Fit Happens: Why CEOs and Leaders Succeed or Fail

Jason Baumgarten 00:00
I'm Jason Baumgarten and you're listening to Fit Happens, the podcast where top leaders, investors and board directors share the stories, surprises and hard-earned lessons behind finding the right fit. Let's get into it.
Jason Baumgarten 00:17
Welcome to Fit Happens, the show built on one crazy contrarian idea, that fit is more important than talent. Not who you are, but whether you're in the right place. I'm Jason Baumgarten, and today's guest is somebody that I have been just so fabulously delighted to have met and gotten to know, and who's a friend and one of the most fascinating people that I've had the pleasure of getting to know, Lexy Franklin. Lexy, welcome to the show.
Lexy Franklin 00:44
Thank you so much for having me. And the feeling is very much mutual. I think you could go many lifetimes and not find someone as brilliant or interesting as you.
Jason Baumgarten 00:56
Well, thank you. Well, I was going to do an intro that was really exciting, but I actually decided I would ask you three questions instead to get your intro.
Lexy Franklin 01:04
Okay, let's do it. I'm in.
Jason Baumgarten 01:07
The most unusual thing about your childhood people don't know about you.
Lexy Franklin 01:12
Yeah, I think the most unusual thing about my childhood is that the way I learned is I actually taught my parents every night what I was learning in school. So I would come home, we lived in a house that was very cold, so my dad would build a fire, and before every test, I would teach him everything I was learning. And this went on for a decade. And he would ask me a bunch of really hard questions and I would try and defend myself. And so that kind of way of learning, where my parents just basically pushed me to understand stuff really well, was really cool. Something I'm super, super grateful for.
Jason Baumgarten 01:56
And you've had a lot of different jobs, many of them in tech.
Lexy Franklin 02:00
Yeah.
Jason Baumgarten 02:01
But what is the common thread that connects them all?
Lexy Franklin 02:03
I'm just such a passionate person. So getting to work on something where, if it works, it can really make a positive difference in a lot of people's lives is so energizing. And I think I've been really fortunate to consistently be the least smart person in a lot of rooms. And so I think the common thread is me being like, wait, wait, wait, wait, can you slow down a little bit so I can understand this? And trying to keep up with all these people who are just so smart and so talented. So that sense of, well, the train is definitely not slowing down and I'm gonna have to figure out some way to get going fast enough to jump on, is definitely something I felt in every spot.
Jason Baumgarten 02:41
And now tell us about the last job you had before this crazy adventure we'll talk about in a minute. But the last job you had, and then we'll talk about what you're doing now.
Lexy Franklin 02:50
So I got to work at Facebook for a long time and it was just the best. I loved working at Facebook because you're just with people who are so smart and they're so driven. And it really was the first place I'd ever worked where you didn't have to change how intelligent you were. You could just bring 100 mile an hour fastball every day. And there's just people throwing 110 around you. And so you really got to work with these people who were so world class at what they did. But it's just really rare to be young and to not know what you're doing and get so much responsibility. I remember there was one moment where one time we're building this feature and I accidentally launched it to the entire United States and it was not ready. And just even the ability to accidentally launch something to the entire United States, and to have what's a few hundred million people. I mean, yeah, a lot of people. And then I remember, because it got written up in TechCrunch, and I was like, oh, that was not ideal, but that was just like a Friday at Facebook. It was a place where you just moved really quickly. You could learn a lot and it was okay to be wrong. And I'd also never worked at a place that was so okay to be wrong. As long as you knew the reasons why you were wrong, and you could document it and learn from that, it didn't really affect you that much. And so it was kind of an amazing place to get a lot of reps at being incorrect.
Jason Baumgarten 04:22
For everybody listening, what was your favorite thing you got to actually build at Facebook?
Lexy Franklin 04:26
We built this app from scratch called Messenger Kids, which was this pretty incredible app. It allowed kids to talk to their friends and their cousins and their parents. And we did so much research, and research was really why it worked. It became this incredible success. It became the number one kids messaging app in the world. The retention was kind of off the charts. Of dozens and dozens and dozens of projects, it was kind of the one home run, and it was just so cool. Kids didn't really have an ability to talk on their Kindles. They didn't really have an ability to talk on their tablets. They were using their parents' accounts. It just was one of those things where it's like, oh, this should work. But all major messaging services were built on the back of a phone contact system. iMessage is built on your phone. WhatsApp's built on your phone contacts. Facebook Messenger was built on your Facebook contacts. So, like, kids' contacts, it doesn't really exist. That's a really hard problem to solve. So that was pretty amazing, to start at the really early days and have it work. It was a pretty incredible experience.
Jason Baumgarten 05:22
Well, it is better than when I was a kid and your contacts had to be in your head. You had to remember all your friends' phone numbers. Do you still remember your buds' phone numbers?
Lexy Franklin 05:33
I remember all the phone numbers.
Jason Baumgarten 05:35
Isn't that so funny? That's what I love about you. So I too remember all the phone numbers. And sometimes you get the fax machine because they have to plug the fax into the phone. Like, my parents are lawyers, so they had a fax machine and only one other kid had a fax machine. But I always used to call and hit the fax number, or you'd hit the dial-up and you just couldn't call. It was like those were different types. When you could out-type your modem connection, that was a good, good day. Did you have to take Mavis Beacon typing in school?
Lexy Franklin 06:06
So I learned how to type when I was really little. One of the gifts my father did was buy a computer. I mean, literally it was an 8 MHz boosted PC. I learned how to type on it and so I was a good typer. But really I think I type in some bizarre way that worked for me. And I'm sure if I took Mavis Beacon I'd fail because they'd be like, you don't type correctly, I don't hold my hands in the right way. But I used to be able to type like 120 words a minute, 130 words a minute. My first job I got because I could type.
Jason Baumgarten 06:31
Really?
Lexy Franklin 06:32
Yeah. I was a summer intern at IBM and they basically hired me because I could type.
Jason Baumgarten 06:37
It's crazy how these little things you do that you think will be inconsequential become so consequential in life. Like when we talk about fit, a job and how well you do is really an amalgamation of all your experience, right? So I had this crazy job when I was in college. I was an intern at the Daily Show, and I almost didn't take it. And I was like, oh, I'm just not gonna take this job. They offered it to me. And I remember being in my dorm room at school and I was like, I don't know, I gotta think about this. And they're like, yo, no one's ever told us that, ever. What are you doing? And I called my mom. I don't know. And my mom was like, you are not the smartest person in the world. You need to take this job. She was like, every job you get in the future will be because of this job. And to this day, no one really cares about anything I've ever done other than interning with Jon Stewart. That's the number one thing. So it's like, your conversation starter, the computer when you were 8 and your typing skills, led you to that. And me running errands in between Jon Stewart and Stephen Colbert in New York really set me up. It's not always the big hard thing we did that matters. All right, we're going to go back to the intro because we haven't finished. So you were at Facebook, you were crushing it, launching new products, sometimes accidentally. And then you decided to do something crazy. You went to be an EIR and then you started a company. Tell us about the company.
