Nirav Tolia: The Lonely Reality Of Being CEO l Trailblazers Podcast Episode 50

0:00Erica Wenger: Today on the show, I am so excited to be joined by Nirav Tolia. Nirav is the CEO, President, and Chairman of the board at Nextdoor, the neighborhood social network he co-founded in 2010 to help neighbors connect and build stronger local communities. Under his leadership, Nextdoor has been adopted by hundreds of thousands of neighborhoods around the world, including the vast majority of those in the U.S., and has launched across the U.K., Germany, France, Italy, Spain, the Netherlands, and Australia. But Nirav's path to Nextdoor was anything but linear. He began his career as employee number 84 at Yahoo, then co-founded and ran ePinions.com as CEO through the dot-com boom and bust.

0:34Erica Wenger: That company became Shopping.com, where he served as COO through its NASDAQ IPO and eventual$620 million acquisition by eBay. He then spent time as an entrepreneur in residence at Benchmark Capital, where the idea for Nextdoor first took shape. Beyond Nextdoor, Nirav serves as non-executive chair of Hito Sophia and is a co-founding director of the William S. Spears Institute for Entrepreneurial Leadership at SMU's Cox School of Business, where he helps shape the next generation of founders. Nirov holds a degree in English from Stanford and lives in Highland Park, Texas with his wife and three sons.

1:05Erica Wenger: Let's welcome Nirov. Thank you for having me. Thanks for being here. You pronounced my name perfectly. Thank you. I appreciate that. I have to redo it. I will let people in behind the scenes, Nirov. Well, I'm so excited to chat with you. We're going to start with a bit of an icebreaker, and then we'll get into it. So we ask all our guests this, and you're welcome to take this question in a personal direction or a professional direction, whatever you want. But when you look back on your journey, I just talked about multiple decades here of amazing work. What has been the hardest part, the part that almost broke you along that journey?

1:36Gosh, I mean, I think as an entrepreneur, and particularly as a founder of entrepreneurial ventures, it's hard to separate personal from professional. And there have probably been multiple moments when I felt either like I'm going to break or that I was broken. A couple of them that come to mind, the first company I started, we were very high flying during the dot-com boom. That was in the late 90s and the early 2000s. But then we had to live through the dot-com bust. And in one particular year, we were three weeks from going out of business. And as the CEO, it's a lonely job. And one of the reasons it's lonely is the worst news is not something you can share, at least not when you get it.

2:21And so when you're the CEO and you're looking around and your employees are, even if they're not happy, they're existing. They have no idea what could be coming. It's a little bit like being on the Titanic and you see the iceberg, but no one else does. So that was really tough. It was very difficult to raise money at that point. And it looked like we weren't going to make it. And somehow we did find someone to invest in the company and we did make it. but that was a very difficult moment. Anytime you do layoffs as a CEO or founder, it's just devastating because you realize at that point, you know, to your question about personal or professional, you realize how professional blends into personal.

3:01And so layoffs are a professional decision, but they are a failure of management because management did not accurately forecast what the business would need. And the result of that is something deeply personal to the people who are let go. And so that was a really, really hard moment. On a personal basis, there have been many times when it has been revealed to me, either implicitly or explicitly, that I'm not good enough for the job. And those are very, very, very hard moments. I like to say sometimes that entrepreneurship, particularly if you're lucky enough to be successful is 999 failures ending with one big success.

3:41And so it's probably easier as a founder to think about the times things didn't work out than the times that they did. And I read something recently that I thought was quite interesting, which is instead of thinking of failure as something to be avoided, think about failure as the opportunity to learn and get better. I actually read that as part of an article on parenting. And so it was, you know, as you talk to your children, you want them to be comfortable trying things and failing because failing as hard as it is, and it is hard. I'm not trying to sugarcoat failing. No one wants to fail. And those moments that I'm talking about felt terrible.

4:20And I wouldn't want to go through those things again. But almost every time they forced me to reassess and they forced me to reflect and they forced me to look in the mirror and say, look, I don't want this to happen again. So what am I going to change to make sure that they don't?

4:36Erica Wenger: Totally. You realize your own toughness. I mean, I think that's so much of it too. It's when you fail and you get back up, you realize, wow, okay, the next thing can be a little harder than that was and I'll be fine. And I think that is so much of the calculus. Who do you lean on? I mean, you talk about like, it's very lonely. There've been moments where you realize you're not cut out for the job or you got to do layoffs. Is it a coach? Is it your wonderful partner? Is it an executive team? Is there an internal practice that you go to? Talk to me about how you soothe yourself in those moments of loneliness because I'm a solo GP.

5:08Erica Wenger: A lot of the people listening to this podcast work for themselves. It's hard to know how to get through those lonely times. I've been really lucky because I've always had a community around me to help me through those low times. And I'll give you a couple of examples. The first is, I was extraordinarily lucky when I was CEO for the first time to have a CEO coach, a real CEO coach. And his name is Bill Campbell. And unfortunately, he's no longer with us. But Bill Campbell, if you don't know the name, is probably the most famous, the most significant, the most amazing CEO coach in Silicon Valley history.

5:42There's a book that's been written about him by the former CEO of Google called Trillion Dollar Coach. And so while Bill was coaching me, he was also coaching Steve Jobs, Jeff Bezos, and Larry and Sergey at Google. A couple of people that you would recognize.

5:56Erica Wenger: Eh, maybe. That I'm certainly not in the same class with. And so you can imagine what it felt like to have someone like that in my corner. And it was amazing. And Bill said something once that was quite extraordinary. When I was going through a tough time and asking him the same question, who should I lean on when things like this happen? I have you, of course, but who else should I lean on? Who can I confide in? Because being a CEO is one of the loneliest jobs. You have people you work for, and then you have people who work for you. But there's no one at your level that you can confide in that really knows what you're going through.

6:31And Bill said to me, you know, you have a board of directors here at this company. It's time for you to start thinking about who's on your personal board of directors. And for me, that has always been my co-founder, Sarah Leary, who I've been lucky enough to to work with since 1999. And so she laughs and says, yeah, we were five years old in 1999 when we started working together and we were a little older than that. But now fast forward 27 years later and to have someone in your life that entire time that has been your professional and personal support, she's like a sister and that is amazing.

