She's Brave Podcast - Kristina Driscoll

Braving Entrepreneurship: Insights from Nextdoor Co-Founder Sarah Leary

April 09, 2024 Kristina Driscoll Episode 81
Braving Entrepreneurship: Insights from Nextdoor Co-Founder Sarah Leary
She's Brave Podcast - Kristina Driscoll
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She's Brave Podcast - Kristina Driscoll
Braving Entrepreneurship: Insights from Nextdoor Co-Founder Sarah Leary
Apr 09, 2024 Episode 81
Kristina Driscoll

In this episode of the She’s Brave Podcast, host Kristina sits down with Sarah Leary, the co-founder of Nextdoor, to delve into the intricacies of entrepreneurship and the journey behind building a billion-dollar company. Sarah shares her invaluable insights on the importance of courage, strategic partnerships, and understanding your audience. From navigating failures to embracing non-scalable tactics, Sarah’s wisdom offers key lessons for aspiring entrepreneurs at any stage of their journey. Join Kristina and Sarah as they explore the power of community, authentic connection, and the relentless pursuit of one’s dreams. Tune in for a captivating conversation filled with actionable advice and inspiration for anyone ready to brave the world of entrepreneurship.

About Sarah:
Sarah Leary is a Venture Partner at Unusual Ventures, specializing in Seed and Series A investments across enterprise and consumer startups. With a rich background spanning over 25 years, Sarah has cultivated extensive experience as an entrepreneur, investor, board member, and technology leader. Renowned for her pivotal role as the co-founder of Nextdoor, the world's largest neighborhood social network, Sarah led the charge in product development, marketing strategies, growth initiatives, and international expansion over a decade. Under her leadership, Nextdoor burgeoned from its inception to nearly $100 million in revenue, amassing a global reach spanning over 270,000 neighborhoods. Prior to Nextdoor, Sarah made significant contributions to industry-defining platforms such as Epinions, Shopping.com, and Microsoft Office, where she spearheaded product and marketing endeavors. Currently serving as an Entrepreneur in Residence at Harvard University and a board member at Spindrift Beverage Co, Sarah remains deeply involved in the startup ecosystem as an advisor and mentor. Beyond her professional pursuits, Sarah finds solace in pursuits like golfing, traveling, indulging in literature, cherishing family time, and navigating the streets on her Vespa.

Connect with Sarah:
Linkedin: https://www.linkedin.com/in/sarahleary/
Instagram: @sarahleary

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Show Notes Transcript

In this episode of the She’s Brave Podcast, host Kristina sits down with Sarah Leary, the co-founder of Nextdoor, to delve into the intricacies of entrepreneurship and the journey behind building a billion-dollar company. Sarah shares her invaluable insights on the importance of courage, strategic partnerships, and understanding your audience. From navigating failures to embracing non-scalable tactics, Sarah’s wisdom offers key lessons for aspiring entrepreneurs at any stage of their journey. Join Kristina and Sarah as they explore the power of community, authentic connection, and the relentless pursuit of one’s dreams. Tune in for a captivating conversation filled with actionable advice and inspiration for anyone ready to brave the world of entrepreneurship.

About Sarah:
Sarah Leary is a Venture Partner at Unusual Ventures, specializing in Seed and Series A investments across enterprise and consumer startups. With a rich background spanning over 25 years, Sarah has cultivated extensive experience as an entrepreneur, investor, board member, and technology leader. Renowned for her pivotal role as the co-founder of Nextdoor, the world's largest neighborhood social network, Sarah led the charge in product development, marketing strategies, growth initiatives, and international expansion over a decade. Under her leadership, Nextdoor burgeoned from its inception to nearly $100 million in revenue, amassing a global reach spanning over 270,000 neighborhoods. Prior to Nextdoor, Sarah made significant contributions to industry-defining platforms such as Epinions, Shopping.com, and Microsoft Office, where she spearheaded product and marketing endeavors. Currently serving as an Entrepreneur in Residence at Harvard University and a board member at Spindrift Beverage Co, Sarah remains deeply involved in the startup ecosystem as an advisor and mentor. Beyond her professional pursuits, Sarah finds solace in pursuits like golfing, traveling, indulging in literature, cherishing family time, and navigating the streets on her Vespa.

Connect with Sarah:
Linkedin: https://www.linkedin.com/in/sarahleary/
Instagram: @sarahleary

Loved this episode?
Leave us a review and rating here:
She's Brave Podcast on Apple Podcasts

Connect with Kristina:
She's Brave Podcast Website
Instagram
Facebook

Curious about podcasting?
Join Podcast Mastery Facebook Group



Hey everyone. It's Kristina with the She’s Brave Podcast. Today's guest is nothing short of amazing, and unbelievably inspiring. We're going to be talking about so many things.

