In Search Of Excellence - Sarah Friar: Taking Risks in Career and Life | E28

Episode Date: September 27, 2022

Sarah Friar learned about the power of community from an early age. Growing up in Northern Ireland during a time of tremendous violence showed her the importance of finding common ground and taught her how to create resilience from within, both of which are lessons that she continues to live by today. Even in moments of fear and despair, Sarah was able to find her resilience and take risks throughout her career.After checking all the boxes that she thought would lead her to become a partner at Goldman Sachs, Sarah received the news that she wouldn’t be getting the promotion she had been striving for. She could have stayed at Goldman, but her husband said something to her that she couldn’t shake — losing the promotion has set her free.From there, Sarah considered what she’s good at, what she’s passionate about, and what the world needs, which ultimately led her to her current role. As the CEO of Nextdoor, a hyperlocal social networking service for neighborhoods, Sarah is now working to strengthen the power of community — a reflection of her lessons learned early on.In this episode, Randall and Sarah discuss how curiosity and resilience are the keys to finding your path; how finding common ground can unlock social capital that allows you to get things done in the world; advice to women today who are working in a sexist environment; what to do when you aren’t passionate about your work but are making good money; why searching for an emotional connection helps to build stronger companies; why you should be taking risks in your career frequently; the role politics has in the workspace; how to use moments of failure to help you rise; and more… Topics include: -The power of community-Why it’s necessary to do the nitty-gritty work-Why it is important to learn both inside and outside of the classroom-The importance of finding purpose at work-How to use your fears to spur you into action-Whether or not you should have a plan B-Why extreme preparation matters -Prioritizing mental health-Why job hopping is a red flag-How to strike the right work-life balance-The secret side of philanthropy-Why having a diversity of experience is advantageousPrior to Nextdoor, Sarah served as the chief financial officer at Square. Under Sarah’s leadership, the company launched its initial public offering in 2015 and added $30 billion in market capitalization.Sarah grew up in Northern Ireland and earned her MEng in Metallurgy, Economics, and Management from the University of Oxford and her MBA from the Stanford University Graduate School of Business, where she graduated as an Arjay Miller scholar.Resources mentioned:NextdoorBooks mentioned: Range: Why Generalists Triumph in a Specialized World,  by David EpsteinSponsors:Sandee | Bliss: BeachesWant to Connect? Reach out to us online!Website | Instagram | LinkedIn

If you are striving and you are in search of excellence, you must be taking risks. A lot of people somehow think that if they go to the thing and it's not successful, they have become less successful. I would actually advise you to think the opposite. People way overestimate the risk to their career by doing something different that doesn't work out, then they estimate the upside, frankly, to their career and to their life of doing something different, even if it doesn't work out. Welcome to In Search of Excellence, which is about our quest for greatness and our desire to be the very best we can be, to learn, educate, and motivate ourselves to live up to our highest potential. It's about planning for excellence and how we achieve excellence through incredibly hard

work, dedication, and perseverance. It's about believing in ourselves and the ability to overcome the many obstacles we all face on our way there. Achieving excellence is our goal and it's never easy to do. We all have different backgrounds, personalities, and surroundings. We all have different routes on how we hope and want to get there. My guest today is Sarah Fryer. Sarah is CEO of Nextdoor, a social media network that operates in 11 countries around the world and which is used in more than 275,000 neighborhoods in the United States, nearly one in three households here. From 2012 to 2018, Sarah was the CEO of Square, which is now known as Block. And under her leadership, the company went public in 2015 and added $30 billion in market value during her tenure there.

Prior to her role at Square, Sarah served as Senior Vice President of Finance and Strategy at Salesforce. She currently serves on the boards of Walmart and Consensus and is a co-founder of Ladies Who Launch, a network that mentors and inspires women entrepreneurs and business owners. She is also a dedicated philanthropist and is on the board of Operation Hope, the nation's largest nonprofit dedicated to financial empowerment for underserved communities. Sarah, it's a pleasure to have you on my show. Welcome to In Search of Excellence. Randall, thank you so much for having me. I'm really excited to chat. I always start my podcast with our family because from the moment we're born, our family helps shape our personality, our values, and the preparation for our future.