Lexy Franklin 07:59
Yeah, so that was a crazy experience, to go from working at Facebook, which I love so much, and to go start a company. But I always wanted to start a company when I was really young. And so I left not knowing what the company would be. And the company we started was actually the ninth idea we worked on. So for two years in the desert, we just tried a bunch of different ideas with a rotating cast of brilliant people. But I was looking for something really specific. I was looking for an idea that felt really atomic. That's one of the things that I think Meta does so well, is they're able to build these things that are kind of fundamental to being human and how you express yourself. And I was looking for a problem that felt atomic, that felt so intrinsic to the human experience that once created, you couldn't imagine it not existing. And the company's called Sidebar. And our first iteration of Sidebar was this idea of kind of peer-to-peer groups. And the thinking was, at work, nothing really gets you better at your job or nothing accelerates you faster in your career than learning from your peers. Like, Jason, when I get to talk to you, I come out now I'm like 10x smarter than I can ever imagine, because you're so brilliant. You're able to impart this hard-earned, tuition-paid work experience that took you two or three years to get and tell it to me in 10 minutes. And I'm able to integrate that and be like, man, that was super useful. This is why I think books are so amazing, is you can spend three hours and read a book that someone spent 20 years on, and you just distill. It's almost like poetry, right? It's like the most distilled form of language and communication. And so I was like, well, this is kind of amazing. You know, at Facebook, I would tackle these new problems like I was the first person to ever have this problem on the planet. And I actually was probably the millionth person, the 10 millionth person to have this problem on the planet. But I just wasn't asking people around me, like, how would you solve this? What would you do if you were me? And so when I did, they would give me these answers that would work. And I, in my infinite wisdom, would be like, should have asked you a year ago. Like, I wasted a lot of time there. And so we wanted to build a product that codified that, and it was a great idea. We have these groups running all the time and they're great. You get with your group, you're in your group for years, you really get to grow with them, you get to learn. It's been pretty incredible. Over the last couple years, this AI has really grown to kind of all be like, okay, how are you using it? What are you learning? What are you growing as leaders? How do you build towards product-market fit? How do you scale? How do you hire? These are things that group intelligence, if the group is really strong, is actually better than individual intelligence. And so that was kind of our first iteration of the product. And then very quickly we kind of expanded from that. And one of the really interesting things is that over the last couple years, a lot of Sidebar members lost their jobs. It's been a very intense time to be in tech. So this concept of, okay, how do you really interview, how do you really hire, became something that really fascinated me and fascinated the team. And how does that really play with AI? How does AI impact that? And so the first step we did is we built probably the world's best AI interview trainer. And so you use the AI when you're applying to a job, and it's amazing. It basically analyzes the job you're applying for, the questions you should get asked, how well you're answering those questions, what the expectations are, who you're interviewing with. You know, 20 to 25% of an interview is actually the questions you ask the person you're getting interviewed by. Like, what do you bring? And how do you ask questions as if you already have the job? It basically is like a crash course in how to go get any job in the world. And we got people like $25 million worth of jobs in like six months. So it kind of blew up. And that was really interesting. And that started to grow really fast. And then we kind of turned our minds to, but what about on the company side? Like, how do you really find the absolute best people to do the work? Because at the end of the day, that's something that's so invigorating to me, is I kind of believe in this world where we're kind of put on the planet to do our best work. And as companies, how do you find the people who would do the best work that are going to fulfill your missions and your dreams and your goals and help you really go in? And that felt like a pretty amazing area to explore. And, Jason, one of the things we've talked about a lot is hiring is kind of broken in a lot of ways. You go, you got 500 applicants at the top of funnel. With AI, it's really easy to apply to all these places. With AI, all their resumes look pretty good. Like, who's really good there? And maybe you look at a hundred of them, 400 of them you just can't even look at. Of the hundred, you maybe narrow it down to 50. You get on the phone, you're calling all these people. It's really hard to have the same criteria across a hiring manager and across a recruiter. Maybe a lot of those 50 go through, everyone goes to the hiring team, and the hiring team maybe likes one of them. And that's just a tremendous waste of time and energy. And why doesn't a world exist where 500 people apply, everyone gets interviewed, and we're like, here's the final three, pick from these three? And so that's kind of what we're building.
Jason Baumgarten 13:05
It's awesome. So I'm so glad you're building it. I'm so glad you're still building on top of the early product, which is still awesome. I mean, I think loneliness at work, the need for groups, the need for community is such a big deal. I need you to now launch Sidebar at home. Need the home edition.
Lexy Franklin 13:23
Yeah, 100%. Think about new parents, all these applications where people are desperate for community. Well, I just think that there's something so fundamental about saying, here's my lived experience, and does that resonate with you? Like, what would you do if you were me? That phrase, when applied to new parents, when applied to money, when applied to what should I do in my career, when applied to leadership, when applied to health, there's just not that much opportunity in the world to be like, here's the sitch, what do you see? And I think that there's something so valuable to be like, here's what I see, and then you can react to it. And in the reaction comes the magic. Because either, if it's you, I'll agree because you're brilliant, and I'll be like, oh, I didn't think about that. Or if I disagree, all of a sudden that sends me down a path too, right? Of like, I had a visceral reaction to that, and that knocks me into, maybe I should go do this. And so I just think that, in a Zen irony, of course it's this way. In a world where there's a lot of noise, actually we're not actually getting kind of the help and the advice we really need.
Jason Baumgarten 14:41
It's so true. And we're very social. I was actually just reading some research out of UCLA that it turns out when our brains are, quote, at rest, when we're at rest state — I don't mean asleep, but, you know, daydreaming, looking out the window, washing your hair — you're actually replaying social interactions. So what our brains do is they try to make sense of our social dynamics. Did that person like me? Did they not like me? Did they do something that dissed me? Did they do something to help me? We replay all that, and we sort of chess out in our heads all these social dynamics around us. So we are inherently very social animals. And so figuring out how to have the right troop around you is so important for anything important you want to do. Lexy, a question about that, because you're probably in the top three most emotionally intelligent people I know.
Lexy Franklin 15:35
Like, socially, all my friends would absolutely disagree, but go ahead.
Jason Baumgarten 15:39
Yeah, no, I think you are. What do you think in your life has been like the most counterintuitive but impactful thing you've learned about that kind of emotional intelligence, social dynamic, having been in these rooms of power and powerful people and dynamics and all this stuff? Like, what's something you've learned where you're like, actually, I apply this all the time, but many of us wouldn't have learned before, or is maybe new to us?
