The Exchanges

Q about kind of doing very little, 10 decisions a year, delegating, giving accountability. Is that from day one? Do you say, hey, go do your thing? Is there a transition process of delegation? Do you start with full trust and it's there to be lost, or none and it's there to be gained? How do you physically approach this as a leader? I need to be more like you. Help.

A Well, remember, I started this business at my kitchen table. It was just four of us for two years at a kitchen table. And now we have 1200 employees, and we're a public company. So a lot has happened. I have an eighteen-year-old daughter and a fourteen-year-old son, and they're always making fun of me for being lame. And I tell them, guys, you never met me. You literally, I am a construct created to be your father. The responsible, tame, calm. This is a persona that I created for you so I could be a good dad to you. You never met me. And what I, I would say to employees at ZipRecruiter today is, you will never meet me. The entrepreneur who started this business, I wasn't hands deep. I was Up to my shoulders deep in every part of the business. I've done every job in the company, customer service through sales, through biz dev. Like I've done it. I've literally done every job. And now I try to do as little as possible because what happens as your organization grows is there's this process that I call increasing specialization. Initially you hire like good marketers. And then eventually you're like, no, I need a TV marketer. I need a radio marketer. I need a podcast marketer. And the people you hire are experts in this very niche field. So if you try to stay involved, They're all better than you at the thing they're doing, but they'll all defer to you, and anything you say, even a…

AI assessment note: “I literally am practicing the discipline of not even giving my opinions anymore.”

Q What have been some of the biggest mistakes you've made in scaling the team? When you think back to that four people around the kitchen, and you look to where you are now, what mistakes are you like, oh my god, that was a big one?

A I mean, I think the biggest mistake that I made is a hiring bias we all have. We love ourselves some people who look like us. Oh, do we love people who look and sound like us? And I was an entrepreneur, I'd done every job in the company, so I wanted gunfighters. Five tool players who could come in and confidently problem solve any part of the business, and I was like, I was looking for these young killers, and then I had this rude awakening. I remember it so clearly. They had me interview someone who had come out of a marketing media company who was a buyer, and the interview I had with him for 20 minutes said not one thing I understood, but they were all excited about him. I was like, guys, you can hire him. That guy, I have no idea what he does or how he does it. Like, he made no sense to me. He spoke in jargon the entire time, so we hired him over mic. Apparent objection. And the first day he's on the job, the first day he's on the job, he goes, hey, where are the audit logs on the ads you're running? And I was like, what's an audit log? He's like, the thing you get from the TV stations that show you that they ran your ad when they said they did so that you can make sure you're not overpaying them. And literally the first day he saved us a million dollars because they had not been running the ads. They said he made us a million dollars in a day. That time we were a company t…

AI assessment note: “I think the biggest mistake that I made is a hiring bias we all have.”

Q Tell me, what's the hardest element of your role with ZipRecruiter today?

A Being the CEO of a public company is that you become more externally facing than you are internally operating, and I was very, very strong as an operator, so that's my wheelhouse talent, and now I'm asked to do a bunch of things that I've never done before. So I've gone from being like the foremost expert in the business and all the things that we do to being like the 50,000th best CEO in America. You know, like I've got to go on TV after earnings calls and explain what the business is doing, and I've got to talk to investors. I'm like a bag carrying sales rep to the investor community now. And so it's just a very different job.

AI assessment note: “you become more externally facing than you are internally operating”

Q Why do you think that is? Is that like youthful naivety and exuberance?

A I think that is the armor of youth. That is both your superpower and your greatest weakness, which is like, you can believe you can do anything. You think all your success is because of you. You think you're some unique animal. I saw this great article, but it was talking about, like, who becomes a successful entrepreneur. All this time, I thought I was really special, and, like, I'd, like, overcome all this stuff, and it turns out I filled, like, nine of the 10 boxes. Middle-class family went to private school, had an early brush with the law. It was, like, every single one of them, I fit, and I was like, oh my god, I'm, like, I'm literally the classic person who succeeds. I'm not special in any way, but I really thought I was special 12 years ago. Like, I was like, Like, I am the person who has the courage to do this and the will to get it done. It's just so funny to me when I look back on it.

AI assessment note: “I think that is the armor of youth. That is both your superpower”

Q Final one for you. What are the next 10 years, like, for you and for ZipRecruiter?