You grew up in Northern Ireland in the small village of Sian Mills, a border town with Ireland that was started by the Quakers and which today has a population of a little over 2,000 people. Sian Mills is only three miles south of the town of Strabane, which was once the most bombed town in Europe in proportion to its size, was also the most bombed town in Northern Ireland during what is known as the Troubles, a very violent 30-year conflict between Catholics and Protestants that killed and injured thousands of people, which ended on April 10th, 1988, with the signing of what is known as the Good Friday Agreement. Your mom, May, was a local midwife and delivered all

the babies in town, most of which were home births, and your dad, Harry, was a local midwife and delivered all the babies in town, most of which were homebrews, and your dad, Harry, was the personnel manager at the Herdman's Flax Mill that made Irish linen thread. The mill was the only employer and was the whole reason why the village existed, which meant that he was essentially the head of people for the village. Then one day, you were sitting in your career room at school, which resembled a bread box, and you read in a career magazine that the accounting firm Arthur Anderson, which you had never heard of before, had a scholarship program where you would go and work for them for a year before you went to college. And as part of that scholarship, they also gave you a stipend where you could travel for five

months. You applied, got it, worked through a year, packed a backpack and went to Thailand, Malaysia, Hong Kong, and Singapore and Australia. Can you tell us what it was like growing up with a tremendous amount of violence near you, the time your best friend Lisa saw bombers plant a bomb and the two of you ran back to school to warn the others, the sense of community and volunteerism your parents had, which later injured your dad, the honor from Queen Elizabeth II, and how all of this shaped your influence as a child. Wow, that is a huge question. Are we going to spend the whole podcast there? Thank you for that. Yeah, growing up in Northern Ireland, certainly you look back at your life, very formative. I did grow up during the Troubles, and yet there was a dichotomy there. On the one

hand, I'd say Northern Ireland was a wonderful community-driven place to live. Very, very safe. We rarely locked our doors. We'd leave our car keys in the car. So that way you'd always find them. And as you pointed out, my parents were really the life and soul of their community. They still are to this day in their 80s. They're still out there doing things like fundraising for cancer awareness, for example.

On the other side, there was this terrible backdrop of the troubles, senseless violence, people died. You talk about Lisa and I spotting this bombing left. I'll give her full credit. We drove past it with my mom as the bombers were literally planting it, didn't quite realize what was going on. She was the one who saw them jump out and get on the back of a motorbike and kind of steam off into the distance and had the wherewithal to start running. I think the bomber actually said to her, better go tell the police. And then both of us together were pounding on that school door to let people know there was danger. And so just learning to live in those two different mindsets was hard.

And you realize, you look back on it, it's not something you'd ever want your own children to go through. But I think it did teach me about resilience. It did teach me a lot about this power of community. It also instills in me, frankly, a need to push against when I see communities getting riven apart and a big

part of why I've come to Nextdoor. But really thankful for that upbringing. And my parents have had an incredible impact on who I am today and continue to do so. And the way they give back is quite inspiring. A lot of us learn very important lessons at a young age that impact our future, particularly from summer jobs. You grew up in a rural part of the country, and your first job, where you worked for many summers, was working on your Uncle Louie's farm, where he would get you up at six in the morning, which is the start of a very long day. Can you tell us about the lessons you learned there, and what's your advice to others who don't want to do the nitty-gritty work because they're too smart to do it, it's beneath their intelligence level, or they think it's denigrating and want to work on more exciting things. And how necessary is

doing the nitty gritty work to being successful in our careers, whether you're working at a company or are an entrepreneur? Yeah, I mean, it's everything. So there's two big learnings from my Uncle Louie, God bless him. Number one was the power of hard work. And number two was act like an owner is how we talk about it today here at Nextdoor. There is no job too small when you are that owner. And so for sure, he got us kids up bright and early to do all sorts of things. There was the day-to-day stuff that had to happen on a farm if we were bringing in cattle to a barn, if we were bringing sheep in because it was lambing season. But then there were the extraordinary things. And I remember so clearly that one of those summers that so stands out, he decided that he wanted to be able

to plant a mountain field that was pretty rocky. He had to clear a bunch of rocks or Northern Irish stones off the mountain. And the only way he could do that using his resources was frankly the people army. It was us as kids. And so he somehow got us in the mindset of being willing to walk along behind this tractor that had a flatbed truck on it to throw these rocks up onto the top of it.

And if you were little, you threw little rocks. And if you were big, you threw bigger ones. And the men would come out and help with really big ones. The incentive was you got to drive the tractor. So he did know about incentives and motivation too, which is a good thing to think on when you're a leader. The second part of that, beyond just the hard work, I think there is tremendous power in being able to go from very deep in the weeds to very high up strategic thinking.

