This isn’t really an essay that’s meant to be read in full. It’s more of a skimmable resource, an archive.

It’s hard to start conversations with strangers. Parties are hard. Bars are hard.

For crypto converts among other crypto converts, it’s fairly easy. At Bitcoin Meetups/crypto conferences/Burning Man, all it takes when you meet a stranger is to ask: “So, when did this whole blockchain thing click for you?”

You’ll get a wry, slight smile, some wistfulness. Usually they will tell you a story about an experience that they had that showed them something that didn’t work about money as we know it today. Usually it’s something personal, like: “I was doing volunteer work around South America and it was clear to me how money just didn’t work for normal people.”

Or: “I was trying to build this mobile gaming startup and the friction on credit card payments just killed adoption.”

You nod. You can see how that would do it. Then, you can tell your story. Bonds begin.

Let me tell you what no one ever says. They never say: “Well, I read this great explainer that someone posted on YouTube/The New York Times/Twitter and once it was all laid out, it just rang true for me.”

It’s never an explainer.

People don’t look for the explainer until something makes it click for them. Then, as Bitcoiners like to say, they go down the rabbit hole. But the explainer doesn’t make anyone want to learn more.

People find explainers because they already want to learn more.

So here’s 16 years’ worth of great explainers that you can take your pick from — annotated.

We’ve got plenty!

(Note that some of these links go to the Internet Archive because they aren’t published in their original locations any longer)

Of course, in the beginning, there was the Bitcoin whitepaper, dropped on Halloween 2009: “Bitcoin: A Peer-to-Peer Electronic Cash System,” by Satoshi Nakamoto. But no one was looking for explainers then, because that paper was the beginning of everything that follows.

“Could the Wikileaks Scandal Lead to New Virtual Currency?“, by Keir Thomas, PC World

The first big use case for Bitcoin was to make donations in support of the leak site, Wikileaks, after all the big payment providers shut the organization out. It was actually more interest than its creator really wanted.

Back in the early days, there just wasn’t much out there really unpacking this stuff. Folks learned in a more word-of-mouth way.

Slashdot was thought of as the last good site on the internet. It leaned techie but there were, I’m told, all sorts of interesting stuff on Slashdot. On BitcoinTalk, the formerly dominant Bitcoin message board, a few members say that early posts on there about Bitcoin opened their eyes to the topic.

I don’t know that Slashdot ca. 2010 converted anyone, but those discussions planted a seed.

“The Rise and Fall of Bitcoin” – WIRED.

“The most dedicated bitcoin loyalists maintained their faith, not just in Nakamoto, but in the system he had built. And yet, unmistakably, beneath the paranoia and infighting lurked something more vulnerable, an almost theodical disappointment. What bitcoiners really seemed to be asking was, why had Nakamoto created this world only to abandon it?”

This is a great historical read, and honestly not a bad backgrounder on the topic. It leans a bit too much too early into how Bitcoin works mechanically, if you ask me, but it’s fun to look back now and assess the expectations.

TL:dr: This thing has been live for almost two years now! Why hasn’t it upended all of global finance yet?

It’s true that on the web, new products usually catch on fast or they never catch on. However, Bitcoin isn’t exactly a new product. Over time it would become more and more clear that it’s more like Bitcoin is a whole new internet.

Honorable mention: Planet Money episode, “Bitcoin.” What’s so honorable about it? This was the first time I ever heard about Bitcoin. I was sitting at my desk in my home office in Philadelphia and drawing a webcomic, listening to podcasts, and I listened to this dispatch on the original cryptocurrency.

• They try to mine it, but that doesn’t work. So the only other option they can come up with is to meet a Bitcoin thinkfluencer in Manhattan and buy the coins in person.

• Then they use it to buy sandwiches.

What is Bitcoin? (v1) by WeUseCoins.

Super simple, 2-minute explainer of what Bitcoin is good at doing. It doesn’t worry too much about how it works and focuses more on what it does. The imagery is basically glorified clip art, like something a startup might make to explain its product.

The website that put it up is still live, but it’s super out of date. If you scroll to the bottom it tells you how to get access to free coins. Yeah... you can’t get access to free bitcoin any longer.

“Explain Bitcoin Like I’m Five,” by Nik Custodio, FreeCodeCamp

This was a rich era for explainers. It was tough to pick, really, because Bitcoin had been around long enough that folks started to feel like they could really proselytize, and there was some community to lean on.

