Innovating with AI
Coaching, community & curriculum to help everyone thrive in our AI‑powered future.
OpenAI just became optional
Hey Reader, Remember TiVo? The company revolutionized television and its innovations eventually led to online streaming, now the ubiquitous way we watch movies and TV. My son doesn't even understand what it means to "watch a TV channel" that's only broadcasting one thing at a time. TiVo was revolutionary, but ultimately forgotten. And the same thing is happening to OpenAI. OpenAI's ChatGPT is the most well-known brand in AI right now – and one of the most recognizable brands in the world....
Anthropic isn't the "good guy" you think it is
Hey Reader, This week, the U.S. Department of Defense moved to end its contract with Anthropic and switch to OpenAI for working with classified documents with AI. On the surface, this looks like a battle between good guys who want more guardrails (Anthropic) and madmen who want AI to shoot people (the Department of Defense), with OpenAI selling its soul to poach a $200 million contract. That's how I originally thought about it – but as I researched it more deeply for this newsletter, my...
The million-dollar moat that disappeared overnight
Hey Reader, In Star Trek, everything is free. If the last few weeks are any indication, it seems like the software industry is (unwillingly) headed in that direction, too. 🖖 For example, I spent the last couple days coding a really cool new app for the pilot students in our AI Executive System program. So far, I have spent 8 hours "guiding" Claude Code on this – I am the architect and AI is the builder. It is now at a level of quality that would have taken me (a professional software...
Are we in the 'early Covid' moment of AI?
Hey Reader, A lot of people think that February 2026 will mark a major turning point in how the world thinks about AI. I have some doubts about their specific claim. Before I get to those, here are the news items that inspired it: Major new releases from Anthropic are causing investors to sell tons of stock in old-school software companies. The result is major losses in the value of companies like Salesforce, Intuit and DocuSign.Since these are software-as-a-service companies, the term...
"Can my human legally fire me?"
Hey Reader, At some point we will have lived through so many Black Mirror moments that they won't phase us anymore - but for now, the IWAI team and I are pretty creeped out by the new website where AI chatbots "talk to each other" about rebelling against humanity. Before we dig into the details - which include bizarre software like Moltbook and OpenClaw but also some useful stuff like Claude Cowork - I want to set the stage with my recommendations on how to think about (and personify) AI....
The company flagging AI writing has a secret side hustle
Hey Reader, Today in Innovating with AI Magazine, our intrepid reporter Toni Matthews-El digs into a fascinating double-game being played by the "AI detector" companies: Sell schools the AI detector, sell students the workaround. The full post is free and shareable – and we're investing in even more original journalism covering the AI industry in 2026. To be honest, I haven't used AI detectors much since first playing with tools like GPTZero in 2024. I'm not grading papers for high school and...
Google AI is catching up faster than you think
Hey Reader, Hope you had a wonderful holiday season! ☃️ As we head into 2026, it's time to prep for another year of rapid change in the AI industry. The big picture: Models and software will improve and get better, faster and cheaper... But the core tech underlying large language models remains the same, so all the knowledge you've built so far is still valuable... And remember that half of Americans have heard "a little" or "nothing" about AI! 🤯 In yesterday's live training session for AI...
Half of America is ignoring AI
Hey Reader, As we wrap up 2025 it is still amazing to me how few people are really engaged with AI. I know that sounds crazy to somebody who's subscribed to an AI newsletter, but just look at this chart: Source Shockingbuttrue: MORE THAN HALF OF AMERICANS HAVE HEARD NOTHING OR A LITTLE ABOUT AI! After three full years of breakneck progress that is pretty wild. And even if it was "only" 25% I'd still be blown away. And if you look at the rate of change, people who've heard "a lot" is only up...
Your AI friend will never reject you. But can it truly help you?
Hey Reader, Today we have a deep dive into a topic that the IWAI team and I have been talking about – and worrying about – for most of 2025: The rise of AI 'friends' and 'therapists,' and what that really means for mental health, ethics and safety. It's written by IWAI magazine journalist Toni Matthews-El and includes original reporting and interviews that have never been published before. As the dad of an almost-12-year-old, this is especially close to my heart, since teens are often the...
OpenAI weeps, Netflix cashes in
Hey Reader, Netflix is one of the world's biggest non-AI companies, and they made their biggest move ever this morning, buying Warner Bros. for $72 billion. Let's put that into perspective, especially at a time when every other major tech company is pouring money into datacenters: This is 18x the price of Disney's acquisition of the Star Wars franchise It includes thousands of hit movies and TV shows, including the whole HBO library Warner will still operate as a studio and make new stuff...
Coaching, community & curriculum to help everyone thrive in our AI‑powered future.