Unicycle #13 - Reflections, Pirates 🏴‍☠️

As a reminder, I’m Alex Grintsvayg and you’re reading Unicycle. I welcome your feedback - hit Reply or message me anonymously. If someone forwarded you this email, subscribe here to follow along.

Hello dear friends :-)

We’ve been riding the Unicycle together for thirteen whole weeks now 💪. Let’s take stock of where we’re headed and how the journey is going.

First, thank you! I’m so grateful to all of you who read my writing, reply with your thoughts, and text me at 11:55 to make sure I’m not about to blow my deadline (we’ve had some close calls, haven’t we). My goal is to consistently put my ideas into writing and share them. I can do the writing on my own, but I can’t do the sharing without you.

Second, a course correction. Writing these emails has been somewhat stressful. I’d like to go deep on something new every week but I don’t have the time. So while optimizing for writing more, I haven’t been writing better. And when a metric becomes a target, beware Goodhart’s Curse!

To be honest, I did this to myself intentionally. When building a new habit, consistency trumps quality. But now that I know I’m going to stick with weekly writing, it’s time to add the quality back in.

My plan is to focus on one longer essay each month. This will give me time to collect my ideas and get feedback before I publish. I already started the first one (it will be about my approach to solving complex technical problems). It will probably be out in November. To make time for longer writing, the weekly emails will be smaller. I’ll write shorter reactions to things I consume or think about each week. If you see something you want me to flesh out, reply and let me know. I’m always open to feedback.

This week’s email touches on the idea that our lives are shaped by our environment and external incentives. I wrote about this observation in a few previous emails, and I keep coming back to it. Enjoy!

Pirates: Startups of the 1700s

The romantic vision of pirates is that they’re bold and charming swashbucklers, seeking a life of adventure on the high seas. This week I watched a funny and insightful video from CGP Grey that recasts pirates as common people living in an era of few opportunities. They are pushed by economic and social forces to take a big risk, in exchange for a shot at riches and a happy retirement. Less Jack Sparrow, more AirBnB.

In fact, many young companies portray themselves as rebels fighting against an oppressive status quo (we do it all the time at LBRY). Watching the video, I was struck several times by how deep the similarities go.

  • Employees at startups trade safety (stable business model, low legal risk, less effort required) for agency (flat hierarchy, higher personal impact, bigger reward for success).

  • These people are often not well-suited for traditional (Royal Navy / BigCo) jobs. Half the people at LBRY don’t have college degrees (some never finished high school), and we see that as a good thing.

  • The privateering/tech opportunity is present in the market. If your ship/team doesn’t take advantage, someone else will.

  • Clever use of branding can be crucial (more below)

  • Legal uncertainty is a big factor in startup life too. AirBnB famously fought several regulatory battles on their way to dominance, especially in NYC.

I feel obligated to add that startups don’t actually threaten or kill people for not handing over their treasure. If that’s what you’re thinking, try to see piracy in the context of the world as it was 300 years ago. The world was 200 times poorer and 50 times more violent than today. One in nine children died before their first birthday. The War of the Spanish Succession had just ravaged Europe and left tens of thousands of sailors unemployed (and there’s no government safety net). People had completely different attitudes about violence and government (and basically everything) than we do today.

With this frame, watch the video. See if you can spot other parallels.

If you’re curious about how pirates take advantage of branding, here's the companion video about that.


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