Month: October 2025
I love to read. I love everything about books. LLMs will not replace good writing anytime soon, although they have mastered the art of slop. Oh, and I love communities of people who love writing and reading.
Authors & Innovators is a free, community-based event happening on October 30th in Newton, MA, for entrepreneurs, students, CEOs, venture and angel investors, and anyone interested in business. I attended in person a few years ago, and this year I will be there virtually with my book Give First: The Power of Mentorship (and a video). Larry Gennari created it a while ago, and if you like books, writers, readers, and entrepreneurship, it’s a blast.
Their overall goal is to introduce new ideas, foster meaningful dialogue, and move their motivated audience to read business books and engage with other like-minded entrepreneurs to learn more about the exciting journey of building a business!
This year, their theme is The Resilient Entrepreneur. They will be celebrating the spirit that drives founders to adapt, evolve, and thrive. Through thought-provoking conversations with visionary authors and business leaders, we’ll explore how resilience fuels innovation, creativity, and growth—both personally and collectively. From navigating uncertainty to cultivating curiosity and courage, this event shines a light on the mindset and community that empower entrepreneurs to turn challenges into catalysts for change.
The event is complementary, but registration is required at www.authorsinnovators.org.
I recently joined Dan Caruso on The Bear Roars podcast, and our conversation brought one thing into focus: we’re living through a shift that’s not just changing what we build—it’s changing how we learn, lead, and collaborate.
We talked about AI, quantum computing, and robotics, but what we kept coming back to was access. How do we make sure every learner, founder, and educator has the tools—broadband, curiosity, and the freedom to experiment—to participate in this next era? The challenge isn’t the technology itself; it’s building the human systems around it that help people adapt and thrive.
Dan introduced the idea of the “super-professional”—someone who doesn’t just use AI, but grows alongside it. What stood out to me is that the real advantage won’t come from mastering the tools themselves, but from staying endlessly curious and open to learning. That mindset of give first—sharing what you learn as you go—feels more important than ever.
Check out the episode here:
Spotify: https://lnkd.in/gMMqrCzH
Apple: https://lnkd.in/gunRWYEH
YouTube: https://lnkd.in/gBzY_fHR
Amazon Music: https://lnkd.in/gkwEvPaY
While “vibe coding” was a catchy phrase when I first heard it, something about it felt like a head fake to me. And, now that I’ve leveled up to “competent individual software developer” again (after 33 years of not writing any code) I think it’s the wrong phrase. Instead, I’d refer to what’s going on as AI Pair Programming.
When I started playing around with AI-related coding tools last Christmas (because, well, I was bored), I had zero skills with contemporary software development. While I hadn’t written any production code since 1992, I played around with a new programming language every few years. Perl. Ruby. Ruby on Rails (sort of, not really). Python. Clojure. I could do Hello World and a few other simple things, but I never really got past basic CSS, tooling, or deployment stuff. I had a Github account and would futz around with it, but quickly get tired of trying to figure out why I didn’t care about a PR. And damn, so many CLI things.
For Level 1, I downloaded Cursor. After trying to figure out how Django actually worked (yet another online course), gave up, and decided to use Next.js. That led me to Vercel, reinforced by a few friends in their 20s who told me that all the cool kids were using Vercel (although Render, Digital Ocean, and AWS all were the beneficiaries of my credit card.) Pretty soon, I was using Cursor to fight with Vercel, Supabase, Clerk, and Github. After realizing Auto was no fun, I shifted to Claude 3.5. Dinostroids resulted (security holes and all …)
For Level 2, I got a little more serious. I discovered Linear, fought with Notion, and came up with a few ideas and a broader hypothesis around how things might work. I built a v0.1 of a thing.
For Level 3, I decided Lovable might be a better way than Cursor given that everyone was talking about it. I wasted about $200 on it, built a really cool design by vibe coding, but then watched it get very, very confused as it tried to go from simple design to something that actually worked that had some data complexity and AI calls. I thought about trying Bolt and Replit but quickly realized, after too much scrolling around on the web, that I’d likely run into the same issues.