7:07If you're lucky enough to find the person that you would call your partner, your true love, and I am lucky enough to have found that person, Megatolia is my wife. you always lean on that person. If you're fortunate enough to have a strong family, you lean on your parents, which is something I've done. And so, if you can say, I've got a CEO coach, I've got a co-founder, I have a life partner, and I have parents and family that will support me, I mean, that's true wealth, you know, because those people make the highs much higher, and they make the lows not quite as low. All that said, it still sucks to go through adversity, And it's still very, very, very difficult.

7:45But you can be around people who help you get through it. Because in reality, nothing makes the pain go away except for time. And so if you can find a way to simply push through, you'll almost always come out the other side.

8:00Erica Wenger: One thing I've learned talking to GPs on the show and in my own experience as a GP, your back office is a signal. How fast you close deals, how clean the LP experience is, how your K-1s land, investors notice all of it. The more buttoned up you are, the more likely they are to give you more money in the future. That's why I want to talk about Sidecar. Sidecar is the SPV platform built for fund managers who want institutional quality execution without hiring a full back office team. They'll review your deal within hours, handle full secondary transaction support and give you transparent pricing up front.

8:31Erica Wenger: No platform carry. Also, your LP relationships stay private, which is super important. It is not a marketplace. If you're running a professional fund, your infrastructure should look like it. Sidecar makes that possible without the overhead. Check them out at sidecar.io slash partners slash trailblazers. Totally. And I think sometimes folks in business underestimate how much non-businessy friends can help. Like I know your wife has done extraordinarily well in entertainment, which we may or may not get to later, but she's very prolific in that world. Not necessarily having a lot of overlap with your work, but it's not necessarily about being in the same sector and the same industry.

9:05Erica Wenger: It's about being there for you and knowing you and knowing your character. Yeah. And almost go a step further. I mean, my wife is an amazing business person. She ran Shonda Rhimes Production Company for a number of years as the president of Shondaland. And so high power job and lots of stress and lots of adversity, just like my jobs. Many times when we would come home, we would tell each other about what happened. And the first instinct is for the person who's listening to start giving business advice. And immediately I would say to her, if I were the one telling her what had happened at next door, Or, you know what, honey, I don't actually want any business advice.

9:41That's a lot of what I've already received today. I just want your support. Or if she were in that position, she would tell me about something that happened at Shondaland and I would immediately start trying to solution whatever she was telling me about. And she would say, honey, right now, I just want you to listen. And so you're exactly right. You don't have to know the specifics. What you have to know is how much you care for the other person. And in those moments, it's not about the specifics and it's not about the solution. it's about just being supported.

10:09Erica Wenger: I love that. Yeah. I imagine she was really there for you as you've had a very long and windy road at Nextdoor. You've been in and out of the CEO seat. So I'm sure she's been part of lots of fun conversations behind closed doors. I want to talk to you a little bit about coming back and we'll kind of work our way backwards. But the past couple of years, you are back in the CEO seat. There is a new wave, a next generation of Nextdoor coming up. Talk to me about why you're back and what you're excited about. Yeah, I've had this incredible opportunity over the last two and a half years to be a boomerang founder, a boomerang CEO.

10:44And so what does that mean? I started the company in the summer of 2010 and was the first CEO of the company for the first eight and a half years of its life. Then things weren't working out as well as I would have liked them to work out. And while the public facing narrative is always, it's time for me to move on. I think I want a different challenge. I want to do something else. I can tell you from being in this position and being on the inside for many of my friends going through similar journeys, it almost always means that the company is going sideways. And the reason the company is going sideways is because the leader has not been able to scale to what the company needs.

11:24And it happens all the time. There should be no shame in that. It's unfortunate because no founder wants to hit a wall or feel like they've reached their ceiling, but it happens and it's okay. It's better to acknowledge it and either decide to work on it and overcome it or to step off and pass the baton to someone else. And so I stepped off the ride. I passed the baton. And after a few years, I was lucky enough to have the offer to come back. And it has been the privilege of a lifetime. And I'll tell you, coming back doesn't mean going back and doing the same things that you did when you were there the first time.

12:00In fact, I think that's probably almost always the wrong way to do it. Coming back means taking the best things from when you were there and the best things from when you weren't there and trying to combine them with the best things you need moving forward. And so it is a new wave. And in our industry, I mean, a 15 or 16-year-old company, and that's next door, I mean, how many are still in existence, right? So rare. I mean, we're in an industry where at various moments, Apple and Microsoft, two of the most valuable companies in the world, were left for dead. And so staying power in our industry is extremely unique.

12:36You either go out of business or you're acquired. You're mushed into someone else. And so coming back to Nextdoor, it's not necessarily a victory lap that I came back to take. It's the opposite. The company wasn't working. It wasn't achieving its potential. And we think its potential is massive. And so we were looking for a way to kickstart things. I'd been on the board even after I left, so I was involved with the company, of course. And we had an incredible person who I'd passed the baton to, Sarah Fryer, who's now the CFO at OpenAI, who had been the CFO at Square, now called Blog. And so it's not as if we brought someone in who wasn't capable, super talented, super smart, right?

13:15It just didn't work out because sometimes it doesn't. And so we needed to kickstart things. We needed to shift things. We needed to have a new way of looking at things. But maybe that new way should be rooted in some of the lessons of the past as well. And that's what a founder coming back gives you. Hopefully some of that magic that got the company off the ground in the first place, but also hopefully the experience to know that it's going to take more than that founding magic. It's going to take some refounding magic. And so I came back and I could not be more excited because we live in an unprecedented time of innovation with the emergence of AI.

13:51And so the hardest thing you can do as a tech founder today is to run a non-native AI company. If any founder asked me today, what sort of company should I start? I would say, well, figure out some area that AI will revolutionize. And it's going to be almost any area you can think of and go figure out a way to start a company in that area. I wouldn't tell a founder, go find an area that is not native in AI and go run that company and see what happens. Right? Nextdoor was not started with AI because there was no AI in the summer of 2010 when we started the company. So the real question is, what are we going to be in an AI emergent and AI dominated world?

