Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

**Keith Rabois** (0:00)
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?

**Lenny Rachitsky** (0:06)
There's a lot of anxiety in the job market.

**Keith Rabois** (0:08)
AI is going to radically reorient lots of people's careers, 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 product.

**Lenny Rachitsky** (0:25)
I want to hit on some contrarian takes that you have your advice. You don't actually want to be talking to customers.

**Keith Rabois** (0:29)
I hate talking to customers. I refuse to allow colleagues to talk to customers.

**Lenny Rachitsky** (0:33)
You have this idea of criticizing in public versus in private.

**Keith Rabois** (0:36)
High-performance machines don't have psychological safety. They're about winning.

**Lenny Rachitsky** (0:40)
You're uniquely great at helping companies build world-class teams.

**Keith Rabois** (0:44)
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.

**Lenny Rachitsky** (0:52)
It feels like it's never been harder to attract the best talent.

**Keith Rabois** (0:56)
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.

**Lenny Rachitsky** (1:12)
Today, my guest is Keith Rabois. 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 two companies and he's currently managing director at Khosla 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 lennysproductpass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. With that, I bring you Keith Rabois. Keith, thank you so much for being here and welcome to the podcast.

**Keith Rabois** (2:07)
It's a pleasure to be with you.

**Lenny Rachitsky** (2:08)
Okay. When we were starting this recording, you told me you're doing this from an iPad, which I've never had, and you shared a crazy fact that you haven't used a computer in years. Talk about what's going on there.

**Keith Rabois** (2:20)
Yeah. When I started working at Square, Jack Dorsey was running the company off an iPad. I immediately converted in September 2010 Have a look back, I haven't touched a computer since September 2010 Everything I do in my life is either done for my phone, my watch, or my iPad.

**Lenny Rachitsky** (2:37)
What's so interesting about this as you're talking is just, there's this trend of engineers starting to code from their phone, like Boris Cherny on and Simon Willison, these two engineers that are like 10x engineers, and they're just coding from their phone, talking to AI. And I feel like you've been preparing for this for a long time.

**Keith Rabois** (2:52)
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, pretty good shape and technology.

**Lenny Rachitsky** (3:00)
And just understand the benefit is to just avoid distractions.

**Keith Rabois** (3:03)
Yeah, partially distractions, partially just the flexibility, like taking an iPad with you anywhere is just super easy. You know, 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'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, there's no reason to use a more powerful, heavier weight, less flexible machine.

**Lenny Rachitsky** (3:34)
Wow. iPad Maxing, Keith Rabois.

**Keith Rabois** (3:36)
See if you got my Apple, as long as it's an Apple product, it works.

**Lenny Rachitsky** (3:40)
So appropriate. This episode is brought to you by our season's presenting sponsor Work OS. What do OpenAI, Anthropic, Cursor, Versel, Replet, Sierra, Clay, and hundreds of other winning companies all have in common? They are all powered by Work OS. If you're building a product for the enterprise, you've felt the pain of integrating single sign-on, skim, RBAC, audit logs, and other features required by large companies. Work OS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Literally, every startup that I'm an investor in that starts to expand up market ends up working with Work OS. And that's because they are the best, whether you are a seed-stage startup trying to land your first enterprise customer or a unicorn expanding globally. Work OS is the fastest path to becoming enterprise-ready and unblocking growth. It's essentially striped for enterprise features. Visit workos.com to get started or just hit up their Slack where they have actual engineers waiting to answer your questions. Work OS allows you to build faster with delightful APIs, comprehensive docs, and a smooth developer experience. Go to workos.com to make your app enterprise-ready today. As I was preparing for this chat, there's just so many directions we could have gone with this. You are so smart at so many things. I want to focus on something that I think you're uniquely great at, which is helping companies build world-class teams. And I want to start in particular with attracting the best talent.