Lexy Franklin 15:56
Oh, that's a good question. I don't know that there's one thing. I will say one of the things I've spent a lot of time thinking about recently, and partially it's because of social media and because of sort of performative leadership, that I've realized humans are wired to follow people in very broken ways. So the way in which we're sort of wired to follow people are very rooted in how we smile and how we command a room and how assertive we are. Quick thinkers, for example, are much easier to get people to follow them than slow thinkers. I don't mean bad thinkers, truly fast versus slow. So as you think about it, what I often look for in a room is, are we following the right person or the right idea or the right concept? And I see this a lot with younger people. They'll follow the carrot. We all have that friend we can immediately think of from high school or middle school where they were the charismatic idiot, where it's like they would get everyone to do something really stupid because they were great at getting everyone rallied around something. And you were like, that is a foundationally bad idea, we should not do that. And so I think one of the things to always check is, are we doing this because it feels good or because it feels right? Because we've thought it through. And it turns out a lot of us are sort of ingrained. This is the funniest example. If you hold a warm drink, or you are warm and you meet someone, you will be more inclined to like them than if you're holding a cold drink or in a cold room. Right now, if you sort of geek out on science, you're like, there's some logical reasons why we would be more inclined to like someone in a warm setting than a cold setting, because it turns out a moderately warm setting is more likely to be a good place for us to be than a cold setting. So there's all kinds of reasons why that might be good in the spirit of the human species, but practically, in a modern environment, it's insane. And yet these are the kinds of things that actually we still are wired to. And so I think it's really hard to go back to, are we following this because it's right or because it feels good? And I see that a lot with hiring. I used to do this thing where I would take famous people and I would pull their old resumes and I would change their name just enough so you didn't know who they were. And I'd be like, hey, do you want to hire this person? And I'd be like, that is the dumbest idea ever. Why would I hire billionaire X or famous person? And I'd be like, well, because that's a really famous person that you'd be desperate to hire now. But before that, there was nothing on paper that made sense until they were supremely successful. And so a lot of my time I've spent recently thinking about this idea of how do you differentiate following someone because they're pleasant, they're nice, they make you feel good — which, by the way, is super important.
Jason Baumgarten 18:39
I mean, I always love, Lexy, that you are super positive, and people get off the phone and feel good.
Lexy Franklin 18:44
Yeah.
Jason Baumgarten 18:45
But I also know you're really smart and you really work the problem. I know people who are really pleasant, make everyone feel good, and they're like, do some heroin. And you're like, no, no, no, no, no. Kids, don't do their job. This amazing ability. There's another thing you said, and, you know, now I'm interviewing you. You articulated that so well, right? Which is like, you can't blindly follow the charisma. But I think there's this really interesting thing, as that CEO who maybe had the bad resume or who maybe wouldn't have gotten hired, there's really this act of becoming in your career. We kind of tell the stories in reverse. So when you have the big exit, or when you have the thing, or when you're famous, it kind of makes all the other things in retrospect make a lot of sense. Like, of course they were amazing, and of course they were that stuff. I think the canonical great example of this is like Abraham Lincoln and Team of Rivals. If anyone hasn't read Team of Rivals, you should read it. It's probably the best non-fiction book I've ever read, for what it's worth. But the beginning of Team of Rivals is so good because it's talking about Abraham Lincoln. It's talking about he's going to get some pancakes. And it's talking about, dude's lost eight elections. And there's this amazing line where he says, nowhere did he have any idea that he was going to become the most famous person of the 19th century. He had no idea that on that Tuesday, eating pancakes, his life was about to change. And I think there's something so interesting in a career. And then when we talk about fit, where did you have those qualities the whole time? Are you becoming? Like, are you there yet? Did you learn the lessons you need to learn, or were you really close and then you got over the hill? Like, if you want to be amazing and you want to be world class, what is that process like? And I'd love to hear your thoughts about that in particular. And I'll just say that there's this great poet called David Whyte, and he has this great saying about Wordsworth, where Wordsworth is writing to his sister, and he is like, this poetry thing is not going that well, no one's reading any of my things. He was like, you know, I think I'm just going to go to the lake country and figure out my life, because this isn't working very well. And then Wordsworth, you know, 150 years later, is like, known for all his poetry in the lake country. Like, he just was about to become, you know, capital-W Wordsworth, and he was, like, hitting his head against the wall. So I'm really curious, how you see that and how you think about that.
Lexy Franklin 21:14
Well, I think that there's a few things to unpack. I think one is you have to figure out your superpower and what you're good at, and sticking with it through what can feel like the world not yet realizing it is actually worth it. And a lot of artists go through that. I think a lot of people go through it in life where they worry about giving up just before it's time to hit it big. I also think there's a lesson in revisionist history, that there's certainly a lot of people where they become famous and then they explain how the fact that they were eating Rice Krispies on June 10th unlocked their whole future. And you're like, yeah, I just don't believe it. So there's that. The third, though, is this really durable notion, which is — and this goes back to your Lincoln story — Lincoln was a failure. Like, Lincoln was an abject failure, even in many ways as a president in the early years. He was a president who was made for a particular setting. And when you look through history, whether it's politicians, military leaders, business figures — and we don't remember most of them, by the way. I also have this quiz where I'm like, who is the CEO of ExxonMobil three CEOs ago? And everyone's like, I have no idea. And I'm like, well, it's one of the three biggest companies in the world for the last 100 years. But it's a little bit of a Percy Shelley, Ozymandias moment for all of us. So I think that the reality of, it's not just a job, it's not just a company, but it's often a moment, it's often a project, it's often one thing that you're uniquely well qualified to do where the timing hits at the right time and you're there. And I think the two things I'd say are one — well, three. One, you've got to know yourself, you've got to know what you're good at. And all these college grads who are now graduating who can't find jobs, a lot of them, you followed what someone else wanted you to be good at. You've got to follow what you're good at. And AI is going to make that even more pronounced. The second thing is really understanding how to create the scenario where you are more likely to have the moment where you can be good. And then the third is to have agency. There's a lot of people who go around saying, well, I would have been really successful except Lexy didn't give me the raise, or I would have been really successful except Facebook was terrible. But at the end of the day, you got to own it. If you don't have that agency to say, I'm not in the right place, I don't have the right boss — this is where I always think having a bad boss early is a gift. Because if you have a bunch of bad bosses, you're like, the world's full of bad bosses, stop worrying about it, move on, figure out what you're going to do, have agency. So I think if you can figure out what you're good at — which is, by the way, the hardest thing. Most people I interview in their 50s and 60s still don't know what they're really good at. They're sort of like catalogers. I'm good at all this stuff. And I'm like, no, but what are you uniquely good at? The second is to try and manufacture that moment where you fit the context. And then the third is have agency. If it's not right, get out, get out, or shift it.
