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Ian Siegel

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2022-05-20
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2022-05-20
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  1. “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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “These are going to be the greatest tenures I've had at Zipper Cruiter because we've 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Make them three times as happy. It just pissed him off because it was more work for them. 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've 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “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 Zip Recruiter. 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 zip recruiters. 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 25 to 35 to 55 to 100. And it turned out that like employers didn't like three times as many candidates.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “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. It has given me a framework in which to talk to people about why I'm insisting on progress against certain initiatives and certain time frames 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 try to talk me out of it.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “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 as my wheelhouse talent, and now I'm asked to do a bunch of things 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, I've got to go on TV after earning calls and explain what the business is doing. And I've got to talk to investors. I'm like a bad carrying sales rep to the investor community now. And so it's just a very different job.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “Living with a seal. It's a story about a successful entrepreneur who married a billionaire, the founder of Spanks, who decided his life was in a rut, so he hires a Navy SEAL who's an ultra thoner. Live with him for thirty days, then 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 asked 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “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 HR team about things like maternity and paternity leave policies, when we're talking about like child care 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “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'm going 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 food and the beverage cart and the Sunday cart came by. And then every time we fly, they now ask 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. 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Older. I'm a little bit older. And so I have 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “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 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 they were like, okay, and then we back with a 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”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “Like, I wouldn't do it just to make more money. I feel like when you get hung up on how is this investment doing versus that indebted, that's extrinsic motivation. Like you pick 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 want to have some measure of success. All my success isn't just based on the success of my businesses.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “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. 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, 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, 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. Because I think we're building something important.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “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 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. And 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 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 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”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “I think that is the armor of Yuf, 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 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 ten 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, 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “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”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “Side, but also on the employer 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. 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “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 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 how I'm always that guy. I never do virtue signaling. I'm never going to be a thoughts and prayers guy. Like, I'm going to 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 zip recruiter, if you start talking to the job seekers who use our service, we have changed lives and save 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. 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 is some incredibly inspiring stories, not just on the job seeker.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “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 a 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 their 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “I've 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “It's funny that word said that. That's really interesting because I can think of a few times that word has caused me to. 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “I guess it's storytelling. It's a little bit of what we talked about before. 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. 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 of jobs. 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”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “They are the ones educ 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 are 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 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 learn 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”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “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 a dinner this awesome interview and 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “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 $100 million in revenue a year when we hired him. So like a million dollars meant a lot. That 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. 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 10Xers. Those are hundred Xers. Hundred Xers every time.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “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 them. 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 my apparent objection. And the first day he's 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”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “It varies by roll, longer leash for engineers than say 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's going to go down because you're not doing your job, then very shortly. 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  30. “Like, I want to tell you what I think is 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 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  31. “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 ZipRitter 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. 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  32. “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 my 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. 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  33. “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 would say to employees at Zipper Cruter 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 BizDev. 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  34. “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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  35. “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 looked 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 mindshare battle because they were first and they were the biggest for a while. I think it's critically important.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  36. “Just start with a thesis around 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  37. “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, I so rare as the 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 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 off optimizing.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  38. “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 to a 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 next couple years we'll be in the billions probably. And so it's very exciting from a revenue perspective. 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  39. “To candidates, so 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  40. “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 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 sucked 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 get dropped into that 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 chubs. We can use the wisdom of the crowd to know who you look like, accurately predict which jobs you should be employing 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 100 other applicants like what we should be doing and what we're now doing as ZipRitter 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”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  41. “For being a big advertiser, I want a brand to be famous for having an awesome product, and I think that's where we're going to be over the next couple years.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  42. “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. 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've said, listen, I want you to have the courage to fail massively. I want you to have the ambition to build something that's never existed before. 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 work, you've got to use Ziff Recruiter 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 5 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  43. “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 barely a thing. And that second step where they mock you, everyone was mocking you. Everyone was like, ah, Zaper is going to burn through all their cash. Zip recruiters 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 on a post 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 you come to ZipRecruiter is because of all the advertising we do. But the reason you stay and are a repe customer”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  44. “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 armor 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 armor 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 lucky. What's the last commercial you saw that you remember?”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  45. “Give a recurring speech about version 1.0s and version 1.0s are the only thing in real 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 1. out there. And when you look at the marketing, that's another example of where we are bereft of version 1.0 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 can insert it. 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 filled with apparel that had technology embedded in it so you could do things like touch your sleeve and a screen would come”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  46. “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 Zipper Cruter 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”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  47. “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 Zipper Cruzer. So I make everybody tell the story of the work that they're doing in a way that a lay person could understand. Because 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.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  48. “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, lock, right place, right time. So I didn't set out to be in tech. I wound up in tech. My background was in writing.”

    2022-05-20 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source