My chat with an AI about Bitcoin, MicroStrategy and possible downstream effects for all of us

I've written a little about Bitcoin here before. This is a much deeper dive, with help from my AI friend.

Background

Before you read this, there are three things you should be aware of:

1. Mapping the present to navigate the future: Almost every piece I write here falls into this category. Everything has changed. Everything is changing still. Some of the things millions of people play with today could become the highly paid careers of tomorrow. Others are just another stepping stone on the road to general delinquency, as we move towards a world where both ever-widening income inequality and universal basic income seem inevitable.

2. Bitcoin: The fundamental starting point for Fee Sheet was money and the way we think about it. No self-respecting publication on that theme can ignore Bitcoin. As yet, I’ve only written a little about Bitcoin. Josh Forti, one of my interviewees this year, spoke about it at length. My one essay dedicated to Bitcoin was written not about its mechanics but about it as a natural extension of Internet technology, a response to the 2007-10 global financial crisis, and as a movement against the financialization of everything. In a way, it felt spiritual. My essay was titled “Bitcoin as religious experience”.

3. AI: I have written almost nothing here about AI. This is embarrassing, because literally no other technology right now — and therefore by extension nothing at all — is having more impact, and will continue to have more impact, on the work you and I do, and therefore the value we can create, and therefore the money we make. (We might debate the definition of “work” in the equation below, but let’s just say hourly rates make up just a small fraction. See “Five tiny bullet points on value”.)

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I use Claude AI, the large language model (LLM) from the company Anthropic, in my day-to-day work and business. And I use it extensively. We — me and “him” — chat every day. We map out plans. We figure out pitfalls and ways to avoid them. We use it as a French grinds teacher for my teenage daughter. And occasionally — like in the long piece that follows below — we go deep on something that’s been making me think to try to figure out where my thinking is inaccurate, where it’s incomplete and what I can do to make it better.

I’ve been thinking a lot about Bitcoin for a while, and I thought a lot about it over the past week. What was making me think about Bitcoin this week was the news about the latest investment splurge by NASDAQ-traded American company MicroStrategy on more Bitcoin.

MicroStrategy was founded in 1989 as a bespoke software company, and continued in that way until 2020, when it pivoted in a big way. The pivot was led by Michael Saylor, its founder and then CEO, now Chairman, who has become arguably the worst’s most persuasive (or most hyped-up, depending on your perspective) advocate of Bitcoin.

And the thing that particularly caught my attention, and which directly led to the AI chat that makes up the bulk of this article, was a Financial Times article last weekend, “MicroStrategy’s secret sauce is volatility, not bitcoin”.

I read the article, and realized I understood — like, really understood — almost none of it.

So I asked Claude to help me learn.

To read the following exchange, it might help if you’re interested in money and Bitcoin. And it might help if you’re interested in stocks and corporate financing. But honestly, even if you’re not, I think this exchange, prompted by me but led in so many ways by Claude, is instructive.

Why?

Because it shows a new way of thinking.

As far as my level of “intelligence” goes — no matter how much Claude says my thinking is “brilliant” or “sophisticated”, and no matter how often it says I ask “Great questions!” — the most straightforward way I have of describing my intellectual fortitude is:

I know how much I don’t know and I know how little I do.

I am curious in lots of ways.

I’m also stupid in lots more.

I’m trying to be less stupid.

And I think Claude, as well as other AI LLMs like ChatGPT and Perplexity, is making everyone who uses them — or uses them well — less stupid, very quickly.

Or maybe it’s just making us more confident and misguided, and still stupid.

I can’t know for sure.

One thing I do know for sure is that when you work with AI, it can take you to fascinating places. One of the fascinating places it brought me below was the section which talks about “The Two Bitcoins” and “The Two Saylors”.

With that, on with the transcript of my conversation about Bitcoin, MicroStrategy and our future.