This one focuses in on the double-spend problem, going from how easy it is to manage with a physical object (apples), to how it becomes much harder digitally. It does this in a super condensed way (a good way, if you ask me), articulating how Bitcoin solved that.

Finance and Capital Markets — Unit 8: Money, Banking and Central Banks, Bitcoin, by Khan Academy

Sal Khan is a legend of the early web, great at making complex concepts comprehensible for young people in a low-stress way.

He put out a unit on Bitcoin in this era. For people who actually do want to get under the hood a little bit with Bitcoin, I recommend going straight to his transactions and proof-of-work lessons.

That said, this gets deeper than most people need.

The Rise and Rise of Bitcoin, Directed by Nicholas Mross

This film is great. Full stop.

You can get a good look at the early days. The most mindblowing part is when they get a drug dealer who was using Silk Road back in the day to talk to them. He says they call him Mr. Bitcoin on the street.

See an extremely fresh-faced Erik Voorhees, Roger Ver and Fred Ehrsam. Bonus points if you catch the moment Charlie Lee just walks through a frame, unnoted.

Honorable mention: The legendary webcomic, Saturday Morning Breakfast Cereal, dealt with mixing up ethics and money. No crypto, but it’s relevant regardless.

Digital Gold: Bitcoin and the Inside Story of the Misfits and Millionaires Trying to Reinvent Money, by Nathaniel Popper (formerly the NYT’s go-to crypto guy)

This was probably the first significant book about Bitcoin. It’s reported, rather than being a long think piece, like 2018’s The Bitcoin Standard. Popper goes out and talks to people in the bitcoin economy, primarily the startups, and wraps his explanations in stories about the people making this thing work.

There is a great scene where a bunch of rich guys text around $10,000 worth of BTC for fun at a party somewhere. They were just demonstrating how easy it was to move value around, but they did it with $10K (iirc). Could they have demonstrated it just as well with $100? Or even $20? Yes. But where’s the fun in that?

The world has come a long way since then, so this is something like a snapshot from the past, but a good one.

Mastering Bitcoin by Andreas Antonopoulos

I’m not going to pretend I have even tried to read this, but if you want to go deep, maybe deep enough to help build the future, Antonopoulos’s book is the place to start. First edition came out in 2015. It’s up to a third edition now.

“Streaming Money“ by Andreas Antonopoulos

They call Roger Ver Bitcoin Jesus, so if we want to continue the Christian metaphor, it would make sense to call Antonopoulos Bitcoin’s first real apostle. He was (and is) a very effective communicator. He’s good at getting you excited about how the thing works.

What’s great about this talk is the fact that Bitcoin is about to have been running for seven years and he comes in focused not on what Bitcoin has always been, but what it’s becoming, how it has changed.

Antonopoulos starts talking about how Bitcoin can scale transactions, using the Lightning Network. He’s very excited about the Lightning Network. This explainer makes the project feel alive, like something that’s still taking shape in the world.

“What is Bitcoin?”, by Nathaniel Popper, New York Times
A simple explainer in the paper focused on why criminals demand Bitcoin when they blackmail people, published in May, just as the initial coin offering (ICO) boom was about to kick in and drive bitcoin to its first new all time high in several years, just short of $20,000.

Bitcoin was only $2,000 when Popper wrote this, though that was still up 100% from the start of the year. The signs were already there.

Bitcoin exploded in price that year because people wanted to buy new tokens on Ethereum that were going to run the next wave of internet technology. To do that, you had to buy BTC to trade it for ETH to then buy into ICOs. The crypto economy has come a long way.

Honorable mention: “Report of Investigation Pursuant to Section 21(a) of the Securities Exchange Act of 1934: The DAO,” by the Securities and Exchange Commission.

This is a different kind of explainer.

In this one, the biggest most powerful investment regulator in the world explains to the crypto world how the agency sees the entrepreneurs. This paper kicked off the still ongoing debate about what kinds of crypto assets are and aren’t subject to transaction limitations under U.S. law.

“Beyond the Bitcoin Bubble,” by Steven Johnson, The New York Times

2018 was a great year for explainers because everyone’s head was spinning from how fast money had poured into it through the last half of 2017.

This was the cover story in the weekly magazine that came with the paper. It couches the whole blossoming of crypto in the growing disillusionment with the worldwide web that had basically taken hold, at least among elites.

