Dear Reader

Time to start whining

Next up: Working on a piece about the Warren anti-trust saber-rattling. Stay tuned.

Thanks for joining the Chaos Monkey. You are the inaugural band of readers that I will forever remember as joining this imprudent lark. If I could dole out ordinal reader numbers, like employee #X at a startup, I would. You are the early Chaos Monkeys.

As I stated in my welcoming salvo, the shameless goal of this is to involve you in my writing process, both benefiting from your feedback, and giving you an early look at what I’m working on (or not going to work on because you collectively think it sucks).

My original plan was to start with a free version and work out the kinks from there, but then this happened on launch day:


I guess we’ve got a paid version to put out too.

The going thinking (based on some best-practices from the kind folks at Substack) is the following:

The public posts will be an even more unvarnished take on what’s going on in technology, social media, etc., along with the more speculative leaps that should be shot to pieces by you, or elevated into columns, books, etc.

The private (i.e. paid) posts will be more of the personal stuff. Me obliterating my laptop in frustration with live gunfire (a la Hunter S. Thompson). Me getting my Jeep stuck on my own land and having to winch it out (this has actually happened ). Think of it as a backstage pass to the ongoing AGM fiasco.

Given the already chaotic nature of everything, I thought I’d impose some order by having at least a few recurring features. Please send me angry feedback on what you like/dislike about the going ideas:

Top Tweet(s) - I tweet a lot (as many of you perhaps painfully know), and some of those go viral or become involved threads that soon morph into columns and (who knows) even books. This would be the 1-2 best Tweets of the week, usually with lots of engagement/discussion, with additional background.

Podcasts of the week - I think podcasts are the new Socratic dialogues of our time, and have some of the smartest and most perceptive commentary on our world, anywhere (including and especially when compared to conventional print media). I listen to a decent number a week, and would flag the highlight few episodes here.

Chaos Monkey Podcast (!) - I’ve gotten a fair bit of questions about ever doing a podcast, and fortunately Substack just launched such a feature. Initially it would be very low-key, personal commentary that could have ended up in a Substack post, but audio presents both a format and tone that favors some commentary. Eventually, I would have guests, likely drawn from tech doers who do the workaday slog of Silicon Valley (don’t think I’m getting Zuck on here any time soon), but of interest to those who want the unvarnished look into this world I attempted in Chaos Monkeys.

Scenes from Orcas Island - I don’t love the title ‘prepping’ as it connotes a survivalist insanity I don’t really possess. That said, having embarked on the misguided lark of homesteading an off-grid property on an island in the middle of nowhere, it is an interesting personal challenge that I think appeals to the post-modern fantasies of many (“If I just left this job staring at screens all day and had a few wooded acres…”).
Well, I was dumb enough to buy the wooded acres, so follow along for the ride. No electricity, no running water, and no apparent skills. If I die of dysentery or a chainsaw accident, you’ll be the first to know.

Into the Deep Blue - Readers of the epilogue of Chaos Monkeys know that I ended that volume with the avowed desire to sail across an ocean, something for which I’d been preparing a boat (and more importantly, myself) for a long time (and many, many dollars). Well, the key thing to doing that is not writing a successful book and fashioning yourself into a begrudging speaker, Tweeter, and ‘personal brand’ (I’ll never not use derisive quotes around that phrase). After sailing the boat from northwest Washington to California (where it’s docked today), I’ve sailed out of the Golden Gate a couple of times, but never not turned around (a key step in getting to, you know, Hawaii). This is still the plan (though here we begin on book two). Follow along as I do the final prep and try to not die getting a small boat across an ocean alone.

Oh, last thing: days of the week. To not exhaust your patience, I was thinking of pubbing afternoonish Friday (when, let’s face it, we’re all zoning out into the weekend), and perhaps once during the week (Tuesday?). All rights reserved to desecrate this by dropping 4,000 words on you on Sunday morning of course.

More soon…