It's mainly about having the courage to start up a business. And it's really, really important. Sarah and I were just talking before I hit record. It's really important who you team up with, who you work with when you're starting up a business. Hers is more of a traditional Silicon Valley story, but her messages and her wisdom are so pertainable to anyone at any stage of any business. Sarah Leary is the co-founder of Nextdoor, currently valued at over 1 billion. She took the company from nothing to over a hundred million in revenue before listing the company on the New York Stock Exchange. In her role at Nextdoor, she led product growth, international expansion, marketing, and operations.

She was previously head of product and marketing for opinions and shopping from prelaunch to IPO through the 620 million sale of eBay. She's currently a venture partner at Unusual Ventures. Welcome. Welcome, Sarah. 

Hi, Kristina. It's such a pleasure to be here and to be a part of this great podcast and talk to your audience.

Thanks. Thanks so much. You're amazing. I'm going to quote you and then we're going to launch into your story because it's so incredible. This quote is so beautiful. It's from LinkedIn. 

The idea of Nextdoor was lofty from day one, to help connect neighbors everywhere so they can help each other. Sounds great. The challenge was it would be hard, very hard. How to build over 200,000 authentic communities covering every neighborhood in the U.S., then on to the rest of the world. Frankly, it was daunting, but we knew it was worth the effort. We didn't shy away from the difficulty. In fact, we leaned into it.

If we could build a network for neighbors, that would be meaningful, impactful, and durable. We embraced non-scalable tactics, which I actually don't know what those are, so we're going to talk about that. We avoided shortcuts. We wanted to build something for decades to come. We insisted on real names and verified addresses.

We embraced a rigorous signup process because it was the right thing to do for neighbors. There were many doubters. But we sought out the true believers and recruited them as our early founding members, employees, city partners, and local advocates. And we found a lot of people who believed in the power of neighbors at their core.

That's incredible. In November, 2021, Nextdoor was officially listed on the New York Stock Exchange, a privilege and a feat that very few companies earn. Sarah. Wow. This is incredible. I want to know more about when you left eBay, because before we hit record, we chatted briefly and you said it wasn't a straight line from leaving eBay to starting Nextdoor.

You had some failures and you've also mentioned the really incredible power of who you team up with, who you partner with, who you are with on this journey. So those are some of the things we want to talk about today. And also just tips on starting a company, scaling it and maybe trying to get those first thousand. Tell us more. 

Wow. All right. Well, um, that quote, uh, you're bringing me back by bringing that up. And obviously it was quite a journey. And I think one of the things when you go on one of these journeys, you don't know exactly where it's going to take you. And You have to be prepared for that.

Um, and I think one of the things that was really important, and I think that quote comes shortly after we were, uh, listed publicly on the New York Stock Exchange. I think a lot of people look at. That type of milestone event. And yet what was overwhelmingly important to me were two things that really stood out.

One was the purpose, the mission, um, having that through all the ups and downs. And you, you didn't exactly call this out, but. That was a 12, 13 year journey. And so if you're not motivated by the mission about what you want to bring to the world, it's going to be really hard to stay the course and to stay energized.

Through the ups and the downs the second thing that I felt in an overwhelming way and I touch on it in that quote is all about the people with whom you go on that journey and that starts with your co-founder and your early employees. Your early customers, your early believers in the community. All of those things are part of, at least for me, the joy of the journey.

And if you don't line those 2 things up early on, it is almost impossible to sustain yourself through the trials and tribulations of creating something that hasn't existed before. So when I reflect on that quote, uh, you can hear for me, at least I hear those themes coming out loud and clearly. And I just encourage anyone who is thinking about going on an entrepreneurial journey to just think about those, those pillars.

Why am I doing this? What is it that I want to bring to the world that isn't there already? And who do I want to go on that journey with? So those are like big themes for me that have stayed true, throughout my career. Your original question, uh, I think was about eBay and about deciding to leave.

And, it wasn't a straight shot and you mentioned it in the intro. I started on this entrepreneurial journey. Uh, the first one that I did was around 1999 and that one eventually led to the creation of a company called shopping. com, which was acquired by eBay. And I found myself in a nice role at eBay as we integrated into their company.

And I have a lot of respect for eBay and it's a great company. But I had to look in the mirror and just be honest with myself. Did I want to be a part of this much larger organization or did I want to go back and start something new from scratch? I had previously joined a company with 15 employees gone on quite a ride, but I hadn't been there at the very, very beginning and so when I left eBay, part of it was I needed to take a little bit of a break and kind of recharge. And then I love that. I have to say, I love and honor that. That's significant. Go ahead. These companies, uh, take a lot of energy and it's really hard to carve out time and space to think when you're running hard, especially at a large company.

