20VC: The Job of the CEO is Do As Little As Possible; How To Hire, What Questions To Ask, Why Pointy People are Always 100xers, How To Tell Great Stories Today & How Leaders Must Determine What To Delegate vs What To Control with Ian Siegel, Co-Founder an

Ian Siegel is the Founder and CEO @ ZipRecruiter, a leading online employment marketplace that uses AI-driven matching technology to actively connect millions of businesses and job seekers to their next great opportunity. Since co-founding the company in 2010, more than 1.8M employers have used ZipRecruiter to find their next great hire and over 500 million job applications have been submitted through the site. Prior to their IPO last year, Ian bootstrapped the company for many years to many millions in revenue before taking venture funding from IVP, Wellington Management and Basepoint Ventures to name a few. Before founding ZipRecruiter, Ian served in key leadership roles at CitySearch, Stamps.com, and Rent.com (an eBay company). In Today’s Episode with Ian Siegel You Will Learn: 1.) The Founding of Olo: How did Ian co-found ZipRecruiter from his kitchen with no venture funding and his 3 friends? Why did they decide to not raise venture funding in the early days? What was the catalyst at $50M in revenue for realising now was the right time to raise funding? 2.) The Art of Great Storytelling What does truly great storytelling mean to Ian? What are the components of a great story? Why do so many people today f*** up their product marketing and messaging? Why does Ian believe Version 1.0 is the only one that takes true courage? 3.) CEO's Do As Little As Possible Why does Ian believe his job as CEO is to do as little as possible? How does Ian determine between the things he, the CEO should do, vs those those he should delegate? Why does Ian believe the art of leadership and the art of parenting are the same? 4.) The Art of Hiring: How has Ian's approach to hiring changed over the years? What does Ian mean when he says, "I look for pointy people"? How does he detect them? What are the two qualities that make the best execs? What questions reveal them? 5.) Parenting and Marriage: Does Ian worry that with increasing family commitments, he loses an inch on work? Why does he believe he is in an advantage as a CEO to those that do not have children? What was the biggest argument he has had with his wife? How did it change his perspective? Item’s Mentioned In Today’s Episode with Ian Siegel Ian’s Favourite Book: Living with a SEAL: 31 Days Training with the Toughest Man on the Planet

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome back. This is 20 VC with me, Harry Stebbings, and I have one core metric when I produce any episode: word to value ratio. Your time is currency and it has to be protected, well spent, and every show has to deliver immense value. Well, no show delivers on that promise like this one today. Our guest blew me away beyond all expectations, and I'm so thrilled to welcome Ian Segal, co-founder and CEO of ZipRecruiter, a leading online employment marketplace that uses AI-driven matching technology to actively connect millions of businesses and job seekers to their next great opportunity. Since co-founding the company in 2010, more than 1.8 million employers have used ZipRecruiter to find their next great hire, and over 500 million job applications have been submitted through the site.

• 0:43Harry Stebbings?

  Prior to their IPO last year, Ian bootstrapped the company for many years to many millions in revenue, before taking venture funding from IVP, Wellington Management, and BasePoint Ventures, to name a few. And before founding ZipRecruiter, Ian served in key leadership roles at CitySearch, Stamps.com, and Rent.com. But before we move into the show today, from websites and online stores to marketing tools and analytics, Squarespace is the all-in-one platform to build a beautiful online presence and run your business. Now, there are three things for me that really stood out about why I love Squarespace. First, mobile optimized websites. All websites are optimized for mobile with Squarespace, so content automatically adjusts, so your site looks great no matter what device it's on. Pretty awesome.

• 1:25Harry Stebbings?

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• 2:10Harry Stebbings?

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• 2:54Harry Stebbings?

  So whether you're running SPVs, a traditional venture fund like me, or even a rolling fund, Angel List has you covered. And I'm also super excited about their new product, Angel List Stack, which is purpose-built for founders. With Angel List Stack, you can create a fundraising-ready startup in just a few clicks. Angel List handles your company's incorporation, banking, cap table and fundraising processes, all in a single place. This allows founders to focus on building. If you're a founder, you can launch your company at stack.angellist.com/20vc. Whether you're a founder or a funder, you're in great hands with Angel List. But that is enough from me and my dulcet British accents. And so now I'm so excited to welcome Ian Siegel, co-founder and CEO at ZipRecruiter.