McKinsey, later training, talked about this idea of porpoising. So if you've ever seen a porpoise going through the water, kind of those dolphin things, right? They're going very deep and then they jump right out of the water. And I think there's tremendous importance to that. Number one, to understand your business or the ecosystem that you're playing in. Number two, it's kind of to prove to everyone around you that details matter. I once had an employee say to me, the thing is, I'm never sure which detail is going to matter to you. And I'm like, that's exactly right. Because if you think

they all matter to me, and I may dig in on any of them, you will make sure the details are well taken care of. But I do think the confounding part of that as a leader can be spending too much time stuck in the weeds and not coming way up for breadth and for elevation, because you are also really tasked with having strong peripheral vision. You're often the leader that's looking most outside the company, that's really clearly seeing what's being asked from by customers, as well as understanding what's going on internally. And so you do have to strike that balance. I think it's one of the hardest things to do as a leader.

People have a tendency to want to sit in either zone, either stuck in the weeds or so high, they actually don't really understand what's happening. I think the great leaders find that balance of how to do both. Let's talk about education, which I think is one of the most important ingredients to our future success. You grew up in a family where education was highly valued and you were always the A-plus student. When people graduated high school in scion mills, most people got vocational degrees. But if you did go to college, the traditional path was to go into law or medicine like your brother, who is now a doctor. Neither of your parents went to a university, and college wasn't something that they talked about. You wanted to go, regardless, to Oxford, which you thought was your one chance to make it out of Scion Mills. But there was a

problem with that. You couldn't afford to go. Then one day, you're sitting in your career school, which resembled a breadbox. You read in a career magazine that the firm, Arthur Anderson, which you had never heard of before, had a scholarship program where you would go and work for them for a year before you went to college. And as part of the scholarship, they also gave you a stipend where you could travel for five months. You applied, you got it, you worked there a year, and then you backpacked to Thailand, Malaysia, Hong Kong, Singapore, and Australia.

When you applied to Oxford, you didn't think you were going to get in. Part of the application was the interview, and you were intimidated because most of the other kids had gone to private feeder schools and were very accomplished. They were also wearing the right kind of suits and looked the part. You didn't. You were wearing your church clothes. When you went to the interview, there were three old men sitting there, and they asked you to solve Boyle's Law, which for those of us who don't know is a statement in physics that says the volume of gas at constant temperature varies inversely with the pressure exerted on it. Great trivia question. So you go to the blackboard and you proved out the theorem. When you look down, you realize you had chalk all over your church clothes. Then you thought they weren't going to

let you in, but they did and you got the scholarship. Can you tell us about playing with Legos as a kid, taking apart the family radio and fixing the Hoover vacuums and the machinery on your Uncle Louie's farm, and how this led to your major in college? And what's your advice about classes students should take if they're like most college students and don't know what they want to do when they get out of school? Yeah, I'm blushing at parts of that because it always brings me back to the sheer horror of realizing I'm not in the correct clothing. And I mean, you're right. There's so much in that question.

I didn't come from a family that had gone to university. So I think, number one, there's a lot of learning about you have to find within yourself the push often. It's not going to come pre-prescribed or packaged for you, even from the people who love you the dearest. And in fact, sometimes they can be the impediment. As I've already said, my parents are a huge influence on who I am today,

but they also were risk-averse in this. They did not want me particularly to leave Northern Ireland. They weren't totally, I mean, they kind of thought I should go to university, but I wouldn't say it was like the be all and end all for them. So I had to find self-motivation, first of all. Second, curiosity. So you kind of led back to things I loved to do as a child.

I was always taking things apart and I loved to put them back together again. And I think that natural curiosity about the world around me got me thinking much more about subjects like engineering. So not the kind of tried and true route that every other kid around me felt like they were taking. And then I think this third part is finding, even in your moments of fear, despair,

like not feeling like you fit in, you have to find your resilience moment and the place that you're going to find optimism and passion from. So for sure, right, that first interview at Oxford was hard. That interview with Arthur Anderson to get the scholarship was hard. But I managed to find common ground,

whether it was with the people I was meeting, the place that I was in. I just managed to find those moments of common ground that made it feel doable. I'll give you an example, right? When I was going to Arthur bond, frankly, in our kind of Irish roots that made me feel more comfortable, but also made me feel like I could find some belonging there. I would say to anyone listening, you got to find within yourself that kind of resilience. And it's not going to come from up above and suddenly descend upon you. It is kind of really self-taught and you need to be explicit about it. And that can come from things like digging in on sports. I played the piano growing up, like things that you really have to strive at that don't just come easily. Second thing is being naturally curious. I wouldn't expect that most people listening, if they're thinking about college right now,