14:31And that's a huge challenge. And I happen to believe that there will be companies that are non-native AI companies that will succeed and succeed in a big way. You already see it. Amazon, Netflix, Apple, Google, Microsoft. These are non-native AI companies, but they're the giants alongside OpenAI and Anthropic and others. And so how do we find that balance? How do we harmonize this incredible innovation of AI with the things that made us successful before AI came along? That's the challenge, not just for Nextdoor, but for every company in our space.

15:08Erica Wenger: Totally. Yeah, it's so interesting. I totally hear you on the non-native AI stuff. And I think there's some companies that are like doubling down on that. There's some companies that are building out completely new businesses internally, and just investing crazy in R &D. And then some that are pivoting completely. And I think it's, you can fall into any of those camps, but it's about authentically figuring out what is best for that company. I want to just talk to you a little bit about fear. So, you know, in your own words, you had built a company for many, many years, and things weren't working, and you brought in someone else.

15:37Erica Wenger: And then many years later, you guys have continued to figure things out and grow and have staying power, you come back to expand it again. But the reason that you were out the first time was because it wasn't expanding. How do you rationalize that? And was there fear associated with coming back of like, wow, what if it doesn't happen? It doesn't work again. And how can I now be the person that takes it to the next level when several years ago, I struggled with that? Yeah, it's a great question. And I think it's a fair question. And so even beyond fear, this was a valid question for our investors and our employees and everyone involved with the company to ask, why would you be the right person to come back?

16:17Now, fear is something that I believe founders feel no matter who they are. I mean, you've heard about the imposter syndrome, right? Some of the most successful people I know still have an imposter syndrome, and I certainly do. And so whether it's fear of failing, fear of measuring up, fear of not being respected, fear of squandering opportunities, fear of anything. That is so much, unfortunately, of what drives us. I wish it weren't. Again, it's not pleasant to feel fear and anxiety. The question is, when you feel those things, how are you going to react? And what I learned in the time that I was gone at Nextdoor is that when I encountered fear, when that turned into anxiety or stress or turmoil, all those things that we do feel when we're trying to build big, great things.

17:08Because if it were easy, it would already be done. When I felt those things, it was effective in getting me to move, getting me to work hard, getting me to focus, getting me to sell out to something that I wanted to do as it does with most people. But it also made me into not the best version of myself. And whether that was the way I was treating people or the way I was treating myself, whether it was physical with sleep and nutrition and exercise, or whether it was emotional, the way that I could make time for other people, the way that I could think of other people and prioritize them. That fear took a lot of my ability to cope with other things away.

17:52And so in some ways, while it was the hardest thing professionally that I've ever had to go through to lose my job from the company that I started, an identity CEO of Nextdoor that was my full identity for many, many, many years. and to think about how to pick up the pieces. That was really, really, really hard. But it was also a gift because it forced me to take a step back and not only try to learn from why it didn't work out, but also give myself the space to start to grow in other areas. I wouldn't recommend this, right? It's not like taking a vitamin, right? But it's a necessary lesson. And I'd never thought I would have the chance to come back to Nextdoor.

18:39But when I did have that opportunity, you better believe I was thinking to myself, if it didn't work out the first time, what am I going to do to make sure that it works out this time? Because no one wants to go into something that didn't work out the first time and think it's not going to work out again. That's maybe the definition of insanity. We're hopeful, optimistic people. We think, okay, whatever happened last time, I'm going to make sure that things are different this time around. But that doesn't happen magically or automatically. That requires work and that requires facing the fear and trying to understand it and making a commitment to not do the same thing that you did last time.

19:18And so for me, that is manifested as if fear in the past sometimes resulted in me tearing people down or making them feel small because I was stressed and I was anxious and I was angry and I was impatient. And these are all natural things that we feel, right? And by the way, being really hard on people, in the short term, it can work.

19:43Erica Wenger: It can actually generate results, right? But this time around, I said to myself, can I find a way to acknowledge that fear and admit it and be authentic about it? Because it's not like happy trails. You go back to a company that's lost 85 % of its market cap and everything's going well. It's the opposite. it. I mean, you are in a crisis. You are walking into the burning building. You've chosen to walk into a burning building, and that's scary. That fear is there. But you can acknowledge it, and you can say to yourself, all right, how are we going to use this opportunity to come together and to lift each other up?

20:24Because crisis can be a time when we tear each other down, as we see a lot in today's world. It can also be a time when we come together. And so that fear, it's always going to be there. It's never going to be pleasant. And it's not something I would wish on anyone. So I'm not saying it's a gift. What I am saying is if it comes your way, figure out a way to use it versus letting it use you.

20:48Erica Wenger: Totally. It's interesting. When I asked that question, I was expecting more of like a businessy answer. And it was refreshing to hear more of a psychological answer. and that like a lot of leadership, I think people believe it to be more skills you need to gain, you know, having done the like, you know, 10 to 100 thing a couple of times before you can do the 10 to 100 thing again. But in reality, a lot of it, you know, especially based on what you're saying is really just about managing your own fear, managing expectations, dealing with your own psychology and being ready for an opportunity. Yeah, the thing I'd say about Silicon Valley is we're pretty good at making the list of objective things that we need to learn, that we need to acquire, the skills list, if you will, right?

21:32What we're not as good at is admitting that so much of this job is about human connection. Leadership is about being able to formulate a strategy, being able to prioritize, being able to make the right decisions, being able to invent incredible things and innovate. Yes, you do need those things. You absolutely need those things. but leading a company is also about courage and it's also about empathy and it's also about team building and it's also about enthusiasm it's also about authenticity and those are things that in Silicon Valley we don't talk as much about I've been really lucky in addition to Bill Campbell who taught me a lot of this you know Bill used to say all the time focus first on who and then on what.

22:19What you just said, which is okay, and make a list of the things that we need to do, that's the what. What about the who? Who am I? Who do I represent? Who do I resonate with? How do I resonate better with those people? Who do I choose to be around me? And how do I carry myself around those people? Bill felt that those were the things that you needed to start with. And this is a guy who coached the most successful people with the greatest skills in our industry, right? And so I think that was an important lesson. The other thing that I've done since I think maybe 2007 or 2008 is I've had a monthly dinner with other CEOs.