• 3:41Speaker 01

  You have now arrived at your destination.

• 3:44Harry Stebbings?

  Ian, this is such a joy to do. I feel like I know you, having heard so much from your co-founder Ward. But thank you so much for joining me today.

• 3:51Speaker 02

  Pleasure to be here.

• 3:52Harry Stebbings?

  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?

• 4:02Speaker 02

  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.

• 4:34Harry Stebbings?

  Was it a tough realization not writing when it was what you always thought you wanted to do?

• 4:39Speaker 02

  You know, that's a good question. I feel like the discipline of storytelling is something that's actually crucial to being successful as an entrepreneur and also being successful as a leader and also being successful as a peer. It's something that I've tried to actually invest a lot of time in with the employees at ZipRecruiter. So I make everybody tell the story of the work that they're doing in a way that a layperson could understand. Cause I feel like if you can't explain it to me that simply, then you yourself don't understand what it is that you're doing. I truly think like writing is an underserved practice in all forms when it comes to entrepreneurship.

• 5:13Harry Stebbings?

  Ian, this is like music to my ears. I think we've lost the art of storytelling. I think with so much money, entrepreneurs don't need to tell the stories the ones we used to. And we had to bring VCs with us on the journey, had to excite people in a way that cash means we just don't have to now. My question to you is, what does great storytelling mean to you? And how do you think about teaching it to your team members?

• 5:33Speaker 02

  A lot of it is about finding empathic points of entry for your audience. In particular, when you're describing, say, product features, a lot of people will describe the product feature. And I always say, no, no, no, don't do that. Give me a user story. Tell me what the experience is for a user and then insert the product feature to show how it made their life better, made the experience easier, whatever it was. That aspect of storytelling where you tell it from the point of view of how it'll impact the audience or how it'll impact the user is one of the great gifts that I feel that we give to the people who work at ZipRecruiter because they go on and then they deploy that technique. And I've heard it over and over again that everywhere they go, people are like amazed by the decks they write and the way they talk about their work. And I'm like, I know, I know. You were drinking champagne here. You didn't even know it.

• 6:15Harry Stebbings?

  My question there is, one thing that I find the biggest challenge with product marketing today and the storytelling is brand, 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.

• 6:34Speaker 02

  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 where we are bereft of version one point O's. Cause 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.

• 7:16Speaker 02

  I don't know if he turns into a video or not, but Under Armour, the apparel company at one point did a TV commercial 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 their future concept car for apparel that they were clearly working on, but weren't ready to bring to market yet. But man, did we all start talking about Under Armour when that happened? And that's the kind of sort of bold, courageous marketing that does storytelling through visuals that I think I totally agree with you is like, we're totally lacking.

• 7:57Speaker 02

  What's the last commercial you saw that you remember is a question that I ask our team internally all the time. Because I am still dissatisfied with the level of memorability in the commercials that we produce.

• 8:07Harry Stebbings?

  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? Well, 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?

• 8:24Speaker 02

  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 saying about startups is first they ignore you, then they mock you, then they try to kill you, then they try to buy you. Distinctively 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's 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.

• 9:05Speaker 02

  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 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 have done. That was very true on the employer side. But so we have a job seeker product as well. And on the job seeker side, I've thrown the gauntlet down to the team and I said, listen, I want you to have to have the courage to fail massively. I want you to have the ambition to build something that's never existed before.

• 9:43Speaker 02

  And when we tell people about it, we're going to meet the expectation we set with the crazy advertising we do when we tell them that we're doing something they've never seen before. And they're going to say to every one of their friends and family who are looking for it, you've got to use ZipRecruiter in addition to whatever else you're using because they do this thing that is so crazy ambitious. We have over 80% brand awareness in America. Think about that. There's five million businesses in America. Most people can name less than 800 of them. All right. Like, we're up there. We're like massively recognized and I am completely unsatisfied with where our brand is at because I don't want our brand to be famous for being a big advertiser. I want our brand to be famous for having an awesome product and I think that's where we're going to be over the next couple of years. But what does it take to change you to make that transition?