would know exactly what they want to do with the rest of their life. In fact, most jobs that you're going to do probably don't exist today. That's the beauty of how fast our world is changing. But stay curious and stay broad. I see far too many people wanting to become experts like when they're 22. And then I think this third thing is common ground. I'm probably going to come back to it later in this podcast because it's a huge underpinning of community and neighborhood, is that even when we disagree with people, finding common ground can be an incredible unlock to building up social capital that allows you to get things done in the world, even when you don't necessarily agree with everything that that person stands for. In your third year at Oxford, you were looking for an internship. You could have worked at British Gas or British Coal or another company in the UK. But a friend of a friend mentioned a company named Ashanti Gold that was based in Ghana,

which you thought sounded interesting because you wanted to get out and see the world. You also wanted to experience what life was like in a gold mine because mining for gold is incredibly damaging to the environment because they use arsenic, a highly toxic chemical, which cannot be removed once it's in the environment. And you wanted to see if there were ways to minimize its use through a process called biox, which would extract gold out of sulfide ores, which would be much better for the environment. Can you tell us about being the only woman there, how you had to make tea for the men, how your experiences there had led you to change your major, and what's your advice to women of any age who are treated any differently than men at work, or who are working in a sexist environment but need the job because they need to put food on

the table and don't want to rock the boat? And separate from that is what we learn outside of the classroom as important or more important than what we learn inside of the classroom. Right. Going back to those words that I used, first of all, finding what creates resilience within you, right? A lot of that comes from what you're passionate about. And I've always had the Irish wanderlust. I love to travel. I got the first peep at it when I did that Arthur Anderson scholarship and they allowed me to head off to Asia. So I was 18, 19 with a backpack on my back, sometimes by myself, sometimes traveling in a group or with another individual, but pretty young, frankly, to be set free around Asia for cell phones.

There was no way to contact home. I recognized that passion. And so when it came to getting that internship, I wanted to weave in travel. And I always say this, like, I love travel. I didn't become like an airline pilot or whatever, but I've always tried to find a way where travel is an inherent part of the job that I do because it gives me kind of the passion and the excitement to keep doing the job. Second thing was curiosity. So it wasn't normal to go off and work on a goldmine in Ghana.

I was incredibly lucky to find an internship that would take me on to do that. But I was incredibly curious about the world and the latter part where you ask about what you learn in the world versus what you learn academically. I was like a microcosm of that because I had clearly read textbooks on how things like metals, my degree was in metallurgy, but really material science, but how metals came out of the ground and got processed. I had done lab processes to see how different metals would react in lab settings, but to go to an actual working mine at scale, Chanticle feels very big, and see just the scale of the operation to understand like when you read about environmental pollution in a book, it's very different from when you see it in action,

when you see water in streams that is polluted, for example, or you see these huge tailings dams that at any moment could literally mudslide down and wipe out whole villages, for example. And so being able to kind of see in real life, not just what you read in a book or experience virtually, incredibly important. So everyone listening, right, we're moving to a world that is increasingly virtual. We're talking about the metaverse, but please don't lose the in real life physicality of

actually seeing something happen, whether it's in an educational setting, a work setting, a personal setting. And then on the being in a tough environment where you're not, you don't have a lot of belonging, you know, advice there. Again, it comes back to what's going to keep you resilient. Figure that out in early age and keep coming back to it, right? So for me, I am a bit of an eternal optimist, but it's waking up every day and being thoughtful about, you know, what am I going to learn this day? What am I going to push myself on? Finding people with common ground to you, right?

Again, that setting, there wasn't a lot of common ground. But what I did find is while there weren't a lot of white women working in that environment, in fact, I think I might have been the only one. There were a lot of Ghanaian women. They did different jobs, but just finding their support and their community was a way to kind of start to fit in a little bit more. And then I think the final part of it was also I had to learn the moment to stand up for myself and the moments when sometimes it's easier to kind of save yourself for the battle that's worth fighting. Did I love being asked to make tea? Definitely not.

And so I would really try to find a way to not maybe go do the thing that needed to get done, back to like acting like an owner, sometimes even the most trivial task, need someone to do it, no matter who you are. But also to kind of show my value and to push. Like there was a moment where they didn't want me going underground because it was deemed not safe, you know, particularly for the girl on the mine. I'll use that word because I was a woman, not a girl, but that's what I was called. And I really pushed so hard they couldn't say no because I realized that was the most important thing in that moment

to be successful. So I figured out what was the most important thing to push on and probably allowed some of the other things to keep happening in some ways to kind of create balance and allow for some acceptance rather than just digging in my heels and saying no to everything that didn't kind of fit my particular worldview at that moment. Do you have any specific advice to women today who are working in a sexist environment? What should they do? Should they stay on the job and go somewhere else? What's your best advice to women today who are working in a sexist environment. What should they do? Should they stay on the job and go somewhere else? What's your best advice to them? It depends a little on your situation.

