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RK Raina Kumra On Masters of Scale

“Some of my agents are smarter than me and better at math than me. And some of them have the judgment of a toddler. So we really have to look at what is that skill that we keep in our toolkit and what do we keep really close.”

Masters of Scale · Startups & Venture · November 2026

“Some of my agents are smarter than me and better at math than me. And some of them have the judgment of a toddler. So we really have to look at what is that skill that we keep in our toolkit and what do we keep really close.” — Raina Kumra, Masters of Scale

Context

Asked whether it has become harder to build a full skill set when everything changes so fast, Kumra describes the team of AI agents she has built and what they can and can't be trusted with.

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Transcript

Masters of Scale Around 07:32 into the episode
Speaker 3

…to give myself an upgrade. And now I have a team of 12 agents. I've got CEOs, CMOs, I've got COOs, engineers. And congratulations, you all have been upgraded as well. You're all CEOs. Whether you wanted it or not, I didn't want to manage a complex team, but complexity is part of life right now.

Speaker 4

And the way to do that was to become like the CEO of your agent team.

Speaker 3

Of everything. Yeah, of everything. And, you know, the problem is that some of my agents are smarter than me and better at math than me. And some of them have the judgment of a toddler. So we really have to look at what is that skill that we keep in our toolkit and what do we keep really close. I

Speaker 4

mean, you would talk to me about certain. Of getting questions from people about being overwhelmed and people feeling like they're being left behind.

Speaker 3

Yes. Okay. So there is no keeping up. There is only keeping calm. And that thing that you're worried about that you are behind on probably came out a week ago. So you're not that behind. I think at any point you can jump in and be two weeks of learning and you can get there. But this doesn't mean…

Speaker 4

Thank you, Raina. Thank you. All right. So if we're all going to become CEOs, then what is it like to be a CEO in an environment like this? It's your turn, Hayden. Hayden Brown is the CEO of Upwork. Hayden, you and I have, there she is. Yeah, you can say hi. You and I talked before about how your…

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

More from Masters of Scale

“There is no keeping up. There is only keeping calm. And that thing that you're worried about that you are behind on probably came out a week ago. So you're not that behind. … You can outsource some of that learning too. You just have to keep your judgment. You have to keep your clarity and make sure that you're not turning AI crap out into the world. That's a responsibility.” — Raina Kumra, Masters of Scale “I'm not sure that's the best way because … if we go down that path as we are, there will be incidents that happen and hopefully they're not too awful, but you don't know. And then there'll be regulation. … We tend to wait till something happens. And then think of the global financial crisis 2008 and then a whole bunch of new regulations come in. So that's the likely case here, unfortunately.” — Reed Hastings, Masters of Scale