When I saw the following sentence I thought: “Maybe this won’t be that bad?”

“Like Bitcoin and most other blockchain platforms, Ethereum is more a swarm than a formal entity. Its borders are porous; its hierarchy is deliberately flattened.”

Johnson went out and explored the possibilities of what folks were trying to fund with ICOs. Sadly, it didn’t come out till after the boom had crested, but it was still a fair, balanced and largely accurate overview of the rapidly expanding cryptocurrency world of that era.

Also, Johnson writes.

Right now, the only real hope for a revival of the open-protocol ethos lies in the blockchain.

Still true.

“Why Decentralization Matters” by Chris Dixon, a prominent investor
Dixon shows a couple of S-curve graphs about how big internet services like Facebook evolve, that really nail the objection to the web as we know it now.

He also tells a compelling story about both why decentralized services can win but also why their victory will not be as smooth as the stories of the big web services that won, such as YouTube or Google.

Basically, making a good decentralized product involves exposing a lot of buggy half-baked work to the world for a long time before anything clicks and becomes useful applications. That doesn’t mean it’s bad, it’s just a very different process.

“The Bitcoin Whitepaper Visualized,” by Scott McCloud.

This is an explainer focused on Bitcoin in magisterial comic form.

Scott McCloud is a true virtuoso of comics. He did the all-time greatest explainer of the medium itself, Understanding Comics. Google tapped him to explain Chrome when it released the now dominant browser. And he also did a really beautiful explainer about the O.G. cryptocurrency.

While it gets extremely in the weeds (unspent transaction outputs!?!), it also has a cute conceit about Satoshi that runs through the whole thing, but the real pleasure of it is the final visualizations of blocks forming and connecting like stars in the sky over the last few pages.

By the way, if you like this kind of work, McCloud made a masterpiece of a graphic novel, The Sculptor, in 2015.

Speaking of comics: I hope by now it is clear to you that this is not true.

“Understanding the crypto-asset phenomenon, its risks and measurement issues,” by Maria Teresa Chimienti, Urszula Kochanska and Andrea Pinna, European Central Bank.

This paper is important because it’s an effort to explain this growing economy to other regulators around the world, detailing what is and isn’t visible about crypto transactions, how regulators should think about monitoring and what kind of risks it might present.

This is the kind of explainer you’re naturally going to see amidst the bust of a boom-bust cycle. The term “Crypto Winter” arose around this time, to name the long lull after the 2017 run.

Bitcoin Rap Battle Debate: Hamilton vs. Satoshi, by Rhyme Combinator

“What Is Yield Farming? The Rocket Fuel of DeFi, Explained,” by Brady Dale, CoinDesk.

In 2020, everyone got stuck inside. Folks were looking for something to do, and a lot of people discovered making magic internet money.

That year, decentralized finance (DeFi) was finding its footing. It was becoming super popular in part because of a new speculative meta: yield farming. These apps needed users to lend them money (liquidity) in order to work well. The apps didn’t need to keep your money forever, but they needed people to put in something for a while so other people could use services like trading, lending and funky derivatives. The more crypto that went in the better they worked.

So entrepreneurs spun up incentives for folks to chip in. It worked (till it didn’t). Like Antonopoulus’s Lightning-based explainer above, this one marked how the space was evolving.

The Infinite Machine: How an Army of Crypto-hackers Is Building the Next Internet with Ethereum, by Camila Russo.

Russo does for Ethereum what Popper did for Bitcoin. It is a fun read.

Money: The True Story of a Made-up Thing by Jacob Goldstein

This book does an astounding job of articulating the fact that money has always been weird, contingent and largely based on nothing. Again and again there’s a ruling class that says money is good as is, must never change, but then a few rebels see something new that’s needed and force a new instrument onto the market.

Sound familiar at all?

It’s also a fast read. Breezy. Compelling. But then he finally gets to Bitcoin though and he’s like: “Naw, can’t ever work.” The cognitive dissonance left me like: “Dude did you even read [checks notes] your own book?”

“NFTs“, by SNL

Obligatory, really. South Park also did NFTs this year.

“Why I’m Less Than Infinitely Hostile to Cryptocurrency”, by Scott Alexander, Astral Codex Ten
One of the frequent criticisms of the cryptoworld is that it’s just speedrunning traditional finance, reinventing what’s already been invented.