I don't think there's a single solve for everything. What I've been working on with a lot of the women, even within my company right now, which I certainly hope is not a sexist environment, is number one, there's a set of traits being very kind of gender stereotypical. But one is women often have a view of like expecting others to recognize good work just serendipitously. No, I want you to really think about what are you working on and why is it important to the business? What's the impact you're having? Create your elevator pitch and make sure you are telling it everywhere you go. That's number one, because in the end, all these isms tend to go away if you're mission critical to the business.

Second thing is think about your brand. How do you want to show up? It's harder for people to go put you in a box, again, of isms, like the woman that can't go down the mine. If you're building a brand that says, no, that's not who I am. It's not what I stand for. I'll often jokingly say something like, I've never met a number I didn't like. It's my backward way of kind of saying, I am a hardcore numbers person. And if you're going to come bring me anything, you better bring me data alongside it. But I do it in a more jokey way. It's a little bit more approachable. And then I think the third trait that I've been working on them with is this idea of connecting your network. So again, women are very good at building networks and building connections.

That's how I found that route to an internship in Ghana. But they often feel like they can't leverage the network. They need to do something before they can ask something in return. Men, I think, have a much more long-term view of their networks where they understand it will be give and take over a long period of time, but they often have no problem asking for something long before they're willing to give or able to give. And so I'm just trying to change the talk track in women's heads that you don't always have to be the giver first to then receive.

Just think about a network as something that over time is going to accrue benefit to both. I'm really talking about your professional networks here, where there's much more extrinsic need to do it because it's going to further your career, the business that you're working in, in some ways, very explicitly. This episode of In Search of Excellence is brought to you by Sandy.com. S-A-N-D-E-E.com. We are a Yelp for beaches and have created the world's most comprehensive beach resource by cataloging more than 100 categories of information for every beach in the world, more than 100,000 beaches in 212 countries. Sandy.com provides beach goers around the world with detailed, comprehensive, and easy-to-use

information to help them plan their perfect beach getaway at home and abroad, and to make sure you're never disappointed by a beach visit again. Plan the perfect beach trip today by visiting sandy.com. That's W-W-W dot S-A-N-D-E-E dot com. The link is in our show notes. Stay sandy, my friends. After graduating Oxford, you went to work at McKinsey, which many consider to be the most prestigious consulting firm in the world. You started in London as a business analyst. And three months after that, they sent you to Johannesburg, South Africa, where you worked in a mine again, this time in a town called Segunda. It was 1996, a cool time to be there in South Africa because it was just coming

out of apartheid. Nelson Mandela had become president two years before on May 10th, 1994, and the whole country had an amazing feeling of hopefulness. You worked at McKinsey for two years, but you couldn't be promoted unless you had an MBA. But if you wanted to get one, they would pay for it. Everyone else was doing it, so you did too. You applied to Stanford, got into Stanford, and graduated as an R.J. Miller Scholar, a distinction that's awarded to the top 10% of your class. While you were there, you realized you didn't want to go back to McKinsey.

You're a doer, and you didn't like handing things over to people to do them for you. When you graduated, the dean of the business school was irate with you that you didn't go to work in a startup. He said you had a natural curiosity and were a builder, and that was where your home should be. Instead, you went to work as an equity research analyst at Goldman Sachs, doing what you later in your career have described as making recommendations that made rich people richer. You chose Goldman over working at a startup for two reasons. You were broke and didn't have any money, and Goldman paid a lot of money.

You had to pay McKinsey back the money they spent on your Stanford tuition because you didn't go to work there after you graduated. The second reason was that you weren't a U.S. resident and you needed a visa, and Goldman was the very safe path to get one. You thought you'd work at Goldman for a couple of years and ended up staying nearly 11 years. You did well there. You covered securities, infrastructure, applications, and then software, and eventually became what was called the business unit leader for tech. You also spent time as an investment banker. And every couple of years, they gave you another mountain to climb and an opportunity to reinvent yourself, which is what kept you there so long. You eventually left primarily for two reasons.

Can you tell us about the importance of purpose at work and in our lives and about a particularly foggy day morning and about a particular foggy morning in 2011 and what your husband said to you as you were crying to him? And in search of excellence, what's your advice to others who aren't as passionate about what they're doing but are making good money? Should they leave and try to find happiness elsewhere? Yeah, wow. It's fascinating to kind of be pulled back into that day. I'm going to go to the foggy morning story first. So I'd come up through the ranks at Goldman. I was one of the younger managing directors. I was on the path to the partnership, which in Goldman terms is somewhat the be-all and end all.