22:58And I mentioned how lonely it is to be a CEO, particularly in Silicon Valley, because you're kind of frenemies with everyone, right? You don't know who you're going to be competing with. I joke and say, you know, if you go to a school like Stanford. I went to Stanford. Everyone's so used to being successful that when you go to that place and you ask people, hey, how's it going? How are your grades? How are your classes? Everyone says it's going well. Whereas you know it's impossible that it's going well for everyone. Silicon Valley is kind of similar. You go to CEOs, hey, how are things going with the company?

23:30Everyone says things are going well, right? When in reality, and you know this because you're one of them, you know that some things are good and a lot of things are not so good and so you got to focus on those things but who do you talk to those things about you know we we talked about that earlier when you get with a group of ceos who can get to know each other and so if we have dinner every month a year that's 12 times we can get together and maybe the first dinner if you don't know someone a few of the walls are up but you know by midway through the year you know these people and you're tracking them and you can start to be honest.

24:06You can start to trust. And trust is this incredible thing because it enables you to be vulnerable. And when you're vulnerable, you can start to ask your peers, hey, what is on the list that I don't have? Not just the things that I can learn with AI, right? Or through a textbook or by going to a course. What are the things that I'm missing from a human perspective? And so getting to know these fellow CEOs that can be part of startups or fortune 100 companies that can be incredibly successful, multi-billionaires or people who keep trying to start companies and never succeed. You can learn from all of them, right?

24:46And it's not an identical experience to the one that you're experiencing, but the feelings are very, very, very similar. And so I agree. I mean, I think there needs to be more exploration of, if we call it the soft side, no one wants to say that, right? Because we're all type A, hard charging, want to be perfectionists and successful people, right? But the soft side in many cases can unlock real success. And I've seen that over and over again.

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26:54Erica Wenger: If I finish a meeting with the potential investor in my fund, I'll ask Granola, what could I have done better to get my point across? If I'm meeting with a founder I like, I'll ask Granola to point out any major green flags or maybe red flags I may not have already caught. For people with a lot of meetings and decisions that require endless context, Granola is a game changer. Actually, we're running Granola on today's episode, so you can read the full show notes at granola.ai slash trailblazers. New users get three months completely free. That's granola.ai slash trailblazers. Okay, so you've changed.

27:23Erica Wenger: We're going to be repping the merch. I know it's very hot in here. I was so nervous that you were making me sweat. I'm just grilling you. Yeah, we didn't want to show that to everyone. Focus on the words. Focus on the words. So the words are about cool people that came. OG Silicon Valley CEOs that like, you know, maybe I would be like, whoa, Nirav. You know, over a series of years, I mean, this has been going on since 2007. So figure almost 20 years, right? There have been some extremely prominent people that have not just come once, but have come for many years. Mark Benioff, for example, Drew Houston from Dropbox, Dick Costolo, right?

28:00But I think what's interesting, they're wonderful people, by the way, those three that I mentioned. But what's interesting is it's not about where they are. It's about who they are. And it's about getting to know them as people. So let's take Drew Houston, one of my favorite people, right? Amazing founder of Dropbox, created a$10 billion public company from scratch, right out of college, right? Feels so lucky to know him and to be his friend and to have gotten to know him through the context of Dropbox. but in the process of that getting to know him as a human being and ultimately go to his wedding and celebrate the two wonderful children that he now has that's what made that ceo dinner and what still makes it so special i mean if you see the same people 12 times a year and you do that for years upon years right think about all the life that is being lived over that time companies start companies succeed they go public they get acquired they fail but alongside that people grow they're in relationships they're out of relationships they get married they have children their children leave home right and the tradition of this dinner is to choose a month of the year when every one of the members of the dinner hosts so you own a month and during that month, the other people learn a lot about you.

29:28Are you going to have it at your house? Are you going to run out of a restaurant? One time we had a really prominent, I'll kind of out him on here, the chairman of OpenAI, Brett Taylor, has been coming to our dinner for many years.

29:38Erica Wenger: Founder of Sierra as well, of course. Founder of Sierra, one of the best entrepreneurs that I've ever met and one of the best product people and now proving that he's one of the best CEOs as well. So incredible human being, both from a business and from a human perspective. But we'd had this crazy over-the-top dinner that someone had hosted at the French Laundry. And the next month was Brett's month. And I remember him saying to me, you know, we got to bring this back down to earth. And so I'm going to do something very different. I have actually found a park where food trucks come and we're going to go have dinner on a park table in that park and we're going to be served by the food trucks and it was amazing because whether it's the french laundry or whether you're actually getting food from a food truck first of all the food was pretty good even with the food trucks better sometimes yeah but it was all about the people it was all about the people and so i go back to what bill campbell told me which is you know if you're really really really lucky you have a successful company but priceless success is the people you do that company with and the people that that company brings you into contact with.

30:50And I'd say one of the best things about Silicon Valley is not just the concentration of talent. It's the fact that you create real relationships with those people. And that's what makes it really hard to leave.

31:04Erica Wenger: Yeah, totally. But now you're back. So you haven't left. You're back. I did have to ask, just during that gap year, you went to Italy, which sounds magical with your three boys. Why Italy? And how was it? I had five years between the time that I left Nextdoor and the time I came back. And I never thought that I would go back to Nextdoor, and I never thought that I would be a CEO again. I was pretty burned out. And I knew that the pressure of being a CEO was something that I shouldn't take lightly because of the kind of person it made me. So I wasn't sure that I ever wanted to take that on again.

31:43In fact, I was teasing my friends saying, I'm going to go to the other side of the table and be an investor so I can watch you being tormented by all this CEO stuff, right? And so I went to my wife and I said, look, I want to support you now in your career. She had just been promoted and we had three really young children, three boys, ages, I think at the time, six, four, and two. And literally, she had just been promoted. I'd stepped down, she'd been promoted. And I said, this is great because you've pulled such a heavy load in addition to your job of raising the children. Let me now make that my priority and your priority can be work.

32:23And she said, great. And so we were going to go to Italy for a summer because it was the first time ever. And a lot of founders will know what this feels like i mean you found a company maybe you take a week of vacation maybe right to take an entire summer off is unheard of and i went to my wife and i said we love italy we want to take the kids somewhere it would be fun maybe we'll do a summer in italy and she said okay that might be hard i was just promoted i'm part of the leadership team now like how am i going to tell them i'm going to be gone for three months it's okay we'll figure out what you can do so we started to talk about it.

