Twenty-five years of circling the same idea: a field guide to this blog

I started writing here in 2005, mostly about bootstrapping software companies. I kept writing, on and off, until 2016, by which point I was writing about Ethereum smart contracts. Then the blog went quiet for the better part of a decade while I went and built the things I’d been writing about. I’m bringing it back now, in 2026, because none of the questions I was circling here ever went away. They just got a bigger stage.

Count it all up — the years before the blog, the years of the blog itself, and the decade since — and it’s the better part of twenty-five years spent circling the same handful of ideas. On the surface that looks like a person who couldn’t decide what his blog was about.

Going back through it to put together this guide, I don’t think that’s what happened. I think I was circling the same handful of ideas the whole time, and the technology kept changing underneath me while the questions stayed the same.

The questions are pretty simple. What is money, really? What is a contract, really? Who do you have to trust, and what happens when they let you down? And why do we keep building closed, complicated systems when open, simple ones work better?

I won’t pretend I saw any of where this ended up. I didn’t. Plenty of what I championed here went nowhere. But the ideas underneath turned out to be durable, and a lot of them read better now than they did when I wrote them. So rather than a chronological list, here is a map, grouped by subject, of the pieces I’d actually send someone to.

Where to start: money is just rights and obligations

If you only read a few things here, read these. This is the idea everything else hangs on.

• Rights and Obligations in and out of blockchains is the keystone. An asset is a right. A liability is an obligation. Money, contracts, and shares are all just bundles of these, with numbers attached.
• Balance Sheets and Blockchains takes that primitive and runs ordinary accounting over Bitcoin, Ethereum addresses, and token contracts. Boring tools, surprising clarity.
• Counter-Party risk on block chains is the other half. Once you hold a right to someone else’s obligation, you’re exposed to whether they can actually deliver. That risk never disappears. It just moves around.

Almost everything below is a special case of these three.

The nature of money and currencies

Long before I touched a blockchain, I was trying to work out what a currency actually is.

• 4 flavors of the mighty dollar argues that $100 in cash, in your bank, in PayPal, and on a Starbucks card are four different currencies wearing the same label. They aren’t fungible, and the differences are the whole business.
• The Geeks Guide to Currencies: Trade, money and value and its follow-up on Trust and Promises build money up from barter, fungibility, and the promises an issuer makes.
• The May Scale of Money Hardness and BitCoin ranks payment methods by how hard they are to reverse. It’s still the cleanest way I know to explain why Bitcoin felt different.

Contracts as code, and the agile lawyer

The same years, I was making the same argument about law that I was making about money: the document is not the point, the relationship is.

• What Lawyers could Learn from Programmers is the manifesto. Plain language, version control, less ceremony.
• Who is supposed to draft your agreements? You are!!! and Pragmatic contract law for entrepreneurs are the practical version: write the business terms yourself, use the lawyer to review.
• Contracts are relationships (with strings attached) is the short one that names the whole idea.

Read these next to the smart contract pieces below and the rhyme is hard to miss.

Open payment standards

By 2010 I was convinced the problem with payments was that the standards were a mess, and that the web had already shown us how to fix it.

• The sorry state of payment standards is the diagnosis.
• OpenTransact a tiny payment standard was my answer: a deliberately small, REST-shaped standard for moving any asset. It did not take over the world. I still think the instinct was right.
• How OAuth beat Chip and Pin is the one I’m proudest of in this group. Revokable, delegated tokens beat rigid credentials, because when something breaks you can respond. That argument has only gotten more relevant.

I never let this thread go. The instinct behind OpenTransact, a small and open standard for moving any asset, is exactly what I’m building now in the open at TAP, the Transaction Authorization Protocol. TAP is royalty-free and open-source, and it does the thing OpenTransact couldn’t yet: connect real-world identities and authorization to on-chain payments without giving up privacy. Same instinct, fifteen years of better tools.

Rebooting banking

Then I got more ambitious, and started writing about replacing the bank itself.

• My proposal to create a new Banking System is the boldest thing in the archive: limit each bank to a single, transparent service with user-managed reserves.
• Benches, Coffee and Bubbles tells the history of where financial innovation actually comes from, and why bubbles follow.
• How the Man finally brought e-gold down is the cautionary tale. A genuinely innovative system, undone by everything around the edges rather than the core. I’ve thought about it constantly in the years since.

Blockchain and smart contracts

In 2016 the tools finally caught up with the questions, and all of the above came together.

• From Contract to Smart Contract in Ethereum is the on-ramp.
• How to make sure a Smart Contract is also a Contract and Simple Convention for Human Readable Terms for Smart Contracts are where the lawyer and the programmer in me finally shook hands: code for what code does well, human-readable terms on IPFS for everything else.
• Ethereum vs Mossack Fonseca: Trusts without Trustees is the one to read if you want a feel for what was genuinely new.

When it meets the real world

The theory is fun. The real world is the test, and the real world is harder.

• What actually happened at Kipochi? is the most honest thing here. We built a Bitcoin wallet for Africa, and it ran into telecoms and regulators rather than technology. If you read one piece about the gap between the idea and the ground, read this one.

The thread that doesn’t quit: keep it small, keep it open

Running underneath all of it is a bias I’ve never shaken: small, composable, transparent things beat big, closed, complicated ones. It started as advice for founders and never really stopped applying.

• 6 simple rules for micro ventures and Small is the new big are where it began.
• Bootstrap globally extends it past the company to the whole world you operate in.

The same instinct shows up later as “small composable contracts beat jumbo kitchen-sink ones.” Same idea, different decade.

So what’s the point of all this?

The point is that none of it was really about Bitcoin, or Ethereum, or even payments. It was about a few stubborn first principles: money is rights and obligations, trust is the thing you’re actually buying and selling, and open beats closed almost every time.

These days those principles have a name and a payroll. I’m now CEO of Notabene, where the whole job is making trust and counter-party risk visible and computable between institutions moving money on public blockchains. If you’ve read this far, you’ll recognise it instantly. It’s the same counter-party risk I wrote about in 2016, the same identity questions from the OAuth and OpenTransact years, and the same refusal to choose between compliant and open. Notabene isn’t a departure from any of this. It’s the latest stop on the same path, and the one where I finally get to build it at scale.

The standards work continues alongside it in the open at TAP, and I still think out loud at Open Stable about bringing stablecoins into the real world and keeping it open. The questions haven’t changed. The tools, finally, might be good enough to answer them.