• 10:22Speaker 02

  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're saying, 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?

• 11:06Speaker 02

  Why do we make them apply to employers who are receiving 100 other applicants? Like, what we should be doing, and what we're now doing as ZipRecruiter, is pitching you to the employer so that they recruit you. And that's a way better experience for both sides, because then the employers are only talking to candidates who they're already excited about. I mean, you take it for granted, and I take it for granted, because we're probably successful enough that recruiters reach out to us. But the majority of people in America will never talk to a recruiter over the entirety of their career. So it's a novel experience. It's intoxicating to be told, like, you're special, you're beautiful, I want you, especially when an employer reaches out to you. That's a story. I'm trying to flip the job market on its head, and like, that's the ambition we have, which is like, let's build a job market where employers go first. That's fundamentally what we're trying to do.

• 11:43Harry Stebbings?

  I just wish my girlfriend would tell me that, not the recruiters.

• 11:47Speaker 02

  That's right. I think that's called Bumble.

• 11:49Harry Stebbings?

  I do want to ask that you mentioned about kind of the tracking and the measurement that you implement in terms of the advertising that you do. It was when I spoke to Ward, he said this was one of your superpowers in terms of really implementing such a data-driven culture and environment. What does it take to implement such a data-driven culture and environment? And what are the challenges that one faces when implementing it?

• 12:08Speaker 02

  That's such a great question, because we're facing the challenge of it right now, which is, I was really proud of myself, because when we built the company, we bootstrapped for the first four and a half years, and we got the company in the north of 50 million in revenue with millions of free cash flow before we ever took any outside funding. And the way we did that, we were incredibly disciplined operators. And we created a culture of disciplined operation, where, like I said, you can make any argument you want, as long as you support it with data. That was the culture we created. People became meticulous about capturing data and talking with data and making logical arguments with data. And it was awesome, and it still is awesome. And now we are like, we do high hundreds of millions, and well, next couple of years, we will be in the billions probably. And so it's very exciting from a revenue perspective.

• 12:50Speaker 02

  But what is the dark downside of being this highly analytical, data-driven culture? It is very easy to use data to optimize an existing product. It is very difficult to use data to innovate and build new product. And so the trap you fall into is before you do anything, you always want to prove with data that you're doing the right thing. And it was so interesting because when we went to tackle the job seeker side of our marketplace, which was the second product we built, the teams were doing scads of research, spending millions of dollars just trying to figure out what the right thing to do was. Actually, it's so rare as a CEO, I mean, we could talk about this if you want to, but I always say like, my job is to do as little as possible to create accountability and autonomy. I want to make less than 10 decisions a year. But one of the times I threw my CEO card on the table and I fully stepped in is when

• 13:35Speaker 02

  we were working on the job seeker product and I said, everybody stop, we're doing this the wrong way. Here's how I want you to build a job seeker product. Here's the only metric I care about. What is the product you yourself would want to use? What is the product that you would recommend to a friend or family member if they were looking for work and tell them with confidence that they should use this? That's the product I want you to build. That's it. Go with your gut, build that, have the courage and the vulnerability to put that version one out there and then we'll start optimizing. Just start with like a thesis around like, what would be different from the way the market works today that would make you want to use a product? Make some bold claim and then make it true. We had a lot of data-driven decision-making and then we got somewhat stifled by it when we got to the innovation phase, but fortunately, we're now powering through that.

• 14:14Harry Stebbings?

  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?

• 14:22Speaker 02

  I mean, that's art, not science. Everything comes down to momentum. When I saw the team working on the job seeker 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

• 15:04Speaker 02

  everybody who mentions one of those sites, that site always gets described as, oh, you mean like Glassdoor? Because they won the mindshare 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 like the biggest email company, the biggest mapping company, the second biggest cloud company. I mean, they're they're in the everything business. It's very important to be identifiable as something in one sentence. Because that is the thing that is going to give you the freedom to do all those other things.