A These are going to be the greatest 10 years I've had at ZipRecruiter because we have such a clarified vision of how we're going to change the world, and I'm so excited about it. Like, it's not about, obviously I have to deliver to the street The revenue numbers that we're talking about, but more importantly, it is very rare in your career. You will work on a product that everyone in the country will use, and it can make everyone's life better. That is not a statement that most businesses can make. And we are all fully cognizant of the opportunity and also the responsibility that brings, because we are truly doing something that has never been done before. And I always say like take an existing business and like put one optimization on it. And it's like a hundred million dollar business every time. But if you want to like change the way everybody does something, It's knife fighting in the jungle. You're a trailblazer. We are trailblazing. Like, we're trying to flip the whole job market. We're trying to get employers to go first. Novel concept, and it sounds easy to describe, but it is so hard to execute on it. But we had millions of job seekers receive outreach from employers before they'd applied last year, and that was the tip of the iceberg. We're going to change the way the job market works, so I'm excited about it.

AI assessment note: “These are going to be the greatest 10 years I've had at ZipRecruiter”

Q Ian, you said about staying calm there. When I spoke to Warden, I asked him the question, what is Ian's biggest superpower? He said, and I'm quoting here, Ian has the most insane ability to stay cool under pressure. Talk to me. I don't have this same ability. What do you do to stay cool under pressure? How do you not lose your shit when shit hits the fan?

A That's funny that Ward said that. That's really interesting, because I can think of a few times that Ward has caused me to... Have an intense reaction. This was my path to it, but it's not everyone's path to it. Once you have children, the art of being a good parent and the art of being a good leader are the same, which is the ability to suppress your natural first reaction to think about the outcome you want to create. And so like with kids, it is literally mastering the discipline of patience, mastering regulation, because, you know, a three-year-old is not someone you can reason with. And if you let yourself get heated, you're always going to lose. The three-year-old is literally cognitively not capable of having a rational discussion with you. So it was through the practice of parenting that I developed this, what I call better listening and thoughtful approach. And then I started applying it at work with tremendous results. I owe so much to my kids because I felt like they made me a better person in so many ways. But I really, really, really try to listen when people talk. And I really try to think before I speak. In good situations and in bad situations, I have told the whole company every year, I only make one New Year's resolution every year. It's the same New Year's resolution every time. Listen better, because the older you get, the more senior you become in your role…

AI assessment note: “suppress your natural first reaction to think about the outcome you want to create”

Q My question there is, one thing that I find the biggest challenge with product marketing today and the storytelling, it's bland, Ian. How many products do you actually feel excited about, where you're for or against it? You could hate it, but you feel something. How do you feel about really bringing A stance to product marketing today and to storytelling.

A I give a recurring speech about version one point O's and version one point O's are the only thing in life that actually take courage because you're effectively putting something out there that's never existed before. It's always deeply flawed. Everyone can look at it and criticize it. And so it takes real courage to be vulnerable enough to put a version one point out, out there. And when you look at the marketing, that's another example of like We are bereft of version one point O is because the most common forms of marketing that you see are all derivative of each other. So people put testimonials up there or they put up like a single feature story, but nobody makes bold claims. Nobody puts out commercials that stun you or make you think. And there's a great example of one that did do this. So I'll quote it and then you can maybe go look it up and then you maybe get inserted. I don't know if you turn this into a video or not, but under armor, the apparel company at one point did a TV commercial and Filled with apparel that had technology embedded in it. So you could do things like touch your sleeve and a screen would come up and you could change the color of your shirt. It was just stuff like that. And when you saw it, you were like, everything in it was futuristic and cool. None of it existed, but man, did it get you excited about Under Armour? Because it showed, it was like…

AI assessment note: “that's the kind of sort of bold Courageous marketing that does storytelling through visuals”

Q Do you give them that responsibility on day one though? Or is it one where they scale into it over time with you and with the team? Do you start with full trust or do you start no trust and it's there to be gained?

A Now I start with full trust. It's like burning in a car. You get a new car. It's how you drive it for the first thousand miles. Determines like how that car will drive forever. Now start with full trust and try to immediately create opportunities for them to learn how much autonomy they actually have. However, it's trust with an insistence on results. And so if you're in your job for a month and there is no momentum, we will intervene. We will not allow you to fail four months at ZipRecruiter when you join. So if you come in and you hit the ground running, fantastic. You're just going to get more and more responsibility and more and more autonomy. But if you come in and And you're stunted, unsure of which direction you should be moving in. Like we're going to move in and help. And then very quickly, we're going to set the expectation. Like we're never going to want to do this again. So if you want to succeed here, you've got to do your own strategy. And I mean, I think that actually is one of the great challenges for founder CEOs like myself, which is to actually give people the space. I do it by having less meetings, by the way, because if you start talking to me, I get too excited. Like I want to tell you what I think so badly. And I'm like a giant, like my voice booms. And when you hear my voice, you can't hear other voices. So, like, I've learned, like, I have to really rep…

AI assessment note: “Now I start with full trust.”