32:57In the meantime, I was speaking to a former Nextdoor board member and a great mentor of mine, definitely someone on my personal board of directors, and that's Rich Barton. And Rich is not necessarily a household name, although he should be in our industry. Part of the reason is he's up in Seattle. Rich is the founder and CEO of Expedia, which he ran as a public company and ultimately sold for$10 billion. And then more recently, he founded and was CEO of Zillow, which is, you know, I don't know,$20 billion public company. In between then, he also was a founder of Glassdoor, which ultimately sold for a billion dollars.

33:32How do we not know about this guy? Crazy. So Rich is phenomenal. You should definitely have him on the podcast. I know. I'll ping Rich after this.

33:37Erica Wenger: Yeah. Rich is phenomenal. And Rich had been on the board of Nextdoor from the very beginning and a great mentor and someone that I've learned so much from. And I called him and I said, look, I got a lot of new spare time on my hands. I'm thinking about going to Italy for the summer. I seem to remember you telling me the story that when Barry Diller at IAC bought Expedia, you had a one-year non-compete. And I seem to remember you telling me that for that one year, you went with your wife and your three young kids to Florence, Italy. What was that like? Because we're thinking about doing that for the summer.

34:09And Rich said, oh, it was amazing. It was life-changing. It was one of the best experiences we ever had as a family. But I wouldn't go for a summer. You can't just go for a summer. That's like being a tourist. You got to figure out a way to go for a year. You got to put your kids in school. You have to actually live like an Italian. And so I went back to my wife and I said, hey, we can do the summer thing if you can get the time off. But at some point in the future, we should figure out a way to do an entire year. And she said, some point in the future, I mean, we should just do it now. And I said, well, you were just promoted though.

34:42Like, are you going to resign from this job that you've been working so hard to be promoted. You're finally promoted, right? And she said, I have to choose the family. I mean, it was really incredible of her to feel that way. But she knew that sometimes you have to take the opportunity when it's presented. And our kids were young enough, and I wasn't working. And so, she made the sacrifice of resigning from her job. And in the summer of 2019, we went to Florence, Italy. I was also very lucky because Rich introduced me to the folks at Stanford in Florence. So Stanford has a very small campus in Florence where Stanford students can go while they're undergrads at Stanford in California just to study abroad.

35:22And as an undergrad, I'd always heard about that program, but I was so intense as a Stanford undergrad, I never would have wasted time by studying abroad. I was a pre-med, you know, I needed to take all my pre-med curriculum. And so Rich introduced me to the folks who run that program, in particular, a wonderful woman named Linda Campani. And I was talking to her and I said, you know, we're going to be in Florence. I'd love to find a way to be involved with this program because I love my alma mater. And I think it'd be really fun to think about going back to the university. And by the way, I think there's a very interesting parallel between Silicon Valley today and Renaissance Florence.

35:59And so at some point, I'd love to tell you my theory of how the Medicis of yesteryear are like the VCs of today. And the Da Vinci and Michelangelo's of yesteryear are like the Elon Musks and Steve Jobs of today. And after a little bit more conversation, she said, you know, I think you should teach a class about that. And so I did something crazy. I put a syllabus together that was approved by the Stanford faculty. And I taught a comparative study at Stanford and Florence between Renaissance, Florence and Silicon Valley today. And it was an incredible experience. And I definitely learned more from those sharp Stanford kids than I taught them.

36:36But it was an incredible first seven months that we had, starting with the summer of 2019. If you remember 2019 and you think about seven months, you know what happened.

36:45Erica Wenger: COVID. COVID, yeah. Right? The big COVID. And my dear friend who I've known as long as I've known my co-founder, Sarah, so multiple decades, Reid Hoffman, the founder of LinkedIn. I remember he called me and he said, I know you're in Italy. and he's part of our CEO dinner as well. And I just want to let you know that they may close the borders. I think you should get back over here. It was the very end of February of 2020. No one really knew what was going on. But Reid, out of the kindness of his heart and the love he had for our friendship, said, if you really want to protect your family, you should get back to America.

37:21And so literally in a day, we left Florence, Italy, and we flew back to San Francisco with our three kids. And I remember them crying and saying they didn't want to leave. And could they just go to school for one more day? And we'd started to see masks on the streets of Florence. And so we knew that something was going on. Within a week of being back in San Francisco, COVID was everywhere. It was the first week of March, and they shut down San Francisco. And it was actually a lot worse, the shutdown in San Francisco. And I think in the United States in general, even then it wasn't a place like Italy, where COVID went from China to Italy.

37:56So Italy was one of the first places. But because of herd immunity, Italy opened back up before the US did. And so while San Francisco was still shut down in the summer of 2020, Italy was opening up. So we went back because we wanted to have more of our time in Italy. So we ended up spending another year there, another entire school year. And that was a magical year because COVID also came back. They did close the borders. And we ended up spending almost a year in Florence with no tourists. And so that was not only an incredible, incredible opportunity to be in a place in a way that no one will ever experience it in our lifetime, it was like a personal renaissance.

38:37And so I was thinking about this class, Renaissance Florence and Silicon Valley, but I was experiencing my own personal renaissance. I was spending time with my wife and children for the first time in a way that I never could when I was working. I was reacquainting myself with my university, my alma mater, and And what a gift to go back and be around those students who are AI natives. They knew so much more about technology in some ways even than I did. And it was just a wonderful experience to live in another country. And I tell a lot of people, there's nothing like living in another country to not only make you love that country, but also make you love America more.

39:18And it taught me something really, really, really important. And it's particularly important, I think, in the context of Nextdoor, because Nextdoor is all about helping you love where you live even more than you do. And we do love where we live. That's why we choose to live there, right? But what I learned living in Florence, you can love multiple places. You can feel at home in multiple places. And what an incredible gift it is to have two or three places where you feel at home. And so for me, I grew up in Texas. I live in Dallas now. We moved back there from Silicon Valley when we came back from Italy because we wanted our children to be close to my parents, their grandparents.

40:00I've spent almost my entire adult life in San Francisco and in Silicon Valley. So I feel very much at home there. And now we have Florence as well. We're in New York right now doing the podcast, right? New York is my favorite city in the world. I've lived here for a couple of years earlier in my life. And so to be able to be in multiple places and have the richest of those places, going back again to the who, the friends you have, the acquaintances you have, and the memories you have, I think that's a really powerful thing. And COVID reminded us that being tied down to one place was a very unnatural state for us, right?