• 15:43Harry Stebbings?

  I want to touch on so many things here. I'm loving this. But you said 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.

• 16:07Speaker 02

  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 1,200 employees and we're a public company. So a lot has happened. I have an 18 year old daughter and a 14 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.

• 16:50Speaker 02

  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 as a suggestion, becomes like an order or a CYA moment where you're like, I'm going to do what he said, just in case. Idea doesn't work. So I literally am practicing the discipline of not even giving my opinions anymore. What I try to do is ask questions. Tell me why you're thinking a testimonial style commercial is the right approach for us at this point.

• 17:33Speaker 02

  I try to just elicit them to explain their strategy to me so that they're listening to themselves, explain it out loud. And then we have a dialogue about their answers instead of me saying like, I don't think we should do a testimonial driven commercial right now. Too many people are doing it.

• 17:46Harry Stebbings?

  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?

• 17:58Speaker 02

  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 I 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 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.

• 18:43Speaker 02

  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 repress my enthusiasm, which is a weird place to be when you feel like you're the expert on the business.

• 19:07Harry Stebbings?

  Again, I have to dig in here. When you say like a month in and that maybe something's not working and you intervene. How long is long enough? Cause sometimes people need ramp times. They need to get acquainted with the business. How long do you give someone before you intervene? And how much data is enough data to know whether a new team member is working or not working?

• 19:25Speaker 02

  It varies by role, longer leash for engineers than say like. Like someone in product and it varies in scope of responsibility. So if you're a person who's hired to be a senior fill in the blank, you get a long runway. If you're hired in as a director, fill in the blank, very short runway. It's about the damage radius. If you're in a position where a lot of people's jobs got harder or morale is going to go down because you're not doing your job, then very short leash. But if you're in a position where we're mentoring and training you, you're just working on a single feature or a single product, long leash.

• 19:57Harry Stebbings?

  What've 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 you're like, oh my God, that was a big one?

• 20:07Speaker 02

  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. In 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 had 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 my apparent objection.

• 20:51Speaker 02

  And the first days on the job, the first days 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 that was doing less than a hundred million in revenue a year when we hired him. So like a million dollars meant a lot. I was like, holy cow. And that's when I started to change my thinking. Instead of looking for like incredibly well-rounded problem solvers, I love pointy people. Show me like someone who went super deep and became an expert at some niche area of business. I will hire that person 10 times out of 10.

• 21:36Speaker 02

  I don't want Michael Jordan, I want Dennis Rodman. I want someone with an elite skill at a Single thing who obsesses about that thing all the time. We talk about like the ten Xers. Those are hundred Xers, hundred Xers every time.

• 21:47Harry Stebbings?

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

• 21:52Speaker 02

  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 I 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.

• 22:37Speaker 02

  So like, I guess I look for enthusiasm, particularly infectious enthusiasm.

• 22:41Harry Stebbings?

  Okay, 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?

• 23:02Speaker 02

  There's a couple of 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 were 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 were 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.

• 23:45Speaker 02

  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, then I feel really confident hiring you because communicating with me is scary. Like I'm the CEO, I get it. When you're talking to me, it's nerve wracking. Like I'm the scariest interview you do. So I love it when they're speaking in plain English. I always talk about the two great gifts that I look for in directors and above. Only two things I really look for. Common sense and perspective. That's it. Common sense and perspective. We're just missing common sense so often.

• 24:27Speaker 02

  And it goes back to like when you talk to elite sales candidates, they're really good at talking to in the room. But do you understand what they say? And perspective is just really like, how bad is anything? Like don't sweat the small stuff and it's all small stuff. Culture and really satisfaction job. So many people key off their manager or their leaders. I really believe your job as you get more senior is to stay calm. Your energy feeds the room. And so I really goal seek people who emulate what I believe is the right way to operate. Perspective is to me like one of the most unheralded superpowers that executives can have. Because by having proper perspective, you're never going to lose it in front of your team. You're never going to start screaming at a team member. I think that's somebody I'd want to work for.

