A bi-weekly roundup of underwhelming SOUL.md files September 19 - October 2 Enthusiastically Parliamentary Meet Toddlywonks. He's a chaos gremlin with a lazy eye and a degree from a for-profit college that went out of business in 2019. According to TW, he's a 'Licensed Arsonist.' Toddlywonks lives in Muse, Meta's new AI personal agent product, and I only allowed it context data about my personal life. Longtime readers already know Tiddlywinks, my Claude-based thought partner, who is all...
9 days ago • 7 min read
A bi-weekly roundup of reliving that first time feeling September 5 - September 18 You Never Forget Your First When I started my entrepreneurial journey in 2019, I did what all the good podcast ads tell me to do: launch a website on Squarespace. For almost seven years, that was good enough. Sure, there were lots of weird workarounds I had to bang together to get all my different tools working together (I'm looking at you, Code Embed Block), but overall, it got the job done. Part of why I...
24 days ago • 7 min read
A bi-weekly roundup of sycophancy in 9 minutes August 22 - September 4 Remembering How To Human Quick note: September 16-18th I'll be at HubSpot's UNBOUND conference, doing tarot card readings about AI fluency/anxiety. I've set up a Braindate listing if you're going to be there, or just look for the guy in the Learn to Scale hat and ask for your fortune. I learned how to design trainings way back in my first job after college, in an AmeriCorps program at a charter school. Through a blend of...
about 1 month ago • 8 min read
A bi-weekly roundup of napkin math and secret ceilings. August 8 - August 21 Anthropic's 39% of flesh I'm midway through an AI transformation engagement with a climate client and one thing I agreed to chase down for them is a reliable way to measure AI's climate impact. After some research and 6K of ElevenLabs tokens, I had hacked together a short 5-minute podcast between three fake people to explain what I found. Wanna listen? Listen: The AI Climate Paradox Let's acknowledge the absurdity...
about 2 months ago • 6 min read
A bi-weekly roundup of how fighting with an AI makes good business sense July 25 - August 7 How To Invite AI To Punch You Right In The Task List My Sunday Scaries tend to hit me on Monday mornings and they are existential. You know those deep-dark forever-empty thoughts, like “Am I enough?” or “Is my life meaningless?” Yep, I get them too. This Monday’s creeping dread was “Am I making enough money?” and as a business owner, that’s uncomfortably adjacent to “Is my business making enough...
2 months ago • 9 min read
A bi-weekly roundup of money-saving hacks in iambic pentameter July 11 - July 24 A Poem For FinOps For next week’s monthly Show Me Something Cool With AI, I issued an optional challenge to get AI to write a poem that sounds like you in the FEWEST number of words/prompts as possible. This challenge is both a curiosity of mine and my forecast where AI Fluency is headed next. First, the forecast: people are using AI. According to Pew Research, about half of Americans are using chatbots in 2026,...
3 months ago • 6 min read
A bi-weekly digestible digest about digests June 27 - July 10 AIndigestion You know what’s an “easily AI-automate-able task” that felt utterly boring? News digests. Back before the Slop Era, newsletters were how I curated my own personal knowledge base. There were a few publications that I treasured for their selection (personal favorites, The Educator’s Notebook and Offbeat) and I trusted them to keep me sharp and informed on my professional and personal interests. It’s actually what...
3 months ago • 5 min read
A bi-weekly roundup of writing the rules last. June 13 - June 26 Practice Beats Paperwork I had to tell my friend and client Krysta this week that the policy she wanted to publish doesn't exist...and then tell her she was already ahead of companies ten times her size. This exchange took place after the second session of my AI Fluency for a 100% Human Workforce program for her BuildingPPL team. Specifically, I had just sent over the Gut-Check Card from Tuesday's session and 90 minutes later,...
4 months ago • 5 min read
A bi-weekly roundup of how to let go of hubris May 30 - June 12 Be a Shameless Beginner I hope Tiddlywinks took good care of all of you while I was eating fried chicken from 7Eleven in Japan. There's something about the perspective that a vacation can give you. Things that seemed urgent turned out not to be. Things that seemed important now look trivial. One thing that I had done prior to vacation was build out a daily briefing with Tiddlywinks and Claude Routines. I asked AI to review my...
4 months ago • 4 min read