Jason Baumgarten 24:04
That's — everyone should underline those three. Like, that was really smart. Well, and I think what's really cool about what you said too is that, you know, as a positive person, is that there's again this really interesting Zen tension between you're kind of always ready, right? Like, that moment and that overlap could happen at any time if you know who you are and you have the agency to kind of go find it. And it might be quite a journey. I mean, Abraham Lincoln, again, as the example, dude lost eight elections. He was so bummed that he wasn't born 70 years earlier and he could have been part of the American Revolution and the constitutional — like, he thought he had missed his time. Maybe we live in interesting times and it just was coming. And so I think that there's this patience, but also this idea that tomorrow could be your day, today could be your day. You just kind of have to be open and looking for it. That's really invigorating. Totally. Well, and we learn a lot when things don't work out. I love the fact that founders and CEOs are always perfect. Now, something that went wrong in their life is usually carefully manipulated to actually be a success. But what, like, really didn't work for you? Like, what's a moment where, like, that was terrible, but I learned a lot?
Lexy Franklin 25:20
Let it be known that my dad actually calls me — he's like, you're the best failure I know. And I'm like, dad, you can't literally tell anyone that ever. Go and introduce me at that. And what he says is that I just fail way more often than most people. Ever since I was really young, I would fail at sports, I would fail at school. I would go and give a speech in front of a bunch of people and it wouldn't really go that well. I wouldn't hit my marks. I would want to get into like advanced class and not make it. I wouldn't get into the college that I really wanted to go to. Like, I am someone who puts myself out there and just fails hard and publicly.
Jason Baumgarten 26:00
By the way, if you're listening to this or watching this, and you know Lexy, this is both true and funny. Because — you know that poster? I had one in, like, my eighth grade science class. You know, don't aim for the moon, aim for the stars, because then you might hit the moon. Lexy's failure is like landing on the moon, not getting to the stars. Yeah, but it's like, may we all be so lucky to fail like Lexy.
Lexy Franklin 26:21
But my dad's point was, we would lose a championship and everyone would be crying. Everyone would be crying, and my dad would be like, yo, you'd be bummed for like a minute and just be like, are we going to go get pizza? Or whatever. And it's just the process of starting a company is like feeling all the time. Oh my gosh, I built so many products at Facebook. Lots of people worked on these products, like hundreds. And it wouldn't work. And I'd be like, ooh, that's bad. And then we would document it and be like, here's what we learned, here's these pieces. But it's just impossible to know these things ahead of time. In fact, the art of building from scratch, which is our job — if you're really good, if you're world class, you only write like maybe 10% of the time. If you're really, really talented. Now you can do all the stuff and you can get better, and maybe over time you're able to visualize and play in your head and predict, and you get right more and more. But it is a lesson in constant failure. I mean, something really specifically is there was this one really, really, really public feature we were working on at Facebook. A lot of people were working on it and it was like right in my wheelhouse. And ultimately it just didn't have PMF. Like, we had hundreds of people working on it. It was in the news, it was like a big deal. It just didn't work. And I was point on it across the whole company. And we did a really good job executing it. Whether it was too early, whether it just wasn't the exact right thing that the market wanted. That's a really good example of something that just was like, man, I put my heart and soul into that for a really long time and it just wasn't right. The process of the startup doing eight ideas before any of these working — that was two years of my life and I bootstrapped it. So that was like so much cash we lay on fire and so much time and so much energy. And every one of these, I think it's really important for everyone to understand, I thought was the best idea I've ever had. It wasn't like, oh, this is a flyer. It was like my heart and my soul and my being. This was my Olympics. And then it feels — and it's just like the worst, where you're like, oh, that was so much time and energy. And I usually give myself a day or two to mourn, max. Two days to mourn, where you just let yourself say all the things. I'm terrible, I'm an idiot, I should have figured this out, why did I do this? That was like somewhat public. No one's ever going to like hire me again, no one's going to like me again. And then I'm like, okay, at the end of day two, it's like, what I learned — write all that stuff down, really kind of understand, okay, what was something I learned, how do I fix it, what do I do better? And then day three, get started on the next one, right? Oh, I have another really good one. This only happened to me, I think, at Facebook. But we used to have to present our ideas to all the exec team. I was the PM in charge of new crazy ideas for Messenger. So I was on the Messenger team really early. It grew from 100 million to a billion people. And think about all the crazy stuff — stickers, GIFs, emoji, the composer, all the fun stuff. I remember my first year of Facebook, you would present what your ideas were to the executive, and I was like, let's go, I had so many ideas. I would come in, I was like, oh, we're gonna do betting, we're doing real-time sports, we're gonna do all these ideas. I literally think they said no to me like eight times. They said no to me so often. And everyone had already had all their plans approved except for me, in remedial class. I think I got eight plans rejected in a row, to the point where the head of engineering, God bless him, pulled me aside and was like, are you okay? Like, no one's ever gotten this many plans rejected. And I was like, not only am I okay, I got 10 more, let's go. And then finally they approved one. And to be clear, all those ideas were actually really good, but they just weren't the right idea for that right time.
Jason Baumgarten 30:04
I think that it takes enormous confidence and spirit. But when you think back as a leader, what have you learned about yourself from that? Like, what's the leadership lesson? You know, in some ways we'll get back to this question of fit, because being able to fail actually does fit being an entrepreneur.
Lexy Franklin 30:24
Yeah.
Jason Baumgarten 30:25
So we'll come back to that. But this idea of, okay, so if you had to pull a lesson out of all that from your Facebook days, is there something that everybody should think about as a lesson? They don't have to relive your experience to glean.
Lexy Franklin 30:36
Yeah, 100%. So there's like an immediate lesson and then there's a longer-term lesson. And I'll start with the longer-term one and get into the immediate one. I think the longer-term one is I think we tend to look at success and the definition of success incorrectly very often. I'm a big Bob Dylan fan, and Bob Dylan has the best quote about this of all time. In his song "Love Minus Zero/No Limit," he says, there's no success like failure, and failure's no success at all. And I think as society, we're kind of in that second camp — like, failure's no success at all. And being raised in a very intense environment, being really intense at school, trying to get 100% on everything I've ever done in my entire life, there's this sense of failure is something that we want to control for. It's no success at all. But actually, when you study the really, truly breakout, super smart, iconoclastic people who we immortalize many years later, they actually fail quite often, and they kind of dance in that failure. There's no success like failure. It's kind of the greatest success, because in that failure, that's the bleeding edge of what we learn. And when you read about people, whether it's Einstein or these people who really matter, they're much more comfortable with failing than your average person. And I think that school actually does a really giant disservice to us, because you have the very false pretense that you can control your environment. But if you're trying to build something really big, you can't control your environment. And while you can do your best to get better and make better decisions and think through how things are going to go and get better at strategy, you're not in control. There's so many things that you're not in control of. And so that Bob Dylan quote of kind of having a longer-term time horizon — like, to your point, if Abraham Lincoln quit in the first two years of his presidency, he would be judged as kind of a mediocre president. If he quit a year and a half later, he'd probably be judged as arguably the best president of all time. Like, there's just a longer-term time horizon to success. And when you look at people who are out of the ordinary, extraordinarily successful, it doesn't tend to come early. And if it comes early, the story is not usually done. One lesson I had at Facebook, as an example — as probably the number one biggest failure at Facebook — was every week I would be like, what's one thing I failed at this week and what did I learn from it? And I would go and write it down in a notebook every single week. Because my thinking was, it's probably going to take me two years to get really good at this job. And that's like 104 weeks of failing at something. And sometimes the failure would be really small, like, don't say this in a meeting because that doesn't work. Sometimes it'd be really big, you know, you couldn't launch the product to the whole of the — yeah, like, check your QAs and make sure it's not rolled out to 100%, accidentally launches tomorrow when it's not ready. But I felt like if I just learned one thing and I could integrate it each week, in two years that's 102 things that I didn't have two years previously. Like, I would bet on that person. Like, someone who's learning like that every single week, I would bet on them. So that's like the longer-term thing of how to define success. I think the shorter-term thing is that — and this one's tricky, because I think we have to be comfortable with things not working out. Like, ultimately you have to be okay with it actually just failing and kind of being not great, and it not being for some larger purpose and not being for some larger thing written across the sky. It just being not good. And I think that if you take a homeopathic dose of that, which is just like, ooh, I really wanted this to be X and it's Y, and there's no sugarcoating it, it's just really not good — I think it allows you to have this confidence of, this story's not done yet, and I'm not really going to be defined by this. And it's okay. If you're actually open fully to something not working out and it's just bad, it actually allows you to be okay with that being the ultimate reason. But it also allows you to kind of be free, to be like, oh, I'm just in the really shitty part of this.