• 25:04Harry Stebbings?

  Ian, you said about staying calm there. When I spoke to Ward and 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?

• 25:24Speaker 02

  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

• 25:32Speaker 02

  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.

• 26:17Speaker 02

  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. Particularly if you start a company, like you never have to listen again. You really don't like you have so much power in these roles that we have. And there's so many people want to hear you speak. So it's a real art to maintain the discipline of listening and then not just listening, but processing. So I always try to think about what I'm going to do before I say it.

• 26:53Harry Stebbings?

  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?

• 27:03Speaker 02

  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. 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.

• 27:48Harry Stebbings?

  Where do you think you're not good at leadership? You've had many years now as CEO. You've changed a lot as this time has progressed. I'd love to know in hindsight now, where do you look back on yourself and go, ah, I could do better here?

• 28:01Speaker 02

  I think the number one thing that I'm working on personally right now, I am probably too cynical. And as a result of that, I distrust when companies. Companies talk about their mission, their vision, their values. Cause I'm like, it's easy to say, don't tell me, show me. That's I'm always that guy. 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 you believe in guy. But it turns out a lot of people like hearing what you aspire to, and particularly in the category we're in, because at ZipRecruiter, if you start talking to the job seekers who use our service, we have changed lives and saved lives. Not exaggerating when I say that, it is dramatic. Their stories are so compelling and I've worked for so many internet businesses, you know, like I helped brides get wedding photos.

• 28:44Speaker 02

  I helped people print postage from their printer. None of those were true mission-based businesses. But when you work in jobs, it's like people's identity. It's where they spend the bulk of their lives. And so there are some incredibly inspiring stories, not just on the job seeker's side, but also on the employer's side. And so the way I've been doing it, we have these all hands. When COVID hit, we went to doing all hands every week, which was a little too much, but we still do them every two weeks. And that means you need a lot of content. And so I started interviewing employers and job seekers and just showing the videos of the interviews to the team. So they could get a sense of what the customers were saying. Highest marks we've ever gotten on any content we've ever produced because it makes it real. It makes it feel tangible and exciting. And I was like, great. I'm doing it. I'm creating culture.

• 29:21Speaker 02

  And people were like, no, encapsulate it, be more specific. What do you aspire to? And that's what I realized particularly values do for you, which is like, it's a way for you as a leader to communicate to people what you want them to aspire to, and who you expect will do well in your organization. And so I've been putting a lot more time into that than my previous cynical self thought was necessary.

• 29:42Harry Stebbings?

  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?

• 29:56Speaker 02

  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. Our 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.

• 30:42Speaker 02

  It's so ironic. I thought I knew so much back then.

• 30:44Harry Stebbings?

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

• 30:48Speaker 02

  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's 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, 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.

• 31:31Harry Stebbings?

  When did that change?

• 31:33Speaker 02

  I think the thing that happens is at various times when you're running a business like mine, and I've been around for 12 years and we've like gone from bootstrapping at a kitchen table to being public. Your team turns over, but there were multiple times I was like, this is the greatest team that has ever been assembled. We will never be a better team than we are today. Like these people are all exactly right for the roles that they're in. Then one thing or another happens and people leave or people get fired and new people come in. And what I keep learning, different ways business can be done. I'm getting a broader perspective on different approaches people are utilizing, all meeting with success. And what I, I went from thinking like there's a right way to thinking there are many right ways. And I went from thinking that I as a leader had to be at the front and showing everybody how to do every job,

• 32:16Speaker 02

  to me being like, I'm going to be at the back and I'm going to be a learner. I'm just going to learn. I'm going to be a spider at the center of the way. I'm going to learn from everybody. And sometimes I'm just going to introduce two people in the org to each other who need to be talking to each other. But my value is as an external storyteller now, much more. than it is as a day to day operator.

• 32:31Harry Stebbings?

  One thing that stuck with me is when you said to your children and to some of your team, you don't know me like this is just a you never met me. One of the biggest challenges that I have is a 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?