Q So what does listening better mean? Does it mean talking less, and saying nothing, and absorbing? What does that mean to you, and how do you measure whether you're successful in your New Year's resolution?

A Well, there's a reason I keep making it over and over again, because I never feel successful enough, I'll tell you that. I think that as managers, there's simple rules you can apply, like, speak last. Let everybody get their words out, because once you start speaking, the conversation's over. That's number one. But number two, I get excited, and when I get excited, and you're talking to me, my tendency is to, like, Yes, and you, and like, I'll cut you off, and I won't let you finish your thought, and I haven't even fully processed what you said, because I got so excited about a piece of what you said. It's probably like when you're interviewing somebody, and you probably have to wait for them to stop there, blah, blah, blah, blah. Like, I'm probably doing it to you right now, and you're like, I want to ask you about that, and you just keep going, you just keep going. I find people feel more confident sharing ideas with me if I can not just listen to them get it all the way out, but if I pause for two seconds and reflect. I'm a big fan of the two-second pause.

AI assessment note: “there's simple rules you can apply, like, speak last.”

Q How do you think about your relationship with money?

A We had a lot of success early on when we were bootstrapping and we could have put millions of dollars in each of our individual pockets at any time. And so we've always had access to a lot of money. And I had to do this exercise with my co-founders. There were three of them to figure out like how much money should we take out of the business and put in our pockets versus how much should we reinvest in the business? And so the way I did it is I had us all sit around the table and I said, all right, not in dollars, but in lifestyle, describe the life you want. And so I'll go first. My life is I want my kids to go to great private schools. I want to be able to take two vacations a year. Ideally, I want to fly business class. What are yours? And then they went around and they said it. And then we were like, okay. And then we back with the napkin that we're like, this is how much money we need right now. And that's how we came up with the amount of money that we would take out of the business versus reinvest. And literally like Money gets stupid. Like, there comes a point where you'll never spend all the money you have unless you start doing things like flying on private jets or buying boats, and like, once you get older, I'm a little bit older, and so, and I have, you know, kids. You don't want to do those things, because the message you're sending your kids is all effed up at that…

AI assessment note: “not in dollars, but in lifestyle, describe the life you want.”

Q Why do you think that is? Is that like youthful naivety and exuberance?

A I think that is the armor of youth. That is both your superpower and your greatest weakness, which is like, you can believe you can do anything. You think all your success is because of you. You think you're some unique animal. I saw this great article, but it was talking about, like, who becomes a successful entrepreneur. All this time, I thought I was really special, and, like, I'd, like, overcome all this stuff, and it turns out I filled, like, nine of the 10 boxes. Middle-class family went to private school, had an early brush with the law. It was, like, every single one of them, I fit, and I was like, oh my god, I'm, like, I'm literally the classic person who succeeds. I'm not special in any way, but I really thought I was special 12 years ago. Like, I was like, Like, I am the person who has the courage to do this and the will to get it done. It's just so funny to me when I look back on it.

AI assessment note: “I think that is the armor of youth. That is both your superpower”

Q My question there is, one thing that I find the biggest challenge with product marketing today and the storytelling, it's bland, Ian. How many products do you actually feel excited about, where you're for or against it? You could hate it, but you feel something. How do you feel about really bringing A stance to product marketing today and to storytelling.

A I give a recurring speech about version one point O's and version one point O's are the only thing in life that actually take courage because you're effectively putting something out there that's never existed before. It's always deeply flawed. Everyone can look at it and criticize it. And so it takes real courage to be vulnerable enough to put a version one point out, out there. And when you look at the marketing, that's another example of like We are bereft of version one point O is because the most common forms of marketing that you see are all derivative of each other. So people put testimonials up there or they put up like a single feature story, but nobody makes bold claims. Nobody puts out commercials that stun you or make you think. And there's a great example of one that did do this. So I'll quote it and then you can maybe go look it up and then you maybe get inserted. I don't know if you turn this into a video or not, but under armor, the apparel company at one point did a TV commercial and Filled with apparel that had technology embedded in it. So you could do things like touch your sleeve and a screen would come up and you could change the color of your shirt. It was just stuff like that. And when you saw it, you were like, everything in it was futuristic and cool. None of it existed, but man, did it get you excited about Under Armour? Because it showed, it was like…

AI assessment note: “nobody makes bold claims. Nobody puts out commercials that stun you or make you think.”

