Essays
New and old writings and ramblings from yours truly. Also check out the annual letters.
August 15, 2026
Entitled: An AI SEO App for Shopify That Shows Its Receipts
Entitled gets your Shopify product data ready for AI shopping in one click, then proves it did something. A free AI-Readiness Score, one-click fixes, and AI mention tracking, no chart that just counts button clicks.
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August 13, 2026
No One Is Excited About Your AI Thing
The excitement of building anything with AI is completely non-transferable. On the eleven-at-night jolt, AI slop, and why the applause was never the point.
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August 7, 2026
Don't Trust People Who Say "I Don't Trust the Data"
"I don't trust the data" is the most expensive sentence in any meeting. On owning your numbers, seeking signal over perfection, and what happens when you hand a model your actual source data.
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July 16, 2026
I Built a Shopify App That Deletes Your Dashboards
Nobody checks the dashboard. You feel like a serious operator for three days, then never open it again. So I built Seam: it reads your store overnight and emails you the one paragraph worth knowing.
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July 16, 2026
Turn Your Meeting Transcript Into a Song (Yes, Really)
Most meeting transcript tools summarize your meeting. Very responsible. Very beige. I built the opposite: a free AI tool that turns your transcript into a one-minute banger.
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April 15, 2026
Sleeping Through the AI Revolution
On biphasic sleep, midnight prompts, and the strange new insomnia of having too many ideas. The pandemic gave us panic insomnia; AI has given us possibility insomnia.
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April 9, 2026
AI Psychosis Is Here. It's Just Not Evenly Distributed.
The chaotic gap between the people genuinely deep in AI and everyone else. Three tiers of adoption, the Twitter/LinkedIn split, and why your tier is a cultural choice, not a resource one.
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October 27, 2021
The Metaverse Is Here, Again
From Snow Crash to VRML to Second Life to Oculus to Meta: twenty years of waiting for the metaverse, and an uncomfortable theory about what it would take for it to actually arrive.
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October 18, 2021
Social Media Is Us and Using Us
A rant about social media like it's 2006 all over again. The annual outrage cycle, the coming age of fake people, and the friend who never signed up at all.
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November 22, 2020
Note to My Future Self: A 2020 Retrospective
Dear Future Self: instead of what you couldn't do in 2020, a catalog of what you did. The proto-annual-letter, with flight miles and mentoring stats included.
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April 26, 2020
Sleeping Through a Pandemic
On pandemic insomnia, biphasic sleep, and the pre-industrial waking period. Your broken 2020 sleep schedule was actually older than street lights. The original — the AI sequel came in 2026.
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March 19, 2020
Coronavirus Tales Under Socialism, Democracy, and Social Democracy
In 30 days I lived the early pandemic under three governments: Vietnam, the United States, and Norway. Who infected it best? Grades were issued.
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February 14, 2020
Marketing Consultant Rules of Engagement
12+ years and 100+ consulting projects distilled: use me like a scalpel, scope like OKRs, 3-month engagements, day rates over billable hours, and the eternal war of getting paid.
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September 19, 2016
Founder Real Talk From the Edge
Written after losing a friend and former Myspace colleague. Why it's OK to quit, why you should write or smash something, and the real talk I gave struggling founders at 500 Startups.
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August 28, 2016
Investor-to-Founder Translator
What investors actually mean, what founders actually mean, and how to read a pitch meeting by its muffins. A decade later, still requires no updates.
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August 11, 2014
No Email August
A month without email, one of my annual experiments in annoying family and colleagues. Email is a to-do list other people can add to — here's what happened when I stopped reading it.
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February 1, 2013
When it's not all good, ask for help
Written after the loss of Jody Sherman. On startup pressure, founder depression, and why asking for help directly and without shame matters. The most important thing I've ever written.
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June 3, 2013
How to Survive the Series A Crunch — From Someone Who Didn't
Lessons from stepping down from my own startup: fundraising mistakes, cutting costs before it's too late, accelerator politics, and falling out of love with your company.
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July 15, 2013
Goodbye, Los Angeles, and Thank You
A love letter to LA on the way out the door: a short history of LA tech, advice for the founders staying, and which streets to take. Written before Silicon Valley, long before Norway.
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August 27, 2011
Subscription Commerce (#SUBCOM) Matrix
The 2011 map of the subscription box gold rush, from Birchbox to Candy Japan. Restored as a historical artifact — fifteen years later it reads like a cemetery with a few castles.
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July 4, 2011
Google+ Brand Page Concept
A concept mockup for Google+ brand pages, sketched up while Google was still figuring out whether brands belonged on the platform at all. Restored from the archive, with a note on where the same question landed fifteen years later.
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September 19, 2010
First Photo of the Facebook Phone
A 2010 rumor post on the Facebook phone, complete with the very convincing photo of a fake privacy dialog that ends in "Watch you pee." Restored from the archive, photo included.
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April 23, 2008
Mahalo Adds Microformats
The 2008 post announcing Mahalo's microformat rollout that briefly made the rounds of the whole blogosphere. Restored with its original comments, plus a look at what came next: Entitled and the AI-readable-data problem all over again.
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March 8, 2008
How I Went From Picking up Your Crap to Reading It
The year was 1997, I was 18 and a janitor. Cleaning a dotcom's offices at midnight rewired how I think about work. The origin story of everything since.
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