The Exchanges

Q Can I ask, I actually had Clark at InVision on the show very, very recently, and we spoke a lot about self-awareness and how to increase it. He spends time specifically everyday journaling with different segmented thoughts that he has and continues to have. How do you think about proactively increasing self-awareness and anything that you do in particular?

A So I think there are three ways you can grow in self-awareness. One is to become more self-reflective, and a great way of actually stimulating this is through meditation, but actually pause and bring almost like a lens of attention back at yourself as if There was something outside of you looking back at you. The other way to grow in self-awareness is some kind of instrument, and I mentioned the Enneagram earlier. I like that one, but there's a few technical instruments like the Myers-Briggs test, for example. And the third way, and my favorite way, is to set up this incredibly feedback-rich environment where the people around you, the most direct form of feedback, are giving you feedback all the time and helping you grow.

AI assessment note: “So I think there are three ways you can grow in self-awareness.”

Q Got it. No, listen, I'm going to do the test for sure. I'm going to send you my results. I do want to discuss the next one, and I'm super passionate about this one. So what is the next one? Talk me through it. Health.

A So health is number one, and I think the issue with the idea of work-life balance is it really implies the two diametrically opposed. I prefer the idea of work-life harmony, where you look at everything holistically. And this means, at Clearbit, we have really healthy lunches. We actually have two full-time chefs, because people just pick the default. If there's shitty food in front of them, they'll pick it. We offer gym stipends. We offer therapy for everyone. We offer the best health insurance. We have on track vacation. You can work from anywhere. We don't track or care about the time of the seat, but it's really, I think health is really about amalgamating it into your work life harmony. It's got to be integrated into everything. You'll see if people at Cleber, they will leave the office in the afternoon to go to the gym because it's a lot more convenient to them. And it means that if they have that habit every day, then they're going to be healthier.

AI assessment note: “So health is number one, and I think the issue with the idea of work-life balance”

Q Can I ask, I actually had Clark at InVision on the show very, very recently, and we spoke a lot about self-awareness and how to increase it. He spends time specifically everyday journaling with different segmented thoughts that he has and continues to have. How do you think about proactively increasing self-awareness and anything that you do in particular?

A So I think there are three ways you can grow in self-awareness. One is to become more self-reflective, and a great way of actually stimulating this is through meditation, but actually pause and bring almost like a lens of attention back at yourself as if There was something outside of you looking back at you. The other way to grow in self-awareness is some kind of instrument, and I mentioned the Enneagram earlier. I like that one, but there's a few technical instruments like the Myers-Briggs test, for example. And the third way, and my favorite way, is to set up this incredibly feedback-rich environment where the people around you, the most direct form of feedback, are giving you feedback all the time and helping you grow.

AI assessment note: “I think there are three ways you can grow in self-awareness.”

Q many in terms of people in the existing role that you're looking to hire for to really determine what great looks like. Is that a sort of process that you look like in terms of hiring for roles that maybe you're not akin or used to as a technical founder hiring marketers, for instance? How do you think about hiring for roles which aren't akin to your maybe natural skills?

A So, what I'll do when I'm hiring a senior role is I will go out and meet the best people in the industry. You know, right now we're hiring a COO, Chief Operating Officer, and during the search, I've spoken to some of the best COOs on the planet. Last week, I was chatting to Adam Bain about it. He was, like, CEO of Twitter. So that really actually lets you tune what excellence looks like. And then when it comes to candidates, I think the key thing is sourcing. It's like the number one thing, because if you don't have enough Candidates in funnel. As you go down, you start compromising, and you're like, ah, we need to fill this role. We haven't found the perfect person, but let's hire them anyway. So the key thing is that sourcing up front.

AI assessment note: “lets you tune what excellence looks like”

Q I love that in terms of the focus on management. I guess the question there is, I've seen too, kind of how poor onboarding can be. How do you think about structuring your onboarding to be as optimal as possible?

A You know, I actually got the feedback last week that our onboarding was pretty bad too, which is kind of sad, but now I know, which is great. So I can fix it. My approach to onboarding in the current system is that we just get people to read. So the first couple of days, it's just reading. And there's like an Asana checklist and people go through and read. And it is a very efficient form of data transfer. But what I've just realized is that it's great for Alex McCaw, not so good for everyone else, because not everyone learns that way. And so we're going to mix things up. We're going to have a Some more videos in there. We're going to have some in-person talks, but I'm not sure I've nailed onboarding yet at Clever.

