YouSaid · the spoken record

Nirav Tolia

lines on the record: 74
first: 2025-09-15
most recent: 2025-09-15
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Entrepreneurs in residence together with the intent of starting a new company. But as part of that, I moved back to Silicon Valley. And I highly encourage entrepreneurs who are coming off of one journey to take a sabbatical because I learned some of my greatest lessons in New York. They have nothing to do with business, right? But about life.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“I met entrepreneurs and I started doing some consulting and I started doing some investing and I started realizing that I was missing being part of the flow. And I called up Bill Gurley, who I talked about before from Benchmark. And he said something really interesting. He said, okay, well, you want to start a company in New York? All right. But let me just ask you a question since you're in New York. How many billion dollar consumer internet companies are there in New York and at the time the entry was zero? And so what he was really saying is, look, if you really want to optimize the probability of success, you should probably move back to San Francisco. And so when it got to be time to get serious about starting a new company, I was lucky enough to have one of my first colleagues from opinions, a woman named Sarah Leary, we went and joined Benchmark as”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Enamored with the city that I thought to myself, gosh, I mean, maybe I'll just live here for a year. And for me, it was always the plan of, I'm just going to go for a year and just see what it's like. And I didn't know what the professor was.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“It was a year later. It was a year later. I decided that I wanted to take the opportunity to live in a place that I always wanted to live in. I had visited New York and I was so”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Without a doubt, all those things go through your mind. And you know, I was definitely in a situation where you get so cooked as a founder, like being in the tunnel. You haven't had the opportunity to take a step back and say, hey, what does all this stuff mean? What have I learned? Like, am I qualified to be a CEO? Am I a good founder? Is that the thing I should be doing? Should I go work for someone else, right? And so leaving While it was incredibly painful also gave me the opportunity to do a lot of self-reflection. One of the hardest things about being a founder, in my opinion, is you never have the space to really absorb the greater lessons. You're just in motion. And so to stop for a second and have a little bit of reflection, it was actually quite valuable for me.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“That's unfortunate, right? I doubt very much given the incredible success that they've had that they're thinking about this ever, right? And that's good. And this is not something I think about on a daily basis, right? But when I go back and think about it, yeah, those were people that were really important to me.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“No, look, this was 20 years ago. And it is for me even today. Huge bummer that those relationships that I had were affected by this outcome. And so I've tried over the years to put myself in their shoes. It took friendships and it fractured them and they've never been repaired.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“No, look, I don't think there's ever any value in justifying things based on the environment or based on some other thing. I think the best thing to do is to acknowledge mistakes, to learn from them, and then to move forward. And that's something that's not easy to do”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Well, look, I think there are always things that we do that we wish we didn't, right? There are times when we have to pay for those mistakes and sometimes we don't, right? I mean, this was the case of me having to pay for it. When you are a company that wants to go public, you want to be as unencumbered by controversy as possible, right? And the best thing for me to do at that point was to step away. Now, did I have a choice? No, not really. I mean, they kind of asked me nicely to do it. I understood that it was the right thing to do. But yeah, I mean, it was devastating for me on a number of levels. One is, you know, you don't want to publicly fail. So that's one piece of it. The second piece of it is I loved my job. I loved working with those people. I love trying to solve that problem. And so when you lose that opportunity, that's the hardest thing.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“A bit of a mixed track record, but ultimately was bought by eBay for, I think, about $620,000, $630 million. So not a terrible outcome. But when we think about our original dreams, we wanted to build something like Yahoo, which at the time was a hundred billion dollar company. But when we think about almost dying, Very improbable that we ended where we did.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Well, you know, around that time, I won another lottery, which is one of my investors benchmark capital, general partner Bill Gurley, who I've worked with for many years, decades, who I think the world of. And he gave me the opportunity to be coached by someone who'd been the CEO of a real public company into it. It was a guy named Bill Campbell. And Bill C, coach, as we call him, became my mentor. And it wasn't just for me, it was for our entire management team because, you know, I was not the reason that opinions ultimately survived. It was all of those people. And so slowly but surely, we grinded our way to being break even, to being profitable. We merged with another private company. We rename the entire thing shopping.com. And believe it or not, Shopping.com ultimately went public.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, all of those things sound bad laying people off and begging for money and being weeks away from shutting down the lights. If they sound bad, imagine how they feel. And I became the permanent CEO probably less because I deserved the role and more because in the middle of the dot-com bust, we had no chance of hiring someone who could be a real CEO.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“And so all around us, companies are going out of business. It was incredibly difficult. And we almost ran out of money ourselves. We lost most of the employees. I think we probably were up over 100 employees. We went down to 20 employees at some point. Many of the co-founders left. And without a doubt, the failure or imminent failure of something was the fulcrum for really learning about what it might take to survive.