40:38Natural state is for us to get out and then love coming home. And that's something that I feel every time I go to any of the places where I've lived.

40:46Erica Wenger: Totally. It's such a beautiful thing to teach your children, too. You know, like two, four, and six. Those are such great ages. And I know maybe you jump a year or two because it was sort of during COVID. But what a beautiful lesson to teach your children, too. That, like, we love our home, but we can find home in a lot of places and it's about each other, not the, you know, the structure around us. Well, one of the really interesting constructs, if you think about family, whether it's you marrying someone or having children, typically when you marry someone, you either go into their life, you move to where they are, or they move into your life, they move where you are.

41:18And so you're not experiencing that life together for the first time because one of you has already lived in that place that you're inhabiting and has memories before you came along, before the other person came along. Children, it's even more extreme. Your children are born and then they come and inhabit your life. They go to your favorite restaurants and they go to your favorite places to spend time, right? On the other hand, when we went to Florence as a family, it was the first time for me and my wife and my three kids to ever live in Florence. And we experienced that first day together. We experienced that favorite restaurant for the first time together.

41:59And it was an incredible bonding experience because when you have fresh eyes, the world looks totally different. And when you're able to share those fresh eyes with the people you love, it's a really special and bonding experience.

42:13Erica Wenger: I love that. I love that construct. It reminds me, I have friends who recently got married, and one is from one place and one is from another. And then they picked this like third place that neither of them have a connection to to get married. And it reminds me a little bit of what you're saying, like this idea that you're not really molding to one person's life or the other, but you're building something completely new, just you guys. Yeah, it's a little bit like, I mean, coming back to Nextdoor, and I mentioned this earlier, a lot of people say, oh, are you going back to the way Nextdoor was?

42:37No, no, that's Nextdoor 1.0. And they say, well, are you going to continue doing what Nextdoor has been doing? And I say, no, no, that's Nextdoor 2.0. We're going to try to build Nextdoor 3.0, and it's got to be better than one and two combined. And so when we do that, to some extent, everyone that was at the company when I came back is a co-founder of Nextdoor 3.0. And that's fun because in reality, pivots and reinventions, they're very hard. They're very, very, very hard because inertia makes it almost too easy to just keep doing what you're doing. But if it's not working, you can't keep doing it.

43:17Unfortunately, human nature is even if it's not working, it's easier to just keep doing it. And so to shock the system a little bit, sometimes it does require moving somewhere else. Sometimes it does require bringing in a new leader. Sometimes it does require creating a new kind of entity inside. you think about the creation of the Macintosh, right? Steve Jobs created the pirate ship inside Apple. We read recently about the sale of Airwalt, right? Or Airtable, rather. I believe that the founders of Airtable had created an AI-centric version of Airtable inside Airtable, and now they're spinning that out.

43:53Hyperagent. Hyperagent. It's going to be a new thing, right? So it's a very, very hard thing to take something that already has life force, whether it's a place you live in all those memories or a company and change that thing, either stop it from spinning and then get it spinning again or stop it from spinning and get something else to start spinning from scratch. That's a very hard thing for us. It's not natural for us as humans because it goes against all the investment that we've already put in. But sometimes you have to force yourself to do it.

44:27Erica Wenger: Yeah. And it can sometimes be under the same name or a new name. Like I do think what Airtable has done is really interesting. I think what Intercom has done with Finn, I think I maybe mentioned. I'm so excited to see this next chapter for you guys. The 2026 primaries are taking shape. And if you have a strong opinion about how they're going to go, Calci lets you actually trade on it. Calci is the largest prediction market in the US, federally regulated and available in all 50 states. You're not betting against a house. You're trading against other people in a live market, taking yes or no positions on real world events, elections, federal interest rates, economic data, you name it.

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45:31Erica Wenger: Event contract trading involves risk and may not be suitable for all investors. Prices, values, and available markets may differ from those mentioned. For more information, see calshe.com slash regulatory. Okay, so a quick experiment. Think about the last long message you typed. Could be a Slack thread, a prompt into Claude, maybe it's a detailed email. It probably took you 10 minutes, maybe even 20 to get it right. Now imagine you just said it out loud instead. That is the whole pitch for Whisperflow. Whisperflow is voice to text that actually works in every app on every device. You speak naturally and it outputs clean formatted text that's ready to send.

46:03Erica Wenger: No setup, no integrations, no fixing weird transcription errors. And it works across Gmail, Slack, NoShan, Claude, iMessage, wherever you type. And unlike the built-in dictation on your phone, Whisperflow removes all filler words, mid-sentence corrections and jargon. What I personally love about it too is that it perfectly matches my style. So I often type in all lowercase letters. So it'll type like that. I also say things like LMK, which means let me know in shorthand, and it'll auto adjust it from let me know to LMK. Like many of you, I also do a lot of brain dumping into LLMs. So instead of typing it all out, I actually just speak my windy train of thought into Whisperflow, which is infinitely faster than trying to get my fingers to keep up with the pace of my thoughts.

46:42Erica Wenger: If you do any serious writing or just send a lot of messages and emails, using Whisperflow is a no-brainer. Get one whole month of Whisperflow Pro completely free at ref.whisperflow.ai. slash trailblazers. I do have one final question I want to ask you before our trailblazer round. I got to ask you about Shark Tank. We were talking about it a little bit before. How did you get that opportunity and what was your experience like on Shark Tank? I was very, very lucky to be a shark on Shark Tank, which is a little ironic because most of my professional career, I've been the entrepreneur, right? And so to be on the other side of the table and be the shark, why would I do it?

47:15Well, first of all, what an incredible honor to be asked to do it. I think Shark Tank in many ways is emblematic of everything that makes Silicon Valley in America great. It's the American dream. It's that idea of, I have a great idea. It doesn't exist. I want to put it into existence. I need help to do that. I'm going to go pitch the powers that be. And if they approve, if they choose to support, I'm going to have an opportunity to do it. That is the American dream to me. And particularly as the kid of immigrants, that's why my parents came to america and so shark tank is one of my core beliefs entrepreneurship and trying to create something new and so i would have loved to be on shark tank even as an entrepreneur pitching the sharks but having the opportunity to go on as a shark i mean i always would tell the producers when they approached me you know i'm probably going to be a little more sympathetic i don't know i don't know if i'm comfortable with this moniker of being a shark because I want to support the entrepreneurs.