Jason Baumgarten 34:50
Totally, totally. I'll connect to two very different things. One is, you know, I love fixing stuff around the house and building. And one of the things I figured out years ago was that most of the people I was hiring to come fix things really weren't sure how to fix it. And they would break stuff in the process of fixing it. It's just, when it broke, they were like, well, no big deal, I'll fix the drywall, I'll paint the wall, I'll put a different plumbing part in. And watching them, I realized, well, I can break stuff too, and that's not such a big deal. But when I started working on stuff around the house and building stuff, I would think, well, if I don't know exactly how to do it, I shouldn't do it. And then in watching people and talking to them, I'd realize, well, they would try stuff, and in the process of trying it, be like, that didn't fit, let me try a different way. And you said something once — you said the 9010 rule, of like, leaders know 90% of the time how to do something, and 10%, they're in totally uncharted territory. And I think what you're getting at is that failure helps you navigate the 10%, because there's no way you're going to get things uncharted, all right? And particularly when we're living in times like this, like AI, where everyone who walks in and goes, the answer to AI is going to be X — like, no way, no way, we're all wrong. I mean, I don't know in what dimension, but we're all going to be wrong. And it helps if you know you can patch the drywall.
Lexy Franklin 36:08
I think the other thing that people really underestimate is how much you learn from exposure. And I think that that was something that I really learned a really intimate lesson at Facebook. Because you would meet these people who are leaders at Facebook, and the leadership team at Facebook is just like A-plus. They're just so talented. They might be the same age, they might be younger than you are. But they're just a world of brilliance, of just — they're so good at what they do. And there's something that you know as a CEO, where you can't know how to do the 10% until you get exposed to it, and you can't be good at it until it just washes over you, like a bunch of — and it's kind of like, I was surfing the other day and I was on a new break and I just was getting crushed. I was like, just getting — I was like flying everywhere, I fall so much, my contact came out, like, I was just getting crushed.
Jason Baumgarten 36:56
You were 10% of surfing.
Lexy Franklin 36:58
I was 10%, right? But I was like, this is the exposure, like, this is awesome. And I think that there's something where at work, it's so easy, especially when you're good and you're smart, to feel like my job is to have the right answer all the time. Your job might actually be to be thrashed against the rocks over and over and over again, just because it's like the world is hitting you over the head to get exposed to this thing that's really hard. In the right measure, it may not be, did I get this right or did I fail? It's like, can I do something today that six months ago I wouldn't have been able to do? So much of being great is just being exposed to your terribleness and not quitting. The way it was described to me is you want to get exposed to your edge, because then your edge expands. Being exposed to your edge is the worst, because you're on your edge, you're super uncomfortable. And if you could just hang in that pocket as long as you can, you push further and you push further and you push further and you push further. And that's a pretty sick existence. Because otherwise you live in the safe middle where you never really see how far you can push. And I think a lot of people do that. And that's how you end up being that person who has the not-good background and who becomes the famous person. Like, they're just like, okay, living on that edge.
Jason Baumgarten 38:20
Here's a great question for you. What was the last thing you made up? Like, a very high-stakes situation where you literally had no idea what you were doing. Someone's looking at you, this very successful, famous dude — what'd you make up? Just like totally made it up, pulled it out.
Lexy Franklin 38:35
I think a lot of leadership scenarios, you are triangulating because they're like snowflakes. A CEO asked me something about a team, and there was no exact example. It wasn't like I'd seen this exact thing before, but I had seen like three patterns that look similar enough where I was like, I think the right thing to do is this. And he did it, and it was awesome, he was really happy. But it's like saying, in this moment in history, if you leave the house an hour later, would something better or worse have happened? Sometimes you just say my best guess. Because I think when you have more experience, it stops being a guess and it starts being more of like a hypothesis or a point of view or something based on something. And then what also is crazy to me is how many times we do something that we know is bad, but everyone does it anyhow.
Jason Baumgarten 39:21
So, like, one of the things I was going to ask you about is you are amazing at being super hardworking, super focused, but you also have a view of how you lead, which is not necessarily the insane, like, 996 approach. And I was going back and I was actually looking through history. There's so many moments — Karoshi in Japan after World War II, where it was literally like, let's work to death. The dot-com death march was a thing in the dot-com era where people were literally like, how much can we work, do we have to go to the hospital? And we know everything about human performance suggests that this is a terrible idea. Like, everything we know is that if you're sleep deprived, if you are not exposed to other things in your life, your ideation will decrease, your productivity will decrease, your efficiency will decrease, you get more stressed in how you deal with other people, you become more miserable. You haven't fallen into that belief that founders need to be, you know, locking cages on their employees at night. How have you navigated that in a world where people are rewarding that?
Lexy Franklin 40:34
Again, it's such a great question. I just think that the biggest gains in a company are non-linear. I think that so much of building is trying to find and really understand exactly the pain points of the customers that you're building for, and really have that deep empathy to put yourself in their shoes and to understand their problems so deeply, and then to turn on your kind of creative execution of what are all the ways you can solve that problem. It's like the empathy times the execution. You know, one of our advisors, Shreyas Doshi, who's like a brilliant, brilliant person, talks about motivation theory, right, which is like, how do you take the motivation of what someone wants to do — and there's intrinsic nudges of what they're aiming for — and how do you subtract the friction of what gets in their way, so they're satisfied and they're doing something that they want to be doing that you can help facilitate? Those things are not things that you can just brute force just by working over and over and over again. It's really like, how do you look at a situation, how do you really amalgamate all of the data that you're getting, how do you really creatively think about the answers? Like, there's always times when you're in execution mode to go work really hard. And one of the things that I love doing, like, more than anything, is that feeling of, you know what, you're all building, the wind's running through everyone's hair, you're all collaborating, everyone's going fast, the sum is more than the parts. Like, I hope everyone who's listening knows that feeling, right, of building from scratch, having a blank piece of paper. I mean, you know this as an author, there's nothing better than having a blank piece of paper and creating in the world. The only other better thing is to do it with other people that you love. I would do that for free for the rest of my life. And so there's always a part of, we have to work really hard to go do this. And no one gives you any of these things in life. Like, if you have these goals to go aim for the moon, you have to go grab them, right? But at the same time, there's wisdom floating around all around you. There's wisdom in deeply listening to a customer, there's wisdom in going to look at a tree, there's wisdom in watching the sunset. Like, there's a universal wisdom in kind of observing the world and letting all that stuff amalgamate. And we all know this, where if you're on a business trip and you don't sleep that well and you have to go do really good — of course you can, because you're charismatic and whatever, but it's not quite magic — versus if you slept really well.
