Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
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Why does Keith Rabois say the product manager role is becoming obsolete in the AI era?
The idea of a PM makes no sense in the future. The skill is more like being a CEO now, which is what are we building and why? There's a lot of anxiety in the job market. AI is gonna radically reorient lots of people's careers, and maybe including mine. What I've noticed in some of the best organizations is the number one consumer of tokens is the CMO. They don't need to rely upon deputies and deputies and deputies to get actual work products.
I wanna hit on some contrarian takes that you have. Your advice, you don't actually want to be talking to customers. I hate talking to customers. I refuse to allow colleagues of mine to talk to customers. You have this idea of criticizing in public versus in private. High performance machines don't have psychological safety. They're about winning. You're uniquely great at helping companies build world-class teams.
If a founder shows the ability early in his or her career to assess talent ruthlessly and accurately, he or she can go very far with no other abilities whatsoever. It feels like it's never been harder
to attract the best talent. Really talented.
people. When things are going well, they're not happy. The morale actually does go down when people are skating. The single role for the CEO is offsetting that complacency. The better you're doing, the more the CEO should push.
Today, my guest is Keith Raboy. Keith's resume, both as an operator and investor, is absurd. He was an early investor in Stripe, Palantir, Airbnb, YouTube, DoorDash, Ramp, and dozens of other companies. He's part of the famous PayPal Mafia, where he was Executive Vice President of Business Development and Policy. He's also been Chief Operating Officer at Square, VP of Corporate Development at LinkedIn. He's also co-founded Companies and he's currently managing director at Kostla Ventures. It's safe to say that Keith is in the 99.9th percentile at identifying talent, building teams, and operating world-class companies. Before we get into it, don't forget to check out Lenny'sProductPass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers.
With that, I bring you Keith Raboy. Keith, thank you so much for being here and welcome to the podcast.
It's a pleasure to be with you.
Okay. So when we were starting this recording, you told me you're doing this from an iPad, which I've never had, and you've shared a crazy fact that you haven't used a computer in like years. Talk talk about what's going on there.
Yeah. So uh when I when I started working at Square, Jack Dorsey was running the company off an iPad. And so I immediately converted in September two thousand ten. And have a look back, I haven't touched a computer since September two thousand ten. Everything I do in my life is either done from my phone, my watch, or my iPad.
What's so interesting about this as you were talking is just there's this trend of engineers starting to code from their phone. Like at Boris Cherneon and Simon Willison, these two engineers that are like 10x engineers, and they're just like coding from their phone, talking to AI. And I feel like you've you've been preparing for this for a long time.
Yeah, trying to be ahead of the curve. Jack's very good at being ahead of the curve. If you just watch what Jack's doing and follow, you can be pretty good shape in technology.
And just understand the benefit is it just avoid distractions.
Yeah, partially distractions, partially just the flexibility, like taking an iPad with you anywhere is just super easy. You know, uh some of the some laptops have improved since then, but like the screen flexibility angles, but like just the weight. Like I carry my iPad with me everywhere. So there's no reason there there's nothing you can't perform unless maybe if you're doing heavy duty engineering, which obviously has not been my forte in life, although I may have to start Um, there's no reason to use a more powerful, heavier weight, less flexible machine. Well,
iPad Maxing, Keith Roboy. See
if you got my Apple.
As
long
as
it's an Apple product, it works.
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Chapters
8 chapters
1
Why does Keith Rabois say the product manager role is becoming obsolete in the AI era?
0:00–10:53
2
What is the ‘barrels vs. ammunition’ framework and how does it help identify top talent?
10:53–21:49
3
Why does Keith argue that talking to customers can be harmful for consumer products?
21:49–32:31
4
How will the roles of product, design, and engineering evolve with AI?
32:31–42:24
5
Why are design and coding merging and what does that mean for product teams?
42:24–51:26
6
How does a CEO keep pressure high and avoid complacency as the company grows?
51:26–1:01:43
7
Will AI‑generated content surpass human‑created content and how will audiences react?
1:01:43–1:11:05
8
Why does Keith prefer giving criticism publicly rather than privately?
1:11:05–1:22:36
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