And so it took a little bit of time off, but I knew that I wanted to be a part of an entrepreneurial journey from the beginning. And one of the co-founders of that first company that I worked for was also thinking about ideas and we just clicked and as a result, we started talking about starting another company and I think, for me, it really started with who, before we figured out what we were going to tour.

That is fascinating. I have actually never heard an entrepreneur say that, that, you know, your first question was, who do I want to go on this journey with? I love this. 

Yeah, and I think it's one way to approach it is a really important piece  of the puzzle. Um,  and that um, that is my next door co-founder , uh, Nirav Tolia and We started on a variety of ideas.

The first idea that we worked on was actually not Next door. It was a precursor to next door a company called fan base that I'm sure no one's heard of Uh, I won't go into the long sorted tail, but I will tell you that we raised money. We hired a team, we launched a product. We were working on it for almost two years before we realized that we weren't onto the next best thing we offered.

Uh, and so we thought, gee, we really need to go in a different direction. We actually offered to give our investors the money back. They said, no, we believe him and, uh, why don't you take a couple of months and work on new ideas? And we took incredible that story right there, like how much faith these people had in you.

And also that's a really powerful message. You worked really hard on this company for two years and then realized it was time to quit. And I've heard that , that's a key sometimes, you have to know this isn't working. We've got to take it in another direction. 

Well, you know, as entrepreneurs, the most precious resource that you have is your time.

And if you don't, um, feel like you're on the path to something as hard as it is to step back. And think that now I will tell you, we tried multiple ways to get things going. And there was a reason why we took almost 2 years to work on it. Um, but, uh, we pivoted in a different direction. And I think 1 of the most important things was. You learn a lot from failures and we learned a lot about how to think about coming up with a great product and finding that elusive product market fit. And  again, I won't go into the long sordid tale, but a lot of it really came back to once you have a team, you have an area that you're focused on, you have an insight about an opportunity.

The really important thing is to figure out the fastest way to test an idea, the fastest and cheapest way to test an idea, to figure out whether your hypothesis about what's missing in the world and your potential solution. Actually resonates with customers and users. And so in the case of next door, we spent a couple of months interviewing, talking to neighbors, trying to understand if they wanted to be connected to one another.

And overwhelmingly we heard, yes, we would love to be able to do that. And at the time, most people. Counted on maybe their local newspaper, maybe it was flyers, or maybe they had a Yahoo group or an email listserv that they were using to share information about what was happening locally. But there was no modern way to be able to stay in touch with your neighbors and to know what was happening in your local neighborhood.

And we saw that as an opportunity. Great. Well, you've identified a problem in that case, but then you've got to come up with a potential solution. And so. We built a very simple prototype of our product and we launched it in a single neighborhood and watched what happened. And sure enough, people had things to talk about.

They were interested in connecting with one another. And at that point we had gotten some signals to tell us that there was interest out there for our particular solution to This problem and the problem being that people had lost, uh, a way to communicate with their neighbors. They had lost that sense of community.

And can we use digital technology to help bridge that gap? And so we proceeded to roll it out to another handful of neighborhoods and, uh, kept working. There were tweaks along the way and what we had to offer. And, we actually were in private beta for an entire year , before we fully launched the product , to the public, and that was a really important year to learn and iterate.

And improve the product to such that it was ready for primetime. And so that journey is one of testing and iterating in a small contained way, uh, before you're ready to really push it out and make it available to the broader public. And I think it's something that. Every entrepreneur needs to be able to do this since we started next door, since a book that's been written called lean startup that talks a lot about this testing and iterating approach to product development and to coming up with something new that I think is worth it for people to read.

But at its core. It basically says you can have a hypothesis about a solution in the world. How can you test it and verify it with real users before you try and market it and get it out to hundreds, thousands, and potentially millions of people. , and I think that's why I try to encourage people to think a little bit when they start.

You can have this, but you've got to almost create the Petri dish for Let's figure out , if we've created a solution that , the customers, the users that we're going after love, and if they do, then we're really onto something. 

Yeah. I have never heard this  and my favorite people to interview are entrepreneurs and I've never heard this and it's a really powerful concept of , what's the least expensive, you Effective way to test this, you know, before we like to throw a bunch of marketing dollars at it.

It's huge. 

Well, you know, it's interesting. I think as entrepreneurs, we're dreamers and. You know, it's a little bit crazy to be an entrepreneur. , you're basically saying, I see something that's missing in the world and I want to bring it to the world. Okay. Well, you have to dream a bit about that and you can have your ideas about how to solve it.