Q Do you give them that responsibility on day one though? Or is it one where they scale into it over time with you and with the team? Do you start with full trust or do you start no trust and it's there to be gained?

A Now I start with full trust. It's like burning in a car. You get a new car. It's how you drive it for the first thousand miles. Determines like how that car will drive forever. Now start with full trust and try to immediately create opportunities for them to learn how much autonomy they actually have. However, it's trust with an insistence on results. And so if you're in your job for a month and there is no momentum, we will intervene. We will not allow you to fail four months at ZipRecruiter when you join. So if you come in and you hit the ground running, fantastic. You're just going to get more and more responsibility and more and more autonomy. But if you come in and And you're stunted, unsure of which direction you should be moving in. Like we're going to move in and help. And then very quickly, we're going to set the expectation. Like we're never going to want to do this again. So if you want to succeed here, you've got to do your own strategy. And I mean, I think that actually is one of the great challenges for founder CEOs like myself, which is to actually give people the space. I do it by having less meetings, by the way, because if you start talking to me, I get too excited. Like I want to tell you what I think so badly. And I'm like a giant, like my voice booms. And when you hear my voice, you can't hear other voices. So, like, I've learned, like, I have to really rep…

AI assessment note: “Now I start with full trust.”

Q How do you know how good they are if it's in a position that you don't know or understand?

A The media guy was the outlier, because what I have found with the truly elite pointy people is that when I sat down in an interview with them, it's like getting an education on their subject, and if they're infectiously enthusiastic about something that I never cared enough to go deep on before, in particular, something I thought was boring. I had a meeting with an accountant who focuses on tax issues, and she was so giddy About all the ways that we could save money on taxes by having a proactive forward thinking approach that I started to get excited about taxes. And then I tried to tell my wife about at dinner, this awesome interview had. I realized like I couldn't repeat half of what had been said to me. I just knew we had someone who lived and breathed taxes and I was never going to be that person. So like, I guess I look for enthusiasm, particularly infectious enthusiasm.

AI assessment note: “I look for enthusiasm, particularly infectious enthusiasm.”

Q lack of detachment, either with my venture fund or with my media company. When they do well, I'm fucking high. When they do badly, I'm on the Floor, and I'm terrible. Like that, you never met me, doesn't really sound like you have much detachment. How do you think about the ability to separate yourself from your business's success, and not be in the bluntly uncomfortable position that I am?

A I mean, it's like, uh, extrinsic versus intrinsic motivation. I remember I was at a company, I'd been hired as sort of like the turnaround guy for this company, and at one point I became like this no-name operator in LA, and so I got twice, I did a turnaround job. And they were negotiating my bonus with me, and they were like, well, if you hit this number, you get X, but if you hit this bigger number, you get Y. And I was like, listen, there is no difference in how I will approach this job or the effort I will put in whether you put X or Y or Z there. So put any number you want. Like I'm going to do the best job I can possibly do because that's just how I operate. You know, all I do is try to hypergrow your business. That's what I'm going to do. There's no throttle that you're going to motivate me with money. I'm not a, and my whole career, people have asked me, oh, you've taken the company public. You theoretically could take a lot of money off the table. Like why do you still do your job? I do it because I believe we're building a product that my children will use to find work and they will like it more than what exists today. That's why I do it. Cause I think we're building something important. Like I wouldn't do it just to make more money. I feel like when you get hung up on like, how is this investment doing versus that? And that's extrinsic motivation. Like you picked tho…

AI assessment note: “That part was out of your control.”

Q What does, like, good values mean to you today? If you're then, if you had the chance again, and you now know that good values is crucial, and it's ZipRecruiter first year, how would you approach value setting and value maintenance with what you know now?