It's not true partnership anymore, but it's what everyone aspires to. And you do get in your head, like you get inside organizations and you can get very kind of blinkered, like you're on a track. And so I was up for that promotion. I thought I'd done everything, quote unquote, right. You know, this is the, we're talking about the perfection, a student here, right? It checked all the boxes. And not only I was doing well from a business standpoint, I was clearly helping the firm grow, but I was also in charge, you know, I was working on diversity and bringing more women in and I was leading in San Francisco,

check, check, check, check, check. And when I got the call that morning that said, this is not your year. And in fact, the partner left us every two years. So this is not your, you're going to have to wait two years minimum. I just remember being so devastated. And I called my husband. It was super early because we both work market hours. So it was before 630 in the morning. And first of all, he said, just walk downstairs. Don't let them see you cry, which I don't know if that's great advice. Today, I'm more willing to be vulnerable. But then he was like, just walk out of the building. I'll come meet you. And we walked around that building. I am Northern Irish, so I won't repeat in full Technicolor everything I said, because let's just say we Northern Irish know how to swear. But I was super upset. And he said

these magical words. He said, they just set you free. And I was like, what are you talking about? And he said, they've set you free. You can, if you want, double down. If you want to go back after this, and this is the most important thing to you, you know I'll support you. But he kind of opened the door to this much bigger conversation about passion and what I was passionate about. And he reminded me of like a few weeks before I'd come home from work so excited because the woman who worked for me had gotten her promotion. It's something we had been working on for a couple of years. She'd missed the first couple of cycles. And he said, I have not seen you that excited about your job in maybe years. He's like, I don't know if I've

ever seen you that excited about a stock call. And it was like, it really like stuck in my head of like, you're right. I'm actually not passionate at all about calling stock movements. I love people. I love technology. I'm so curious about that. I love when I feel like I'm building something up. As the business unit leader for the group, there was a lot of kind of building of the group. But I wasn't super passionate about the day-to-day mechanics, potentially the most important thing of why I was doing my job. And so today, I can now articulate it in a great framework called Ikigai for overlapping

circles. So finding the place of like what you're good at, what you're passionate about, what the world needs, and then what you can get paid for, right? Without the fourth, it's a hobby. If you can find yourself in the center of those four circles, then you're in a moment of flow. It has a Japanese name. It was discovered in these blue zones. People live not quite forever, but until they're quite old. And a lot of it is around this discovery that when you're in flow, you're not facing a lot of the stress of day-to-day because

everything's just kind of working. You don't have those cortisol releases in your body, the things that cause inflammation and so on. So it's really good for your health. And so I think that's the passion moment. So you asked, you know, should people just leave their job right now if they don't feel passionate about it? I mean, frankly, I am a big advocate to kind of get up and take the risk. Nothing's going to change if you just come to work and do the same thing every single day. Now, I went extreme. I literally just left my job right after that happened. I think I had like two months and then I was like, I'm out of here. I didn't have another job to go to. It was actually quite scary.

It sounds daft and in hindsight, of course, I was completely employable. But in my head, I wasn't. But it was the best thing I ever did was to just go take that leap because then I had to go on a quest for what was going to be this next kind of era of my career. And I don't think I would ever have done it just sitting in the same seat. So it was a gift. Your moment of maximum despair may turn out to be the best thing that ever happened to you. While you were at Goldman, you met Mark Benioff, the founder and CEO of Salesforce, after he became furious at you for putting a sell rating on his stock.

But the two of you soon became friends. And among different topics, you would debate trends in Silicon Valley. He eventually became a mentor to you. And when you left Goldman, you called him for advice on whether you should join a startup. And he told you to go work with him because you had learned far more working with him than you would at a small company. It was a step down for you from your title at Goldman and in your salary, both of which were ego blows for you.

But the pitch works. Salesforce had 5,000 employees at the time and was growing like a weed. And you joined there as their senior vice president of finance and strategy, which was your first operating role. You're there for a little over a year. Then you get a call about a new payment processing startup called Square that was co-founded by Jack Dorsey,

who was also the co-founder and CEO of Twitter. You met Jack for the first time at breakfast on Mother's Day, which you weren't too happy about. The two of you clicked and had a very strong emotional connection, spending four hours talking about your childhoods before moving on to other things. You were scared about going to work for a 200-person company, but Jack told you over and over again that you shouldn't be afraid to fail in public, which you consider good advice, particularly for women. And also given your background, that you always had the sense that you had to be perfect and be the best student or an A-plus student. We're going to talk about your experience at Square in a minute, but before we do,

I want to freeze frame it here. And I have two questions about this. First, is it true that you build stronger companies and have stronger people around you when you search for that emotional connection? And in search of excellence, is fear of failure necessary on our path to success? And what's your advice to those listening and watching who want to try something new, but don't because they're afraid to fail? Great questions. On the fear of failure, I don't think you can be successful without having some inherent, intrinsic kind of fear of failure or something that's driving you, right? I think I would be spinning you a wrong bill of goods right now if I told you, don't worry, you can aspire to the dizziest of heights and you'll never have a moment of fear. It's just not true.