Jason Baumgarten 42:47
This would be the right time to mention that you just got back from Europe and are very jet lagged.
Lexy Franklin 42:57
But I had all these magical moments. The flight attendant was such a nice person, we became really good friends. He gave me his meal. I'm vegetarian, and there was somehow no vegetarian meals on the flight. He was like, you can have one of my three meals. And I was like, dude, that's like the kindest thing ever. I was watched over on the 22-hour travel home.
Jason Baumgarten 43:17
I want to go back to that, Lexy. This idea of making connection — and, I mean, you do it so naturally. One of the things that I really love about the first product out of Sidebar is this idea of connecting people. And I know there's a bigger purpose around wisdom and getting advice from others, but I also think at its core, work and leadership are lonely, right? Whether you're leading thousands or you're leading five. And it's gotten worse in a remote world, right? And one of the things that I've noticed — and I'm going to ask you two questions, I'll do them one by one. So one is that loneliness and bad fit can often look very similar, right? Those things like feeling isolated, having self-doubt, the sense that the people around you don't get what you're up against. Like, how do you think about loneliness versus, like, I'm in the wrong fit? Maybe it doesn't even matter if you can distinguish, but you've been in so many of your groups now, hearing people talk. What would you tell people about, hey, you're in the right place, you just need to find your tribe, versus, you actually might be in the wrong place, it has nothing to do with finding other people?
Lexy Franklin 44:24
It's such a great question. I actually think they're very different, but, like, to your point, they look really similar and they smell really similar. And so you can get confused on that journey. I mean, I think it boils down to passion. Like, if you're passionate about what you're doing and you're passionate about what you're trying to create in the world and you're passionate about the area that you're working in and you're leading, there's a really good chance you're going to feel lonely. And I learned this from a mentor, actually, when we were raising money. When we went to go raise money, I was just pitching as well as I'd ever pitched in my life. Like, I believed in it, I had the vision, I was ready to go. And people would say no, and I'd be like, wait, but I don't understand, I've never pitched that well. Like, how? They would be like, no, I'm not interested. This person, she said this amazing thing to me — I'm never going to forget it my whole life. She was like, did you, A, expect it to be easy? And I was like, not really, but kind of. And she was like, well, it's going to be hard, A. And B, the hardness is how you know you're in the right spot. And I would make the same analogy for the loneliness. Like, if you're trying to build something that no one's ever built before, if you're trying to create something from scratch, if you're trying to write a book, if you're trying to put something out into the world, if you're trying to lead, the loneliness is almost a demarcation that you're in the right spot, you're on the right path, that it's actually a positive feedback signal. And I think the distinction between that and being in the wrong spot is the wrong spot is going to throw negative feedback signals. So the loneliness hurts and it doesn't feel great and it can feel isolating, but it's actually positive in a lot of ways, because it means that you're on the right path. But I think that when you're on the wrong path, there are some telltale early signs. One, you feel like every day you need to change your essence. You need to put on your armor to go to war, right, to go do that. And sometimes that could be really fun, to put on a different version of yourself and learn. But when it starts to feel negative and like it's a lot of energy, that's a really good example. Two is that you're just in an environment where you're not around your people. Like, when you're throwing out ideas, when you're telling jokes — you know, the word toxic is kind of thrown around, and I think you got to be careful, because sometimes things are just hard. But you know that you're doing your work, you start with a full tank every day, and you're not leaving with a full tank every day. It's draining you more than it's filling you up. Because loneliness actually is not draining. It's like a different feeling. I think it's isolating and it's disorienting, it's scary, but it's not necessarily draining. So that's another second leading indicator. And then I think the third leading indicator is that if you listen really deeply — and I can only speak for myself — the voice inside is different. The internal voice when you're lonely is like, this kind of sucks, I'm lonely, I'm isolated, this is really hard. But when you think about, would I rather be doing something else? The answer to the question is like, no, I'm just in the tunnel now. When you ask yourself, are you using your full capacity, and it's not a good fit, the answer is usually no, I'm not using my full capacity. And when you ask yourself the question of, am I doing my best work, the answer is usually no. And then when you ask the follow-up question, which is, am I doing my best to be doing my best work — because sometimes you just get dealt a hard hand and you got to go work for it, and, you know, your boss isn't good, so you got to go around your boss to go do your best work — am I doing all the work to do my best work? The answer to that is usually yes. And so if you're doing your absolute best work to do your best work, and it's not clicking for a substantial period of time, and you're leaving every day more drained than not, there's just these little things you can ask yourself to get much more ground truth to kind of compare against those two.
Jason Baumgarten 48:25
I think a lot about leadership and what it means to be a good leader. And obviously there's all kinds of cheesy things, like, well, you need followers. One of the things that I've realized is this idea of finding fit for people is actually the genesis of a great leader. Like, you're great at figuring out what somebody's superpower is, but importantly, you're great at then putting them in a role that makes that superpower a reality. And I think not enough leaders ask the people working for them those questions you were just alluding to, like, do you feel more drained or recharged at the end of your day? I mean, what business doesn't want to get the best out of their employees? But it turns out that like 60, 65% of American employees would say, not at all, right? And many of them would say, I don't even know what they want out of me, let alone whether I'm giving it. So I think for the leaders listening, really take a moment and find a way to get ground truth on the people working for you. You know, if you think they don't have any more capacity to give and they're doing the best they can do, fine. But I think most leaders I talk to deeply wonder whether they're actually getting the most out of their employees and out of their peers and out of the organizations they're a part of. And it may not be that they're getting nothing, right? Usually they're getting something, but they may not be getting that extra amount. I always remember a very famous founder I worked with. We were building his board in the early days, and we asked him what he wanted out of his board members. And we were expecting some complex answer. And he paused, and he said, I want generosity. And it sort of threw us because it was such an unusual answer. And I said, well, what does that mean to you? How would you know if you had it? And he said, you know, if somebody was in the shower washing their hair in the morning, thinking about how to make this a better company, that's them being generous. And it was such a good example of, you want employees who are thinking about making the company a better place. I don't mean just, you know, bringing muffins in on Fridays, but like, making the product better, making the customer experience better, making whatever the levers you have as a business — if you have employees who are always thinking about that, and it's not, you don't have to prescribe it on a list, I think that's pretty special. And I would urge everybody to be like, do you have that or not? And you've been able to manifest that in a remote environment, which is even harder.