48:13I've been in their shoes. I know what it feels like. I know how your stomach sinks when you pitch something and it doesn't land. I know that feeling of anticipation before you walk out to make the pitch. I've been there so many times. And so it was an incredible honor. And it was really more than anything about expressing my love for entrepreneurship. Now, the show is super fun too. And so I'll tell you a couple of things about the show that people may not know. The first is it's not scripted at all. And so while sometimes it may seem like it's scripted, the sharks don't know anything about the companies that they're going to see.

48:52There is no guidance around the kinds of deals that you might want to make or whether or not you would want to make a deal, et cetera, right? It's real time and it's happening for real. And so it is reality television, but I think about it almost like it's a pitch show that happens to be recorded and shown, but the pitches are real and they're happening. So that's one thing. The second thing I'll tell you, I'm not sure if I'm supposed to share this, but I will share it anyway. At the end of a long day of filming and the sharks work really hard. I mean, you hear, I don't know, something like six or 10 pitches a day and it goes from the morning all the way to the night.

49:29Towards the end of the day, the water at the tables next to the shark seats, I think it's filled with something that's not water. And they refer to it as shark juice. I think it has some alcohol content. I'm not sure exactly what alcohol content. So if you're ever watching an episode and you notice that some of the sharks who are really intense and almost feel a little uptight sometimes, if they look a little bit more relaxed, chances are that was a pitch that was taped towards the end of the day. But look, in all seriousness, I mean, I was lucky enough to sit next to Mark Cuban on the set and to be around those people.

50:07I've become friends with Mr. Wonderful Kevin O 'Leary. We did a couple of deals together. And recently I brought him to SMU where I'm part of the Entrepreneurship Institute because I wanted him to tell a story to entrepreneurs. The lessons of Shark Tank are the lessons of business. And the sharks, the permanent sharks, even the guest sharks, they've lived those lessons. And so for a show to teach people how to pitch, how to think about negotiation, how to think about the gaps in your idea, how to think about evaluating a new opportunity, I think it's an incredibly entertaining way to learn some really important things.

50:46And particularly for my children, I love it when they watch the show because there are many things that you would feel okay as a parent with them doing from a screen standpoint. But watching Shark Tank is definitely approved in our household.

51:00Erica Wenger: I'm really happy to hear that. And sometimes you pop up on the screen, which I'm sure that's very fun, too. You know, I'll tell you one funny story. We did this event with Kevin O 'Leary and my eldest son, who's now 14, was there at the event and he was meeting Mr. O 'Leary, Mr. Wonderful. And it was a big deal for him. And after the event ended, we went to have dinner at our house. We had a small dinner with Kevin and some other folks in Dallas. And in the car, it was me and Kevin and my son. And my son started asking Mr. Wonderful for tips on a business idea that he had. And of course, Kevin is very patiently listening and answering and encouraging.

51:37And you can imagine how my son felt, right? I mean, his chest was puffed out and his smile was like from ear to ear. and we finally get home and Mr. Wonderful walks in and my son's kind of trailing behind and and I say hey Devin was that cool was that was that kind of awesome talking to Mr. Wonderful and he looked at me he said daddy all I want to do is grow up and be just like Mr. Wonderful and so it was a great moment it was a really cool moment I was a little hurt that he didn't say I want to grow up and be like you that's where I thought I was going to end yeah but that's okay second best thing is Mr.

52:08Wonderful you know what Mr. Wonderful is not a bad place for him to end So, you know, that's the inspiration, though, that I think in many cases makes entrepreneurs do what they do. I'll tell you one last funny story. When I started my first company, Opinions, it was definitely a high flyer of the dot-com boom. It was also almost a bust during the dot-com bust, but it was a big high flyer. And when we launched the company, there was a big, splashy New York Times magazine article about the launch of Opinions. The name of the article is Instant Company. It was about just how fast we started this company at internet speed.

52:44And I got a call about two years into ePinions from a guy named Josh Koppelman. Josh is the founder of First Round. Yeah, he's the best. But some people may not know that before he became an incredible, maybe one of the best early investors in the history of Silicon Valley, he was an entrepreneur. And he started a company called Half.com, which he ultimately sold to eBay. And when I was talking with him, because we were talking about doing a business development deal, he said, hey, you know, I got to tell you something. I started Hap.com because I'd had this idea for a couple of years. And then I read about your company, the instant company.

53:21And I thought to myself, if this guy can start a company that fast, surely I can as well. And it was an incredible compliment. It was also a little humbling because at the time, Hap.com was a lot more successful than what he opinions was. Now, Opinions, which became Shopping.com, ultimately was also purchased by eBay, just like Josh's company. But it reminded me that we do get inspired by seeing things that other people do. And Sarah Fryer used to say, if you can see it, you can be it. And I think that's a really powerful expression. And it's why listening to these stories, it's why I love podcasts.

54:01It's why I love listening to your podcast and learning about the journeys of the guests because it makes me think about my own journey. And it makes me think that maybe I can do some of the same things.

54:12Erica Wenger: I love that. Well, I'm so glad you and Josh know each other. And I appreciate the kind words about the podcast. I think that's the power of media. You know, whether it's Shark Tank or it's stuff like this, we never know who we're about to inspire. And someone listening to this right now literally might go start their company because they've heard what you're saying and build the next great thing. I'm sure they will. and I'm sure whatever they're building is going to be way more successful than anything I've done. And that's great. Well, we can only hope. We can only hope for both of us. So here's a problem I hear constantly from operators.

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55:15Erica Wenger: It's game-changing for people like me who want to understand what's going on under the hood, but we are not the data experts. It's funny, too, because I feel like every time I look over my operator friend's shoulders, whether they're in product or marketing or ops, they often have a Hex dashboard pulled up. It's a great tool. Trailblazers listeners get an exclusive 30-day free trial at hex.ai slash trailblazers. All right, let's get to our Trailblazer trade-offs. Okay, let me know what comes to mind. Book in hand or podcast in ears? Book in hand. I'm old school. Okay, any favorites? There was an article that I just read, which was the 25 books that you must read in your lifetime.