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Certainly had a business model, and that was the same business model that most of the experts at the time had when they would publish content as well. And that's advertising. So it was going to be a free service. And if we had enough eyeballs, we were going to monetize. Now, this was something that was very familiar to me because I'd been at Yahoo. This was not a far-fetched thing. And so opinions, yes, we launched in, I think we started the company in April of 1999, we launched a couple of months later. And I would say about a year to the day after we launched the dot-com bust started.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, Naval had this great expression nobody is smarter than everybody. And so way back we would make purchasing decisions based on periodicals like consumer reports. Would make our purchasing decisions or our decisions around where we wanted to travel or how we wanted to spend our time. We would make really important decisions based on these so-called experts. And Naval had this idea that expertise is distributed. Can you create a place where people can submit their opinions on a wide range of things, products, services, experiences? And then you put in certain mechanisms that will ensure that the best opinions float to the top and the worst opinions sink to the bottom, you will get the most valuable database of information that exists. And it's freely available online. And that idea and that notion, I don't think opinions was the first, but it was one of the first and it was certainly one of the first mainstream examples of user generated content and online community.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Yes, I mean, at round zero, I had met several people who ultimately became my co-founders of opinions, and one of them is Naval Ravakan, who's gone on to incredible success and numerous other co-founders and opinions have gone on to do amazing things. And I can't imagine how difficult and lonely it is to start a company by oneself. I never would have the courage to start this thing without Naval and Mike and Guha and our other co-founder Dion. And opinions was Naval's idea. And I wouldn't have jumped if it weren't for those other folks. And so for me, the journey has always been more about who and then what.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“I'm wondering, why are you leaving? Because you know, you got a great opportunity here and you're doing good work and we're doing so many exciting things and the company's on an amazing track. And I said, Jerry, when I walk into the office every day and I look around and I think about what you built, I would love to do the same thing. Like I would love to build a Yahoo myself. And he was dead quiet. And he kind of looked at me. And Jerry's got a bit of a sarcastic sense of humor. He's a great guy, but he will definitely shoot you straight. And he looked at me right in the eyes and he said, you're a lot less intelligent than I thought you were. You have any idea how hard it is to build something like Yahoo? You're about to find out.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“100%. And so Jerry Yang, the founder of Yahoo, is at my going away party. Was so nice of him to stop by. And he came up to me and he said, you know,”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Know it always depends on where the stock is, right? So ultimately, depending on when I would have sold it, it would have been some number of millions of dollars. That wasn't ever part of the consideration. Always wanted to start something. And I was crazy enough to think maybe I can create my own Yahoo. And I remember at my Goodbye party from Yahoo because I was one of the first people who left. No one was leaving Yahoo”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“And this thing did turn into a pretty big organization. And so we picked this name round zero that's really about entrepreneurs coming together before they go and get round one financing. We then incorporated it as a nonprofit. We got some sponsors. And yes, Reid Hoffman, Larry Page, many of the other stars of today were just attendees at round zero”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Well, when I was at Yahoo, I realized something really striking. As fortunate as I was to be there, the thing that was gnawing at me was I'm not actually building what's here. And so then you start thinking, okay, well, what else can I do? Because this is a great job. But, you know, I'm a young person and I want to create my own Yahoo. But that was a really scary thought because who would be stupid enough to leave Yahoo to start a new company? And so the way that I decided to de-risk that is I started talking to people first, one of my colleagues at Yahoo, and we would talk together about our dreams of being entrepreneurs. And when we got together for dinner, ultimately in about six months, we realized we were on discrimination.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Was marketed much better than data entry, and the job was actually pretty cool. It was called being a Yahoo surfer. So at that time, and I was employee 84 at Yahoo, so there weren't that many people there. We would go and surf the web and we would get submissions into the Yahoo directory, which we were responsible for reading and categorizing. And then I would say the true job was more like being a librarian, but it was way cooler. We would joke, can you believe they're paying us to surf the web every single day? And so, again, it was the break of a lifetime. And that paved the way for everything that's happened since.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“Interestingly, in a series of months after I joined Yahoo, the dot-com boom really ignited. And at that point, people were watching CNBC and they were seeing Yahoo as a public company and they were seeing the stock double and triple and quadruple. And I was part of that. It was like I had won the lottery. So it was not something I earned being at Yahoo. I was not qualified. I don't think they had their pick of the best candidates back then because it was such an unorthodox job choice and it was magical.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT
“I ultimately stumbled upon this thing called Yahoo, which in the early days of the internet was the guide to all the websites that existed online. And it was started by a couple of Stanford grad students in a trailer on campus. And so, yes, ultimately I was able to meet them, join there as an early employee. You know, the funny story is there happens to be a chocolate milk company called Yuhoo. And true story, I think my parents believed for the first few weeks when I was working at Yahoo that I was working for a chocolate milk company.”
2025-09-15 · How I Built This with Guy Raz · Nirav Tolia: Nextdoor. How neighborhood chatter went global · IDENTIFIED FROM THE TRANSCRIPT