So, I went back to Cursor and put a lot of efforts into my system prompt, tuning things, watching Cursor evolve quickly on a number of fronts (MCPs – yippee!, Agent mode as default – finally) while simultaneously watching my Cursor bill go up. It was easy to decide to go to Max mode and spend $200 / month instead of $20 / month when dinner in Aspen costs at least $100 / person no matter which restaurant you go to.
I hung out at Level 4 for a while. Cursor kept improving. Claude 4 came out. Auto mode still went off the rails and broke all my code. I started refactoring things and realized that the amount of cruft in my code was absurd. Little bugs turned into fatal flaws when I tried to have Cursor fix something. I learned about “git reset –hard HEAD”. I spent way too much time fighting with config issues on localhost:3000 (at least I’d figured out how to make Cursor always start the server on localhost:3000). I started using Docker. I was baffled that Cursor couldn’t remember stuff I told it the prior day, but intellectually understood why this was. I mean, memories.
The end of my joy at Level 4 was when ChatGPT 5 came out and was free on Cursor for a week. At first, it felt fast. Wheeee. Lots of stuff changing. It seems to be working. And then, after a few days, holy shit what a tangled mess of code it generated. Why are all my API routes suddenly broken. Console statements everywhere. UI elements in different parts of the application doing the same thing but look totally different. I went back to Claude and did another code review and major refactor. So many Vercel build errors. I finally embraced CI/CD. And Prettier. And Husky. Suddenly, I ran out of my monthly Cursor credits and shifted to usage-based pricing. $800 later, I realized that there was no reason for me to be using Opus or the thinking models for what I was doing.
Level 4 was a huge drag. But it was also when I started thinking of this as AI pair programming. The AI (or agent, or sub-agent, or whatever you want to call it) is my pair with hands on keyboard. It can type much faster than me. But I have to watch and constantly look over its shoulder, give it feedback, point at the stuff that needs to be done differently, and document what is important to remember to do.
And then I discovered Claude Code. This didn’t happen until Claude Code 2 came out at the end of September and corresponded with Sonnet 4.5. After my ChatGPT 5 I went back to Claude (and Sonnet) and started referring to Claude Sonnet as “Claudia” since she was my pair programmer. I thought about Claudia as a pair, related to her as I would a human pair programmer, and changed my approach. But when I loaded up Claude Code 2 in my terminal (I mean, just type “Claude”) I immediately leveled up again.
So – I’m now at Level 5 in the video game. It’s changed from a game of vibe coding to AI pair programming. And, it’s still fun!
I approached Echoes of October with trepidation. A graphic novel about violence and grief isn’t easy terrain. But it succeeds in a haunting, urgent way. The creators have chosen to explore the year leading into the October 7, 2023 massacre through the lives of four children who each lose a parent. The children are from different locales (Gaza City, Toronto, Tel Aviv, and Daliyat al‑Karmel) which enables a textured, multi‑vantage narrative.
What impressed me most is the restraint and care in which the story is told. The voices are calibrated: they carry sorrow, confusion, hope, anger, but rarely descend into melodrama. Because the characters are composite (e.g., everything that happens in the book is true, the characters are not), the authors manage to create space for truths without claiming to own them.
I love graphic novels (scifi and history) and regularly have them in my reading diet. The panels breathe. There are silences, negative space, quiet facial expressions, and moments of violent disruption. The juxtaposition of children’s everyday worlds (school, family, and play) with the encroaching shadows of conflict makes the tragedy more palpable and intense.
This is not an easy read, nor should it be. Echoes of October is demanding: it expects the reader to engage, be uncomfortable, and reckon with stories that hold no clean resolution. But in doing so, it honors the complexity of memory, the weight of loss, and the imperative of bearing witness.
I recommend it to anyone willing to engage deeply with how conflict impacts children and the possibility (however fragile) of empathy.
I’m not aware if there has ever been a book launch associated with a Yom Kippur Break Fast, but we are going to have one as part of the launch of Sue Heilbronner’s excellent new book, Never Ask for the Sale: Supercharge Your Business with the Power of Passionate Ambivalence.
It’ll start at 6:30 pm on Thursday, October 2, at Greeley Sachs’ bookstore, Composition Shop, in downtown Longmont.
Sue and I will do a fireside chat about her book and my latest book, Give First: The Power of Mentorship. We will both be signing books. And … food!
Come join us at Composition Shop for the Break the Fast.