55:50And one of the ones that I thought was particularly interesting was a John Steinbeck book, East of Eden. And it reminded me because I did take English literature classes at Stanford. I had to negotiate with my Indian physician immigrant parents, you know, to them, English literature. My mom says, don't you already know how to speak English? Why don't you take an English class? I was like, no, mom, it's English literature. But it just reminded me that the power of a book to create a movie in one's mind is really, really, really special. And we all know that feeling of losing ourselves in a book i think that can happen in a podcast but there's something about a book that's almost metaphysical that i think is really powerful i agree with also the length of it too

56:33Erica Wenger: it's like you buy yourself like you know what is it six seven eight hours of real depth um you can't focus on anything else but the thing you can't speed it up to 1.25 exactly and work out while you're doing it or something else yeah yeah yeah that's amazing um higher slow or fire fast It depends on the position. But I think the most important thing is to know what you've done so that you can react accordingly. And so if you have a burning need in a company, sometimes it's very, very difficult to hire slow, right? And you just need to know that when you hire fast, you may have to fire fast and that's okay because you've made that trade off.

57:09sometimes the role involves so many what jeff bezos would call one-way doors where the person's going to make really important decisions that cannot be undone if they're the wrong decision then you have to hire slow and you just need to be patient enough to understand that hey this is going to take time but we need to get it right i would say when you're talking about a board of directors go slow yeah they'll be there forever exactly i also think as a public company it's

57:36Erica Wenger: just a different calculus because everything is just so much more out in the open that like any little subtle leadership change has ripple effects would you know it it does but it comes back to that idea that it would be easier whether it's a public company where everything is examined with a microscope or even when it's a private company it would be easier to not admit a mistake but the best CEOs in the world probably are getting seven out of 10 hires correct, right? And so if the best CEOs in the world are having to part ways with 30 % of the people they hire to be on their executive teams, what does that mean for normal people like us, right?

58:16It means we're going to make mistakes. We should admit those mistakes. We should treat those people with dignity. And then we should actually make the decision. Because if you have someone on your team who's not the right fit, it's not good for them either right i mean that's the thing that i think we sometimes forget we think oh gosh i could never do this to that person right but if you do it with dignity how many times has someone been in a bad place for them but then left with dignity and then gone on to do amazing things it happens all the time it's about fit rarely is it a bad person right if it's a bad person okay get rid of the person immediately and move on right but most of the time it's about fit.

58:55Let's find people their best fit. And if it's not the right fit, let's figure out how to make it the right fit or figure out how to exit the person with dignity.

59:03Erica Wenger: Totally. Totally. Yeah, you'd be surprised when people have gotten fired that then go on to do big things like Oprah is the classic, you know, which and she's obviously such a legend. 10 small wins or one big moonshot? I always want to do one big moonshot because it's more romantic and it's more ambitious. but I have found that success is almost always the result of small incremental things leading to what appears to be a giant moonshot. So even when you study business and you see things that look like big moonshots that worked out, if you start to scratch below the surface a little bit, what you realize is there were lots of things that contributed to that one big thing.

59:44So the power of compounding is I think the story of business success. Absolutely.

59:50Erica Wenger: I love that reframe too, that they go hand in hand. Being early or being right? You got to do both. I mean, I think if you're early, it's not good enough. If you're right, but you're not early, the opportunity may be gone. The magic of a startup is when you do enough that's right and you're early enough that the incumbents who have more resources aren't there yet. So to truly be innovative, you have to be early and right. That's so much of the VC game too. We always look for that. What's the best teacher, a mentor or a mistake? That's a great one. I mean, I hate to answer all of these questions by saying both, so I'll choose one here.

1:00:37The mentor is more friendly. The mistake is more impactful. Mistakes, if we can truly find a way to contextualize them and learn from them can be very, very powerful in terms of helping us move forward.

1:00:53Erica Wenger: Yeah. Very painful though. Painful, but impactful. Yeah. No pain, no gain. No pain, no gain. Exactly. Is the future of AI abundance or chaos? For me, definitely abundance. We may have to live through some chaos to get there. We almost certainly will. That is actually, in many ways, the tradition of innovation. It seems chaotic. It's hard for people to understand. We don't know who the winners are going to be. We don't know what the disruptions will be. We don't know what the positives and negatives will be. But I love that word abundance, because to me, the power of technology is democratizing access to something that gives human beings leverage.

1:01:29And to me, AI is the single most powerful example of that in our lifetimes. And I truly believe that it will bring abundance. And I'm very excited about that. There will be some bumps before we get there.

1:01:42Erica Wenger: Totally. I do want to just mention that you talk about AI democratizing access, which I agree, but to your earlier point, Nextdoor is a non-native company and used by 99 % of cities, something like one in three households in 99 % of cities. So there's also an interesting counter argument, right, of like, you can do it as a non-native AI company to be truly democratizing access and creating software and interesting products for everyone that you guys have done. Well, my most powerful inspiration with Nextdoor is that we should use the power and leverage of AI as a tool, not as a substitute. It's not a substitute for human connection.

1:02:19Nextdoor is not a substitute for getting to know your neighbors or a substitute for getting out in your neighborhood in the real world. it's a tool that may break the ice, that may give you more leverage because you can hear more points of view, that may help you discover things and be introduced to things that you're not aware of, right? But ultimately, we need to pair the age of intelligence, which is this great abundant AI world that we're living in, with human connection. And human connection is really where it's at. But I think AI will help us get there versus take it away.

1:02:50Erica Wenger: I love that. Nirav, thank you for being here. What a great note to end on. I feel like that perfectly sums up what's next for you guys and next door. Thank you for having me. Thank you. Thanks so much for listening to the Trailblazers podcast. If you found this conversation valuable, please follow along on socials, share with a friend, leave a review, all the things. Most of all, please subscribe to our channel. It helps more contrarian builders find us and supports the work we're doing here. To learn more about what we're doing, you can visit trailblazerspod.com or my venture capital firm parkrangerscap.com or just follow along on socials at Erica underscore winger.

1:03:21Erica Wenger: Until next time, keep trailblazing.