I actually think fear is an incredibly strong motivator, too. I think when it gets dangerous is actually when you're in too much fear that your entire fight or flight mechanism is kicked into gear and you actually can't function. I think it's also, for me, it tends to manifest as this need for perfection in everything. And that's when probably I lean into overwork to begin with. Like I always feel like I cannot work anyone, back to my Uncle Louie. So I need to be careful of that because in the end, sometimes it's not quantity, it's quality of the work. And maybe taking some time away would allow my brain to go a little broader, wider, freer. I think it also can manifest in when you are afraid of failure in

public, which is what Jack was pressing me on. You're just inherently going to be a little bit more risk averse. And I think to really build big things, you have to lean into that risk taking. I'd refer to it as educated risks, right? You shouldn't just take a risk for the sake of a risk. You can do a lot of data, a lot of analysis to say, here's why it makes sense to take this path over another path in a business context. But at some point, the data is going to stop because if it were, could all be data driven, everybody else would do it. It would be relatively obvious.

And there's this moment where you have to tip into a belief bat. So you're out of kind of data directing you and into a belief bat. And it's part intuition. It's experience. It's frankly, when you're building things, it's being very close to your customers and kind of really intuiting and feeling what job they're trying to get done. Not the, you know, don't do the buggy with industry thing of like, you know, they want horses and different ways to get. You would never create it the car, get from A to B.

You would never create it the car. At the same time, you should be listening intently to what your customers are doing and watch what they're doing. So I think that's the moment where you go from using the fear to spur you, but not allowing it to kind of hold you back from the final kind of take flight moment. Super good advice. And I think about it all the time, including in the current environment, right, where it's clearly gotten a lot choppier and rougher as a leader. On the former, you asked me about building great teams, right?

Do you need that emotional connection? Hell yeah. I think the leaders who excel don't just grab people by their head, like intellectually, they grab them by their heart. And I think it is so important to really think about the why your company is doing what they're doing. And how do you turn that into a purpose that really would make people run through walls,

not just for you, but really for the purpose and for the customers that you're serving? I got to work with two amazing leaders. You mentioned them. Mark did this with Salesforce, really around, if you think about it, originally with Salesforce automation tools and then customer relationship management tools, right? Software. But Mark's was like a crusade against software as a service versus on-premise software. And it had a Star Wars-esque element to it, right?

The good and the bad. He even had like a Han Solo frozen statue in his office to kind of really bring that dark side to light side to the forefront. In Jack's case, right, we could easily have built Square as a point of sale software system. Like we're building points of sale. No, like Jack really saw this vision of economic empowerment. And so I think learning and getting to be curious and sit right alongside these big businesses being built really kind of taught me that moment of like the purpose. And when you see it in action, it's in tough times, actually, because the people that you have both heart and head do extraordinary things.

They rise to meet the moment in a way that people who are just there with their head, they often actually are the people who most experience a lot of fear because the data runs out for them and they can't make the leap to the other side because they actually don't have the kind of purpose, the emotional context that carries them over the chasm. When you hire someone, you look at three main things.

Intelligence is number one, loyalty is number two, and experience is a distant third. When Mark hired you at Salesforce, you had taken a chance on you and you felt deeply loyal to him. When you got the call to interview at Square, it was a hard choice for you even to take a meeting with them. But it was a unique moment in time and Square was a different kind of opportunity. When the call came in, your husband told you that if you didn't call them back, he was going to call them back for you. You were offered the position, and on June 14, 2012, you joined Square as their CFO. It was a great choice for you, both from an experience perspective and also from a financial

perspective. From the date of Square's IPO on November 19, 2015, until just before you announced you were leaving to be the CEO of Nextdoor, Square stock increased 10x, and the company had gained more than $30 billion in value. And the day Square announced you were leaving, its stock dropped 10% of value, billions of dollars in value, gone. One of the themes of your career has been the risk, as we talked about, you have taken, starting with going to work in gold mines in Ghana when you were 18 or 19 years old. What's your advice to others specifically about taking risks in their career, whether they're working at a company or thinking about starting a company or have already started a company? Should they take risks earlier in their careers when they don't have responsibilities like family

