“VCs want you either to go crazy or die.” Toby on investor incentives when growth no longer supports the old multiples. Full conversation: youtu.be/SuZLAoRr2-E

“What do you think your valuation is?” Ray asks what Miro’s announced deal and Airtable’s sale mean for a smaller SaaS business still losing money. Full conversation: youtu.be/SuZLAoRr2-E

AI may restructure a market before it restructures the company inside it — AI-native entrants start from a lower interface and move value from vendor to customer. Full conversation: youtu.be/MZwIHkmcDmg

Someone who works with a lot of Fortune 500 CEOs says their most common question about AI isn't strategic — it's "when do I get to retire?" Full conversation: youtu.be/MZwIHkmcDmg

CEOs aren't just cutting costs — they're handing headcount to AI. The honest answer to "when do I get to retire?" turns out to be: reduce headcount, and let AI carry the load. Full conversation: youtu.be/MZwIHkmcDmg

Frontier AI models are becoming interchangeable gears in a larger machine — the practical move is choosing the right model-plus-harness fit per job, not loyalty to one model, since new frontier leaders keep displacing the last favorite. Full conversation: youtu.be/p6PijF6Vci8

“The token efficiency is much better — token cost seems to be lower because it's more efficient.” Full conversation: youtu.be/p6PijF6Vci8

“It's actually the thing that surprised me the most about it is how fast it is.” Full conversation: youtu.be/p6PijF6Vci8

Where does value survive when AI models get commoditized? Specialist data, regulated context, or proprietary process — otherwise you become an invisible extension of someone else's prompt. Full conversation: youtu.be/esvm0CLeT0s

“Unreal Engine creates bigger unlocks when working with models, which then increases the value of Unreal Engine as more people are able to make more extraordinary stuff with a whole lot less labor.” Full conversation: youtu.be/esvm0CLeT0s

“The differential for me comes from specialist knowledge or regulatory environment — where it's not as easy to just do a straight substitution.” Full conversation: youtu.be/esvm0CLeT0s

AI subscription pricing will pass through three phases before it settles: generous today, expensive and metered next, then cheap once infrastructure matures — the same arc that took phone plans from per-minute billing to unlimited data. Full conversation: youtu.be/KuBmIm4QMyE

"That creates predictability for the customer, and the customer is willing to pay a premium for that predictability." Full conversation: youtu.be/KuBmIm4QMyE

"The iPhone comes along and the thing that becomes much more important is data — and we stop getting subsidization. Phones become much more expensive." Full conversation: youtu.be/KuBmIm4QMyE

I sometimes work on ideas by making songs about them with Suno. I thought this one was a lot of fun while also a cautionary tale for an eager software founder. suno.com/song/73b00075-6720-…

A subscription vendor exchanges cash now for cash later. When the price of time rises, those future receipts are worth less today—and carrying the wait costs more. Full essay: youtube.com/watch?v=Ya7PV-ce…

Don't build your plan around the return of a decade-long near-zero-rate regime. Study how software was sold before it, then build business models for the macroeconomic environment we actually have. Full essay: youtube.com/watch?v=Ya7PV-ce…

SaaS is not the natural state of software. It is a recent model shaped by a specific macroeconomic environment—and interest rates help explain both its rise and where it goes next. Full essay: youtube.com/watch?v=Ya7PV-ce…

The real shift in AI isn't about better prompting, it is about building the infrastructure that gives agents hands to interact with your software. pro.statechange.ai/c/weekly-…

One incumbent becomes two economically opposed businesses: a cash-generating legacy business and a faster, smaller growth product. Full conversation: youtube.com/watch?v=cXCPWYSQ…