Lexy Franklin 50:44
Well, I think one thing you said that's so brilliant is that it's okay to talk about this stuff. Like, even the question that you said is somewhat taboo, right? Like, are you feeling more drained than not? Or what are you really great at? How can I set you up to get into the right place to go get that greatness? And I think this is the difference between being an employee and really leading. So one of my big lessons to share here is that, you know, when you're working with someone as an employee, you make a really snap judgment if someone's good or not, very fast. You ask them to go do something, and you're like, they do it really well, they're great, or they don't do it well, I really like working with that person, they're not that good, right? But those snap judgments are actually wrong on a bunch of different levels. They're wrong because it's just a moment in time and people change, but they're also wrong because it's not asking the right question. If most of the people in your company are actually pretty good, they're very smart, they're driven, they want to contribute, and they're not to the extent that you think they should be, it's probably because they're either not in the right spot, they're feeling drained, there's a conversation, or there's a question that needs to unlock. Like, one of my best buddies, who's an amazing founder, used to say, every time someone's stressed or worried, I'm so happy. Like, it's the happiest moment as a founder ever, because then I can talk to them and get them unstressed and unworried and in the right place and super bought in. Like, he just was like, that's the signal for them to move. You know, Peter Drucker, he used to do these seminars, and he'd have very senior executives in the room, and he'd say, how many of you have deadwood in your organizations? And they'd all raise their hand. And then he'd say, how many of them were deadwood when they got to your company? And everyone sort of sheepishly lowered their hand. Like, we very rarely hire people who we think are bad. And so I always say, if you've got somebody who's not doing the thing you want them to do, it's possible you made a bad hire. It's possible you put them in a role that wasn't well suited. It's also possible you aren't giving them clear direction or clear outcomes or something else. And so it does have that moment of reverb back to you as a leader.
Jason Baumgarten 52:44
All right, Lexy, we should do a speed round, because those are fun.
Lexy Franklin 52:47
Let's do it.
Jason Baumgarten 52:48
Okay. You're down to the wire in a critical hiring decision. All the data — psychometric, structured interview scores — tell you one thing, but your gut is saying don't do it, or whatever the opposite is. Which one do you trust?
Lexy Franklin 53:00
This is a really hard question. If your gut says that you're a no and the data says that you're a yes, I think that most of the time you go no. But if you go against your gut as the leader and you hire someone against your gut, very rarely does that work out. But I suspect you're going to say, if your gut is the other way, you're going to go with it. If your gut is a yes and the data says no, I actually would spend a lot of time thinking about that one personally, because that's usually a really good sign of you need more information. If the data says you should hire someone and your gut says no, my advice would be, is that you're a founder for a reason, your gut's gotten you to a really good spot, ignore it at your peril. So I would probably go gut related regardless of all the data.
Jason Baumgarten 53:44
All right, so I've got a lesson for everyone listening who wants to go with their gut, which is fine, that's your prerogative as a leader. Keep track. So keep a scorecard on everyone you hire. But it's important, not just the people you hire, but the people you don't hire. What was your gut, what was the data, what was the outcome, whether you hired them or not? If it turns out you have a great batting average, if you're great at it, then your gut is telling you something you haven't figured out how to measure. But I would say a lot of people that I talk to over the years that do this, when I say, well, okay, let's go back through every single hire, they realize they're really bad at it. And one of the things you learn from forecasters is most people are really good at prediction — they actually measure whether they're good, and they tune. And again, the gut is one signal in the data, but keep track. So for everyone listening, keep track of your results. So one other thing I noticed from probably interviewing a thousand people, you tend to reject a lot of people who would do really well at the job. So I think that's another thing to be really, really mindful of. If you did that tuning, my guess is that in retrospect, you probably rejected a lot of people who would have been great at the job for not a great reason. And I think that's another really important thing as well. The other problem with this conceit is, what is the data, right?
Lexy Franklin 55:11
Totally.
Jason Baumgarten 55:12
We're assuming in this case you've got good data, but you and I both know, career and history — a lot of interview data is super, super meaningless. All right, we're going to go really fast. What is the single biggest non-negotiable red flag for you during an interview or reference check that just ends the conversation?
Lexy Franklin 55:18
So this is completely learned behavior, so this might be totally not the right way to do it. But I love reference checks. And I think that if someone in a reference check was like X, Y, and Z, the truth came out — I don't necessarily make the decision based off that, but that reference check information is so valuable, because they had so much experience with that person. And if it's kind of a BS reason, then it's great, I'm like, cool, the best I can come up with the BS reason, I'm definitely hiring this person. But if it's like a legit reason, yeah, it's really hard to hire, I'm not gonna hire.
Jason Baumgarten 55:57
All right. One piece of conventional, widely accepted leadership advice that you think is utter nonsense.
Lexy Franklin 56:04
I think any questions on how you're gonna scale before you have something that people love more than anything in the world is very silly. Like, I think that we spend a lot of time being like, well, this is the TAM, and how is this going to grow, and what's this going to look like, and what are the pieces, and how are we going to get to all those people? And I think as long as you're in a relatively big market, none of it matters unless you have something that people would be like, I love this so much, I want to tell my friends about it. Like, I think the bar for greatness is so underestimated. It has to be so good in order for you to build $100 billion. It has to be so strong. So I think anything related to growth, how this is going to scale, what is our huge differentiator — all of this stuff, which is stuff we fall into even today. I was having conversations about this. It's so easy to get seduced by this stuff. None of it really matters if you're just looking at it from a really hardcore way. And I think it's BS. It's funny, when I was a kid, whenever a commercial came on for some product, I'd always be like, oh, you know, such-and-such must be good. And my dad would always say, well, you know, if it was really good, they wouldn't need to advertise it so much. And there's a kernel of truth in that.
Jason Baumgarten 57:29
Where you're pointing to this idea of, like, get to the scaling once you've gotten to the product. You know, don't get ahead. Okay, best career advice you've ever received, one sentence or less.
Lexy Franklin 57:38
One of our investors basically says that the best CEOs actually get the most advice. Have that self-confidence in yourself that of course you're going to figure it out, but also have the ability to just be like, what do you think? What would you do in this situation? How would you look at this? Like, can you look at it through my eyes? What do you see? And be okay with all that conflicting stuff coming in.
Jason Baumgarten 58:05
I think that's great advice. As you were saying that, I was thinking about all the great CEOs I've worked with, where they would ask me questions about things that they didn't need to, but it was just their way of being. And then so many CEOs that are not very good, that would be like telling everyone in the room what the answer was, even when everyone in the room knew it was the wrong answer. So I think that idea of being open from a wide range, right? Like, it's not just — don't just ask the obvious person, ask the non-obvious person. I think that's really powerful. AI obsolescence question. And by the way, for anyone listening, Sidebar is a totally AI-native company, Lexy's like in it. One skill or leadership trait that you think is going to be obsolete with AI.
