FOBO - The Fear of Becoming Obsolete (And How to Navigate It)

There are two ways to build backwards. One starts with the answer you actually want and works its way toward the plumbing. The other starts with the plumbing and hopes the answer is in there somewhere...

29 Sep 29min

Rob has a lot of Claude folders now. One knows the book. Another knows the company planning. Others have picked up meeting notes, briefing docs, LinkedIn ideas, strategy work, and whatever else was us...

22 Sep 35min

For a minute there, it looked like the AI wars would come down to who built the smartest model. Rob's not buying that anymore. Take Claude. Rob's increasingly convinced that what makes Anthropic so st...

15 Sep 25min

For years, businesses learned that having data and being able to use it are two very different things. We cleaned it, structured it, modeled it, argued about which version was the truth, and built ent...

1 Sep 22min

There's a new word for what your team is doing with the AI you bought them. You're not going to love it. "Botsitting." Babysitting, but for bots. Journalists are suddenly all over it, and not one of t...

18 Aug 38min

For most of tech history, the new thing belonged to the new people. Then AI showed up and ruined a perfectly good pattern. Because the smartest model on the planet can know darn near everything and st...

12 Aug 1h 24min

There have always been people who can't help themselves. Give them a clunky process, a messy spreadsheet, or a problem nobody owns, and they're already halfway to building something better. Rob calls ...

4 Aug 1h 24min

AI headlines have already moved on to the deep end. Most businesses haven't. Every week brings another headline about what's next for AI. Build your own model. Train your own LLM. Customize everything...

14 Jul 32min