• 33:03Speaker 02

  I mean, it's like 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 known 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. 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, Y or Z there. So put any number you want, like I'm gonna do the best job I can possibly do, because that's just how I operate. You know, all I do is try to hyper grow your business. That's what I'm gonna do. There's no throttle that you're gonna 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?

• 33:48Speaker 02

  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, because 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 those stocks for a reason. There was probably a very good thesis behind why you picked them. That was you doing your job. How they performed, that part was out of your control. So like, I think I would be more excited about the businesses that I picked if I were an investor. I'd be prouder of the types of businesses I was investing in than necessarily the portfolio's results. Because that would say something about who I was as an investor. Obviously, I would wanna have some measure of success. All my success isn't just based on the success of my businesses.

• 34:31Harry Stebbings?

  How do you think about your relationship with money?

• 34:33Speaker 02

  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 in 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.

• 35:18Speaker 02

  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 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 point, if that's what you're doing. I said, like, I made money too late to do anything super fun with money.

• 35:40Harry Stebbings?

  I'm diving in and maybe I have the most douchey friends in the world, but my friends who are GPs would be like, the one thing, Harry, that you never ever take for granted, but it's so worth it, flying private. And they have kids. You think it sends a douchey message to kids?

• 35:54Speaker 02

  Well, here's what I know.

• 35:55Harry Stebbings?

  I don't have kids.

• 35:56Speaker 02

  I would do a little reveal into my personal life. One of the biggest fights I had with my wife was when we were flying cross-country, which was like, it's a five hour flight. I said, I want to get business class seats for everyone, including the kids. And she was like, you're going to ruin our children. Like you're going to set the expectation. I was like, you're being ridiculous. I'm glad you can't hear me right now. So then we do it. I buy the tickets, they fly, they get the like, the food and the beverage cart and the Sunday cart came by. And then every time we fly, they now ask her, are we flying business class? Every time. And then they complain if we're not. And she was right. Like the attenuation was one trip. It was one trip and they were like, this is life. This is how life should be lived. I never flew business class till I was an executive at a company. My whole life I hadn't done it.

• 36:41Speaker 02

  So I'm sure flying private is awesome. I'm sure particularly like during COVID, life changing, like because you felt safe. But maybe when my kids move out, I'll experiment with it and then I'll report back to you. But for now, I'm trying to raise people who value intrinsic goals versus extrinsic signals of success and happiness.

• 37:00Harry Stebbings?

  Man, I love that. I mean, the other thing is just listen to your wife, actually.

• 37:04Speaker 02

  Right. I should have listened to my wife. I should have.

• 37:07Harry Stebbings?

  One final thing before a quick fire round, but it's something that I think about a lot, 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?

• 37:30Speaker 02

  I will tell you the truth. I think you are at a disadvantage to me. I not only have the perspective 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 H R 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 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.

• 38:15Speaker 02

  And being older and having a family. That is what I've learned. But by the way, fifteen 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 fifteen years ago.

• 38:34Harry Stebbings?

  Yeah, I think actually, do you know what? Being an interviewer forces you so much to be a better listener. And I think that's been a big learning for me in doing the shows and doing three thousand. I do want to move into my favorite. I've so enjoyed this. I want to move into my favorite there, which is a quick fire round. So I say a short statement. You give me your immediate thoughts. Does that sound okay?

• 38:51Speaker 02

  Let's do it.

• 38:52Harry Stebbings?

  So what's the favorite book?

• 38:53Speaker 02

  Living with a SEAL. It's a story about a successful entrepreneur who married a billionaire, the founder of Spanx. Who decided his life was in a rut. So he hires a Navy SEAL who's an ultra-thonner. Live with him for thirty days and the SEAL says, I'll only do it if you do everything I tell you to do, because I'm going to break you out of your rut. And the SEAL just tortures him for. Thirty days and I feel like it's like one of the great books on life that you can read because it's exactly what happens to all of us after we've it's like life is about being uncomfortable. Life is about pushing yourself to limits and whenever anyone asks me for a business book, I say, read that one because it's also like the best story of entrepreneurship I've read because he talks about his own personal journey, but while he's suffering and being tortured by the seal. So I strongly recommend it. Like a reflection on marriage. Yeah. Charlie, what's the hardest element of your role with ZipRecruiter today?