And if you're not careful, you can convince yourself that you're right. , and I think that part of being an entrepreneur is being able to have that ability to suspend disbelief of all the things that could be hard or could go wrong and basically say, well, what if everything went right? Okay, does that seem like a future?

I want to create. Yes. But then you have to park that aside and be a hardcore realist to say, all right. How can I test all those assumptions and figure out how I could make that a reality? And the honest truth is you come up with a plan in your head almost without fail. There's something about it that's wrong or you're off.

But the trick is how do you take those insights that you have and start testing them with users to figure out The right path through. And in our case, we spent almost a year in private beta testing and iterating so many facets of the platform and , how neighbors would use it, the direction that we go in, and even at the time that we launched, that was just the beginning of the journey of iterating and learning how people were going to use it and how we could continue to improve it along the way.

And so. A lot of the things that we really focused on early on was taking our ideas and testing them in practice, maybe 1 neighborhood to 10 neighborhoods at a time - before we really perfected it and brought it into existence. I think. One piece of it that really helped me in thinking through this was to really think through these non-scalable ways to test something.

And you mentioned this in your intro. If I could explain a little bit about what that means, I think as an entrepreneur, a lot of times people are thinking about how to scale, how do I get to a hundred customers, a thousand customers, 10, 000, a hundred thousand, a million. And certainly in Silicon Valley, you would hear people talk about millions, but we had to really shrink that back down and say, well, how do we get the first 10 neighborhoods?

And then once we figured that, how do you get the next hundred neighborhoods? And in the beginning, someone might say to you, Oh, there's all these marketing campaigns that you can use and these different paths. For me, I was like, well, first of all, I need to learn who my customers are. What do they really care about?

How can I provide their solution? And so for me, I found it much more useful to sit down across the table from someone in a coffee shop and talk to them. 

That's fascinating. I love this. 

Now, of course, that's not the way you're going to grow to 200, 000 neighborhoods. That's not a repeatable process, but those first hundred founding members that were the ones that brought next door to their communities, talking to them and hearing what mattered to them, what they cared about, what they were concerned about, that was pure.

Gold in terms of understanding users and doing that primary research. And so there are all these things that you could learn. From having these one on one conversations. In many cases, it can be better than doing a survey to a thousand people where you get the emotional connection that people have with things.

And that approach to early product development stayed with us. Even as we moved into, okay, we now have a product. How do we make it something that people in neighborhoods across the country are aware of? And for a lot of people, they think of marketing like, oh, I don't know, take out a billboard or run an ad or, um, you know, run Google ads or something and none of those felt Really authentic to next door in the early days.

This was a platform where communities came together and neighbors would tell each other about next door. And that's how the word would get out. And so we spent a lot of time trying to understand. Who were the people in the community that others turn to and how do we get in touch with them? At one point, we had community organizers that would help get neighborhoods started in cities across the country.

This is not something that you typically would see in a Silicon Valley company. Uh, it was actually a page that was taken out of, um, a, uh, campaign style, uh, rollout, a ground grassroots approach to things that was more authentic to next door than. Maybe some of the ways that other companies from Silicon Valley might've grown.

And so the only way that you come up with those ideas is to really understand who your users are. What is the context that makes sense for them to be introduced to your product and then be innovative about how to roll that out and then how to eventually scale it. And I just encourage people, the more time that you can spend one on one with your customers and really understanding their motivations, uh, that's where you're going to get the insights that will help you figure it out.

Innovative ways to approach the market. If you're just looking over your shoulders and what everyone else is doing. Um, I think that that can be valuable to like, learn about how other people have done it, but you've got to understand your market well and understand what really is going to be. A message that resonates with the customers that you're going after.

And that applies to every business that's out there. 

I love this so much because we live in a world right now where even for me, I've only been podcasting a year. I'm in the top 2 percent globally. And marketers want to work with me, but they just want to put in as little effort as possible. They don't care who my customer is.

They don't want to take the time to learn it. So I have found that I've had to do the grassroots work myself. Kind of like what you said, I've had to think outside of the box on how I'm going to grow this business, that kind of a thing. And we live in a world where we are bombarded with people saying, let me help you.

Let me help market you. Let me, you know, but they're not, they're not you. And they are approaching things differently. And like what you said, they make it sound like put. This amount of money, give it to me and I'll fix it for you. And it doesn't work that way.

Well, I mean, ultimately, for any business out there, uh, or just about any business, maybe there's a few exceptions to this, your ability to connect with a user, a customer, or in your case, an audience, it's all about the longevity of that connection and how long are they going to stick around? And the only way that that works is if you are delivering useful content to people that they find valuable, because then they're going to come back again and again and again.