AI assessment note: “My approach to onboarding in the current system is that we just get people to read.”

Q Got it. No, listen, I'm going to do the test for sure. I'm going to send you my results. I do want to discuss the next one, and I'm super passionate about this one. So what is the next one? Talk me through it. Health.

A So health is number one, and I think the issue with the idea of work-life balance is it really implies the two diametrically opposed. I prefer the idea of work-life harmony, where you look at everything holistically. And this means, at Clearbit, we have really healthy lunches. We actually have two full-time chefs, because people just pick the default. If there's shitty food in front of them, they'll pick it. We offer gym stipends. We offer therapy for everyone. We offer the best health insurance. We have on track vacation. You can work from anywhere. We don't track or care about the time of the seat, but it's really, I think health is really about amalgamating it into your work life harmony. It's got to be integrated into everything. You'll see if people at Cleber, they will leave the office in the afternoon to go to the gym because it's a lot more convenient to them. And it means that if they have that habit every day, then they're going to be healthier.

AI assessment note: “at Clearbit, we have really healthy lunches. We actually have two full-time chefs”

Q many in terms of people in the existing role that you're looking to hire for to really determine what great looks like. Is that a sort of process that you look like in terms of hiring for roles that maybe you're not akin or used to as a technical founder hiring marketers, for instance? How do you think about hiring for roles which aren't akin to your maybe natural skills?

A So, what I'll do when I'm hiring a senior role is I will go out and meet the best people in the industry. You know, right now we're hiring a COO, Chief Operating Officer, and during the search, I've spoken to some of the best COOs on the planet. Last week, I was chatting to Adam Bain about it. He was, like, CEO of Twitter. So that really actually lets you tune what excellence looks like. And then when it comes to candidates, I think the key thing is sourcing. It's like the number one thing, because if you don't have enough Candidates in funnel. As you go down, you start compromising, and you're like, ah, we need to fill this role. We haven't found the perfect person, but let's hire them anyway. So the key thing is that sourcing up front.

AI assessment note: “I will go out and meet the best people in the industry.”

Q I totally agree. And a healthy team is a happier team and a more productive team. I guess That's kind of the question for me is, a lot of founders who maybe would hear this would say, that's great, but I can't afford it. What would you say to them who say, I can't afford the gym style, and I can't afford the healthy food? How would you advise them?

A Well, I would say, as for affording it, I don't think you can afford not to. Health was a priority from day one. It has to be. As a founder and CEO, you have to look after yourself. You need to be exercising every day, and you need regular therapy. I think when you, as soon as you raise a round, let's just say you're a seed founder, you're struggling at the start, and maybe you're finding ways of being healthy, like going for a run, or trying to eat healthy, but as soon as you raise that first round, or you get to profitability, then put a personal trainer on the company card, put an exec coach on the company card, put a therapist on the company card. These are absolutely legitimate expenses, and you should be spending a company money on the stuff, because if you're not in tip-top condition, then the company's not going to work.

AI assessment note: “I don't think you can afford not to. Health was a priority from day one.”

Q I totally agree. And a healthy team is a happier team and a more productive team. I guess That's kind of the question for me is, a lot of founders who maybe would hear this would say, that's great, but I can't afford it. What would you say to them who say, I can't afford the gym style, and I can't afford the healthy food? How would you advise them?

A Well, I would say, as for affording it, I don't think you can afford not to. Health was a priority from day one. It has to be. As a founder and CEO, you have to look after yourself. You need to be exercising every day, and you need regular therapy. I think when you, as soon as you raise a round, let's just say you're a seed founder, you're struggling at the start, and maybe you're finding ways of being healthy, like going for a run, or trying to eat healthy, but as soon as you raise that first round, or you get to profitability, then put a personal trainer on the company card, put an exec coach on the company card, put a therapist on the company card. These are absolutely legitimate expenses, and you should be spending a company money on the stuff, because if you're not in tip-top condition, then the company's not going to work.

AI assessment note: “as for affording it, I don't think you can afford not to.”

Q How do you think about building the candidate pipe there? Is it something you do manually? Do you work with recruiters? How do you think about getting the best candidates in pipe?

A I'll tell you our secret, and this is something that sounds, maybe sounds obvious in retrospect, but we didn't do it for a long time, and when we started doing it, our business transformed. So the secret is sourcing sessions. Sit down with your engineers or whoever is relevant for the role and then use tools. There's tools like teamable, or you can just go through the LinkedIn and use LinkedIn recruiter. You literally just got to sit them down because sourcing is so boring. It's so boring. Everyone hates it. So you, you literally have to, people are not going to go through their network themselves. So you sit them down and you do this every now and again. And you also do this with all your new hires as well. And that is the best way of growing the business.