Yes, Alexander, something of a Silicon Valley blogger guru but not really a crypto guy, agrees, that is true, but it’s doing it out in the open. Finance as we know it today is not open. It is very siloed, highly controlled. Comparing cryptocurrency to finance like that, he argues, is like saying NASA is just another home developer.

It is, it’s just that it’s developing homes in space.

“The Crypto Story,” by Matt Levine, Bloomberg.

Cover story of Bloomberg magazine, in which the writer of its super popular daily financial news column really goes out and tries to understand the space, in a piece that would come out just before FTX blew up.

• The part under the sub-heading “enterprise blockchain” made me IRL laugh.

SBF: How the FTX Bankruptcy Unwound Crypto’s Very Bad Good Guy, by Brady Dale. Wiley.

The idea of this book was to tell a story people were interested in, the downfall of Sam Bankman-Fried, but to go back further than the news accounts were doing. And then through that to explain in simple, fun terms the kinds of crypto businesses SBF bent his considerable powers of market manipulation into.

Will you find another book that uses a Dungeons & Dragons-like setting to tell you about automated market makers like Uniswap? No, you will not.

Of the various SBF books that came out, it’s the only one that makes a good faith effort to really unpack the industry that Sam torpedoed.

“Stablecoins: The Emerging Market Story,” by Castle Island Ventures and Brevan Howard

The world in 2025 started to realize that stablecoins were the first real killer app for this technology, but many inside had known that for a while. In this report, researchers just go out and ask people around the world what they are using stablecoins for.

Lots of them are using them to trade crypto of course. That’s still the main use case. But lots of people were also using them to save money in a medium that wouldn’t inflate away value and to access yield in parts of the world where that’s not as easy as buying some treasuries in a brokerage account.

This research is now ongoing, in collaboration with Artemis Analytics.

Notably, we are entering an era where it’s not the protocols themselves that need to be explained (Bitcoin, Ethereum) but the applications built on those protocols (which, of course, has been the end goal all along). Stablecoins are an application of blockchain technology.

After all, if you decide you’re going to use a dating app, you don’t first ask what database structure it was built on, do you?

Resistance Money by Andrew Bailey, Bradley Rettler and Craig Warmke

Here’s a vibe shift: Philosophers, rather than engineers, skeptics or touts, explain Bitcoin and why it matters.

“What is Cryptocurrency and How Does It Work?“ by Nathan Peterson, Charles Schwab

Doesn’t matter so much what’s in here as it does the company that published it. As of this year, people can actually hold crypto-backed instruments in their Schwab accounts. Better break the stuff down, right?

“The Death of 60/40 – and Why Your Crypto Allocation Should Be 10% to 40%,” by Ric Edelman, Digital Asset Council of Financial Professionals

A guru of financial advisors explains why today’s investor needs to start aggressively allocating to investments with “exponential” potential, especially bitcoin. Not long after this came out, major portfolio management companies would begin permitting their advisors to recommend allocations into crypto ETFs and to include those investments in model portfolios.

It’s been a tectonic shift.

• Note: Many of these stories are behind paywalls, but if you go to this site and put the link I’ve shown in here on the second box shown on the front page (in gray) you will be able to access archived versions of all of them. I’ve checked.

I want to write about interesting things for people who are into interesting things; however, editors have always told me that I should write for people who don’t understand those interesting things.

This despite the fact that I’ve never seen any evidence of people coming to read pieces I wrote about things that they were not, in fact, interested in.

It didn’t seem to matter how well I explained the topic. If the topic wasn’t something they were looking for, they never found my 101 explanations. This is the nature of writing on the web.

I understand the theory. If there’s a million people who understand the thing you are writing about and a billion who don’t, well, it might be better to at least leave the door open for the billion.

Sure, but it seldom works out that way. Yes, sometimes you find a really great story that does bring new people in. Usually it’s because that story has a human who is interesting in it. And people find other people interesting.

More often than not I think it’s better to just write with an audience in mind (I’d take the million — that’s fine. I’m not greedy). And the audience that makes sense to me are those who have already bowed their heads before the altar of Satoshi or within one of the temples built by his plethora of apostates.

Heretics, prophets, acolytes, evangelists, hermits and pilgrims of decentralization, I welcome you all!

But I don’t see a good reason to write for your grandmas. I’m sure your grandmas are lovely, but I don’t see the point.

But if your grandma really wants to know about this stuff, hey— surely one of these will work? I don’t think anyone ever needs to write any more of these though.