A That's a really good question. Well, now that we've put some work into defining just three values, just three, we've started to incorporate them into our recruiting process, and what it does is it acts as a filter. That's proving incredibly effective. It's attracting the right people, pushing away people who don't want to operate in that kind of environment. I think we would have been a better, more united team. Ironically, a more diverse team had we instituted those values sooner in our recruiting process, like literally talked about them in our job ads, literally made them part of the interview process, which we have now done. I'm seeing the power of it. It's one of those things I was really slow to, though. It would have been a real struggle for me back then, because I was so confident back. I'm so much less confident now than I was 12 years ago when I started the business. It's so ironic. I thought I knew so much back then.

AI assessment note: “literally talked about them in our job ads, literally made them part of the interview process”

Q I completely agree. I'm sorry. I'm thinking, and I can't remember. I often ask actually like, what was the last Instagram ad that you clicked and why did you click it? When you think about the ZipRecruiter brand today, how do you reflect on that? Are you happy with the current state of the brand? What would the stance be for you?

A We were first to do many things, and in particular, one of the things we were first to do was big, multi-channel advertising campaigns before it was cool. My favorite thing about startups is, first they ignore you, then they mock you, then they try to kill you, then they try to buy you. Distinctly remember that when we started doing all this marketing, in particular, when we went on television, and then we did crazy stuff, like we went on advertised on podcasts, back when podcasts were like barely a thing. And that second step where they mock you, everyone was mocking it. Everyone was like, ah, ZipRecruiter is going to burn through all their cash. ZipRecruiter has gone crazy. And meanwhile, we're being these disciplined performance marketers. We're running all these ads and measuring the rate of return, and we're just rabbiting the category because nobody realizes how effective this is because we're running unopposed at this point. I think what happened as a result of that, our brand very much became, this is a company that does a lot of advertising. And it's so interesting to me because the reason that You come to ZipRecruiter is because of all the advertising we do. But the reason you stay and are a repeat customer of ZipRecruiter is because of just how well it works. And so I feel like the awesomeness of the product we built has been lost in the quantum of marketing that we …

AI assessment note: “I am completely unsatisfied with where our brand is at”

Q about kind of doing very little, 10 decisions a year, delegating, giving accountability. Is that from day one? Do you say, hey, go do your thing? Is there a transition process of delegation? Do you start with full trust and it's there to be lost, or none and it's there to be gained? How do you physically approach this as a leader? I need to be more like you. Help.

A Well, remember, I started this business at my kitchen table. It was just four of us for two years at a kitchen table. And now we have 1200 employees, and we're a public company. So a lot has happened. I have an eighteen-year-old daughter and a fourteen-year-old son, and they're always making fun of me for being lame. And I tell them, guys, you never met me. You literally, I am a construct created to be your father. The responsible, tame, calm. This is a persona that I created for you so I could be a good dad to you. You never met me. And what I, I would say to employees at ZipRecruiter today is, you will never meet me. The entrepreneur who started this business, I wasn't hands deep. I was Up to my shoulders deep in every part of the business. I've done every job in the company, customer service through sales, through biz dev. Like I've done it. I've literally done every job. And now I try to do as little as possible because what happens as your organization grows is there's this process that I call increasing specialization. Initially you hire like good marketers. And then eventually you're like, no, I need a TV marketer. I need a radio marketer. I need a podcast marketer. And the people you hire are experts in this very niche field. So if you try to stay involved, They're all better than you at the thing they're doing, but they'll all defer to you, and anything you say, even a…

AI assessment note: “I was Up to my shoulders deep in every part of the business.”

Q I completely agree. I'm sorry. I'm thinking, and I can't remember. I often ask actually like, what was the last Instagram ad that you clicked and why did you click it? When you think about the ZipRecruiter brand today, how do you reflect on that? Are you happy with the current state of the brand? What would the stance be for you?

A We were first to do many things, and in particular, one of the things we were first to do was big, multi-channel advertising campaigns before it was cool. My favorite thing about startups is, first they ignore you, then they mock you, then they try to kill you, then they try to buy you. Distinctly remember that when we started doing all this marketing, in particular, when we went on television, and then we did crazy stuff, like we went on advertised on podcasts, back when podcasts were like barely a thing. And that second step where they mock you, everyone was mocking it. Everyone was like, ah, ZipRecruiter is going to burn through all their cash. ZipRecruiter has gone crazy. And meanwhile, we're being these disciplined performance marketers. We're running all these ads and measuring the rate of return, and we're just rabbiting the category because nobody realizes how effective this is because we're running unopposed at this point. I think what happened as a result of that, our brand very much became, this is a company that does a lot of advertising. And it's so interesting to me because the reason that You come to ZipRecruiter is because of all the advertising we do. But the reason you stay and are a repeat customer of ZipRecruiter is because of just how well it works. And so I feel like the awesomeness of the product we built has been lost in the quantum of marketing that we …

AI assessment note: “I am completely unsatisfied with where our brand is at”

Q I always love to have a little bit of storytelling, and so when we think back to the origins, how did you make your way into the world of startups? And then tell me, how did ZipRecruiter come to be? What was that aha moment?

