Ilana

So you start with what helped you personally, and you start an email list and you run also, I think I ran into, you run into all these funny limitations, like 250 address limitations and things that the internet wasn't ready for Mr. Craig, yes, but Craig found a way. So talk to us, how did you decide eventually to jump all in and do this?

So you start with what helped you personally, and you start an email list and you run also, I think I ran into, you run into all these funny limitations, like 250 address limitations and things that the internet wasn't ready for Mr. Craig, yes, but Craig found a way. So talk to us, how did you decide eventually to jump all in and do this?

So before that, before that, so you have an email list. I'm still stuck there. You have just an email list. Like how does that become so big? I know in 1996, you say, okay, maybe I need to create a web-based platform, but how do you move from one to the other?

So before that, before that, so you have an email list. I'm still stuck there. You have just an email list. Like how does that become so big? I know in 1996, you say, okay, maybe I need to create a web-based platform, but how do you move from one to the other?

So your moral compass was there all along. And I do want to touch that as well, because I think for a lot of leaders, yes, that can get wonky pretty quick, you know, with business. So a few things. So first of all, you have an email list. You run into a 250 address limitation or whatever.

So your moral compass was there all along. And I do want to touch that as well, because I think for a lot of leaders, yes, that can get wonky pretty quick, you know, with business. So a few things. So first of all, you have an email list. You run into a 250 address limitation or whatever.

You realize that you have to create a web-based platform for classified, you know, if you really want to do better. You decide to... leave the name Craigslist, right? Why? I mean, it basically catches, but I want to hear that.

You realize that you have to create a web-based platform for classified, you know, if you really want to do better. You decide to... leave the name Craigslist, right? Why? I mean, it basically catches, but I want to hear that.

And you literally created a movement. And I think this movement is still alive, which is pretty mind-blowing. But in 1996, and by the way, congratulations, Craigslist is 30.

And you literally created a movement. And I think this movement is still alive, which is pretty mind-blowing. But in 1996, and by the way, congratulations, Craigslist is 30.

Very exciting. Huge congratulations. That is a very happy birthday. Okay, so it's 1996. You decide to move it into web-based. You understand that Craigslist essentially is catching on in a big way. And I think it starts from covering categories like jobs and housing services and personnel, right? How did you see it taking on? And were there moments that you're like, what the heck am I doing?

Very exciting. Huge congratulations. That is a very happy birthday. Okay, so it's 1996. You decide to move it into web-based. You understand that Craigslist essentially is catching on in a big way. And I think it starts from covering categories like jobs and housing services and personnel, right? How did you see it taking on? And were there moments that you're like, what the heck am I doing?

Why am I not enough in Charles Schwab? Like, were there like big moments that you're scared of this thing?

Why am I not enough in Charles Schwab? Like, were there like big moments that you're scared of this thing?

Well, I will correct this a little bit, Craig, because a million page views was very rare at the time. And I was in Intel. So we, you know, knew how to measure these things. And that was very rare. So you created something that was catching on really fast for that era. How did that feel? And what does it feel like to scale something like this? I mean, I'm sure it comes with challenges.

Well, I will correct this a little bit, Craig, because a million page views was very rare at the time. And I was in Intel. So we, you know, knew how to measure these things. And that was very rare. So you created something that was catching on really fast for that era. How did that feel? And what does it feel like to scale something like this? I mean, I'm sure it comes with challenges.

But you did have some scaling challenges, right? There's fraud when you scale, there's monetization issues, right? So let's talk a little bit about this thing is growing and you're probably starting to see fraud or things that you don't like on the site. What was it like and how did that make you feel and what did you do about it?

But you did have some scaling challenges, right? There's fraud when you scale, there's monetization issues, right? So let's talk a little bit about this thing is growing and you're probably starting to see fraud or things that you don't like on the site. What was it like and how did that make you feel and what did you do about it?

Oh, I agree. And we actually had a full episode with somebody called Don Ariely about hate in the digital world. But let's talk about this then. I mean, you're talking about all these things that you needed to spend money on. But on the other hand, you're very, very lean in Craigslist and you decide not to raise capital. How do you have enough capital for a team or to run this thing?

Oh, I agree. And we actually had a full episode with somebody called Don Ariely about hate in the digital world. But let's talk about this then. I mean, you're talking about all these things that you needed to spend money on. But on the other hand, you're very, very lean in Craigslist and you decide not to raise capital. How do you have enough capital for a team or to run this thing?