A recorded conversation between Jason M. Lemkin and another speaker about how the enterprise software landscape has shifted from 2021 to the present AI era. They discuss historical playbooks (e.g., Netscape-era tactics), note a recent OpenAI stack reveal that omitted Microsoft/Azure branding, and frame Microsoft and OpenAI as moving from partnership toward competition—highlighting Microsoft’s acquisitive, control-oriented approach to hot startups.
Chapters
2021 is like a generation before AI. Right. It's almost a different world where it seemed slack and zoom probably seemed like these huge. They were going to bring down Microsoft when it's ridiculous to think about that today. You should support these applications in 2021. They seemed like they were taking over the world.
You can see that Playbook being used. We saw it on Netscape. We saw it on many things.
Yeah.
Over time. And it's like. And that's that. That. That playbook should get ripped up and thrown away.
Yeah, yeah. The. There is an inherent aggressiveness in enterprise software, but there's limits as well.
You can see it, by the way getting played out right now between OpenAI and Microsoft. So it's a weird dynamic. We saw over the weekend this kind of really interesting presentation that Sarah Fryer, who used to work at Salesforce and she's the CFO at OpenAI, I did, and they revealed their stack for the first time, their data center, their apps, their APIs, all the different aspects of the future of OpenAI and the word Microsoft and Azure and Copilot weren't on the stack. And that was extremely interesting. And you can see how Microsoft is really starting to run a separate playbook against OpenAI. And it's a fascinating moment, I think, in the. In the history of Open OpenAI because of that.
Yeah, it's great. It has. It's so funny to think about Microsoft taking potshots at Slack because Azure is so rejuvenated. Right. And the world's changed 11 times since. It's keep it as competitive, but as open as you can.
It's amazing. Right. And I think that, yeah, that's not how Microsoft thinks. Microsoft is a company that wants to own it all, control it all. If they see a hot company or hot startup, they ask themselves, hey, why is that not in our world. And. And in the case of. They usually they like to either try to feign an acquisition and then based on that, they execute a Playbook or in the case of OpenAI, a partnership is going to become a competition.