A Well, I actually went to college, practiced the art of writing, thinking that I wanted to become a writer. I grew up in Hollywood, so I came back to Hollywood wanting to write movies. I went and worked for a very famous production company that was on the Warner Brothers lot. And in the first year I was there, they treated me so badly that I said, I will take any job I can get to get off this lot and get out of Hollywood. And the first job that I happened to get was at a tech startup. The rest was just serendipity, luck, right place, right time. So I didn't set out to be in tech. I wound up in tech. My background was in writing.

AI assessment note: “And the first job that I happened to get was at a tech startup.”

Q But what does it take to change it and make that transition?

A The onus is on us to deliver on that ambitious idea that we're putting out there, which is nobody trains you to be a job seeker, so you get dumped in front of a search engine, and then they say, hey, go write a Boolean expression and find the right jobs to apply to, and you suck at it. Everyone sucks at it. That's why everyone hates looking for work. So like, why does it work that way? It doesn't even make sense. We have all these amazing modern matching algorithms. Like you go on YouTube in like 10 minutes, it figures out all the videos you should be watching. And then you just, you get dropped into that like wormhole. You can't get out of it. You go on TikTok. You can't stop scrolling. Like we can do the same thing with jobs. We can use the wisdom of the crowd to know who you look like, accurately predict which jobs you should be applying to and which employers will like you. And that's a completely different experience for job seekers. More importantly, why do we make job seekers go first? Why do we make them apply to employers who are receiving a hundred other applicants? Like what we should be doing and what we're now doing as a recruiter is pitching you to the employer so that they recruit you. And that's a way better experience for both sides. Cause then the employers are only talking to candidates. So they're already excited about, I mean, you take it for granted and I …

AI assessment note: “what we're now doing as a recruiter is pitching you to the employer”

Q But what does it take to change it and make that transition?

A The onus is on us to deliver on that ambitious idea that we're putting out there, which is nobody trains you to be a job seeker, so you get dumped in front of a search engine, and then they say, hey, go write a Boolean expression and find the right jobs to apply to, and you suck at it. Everyone sucks at it. That's why everyone hates looking for work. So like, why does it work that way? It doesn't even make sense. We have all these amazing modern matching algorithms. Like you go on YouTube in like 10 minutes, it figures out all the videos you should be watching. And then you just, you get dropped into that like wormhole. You can't get out of it. You go on TikTok. You can't stop scrolling. Like we can do the same thing with jobs. We can use the wisdom of the crowd to know who you look like, accurately predict which jobs you should be applying to and which employers will like you. And that's a completely different experience for job seekers. More importantly, why do we make job seekers go first? Why do we make them apply to employers who are receiving a hundred other applicants? Like what we should be doing and what we're now doing as a recruiter is pitching you to the employer so that they recruit you. And that's a way better experience for both sides. Cause then the employers are only talking to candidates. So they're already excited about, I mean, you take it for granted and I …

AI assessment note: “what we're now doing as a recruiter is pitching you to the employer”

Q Ok, so infectious enthusiasm, also teachability, like where they are the ones educating you, and pointy people. Any other big lessons, like I've relied too much on CV and logos, using that as a predictor of future success when it really wasn't biggest mistake for me. Any others for you where you're like, glaring, why did I do that?

