices made WAR stick. Somebody still has to build it first.
When I finished explaining all of this to my son on that walk, he had one question for me. “What’s more boring, football or baseball?”
‘Nuf ‘ced.
Originally published on the MoneyNeverSleeps newsletter on 5 November 2026.
