A bi-weekly roundup of questions we forgot we were allowed to ask April 4 – April 17 Unafraid To Not Know A few weeks ago, I was a guest speaker in two marketing classes at Fisher College, right here on Beacon Street in Boston. Two classes. Thirty-five students. Seventy-five minutes each. Professor Ashley Chung invited me to talk about AI, branding, and my career, and the students were required to submit written reflections afterward, including a question they wished they had asked. She sent...
16 days ago • 6 min read
A bi-weekly roundup of personalizing your perfect robot companion March 21 - April 3 Bonsai or Lego Blocks Remember when Keanu Reeves in The Matrix learned kung fu by plugging a USB into his head? AI skills are kind of like that, except it's your ChatGPT/Claude that's Keanu Reeves and the kung fu is a simple guide that anyone can read. Here's one of the more popular skills on Skills.sh, an open source library of downloadable skills: front-end design. You can see that it's simply a 500-word...
about 1 month ago • 7 min read
A bi-weekly roundup of intimate interviews with machines March 7 - March 20 Welcome to the Stage, Tiddlywinks! I'm excited to bring you an exclusive interview with my newest AI agent, Tiddlywinks. Built using OpenClaw- which is about as bleeding-edge as you can get right now in March 2026- Tiddlywinks isn't a standard chatbot. It is a highly configured digital thought-partner. A lot of leaders are feeling the pressure to integrate AI into their operations, but they are rightfully terrified of...
about 1 month ago • 9 min read
A bi-weekly roundup of wisdom from the Major AI-rcana February 21 - March 6 Let's Read Your AI Future Everyone "knows" the future and how AI will disrupt it: AI companies says it will be gloriousPrivacy experts says it will be a hellscapeCopyright holders says it's still illegalYour boss says you will use AI (whether you like it or not)Your CEO says "More AI- all gas no brakes" and Dan Newman from Learn to Scale says this is a perfect time for a tarot card reading. Let's ask the cards what...
about 2 months ago • 4 min read
A bi-weekly roundup of why AI fluency needs to be on your strategic plan for 2026 February 7 - February 20 You can't ignore the shift. But you can control it. I was overjoyed when the New York Times' podcast The Daily did a feature on AI this past Wednesday. Go listen, it's a great primer on how AI is changing/has changed EVERYTHING. Welcome back. Aren't you excited to vibe code your own website in 2 minutes, like Natalie did during the interview? This very moment, in February 2026, is a...
2 months ago • 4 min read
A bi-weekly roundup of 1-2-3-HOP January 24 - February 6 When AI Is On Everyone's Dance Card, You Must Dance With AI In the 19th and early 20th centuries, a dance card was a tiny, decorative booklet used by women at formal balls to keep track of their dance partners for the evening. The dance card was a high-stakes social tool. A "full card" was a sign of great popularity, while an empty one was every Victorian socialite's nightmare. It also provided a graceful out: if a woman didn't want to...
3 months ago • 5 min read
A bi-weekly roundup of metrics that makes your CFO go brrrrr January 10 - January 23 Numbers, Glorious Numbers I've been working on an app that helps agency owners answer the existential question: is my business doing ok? As I was vibe-coding my way through Cursor to build this cozy business visualization app, I realized that I needed to provide users with more concrete guidance to help them with the very-confusing parts of setting revenue goals, sales goals, and calculating how efficient...
3 months ago • 1 min read
A bi-weekly roundup of how to fit your business on a single sheet of paper December 27, 2025 - January 9, 2026 Nine Boxes Closer To Nirvana Skip the New Years Resolution, To-Don't List, and Accountabilibuddy Pact. Do a Lean Canvas instead. The Lean Canvas is a one-page business modeling worksheet that should take about 15 minutes for you to fill out if you know your business model and a couple years if you don't. Think of it less like a business plan and more like an annual physical for your...
4 months ago • 3 min read
A bi-weekly roundup of everything TL;DR from the past year December 13 - December 26 A Brief Year In Review Don't forget to enter my end-of-year holiday Cliftonstrengths & 1-1 Giveaway! Contest ends on Monday the 29th. Enter now! The end of the year always puts me into a reflective mood, and out of all my content channels, this newsletter has always been the place I feel most present. The ritual of waking up early on a Friday, putting on vibe-y instrumental music, and setting the lights to...
4 months ago • 4 min read