• 39:38Speaker 02

  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 at 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 all that. I'm like a bad carrying sales rep to the investor community now. And so it's just a very different job. What's the biggest surprise about being public? Everyone tried to scare me and like, you don't want to go public. You don't want to operate on a quarterly cadence. And the reality is it's been awesome. It has been clarifying. It has made us a better business.

• 40:23Speaker 02

  It has given me a framework in which to talk to people about why I'm insisting on progress against certain initiatives and certain timeframes that is more credible than the way I used to do it. Because they have a personal stake in it. Honestly, I strongly recommend going public to every CEO and no one told me I should go public. They all tried to talk me out of it. Why did it take four years to raise funding? Why did you bootstrap for so long? You could have got it earlier. I mean, we never needed to raise funding. That was the. So why raise? Why dilute? First off, why did we not raise right away? Because we actually had term sheets when we were pre-product, like unsolicited term sheets were dropped on us. I had worked for VC-backed businesses for 17 years prior to starting ZipRecruiter.

• 41:06Speaker 02

  And what I learned about that was no matter how much success you had, no matter how well you did, they only said one word to me, which was more, maybe it was faster, maybe it was mush. It was just never enough. It was like celebrate for a millisecond and move on. And so I wanted to run a sensible startup. I unconsciously wanted. To run a lifestyle business and I just happened to assemble like the worst team in history. Like every one of us were hyper growth hackers. Like we were really good at this. So like, once we had product market fit, we were off to the races. But then four and a half years in, we were ZipRecruiter, so we distributed jobs to a hundred different job sites. And we actually, at that point, were distributing to nearly a thousand. We didn't tell people because it freaked them out. But what was happening is the number of candidates jobs were getting went from like twenty five to thirty five to fifty five to a hundred. And it turned out that like employers didn't like three times as many candidates. It didn't make them three times as happy. It just pissed them off because it was more work for them.

• 41:51Speaker 02

  And so we had to move from quantity to quality. That's when we started experimenting with things like machine learning and deep learning. And back then it was like bleeding edge. No one had ever done it before. We weren't even sure it would work. And it was so hard to find the engineers and they were so expensive. And I was like, guys, this is the right thing for us to do. But if we're going to move into this quality world, we need to have a huge war chest to go after it. So that's what really pushed us into raising the first round of funding. When people say, what do you wish you'd done differently? I wish I'd raised that money sooner, knowing now like how much further we could have pushed our advantage had we had a larger war chest back then.

• 42:23Harry Stebbings?

  Final one for you. What are the next ten years like for you and for ZipRecruiter?

• 42:28Speaker 02

  These are going to be the greatest ten 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.

• 43:10Speaker 02

  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.

• 43:30Harry Stebbings?

  Ian, this has been such a fantastic conversation to do. I'm so glad that I didn't actually send you the schedule because it looked very, very different to the conversation that we had. But thank you so much for joining me and this was so much fun to do.

• 43:41Speaker 02

  It's been a pleasure. Thanks for having me.

• 43:45Harry Stebbings?

  I mean, what an incredible interview. Can we just agree? That was such an amazing show with Ian. If you'd like to see more from Ian, you can see him at ZipRecruiter CEO on Twitter. That really is a must. I'd love to hear your feedback on the episode because to me, that was just such a great discussion. As always, you can find more from us at 20vc.com. We always love to see you there. But before we leave you today. From websites and online stores to marketing tools and analytics, Squarespace is the all-in-one platform to build a beautiful online presence and run your business. Now, there are three things to me that really stood out about why I love Squarespace. First, mobile optimized websites. All websites are optimized for mobile with Squarespace, so content automatically adjusts so your site looks great no matter what device it's on. Pretty awesome. Second, email campaigns.

• 44:30Harry Stebbings?

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• 45:14Harry Stebbings?

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• 45:57Harry Stebbings?

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