A There's a couple questions I ask in every interview, and one of the questions I always ask is, tell me about your competition and how you were different. If you can't answer that question, you are someone who everyone Was telling what to do. Success for you was being told what to do. You weren't thinking like an internal owner. So that's one of my favorite questions to ask people. And then another question I like asking people is tell me about your biggest failure and the honesty with which they answer tells me a lot about like how they think about failure and what they learned. I tended to get fooled in the room. Like I think we all do by extroverts who presented incredibly well, and we're really confident and that definitely doesn't work on me anymore. I look for people who can teach me something in an interview. I look for people who are reflective about the lessons they learned from each of the places they've been. And then I look for people, this is going to sound crazy. This seems so obvious who I understand what they said well enough that I could repeat it. Meaning like so many people blitz you with like information. That's it. I guess it's storytelling. It's a little bit of what we talked about before. Like if you can speak to me in a way that I understand everything you're saying, that I feel really confident hiring you because communicating with me is scary. Like I'm …

AI assessment note: “I tended to get fooled in the room. Like I think we all do by extroverts”

Q which is, I think we're both fucking drivers and execution machines, and the thing that I worry about is, like, with a loving relationship with kids, I will become mediocre, because I will spend the weekend with them, and I will spend the evening with them. Like, now, nothing stops me grinding. How do you not lose an inch on performance, and be a good dad and a good husband?

A I will tell you the truth. I think you are at a disadvantage to me. I not only have the perspective of Of what it's like to split time between a family and work. I live that truth. And so the best people you will eventually hire wind up being older, get married and have kids. And when I'm talking to my HR team about things like maternity and paternity leave policies, when we're talking about like childcare benefits, like it's personal to me, the people I'm recruiting, understand that. And it gives us another point of connection. All companies end up gravitating to is the more senior people they can possibly hire over time. And those people Probably are going to vibe with me in a way that would be harder for them to vibe with you. There are intrinsic advantages when it's not just about you operating, but you trying to build a team that operates and being older and having a family. That is what I've learned. But by the way, 15 years ago, if you'd asked me, I'd have said exactly what you said. It's been part of my arc, and I would have been a lot less patient, and I would have probably interrupted you three times while you were speaking to me. Like, I was just a different guy. Like I said, you never met me. This is probably a better version of me than the one I was 15 years ago.

AI assessment note: “There are intrinsic advantages when it's not just about you operating, but you trying to build”

Q I always love to have a little bit of storytelling, and so when we think back to the origins, how did you make your way into the world of startups? And then tell me, how did ZipRecruiter come to be? What was that aha moment?

A Well, I actually went to college, practiced the art of writing, thinking that I wanted to become a writer. I grew up in Hollywood, so I came back to Hollywood wanting to write movies. I went and worked for a very famous production company that was on the Warner Brothers lot. And in the first year I was there, they treated me so badly that I said, I will take any job I can get to get off this lot and get out of Hollywood. And the first job that I happened to get was at a tech startup. The rest was just serendipity, luck, right place, right time. So I didn't set out to be in tech. I wound up in tech. My background was in writing.

AI assessment note: “And the first job that I happened to get was at a tech startup.”

Q Ok, so infectious enthusiasm, also teachability, like where they are the ones educating you, and pointy people. Any other big lessons, like I've relied too much on CV and logos, using that as a predictor of future success when it really wasn't biggest mistake for me. Any others for you where you're like, glaring, why did I do that?

A There's a couple questions I ask in every interview, and one of the questions I always ask is, tell me about your competition and how you were different. If you can't answer that question, you are someone who everyone Was telling what to do. Success for you was being told what to do. You weren't thinking like an internal owner. So that's one of my favorite questions to ask people. And then another question I like asking people is tell me about your biggest failure and the honesty with which they answer tells me a lot about like how they think about failure and what they learned. I tended to get fooled in the room. Like I think we all do by extroverts who presented incredibly well, and we're really confident and that definitely doesn't work on me anymore. I look for people who can teach me something in an interview. I look for people who are reflective about the lessons they learned from each of the places they've been. And then I look for people, this is going to sound crazy. This seems so obvious who I understand what they said well enough that I could repeat it. Meaning like so many people blitz you with like information. That's it. I guess it's storytelling. It's a little bit of what we talked about before. Like if you can speak to me in a way that I understand everything you're saying, that I feel really confident hiring you because communicating with me is scary. Like I'm …

AI assessment note: “I tended to get fooled in the room. Like I think we all do by extroverts”

Q Can I ask you, how do you know when you're in the data-driven decision-making phase versus the innovation phase? How to know whether it's Gut or data time.