to support and spend time with? And when you left Square, did you have a plan B if things didn't work out? And should others also think about having a plan B if their risks don't pan out? So hell yeah, on taking the risk. Absolutely. So as a little litmus test for anyone listening, I often think about adrenaline rushes. Am I getting an adrenaline rush every single day? My brother's a doctor and he always reminds me that when you're right on the table and maybe time to leave the planet, the thing they shoot into you is adrenaline. So

not to be extreme about it, but I actually think you should test yourself to say, how much do I feel adrenaline in my work situation every day or every week? If you're just comfortable, maybe that's okay for you. For some people, comfortable is okay. But if you are striving and you are in search of excellence, you must be taking risks very, very frequently. Now, when you're a junior in your career, what can that look like? First of all, I think it's not getting stuck or pigeonholed into one particular area, right? I joined the marketing team. Therefore, I'm going to be a marketer for the rest of my life. Or I've joined the finance team. I'm only going to be a finance person. I'm a coder, right? I'm in tech. I'm only

an engineer. I do software engineering. No, companies are these beautiful, big, organic structures. There's always gaps unfolding. And when you have that owner mindset, you see them. And I think those are moments when you can put your hand up and say, I want to learn a new skill. Let's go take another tour of Judy somewhere else across the company. Business school was a moment to go back and do that a little bit more academically. But frankly, I think you can create your own MBA, your own business school experience, just moving around the environment that you're in. And those for me were always moments when I both got a massive adrenaline rush, but also really learned the most. Like if you were kind of graphing my learning, there were always those moments where I made a shift into a new environment. So for example, you mentioned

that McKinsey, when I first joined, I did my first study based out of the UK, but I had this opportunity suddenly to go to South Africa. It drew on a place I had a little bit of expertise, but it also threw me into a completely new environment. And for sure, it was scary as hell for the first probably a couple of months, probably the first six months. Similarly, if you look at my career, right, it is a lot of zigzags. It's more of a lattice than it is a straight up. And that's very on purpose because I think I get

good at pattern recognition. You see a lot of the same kind of issues crop up in very, very different circumstances, maybe around different areas of expertise. They have a similar pattern to it. And I think it's really good to think about problem solving using patterns that you've seen elsewhere. There's a book by David Epstein called Range that I always recommend to anyone who comes to me for mentorship. The second part of your question was, I'm forgetting now. Plan B. If it doesn't work out, should you have a plan B? Honestly, I just don't know if you have time in life for a plan B

because you should just be so all in on making plan A work. Now, if plan A doesn't work and you start to have to pivot, that's a good time to start contemplating plan B. Like, what could it be? But I think going into a situation with a plan B already in mind, in some ways, I think might actually make you naturally unsuccessful because you don't have the adrenaline rush of having to make it work. I often joke, you know, life is not an A-B test. So the good news is, what if I had stayed at Square and I was still now at Square four years on? Or what if I had gone back to McKinsey? I actually, it's joyous to not have to know. And I love where I'm at. Therefore, I don't look back with regret.

So I don't think you can get caught up in your head in a plan B. Now, what I will say is a lot of people somehow think that if they go to the thing and it's not successful, they have become less successful. And I would actually advise you to think the opposite. Number one, by going to do something different, you have now incremented your value in the world. Frankly, you have more experience, you have more diversity of experience. When times are tough, you learn far more than when times are good. Times are good, you fool yourself into thinking you're really good. Times are bad, you actually really see who is good and if you are good.

And I used to get it a lot, actually, from people on Wall Street who'd come and say, oh, I really want to go to a company. I really want to do this thing, but I don't know if it's going to work. And I feel like I'm well-paid over here. And I always say to them, why don't you go do it? Do you think you would be a better investment banker, a better research analyst? You name the position in a financial company if you had operating experience, and they always say, yes, of course you would be.

So I'm like, okay, so I don't get your downside. Because if you do say, okay, I did this and it didn't pan out, and now I want to go back, I think you're more valuable. You can pitch yourself. Your brand just got X amount better because of this different experience you got. You're going to be more empathetic to your clients and so on. So I think people way overestimate the risk to their career by doing something different that doesn't work out. Then they estimate the upside, frankly, to their career

and to their life of doing something different, even if it doesn't work out. Hopefully that makes sense. It does. Thanks for listening to part one of my amazing conversation with Sarah Fryer, the incredible CEO of Nextdoor.

Be sure to tune in next week to part two of my awesome conversation with Sarah.