Lexy Franklin 58:44
I think the most important thing to doing a good job at work is having context. Like, you have to understand how all the pieces of a company and all the things fit together. I think the hardest thing as a CEO is you have more context than everyone naturally, because you're bubbling all of the information to you. I think a large part of the reason to have upper executive management, mid-management, is context distribution, right? Of just being able to be like, oh, I was in this meeting you were in, let me kind of explain this to you, let me think about this, let me think about all these things, like, very, very, very quickly. In a world of AI, context is going to be distributed much more effectively than it's ever been before. It's already insane. You record all your meetings, you upload it to a central knowledge base, anyone can query that, every single meeting you're getting better and better and better at it. Like, this idea of, oh, today we're thinking about pricing in a new way, we're thinking about — you know, yesterday, well, in the world from T-minus a week ago, you had to be in the pricing meeting in order to understand that context. And then someone needs to go explain it to you, you need to do an HPM to be like, here's how we're doing pricing now. Like, all that stuff is so important, but it requires a lot of people, and people whose jobs are to just communicate over and over and over again. You know, AI is the best at holding context, right? Like, the context window is what makes it insane. But I think what's crazy about it is that if everyone has all the context that's updating all the time, you end up having these conversations with context as an entity in a way that you never had before. Like, the reason that the more senior you get, you end up talking to people in smaller and smaller groups in a lot of ways, is because they're the only people who have all the context that you do in order to have that conversation. But if you can kind of talk to the entity of the company as context, it enables the creativity of everyone across the organization 100 times, a thousand times more. Because someone can be understanding what's going on in the pricing meeting, having not been there and not having to wait three, five, seven — you know, for the company update, for the monthly meeting, to understand all of that. Like, the speed of learning is going to grow so much. And so I think these context bearers in companies are going away, and I think they're going away really fast.
Jason Baumgarten 61:08
It's so interesting. One of the things that when I was in consulting, I realized you always have to tell people why. So if you say, like, hey, we should build this model, or we should do this, you'd always give them the why. And not in a — I mean, there's the Simon Sinek, like, "why," but there's also the context why. Like, they should know how this fits in, because they might see a different, better way to do it. It was really starting — pushing the context layer down.
Lexy Franklin 61:31
You're spot on.
Jason Baumgarten 61:33
Okay, one book or movie that has had the biggest impact on you in the last five years.
Lexy Franklin 61:38
I think Moby Dick has had the biggest impact on me in the last five years. So when I was in school, I got to read a lot, and then there were probably, you know, 30 books or so that I didn't get to read in school for whatever reason — that, you know, these canonical books, like many people call Moby Dick the great American novel, right, the best one. And I was like, man, I just missed it. Like, I didn't get to read it in school. And so I bought it, and, oh man, Moby Dick, if anyone hasn't read it, is quite the book. It is very hard to read. There's no punctuation in Moby Dick. Like, it just goes on forever. Also, Moby Dick doesn't show up for like hundreds of pages. So you're just reading Moby Dick, you're learning about all this maritime history, there's no punctuation. I think there's some sentences that are a page and a half long. But in five seconds, you can kind of tell, like, oh, this is a singular creation. But the reason I chose it was for two reasons. The first is, there's this one line in Moby Dick — "death, trellis, life." They're talking about this whale's bones, and they're on this island, and all these flowers are sprouting from the bones. And I was like, wow, you could go hundreds of lifetimes and not write a line like that. "Death, trellis, life." And it was just so cool to fight your way for nine months through this book, on audio and on written, and read a line like that and be like, wow, that might be one of the best lines I've ever read in my entire life. In this book of words, to find something that beautiful was really inspiring. I think about it probably every day. Actually, maybe one day, many years in the future, or maybe today, I have a "death, trellis, life" in me. Can I go find it? So that's part one. And then part two is it's just really cool to do really hard things. You know, I've been a really good reader my whole life. This book was hard, and it was brutal to get through it. But it just kind of changed me, because afterwards I was like, oh, I read Moby Dick. Like, it's just something that I've always wanted to do, I didn't believe I could do it. And I think it just inspired me to lead in a different way, which is like, today, maybe I'm one one-hundredth of who I'll become. Like, I haven't even read my Moby Dick yet.
Jason Baumgarten 64:00
Well, my favorite line from Moby Dick — you and I did not talk about this — is, it is not down on any map; true places never are. And, you know, I think that is a little bit of the spirit of entrepreneurship and finding great products. Like, you've got to discover your fictional island. Lexy, before I let you go, if people want to find you or want to learn more about what you guys are building, where should they go?
Lexy Franklin 64:19
Yeah. So you can just connect with me on LinkedIn. I'm just Lexy — L-E-X-Y — Franklin. Or you can email me, lexy@teamsidebar.com. I'd love to talk with you. And I just want to make a quick plug for all the listeners. I have the pleasure of getting to meet and talk to lots of different people in my life. I'm a very lucky person. And, Jason, you're one of one. Like, just how you think about the world, how you think about your work, how you think about fit, how you think about career — for all of your listeners and all of your readers, they're so lucky to be in your orbit. Because I'm so lucky to be in your orbit.
Jason Baumgarten 64:59
Well, Lexy, thank you. And for everyone listening, if today's conversation landed for you, share it with one person in your life, and ideally somebody who's maybe a little stuck in their role because they haven't found that fit. Because what we figured out on the show is that fit doesn't happen to you — you have to build it, you have to find it. And sometimes you have to take a little risk, like Lexy leaving Facebook to find perfect fit for him at Sidebar.
Lexy Franklin 65:21
And, Jason, can I have one thing at the end? Which is just, like — what I want to say is, for anyone who's listening who's at one of those moments, right, where you're like, whether you're feeling lonely, whether you're feeling lost, whether you're feeling found and it's all going well — I just want to say that Jason and I super believe in you. Like, we just believe that you're going to go get what you want. We believe you're going to become whoever you're supposed to be. And there's this great line that someone taught me, which is called "borrow my confidence." So whenever you feel like you're a little bit lost, or it's maybe not going to work out, or you're in the tunnel, I was taught that you could just borrow someone else's confidence, that it's going to figure it out. So, like, I just want to offer that you can borrow our confidence. Like, we believe in you. We think you're genius. Like, you obviously are going to figure it out. It's obviously going to all work, and it's going to be spades or aces. And so I just wanted to share that, because for anyone who needed to hear it, we believe in you. Borrow a little swagger.
Jason Baumgarten 66:21
See you next time on Fit Happens. Lexy, thank you, as always. Thank you for being here and for sharing your wisdom.
Lexy Franklin 66:30
What a pleasure. Thank you so much, Sam.