The first time Tim Ferriss met Naval (and his girlfriend)

I want to leave with one thing, which is Naval. You're friends with Naval. Do you have any stories about Naval? Anything that you noticed early on or the sort of the insightfulness that he has?

Actually, the first time I met Naval, I went into a coffee shop in the Mission in San Francisco and I ordered a coffee and I'm waiting at the counter and there's this very attractive girl standing next to me and she's very friendly and smiles and I start talking to her and I'm chatting her up, hitting on her, hoping to ask her for her number and take her out and maybe dinner, maybe drink, who knows. And then I see Naval walk up with this huge grin on his face and he's like, "I see you met my girlfriend." And I was like, "Oh, Tim." And he's like, "Naval." And he just had this huge grin on his face.

Did he know who you were or he was just like—

I don't think, I'm not sure. I don't think so. Didn't lose his cool, was just like—

Wow, what a good way to address it.

Just like totally calm. And then we started talking and like, hit it off. And, you know, that was probably— God knows when that was. I don't know, 2008 or something.

Yeah, you're like a man crush, actually. Move out of the way.

Yeah, face palm. Yeah. Uh, and I, I just— I admire Naval for his ability to speak truth and ask uncomfortable questions and is less inclined to the type of people pleasing that I'd say many people are predisposed to, myself included. Like, there are definitely times when I'm maybe too polite or tell white lies to make people feel good or whatever, like normal human social lubrication, right? Nothing major, but it's like, you know, if my girlfriend's put on a few pounds, she's like, do I look fat? I'm like, no, I'm not gonna say, yeah, you look really fat. Not to say that Naval would say that, but he's direct in a way that cuts through the noise and is very refreshing to me.

Have you been able to pick up or learn anything from him in terms of tactical stuff on the investing side or—

Tons of stuff on the investing side. I mean, I think the site was way back in the day Venture Hacks.

Oh yeah.

That he and Nivi co-authored. That was basically the kind of Wikipedia Bible of angel investing and advising for— and inside game on venture capital. I mean, Naval is Jedi level. When it comes to early-stage investing. Very technical. He just ends up in every deal you would ever want to be in. It's the sort of, you know, Pinky and the Brain meets like Forrest Gump meets, you know, Siddhartha. You're just like, how is he in every cap table? Right. He's incredibly skilled as an angel investor. He's very curious. He's very interested. And it's not at all limited to business. So if it's David Deutsch or other thinkers, he introduces me to a lot of eclectic thinkers from different disciplines. And his exploration is certainly not limited, as it is with a lot of people, to say the sport of business or finance or investing. A lot of people are one-trick ponies that way. He is not a one-trick pony. I admire that as well.

I have a funny Naval story, which is I have a buddy who was doing some— like when Facebook launched its platform My buddy made an app and it was like one of the silly apps. I don't remember back then. It was like people throwing sheep at each other and stuff like that. He was doing one of the like silly apps, but it was clear that, oh, Facebook platform, that's like an opportunity. And so smart Silicon Valley people were interested. My friend's sitting in Georgia and Naval's in San Francisco and he gets an email from Naval. Basically, he found the Contact Us page or whatever and was like, hey, I'd love to meet with you sometime, talk about your app. I'm a venture capitalist here in San Francisco. Friend doesn't know who Naval is, doesn't know what venture capital is, but okay, sounds interesting. He's, "Oh yeah, like, sure, I'm open to that." Next email is a plane ticket. Like, "Here's a plane ticket, goes out tomorrow." So friend's like, "Okay," gets on a plane, flies out here, meets Naval, meets him in his office. He's like, "He asked me questions for like 30 minutes." And he's like, "I had no idea what the right answer should have been, but I'm saying whatever's my honest answers." Naval was like, "Hold on," goes into the other room, comes back, has printed out like a term sheet. And says like, here, you know, I'll give you whatever, half a million bucks or something, whatever it is, like some amount of money for, you know, some percentage of your company. And my friend who's like 23 or something like that is just like, I don't know who this Indian guy is. I don't know what the deal— I don't know any of the words on this page. My app is stupid. I don't know why he wants to invest in it. I don't really understand this. So he's like, I just don't feel comfortable right now. And he's like— and Naval at the time was like, I think Facebook is going to be, you know, huge. I think it's going to be the platform where you do lots of things. You're not just going to talk to friends on there. You're going to be able to do X, Y, Z. That's my thesis. That's why I want to invest in this. Because my friend was like, honestly, this is a stupid idea. Why are you— this is not a business. And so he gave him that pitch. My friend was like, wow, that sounds awesome. I didn't realize all that. I had stumbled into this goldmine potentially. So he's like, listen, man, I just— I don't understand what this thing is. I just need to think about it. And I was like, no problem. By the way, that same week he meets Keith Raboi, Max Levchin, a bunch of other people who are also giving him the same pitch but in different flavors. Like Keith Raboi was like, You should come work for us. He's like, I don't want a job. He's like, see all those people right there? All those programmers? They're going to put you out of business like tomorrow. And he was like, this is a stupid app. It's not a business to do it. It wastes your time doing this.

You're going to put me out of business. That isn't a business.

I live in my mom's bedroom. What are you talking about? And so he goes, you know, the great thing about Naval though, is that like 15 years later now, my friend's very, very successful tech entrepreneur. He's like, I actually dug up that old term sheet. It was so fair. He could have taken advantage of me and I didn't know anything. And he's like, it was incredibly founder-friendly and fair. That told me a lot about Naval that at that time when a lot of people were in the heat of the moment about this kind of gold rush in that Facebook app days, and I was clearly a novice, he operated with very high integrity, and I thought that said a lot about him.

Yeah, that matches with my experience. I've always seen that in Naval. Yeah, for sure.

Right on. Well, Tim, thanks for doing this, man. I really, really appreciate it.

Yeah, my pleasure, man. Thanks for taking the time.

Yeah, mission accomplished, I hope.