And so if you can create a product, a service. A podcast that is producing unique content that folks want to come back to again and again. Well, the value of that audience is immeasurable, right? It's infinite. And so , to me, it has more to do with the quality of the customers and the users. You bring on board versus the speed with which you bring them on and so until you're ready to receive those users, you shouldn't be turning the crank on the marketing because.

What will happen is people will come, they won't find exactly what they were looking for, and then they'll leap, , and those people become twice as hard to be able to bring back in the future. 

Wow. And that's exactly kind of what happened to me, if I was, you know, experimenting a little bit with marketing, but it's all about authenticity and I love how you keep talking about figuring out what is it my customer needs, you know, how can I help them?

And that's basically what I've been working on too. What do my listeners want to hear? What do they want to know? So every question that I ask you is, you know, , how can my listener benefit from your expertise and knowledge? This has been incredible, I mean, I can't believe how much we've packed in, in such a short time.

Amount of time, and  it's a very different angle from. Entrepreneurs that I have interviewed in the past and it's fascinating and I want to commend you on building next door because community is a huge issue that we are continuing to have in our society. And I love this whole concept of can we use technology to help create more community?

And here we are after COVID and, you know, We need it more than ever. Right. 

I think human beings have this innate desire to be connected to others, especially with people who are proximate to them. And that isn't something that next door invented. I think that that's just core to who we are as human beings.

And I think creating a platform where people can learn about what's happening in their local community so that they can further engage still remains a huge opportunity and something that, as you mentioned, is probably in higher demand now than it has ever been. Lifetime coming off the heels of COVID.

And so, uh, it's still an amazing, uh, opportunity to be able to shift the way that people engage in their local community and it's part of why the mission of Nextdoor continues to resonate. 

Yeah, definitely. And you continue to do many, many amazing things. I'm going to ask you. If you could teach one thing to everyone in the world, what would it be?

I think that there are so many times in our lives, whether we're entrepreneurs, or not, where we have an idea about doing something and we start to dream. And then there's a part of our brain that starts to think about everything that can go wrong. And that's a very normal thing  to do. But. I would just encourage anyone out there that when you have these moments of dreaming about a possibility, professionally, personally,  you name it to park it and start writing it down, well, what would have to be true for this to happen?

So , when all of a sudden you start hearing the, oh, that'll never work. That'll never work. Is there a way for you to run a little experiment? To figure out whether or not it's truly possible and instead of getting wrapped up in the anxiety of it all, think about how I could test my theory here and either gain more confidence about what I was that I thought we could do.

I could change it, tweak it just a little bit. Or maybe you're right, , it's not gonna work and I should move on to something else and just move out of just thinking about things and move into some systematic way of testing out the assumptions and figuring out whether , you should actually go for it.

Because I think so often we get. In the way of ourselves, and I get it life's complicated. You don't want to be taking risks every single day. But are there ways that you can break down a problem and really think it through and gain confidence as to whether or not it's a bet you want to go for.

It's something that you want to change in your life . And I think it's just a way to take ideas and empower yourself , to have agency over your life in whatever direction you want to take it. And so much about entrepreneurship to me is about having that agency in your life to create a future that you dreamed up.

And the reality is a lot of people get in their own way and stop themselves from actually executing on the dream. And then they're like, Oh, I had that idea. I wish I had done that. And I think if you can go through life saying when you have those ideas, you have a process by which you think through whether or not it's a really good idea, or it needs to change a little bit, or it's just not a good idea, then you can be.

Yeah, much more captain of your own ship, which I think at the end of the day for a lot of us, we want to just have agency about realizing all the dreams that we have in our minds and figuring out the right ones to follow. 

Oh my gosh. Sarah Leary, you are my absolute favorite podcast  guest that I have ever had.

You're sweet. Well, I'm excited to be here. Thank you for creating this platform and an opportunity to meet you and connect with so many people out there. It's great to be able to have a place where people can learn about opportunities and ways that they can improve their own lives.

Absolutely. And that's what I'm doing for women all over the world saying, yes, you can. So that, that being said, please let. My audience know how they can follow you, you know, stay in touch with you, reach out to you. 

Well, uh, you can find me on LinkedIn. You can find me on X formerly known as Twitter at Sarah Leary, um, or, uh, just sign up for next door in your own neighborhood.

Ah, wonderful. We will put everything in the show notes. You are a true, true gift to this world, Sarah. Thank you. Thank you. I can't thank you enough for your time today. 

Well, I appreciate the opportunity to chat with you and to connect with your audience