Accumulated organisational context in AI enterprise tools creates strong switching costs that lock customers in.
The case
Bending Spoons may lose 20% of Airtable's customers when it triples prices, but it will still be a good deal for Bending Spoons.
“Bending Spoons may lose 20% of Air Table's customers who finally spend a week lifting off of Air Table, but when they triple prices, it's a good deal for Bending Spoons, right? But it's gonna happen a lot faster than workday.”Harry Stebbings · 20 Aug 2026
Future versions of ChatGPT will support durable, reusable workflows, contrasting with the current experience where users start from scratch each session.
“You'll start to build more durable kind of workflows with attribut that you can kind of use over and over. Right now, you know, it a lot of times it feels like you're coming and starting from scratch each time.”Ian Silber · 16 Aug 2026
Setting up a 'session end' skill in Claude Code that logs every session to Obsidian allows AI work to compound over time.
“If you set up one skill that's going to like let your work compound, it's what I call session end.”Matt Swulinski · 15 Aug 2026
The legal AI market has consolidated from many competing players to essentially two dominant players in the last two years.
“Seems like there were a lot of those companies around two years ago but now it's pretty much two.”Lin Qiao · 20 Jul 2026
In AI products like Granola, accumulated context within an enterprise acts as a powerful switching cost that prevents customers from leaving.
“What I've also learned about AI products and granola is that context is extremely valuable. Right? If granola gets inside of your organization and everyone in the organization starts using it and producing and accumulating all of this amazingly rich and valuable context, that's not something you as an enterprise want to give up.”Mike Mignano · 6 Jul 2026
Within two months, every one of Sierra's engineering interviews will include a strong AI-native component.
“I will be disappointed if in the next no more than two months not every one of our interviews has some strong AI native component to it.”Clay Bavor · 4 Jul 2026
The pushback
CIOs are actively trying to cut spending with vendors they feel locked into, targeting 80-90% of last year's spend.
“The CIOS want to cut what they spend with their when they're hostage, right? They're like, "Okay, I want to spend 90% 80% of last year. What can we cut from our bill from the vendors we're stuck with?”Harry Stebbings · 20 Aug 2026
AI has made database migration nearly trivial, inverting the traditional stickiness of database businesses.
“It turns out that now all of a sudden database migration which used to be like the like number one thing you would not do in is like kind of trivial.”Eric Vishria · 11 Aug 2026
Suno's CTO stated he would not hesitate to swap in a better large language model, indicating that Suno's real product is the consumer experience, not the underlying model.
“Without missing a beat Martin goes wouldn't think twice about it.”David Frankel · 8 Aug 2026
Curative plans to cut approximately 80% of their SaaS spend in the current year.
“We're cutting about 80% of our SAS spend this year.”Fred Turner · 18 Jul 2026
90% or more of enterprise AI use cases can now be fully handled by many different models, including open source models.
“90% or greater of use cases can now be fully handled by many different models including open source models.”Arvind Jain · 11 Jul 2026