A I mean, that's art, not science. Everything comes down to momentum. When I saw the team working on the JobSeeker product, our momentum was very slow. We were building a lot of features that look like features that existed on other job boards, but slightly improved, and I always talk about those as jeweler's glass features. If you need to be an expert looking through a jeweler's glass to see the difference between my site and another site, we've done nothing. We're never going to be considered the best at a feature we were 50th To deploy. We need to have the boldness to put something out there where we win not just market share, but mind share. I say this about, there's a site called Glassdoor. It's the review site for employers. You want to see reviews on employers? Well, guess what? There are sites out there that have more reviews about employers than Glassdoor, but everybody who mentions one of those sites, that site always gets described as, oh, you mean like Glassdoor? Because they won the mind share battle, because they were first, and they were The biggest for a while. I think it's critically important to be famous for something. And my argument is most companies only get famous for one thing. And I can prove it to you. I can say like, Hey, what's Google. And the first thing that pops into your head is like, it's a search engine. That's what everyone says. They're also li…

AI assessment note: “that's art, not science. Everything comes down to momentum.”

Q Okay, listen better and more. Well, what can managers and parents do to listen better and more effectively?

A As managers, a simple, like, there's simple rules you can apply, like, speak last. Let everybody get their words out, because once you start speaking, the conversation's over. But number two, I get excited, and when I get excited, and you're talking to me, my tendency is to like, yes, and you, and like, I'll cut you off, and I won't let you finish your thought, and I haven't even fully processed what you said, because I got so excited about a piece of what you said. It's probably like when you're interviewing somebody, and you probably have to wait for them to stop there, blah, blah, blah, blah. Like, I'm probably doing it to you right now, and you're like, I want to ask you about that, and you just keep going, you just keep going. I find that people feel more confident sharing ideas with me if I can not just listen to them get it all the way out, But if I pause for two seconds and reflect, I'm a big fan of the two-second pause. I think the number one thing that I'm working on personally right now is I am probably too cynical, and as a result of that, I distrust when companies talk about their mission, their vision, their values, because I'm like, it's easy to say, don't tell me, show me. That's, I'm always that guy. Like, I never, I never do virtue signaling. I'm never going to be a thoughts and prayers guy. Like, I'm, I'm a like, take action and show through your actions what…

AI assessment note: “there's simple rules you can apply, like, speak last... fan of the two-second pause.”

Q Can I ask you, how do you know when you're in the data-driven decision-making phase versus the innovation phase? How to know whether it's Gut or data time.

A I mean, that's art, not science. Everything comes down to momentum. When I saw the team working on the JobSeeker product, our momentum was very slow. We were building a lot of features that look like features that existed on other job boards, but slightly improved, and I always talk about those as jeweler's glass features. If you need to be an expert looking through a jeweler's glass to see the difference between my site and another site, we've done nothing. We're never going to be considered the best at a feature we were 50th To deploy. We need to have the boldness to put something out there where we win not just market share, but mind share. I say this about, there's a site called Glassdoor. It's the review site for employers. You want to see reviews on employers? Well, guess what? There are sites out there that have more reviews about employers than Glassdoor, but everybody who mentions one of those sites, that site always gets described as, oh, you mean like Glassdoor? Because they won the mind share battle, because they were first, and they were The biggest for a while. I think it's critically important to be famous for something. And my argument is most companies only get famous for one thing. And I can prove it to you. I can say like, Hey, what's Google. And the first thing that pops into your head is like, it's a search engine. That's what everyone says. They're also li…

AI assessment note: “I mean, that's art, not science. Everything comes down to momentum.”

Q Okay, listen better and more. Well, what can managers and parents do to listen better and more effectively?

A As managers, a simple, like, there's simple rules you can apply, like, speak last. Let everybody get their words out, because once you start speaking, the conversation's over. But number two, I get excited, and when I get excited, and you're talking to me, my tendency is to like, yes, and you, and like, I'll cut you off, and I won't let you finish your thought, and I haven't even fully processed what you said, because I got so excited about a piece of what you said. It's probably like when you're interviewing somebody, and you probably have to wait for them to stop there, blah, blah, blah, blah. Like, I'm probably doing it to you right now, and you're like, I want to ask you about that, and you just keep going, you just keep going. I find that people feel more confident sharing ideas with me if I can not just listen to them get it all the way out, But if I pause for two seconds and reflect, I'm a big fan of the two-second pause. I think the number one thing that I'm working on personally right now is I am probably too cynical, and as a result of that, I distrust when companies talk about their mission, their vision, their values, because I'm like, it's easy to say, don't tell me, show me. That's, I'm always that guy. Like, I never, I never do virtue signaling. I'm never going to be a thoughts and prayers guy. Like, I'm, I'm a like, take action and show through your actions what…

AI assessment note: “there's simple rules you can apply, like, speak last.”