AI assessment note: “So the secret is sourcing sessions. Sit down with your engineers”

Q Totally. No, I agree. I think the competitive element will always drive a lot more participation. Okay, next one. What's the next pillar, Alex?

A Well, the last one is, is management. So most companies, and most companies our size, they just don't put much thought into management and training, which I think is a complete travesty. You know, I can't emphasize enough how important management is. At most companies, people join, and it's just, it's complete crapshoot as to if they get a good manager or not, and that affects their entire experience of the company, then they leave the company. People don't leave companies, they leave managers. So we put so much Thought into management training, and we've got a, actually a whole handbook that we've written internally, and we do regular management trainings, and we are trying to get to a place where Clearbit has world-class managers.

AI assessment note: “Well, the last one is, is management.”

Q I'm totally with you in terms of the heaviness and weight of references. But if we stay on the element of the company is a vehicle for growth. When we chatted before, you said to me, when you hit product market fit, it's time to move into the company making phase. So I guess, what does company making really mean to you? And does this not happen from day one?

A At its essence, company building is building the machine that builds the machine. So it's scaling up the company while ensuring that communication and culture is Doesn't go to shit. It's a real art and a rare one, and I think that's why you see founders who've demonstrated they've done it before, they've just come on such huge valuations in the next company they build, because it's such a rare talent. And for first-time founders, it's a really tricky transition. You have to change how you think about your time, how you think about hiring, you have to start dealing with human problems rather than bits and bytes. And I actually think it's really difficult, especially for technical founders. Well, it certainly was for me. You've had your head down this whole time building, building, building, and now you stick your head up, and you realize the company needs a real CEO, but you, you have no idea where to start, and I was exceptionally lucky to have coaching from this guy called Matt Mashari, and he came in, and he held us early on when we were about 25 people or so, and now we're about a hundred, but he taught me the love of company building, and the love of management, and operations and management are the unglamorous side of company building, sure, but after product-market They are the difference between success and failure.

AI assessment note: “At its essence, company building is building the machine that builds the machine.”

Q How do you think about building the candidate pipe there? Is it something you do manually? Do you work with recruiters? How do you think about getting the best candidates in pipe?

A I'll tell you our secret, and this is something that sounds, maybe sounds obvious in retrospect, but we didn't do it for a long time, and when we started doing it, our business transformed. So the secret is sourcing sessions. Sit down with your engineers or whoever is relevant for the role and then use tools. There's tools like teamable, or you can just go through the LinkedIn and use LinkedIn recruiter. You literally just got to sit them down because sourcing is so boring. It's so boring. Everyone hates it. So you, you literally have to, people are not going to go through their network themselves. So you sit them down and you do this every now and again. And you also do this with all your new hires as well. And that is the best way of growing the business.

AI assessment note: “So the secret is sourcing sessions. Sit down with your engineers”

Q Totally. No, I agree. I think the competitive element will always drive a lot more participation. Okay, next one. What's the next pillar, Alex?

A Well, the last one is, is management. So most companies, and most companies our size, they just don't put much thought into management and training, which I think is a complete travesty. You know, I can't emphasize enough how important management is. At most companies, people join, and it's just, it's complete crapshoot as to if they get a good manager or not, and that affects their entire experience of the company, then they leave the company. People don't leave companies, they leave managers. So we put so much Thought into management training, and we've got a, actually a whole handbook that we've written internally, and we do regular management trainings, and we are trying to get to a place where Clearbit has world-class managers.

AI assessment note: “Well, the last one is, is management.”

Q So agreed in terms of feedback being a gift, can I ask, what do you do internally to create an environment where people feel safe enough to give Maybe raw, unvarnished feedback, which in most cases is the most constructive. Is there anything that one can do to make people feel open enough to share to that extent?

A You know, there's a real skill to giving and receiving effective feedback, and we could do a whole podcast about this. Fundamentally, there are two steps, and I recommend reading a book called Radical Candor on this. The first step is you need to have a real, genuine relationship with each other, such that the person you're giving feedback to really trusts that you have their best interests in mind. So you've got to have that real genuine relationship. The second is that you need to be absolutely candid. State the facts. State the story in your head. Don't sugarcoat things to make people feel better. You're just doing them a disservice by watering down the feedback. That's what I see the most is managers operating in what I call ruinous empathy, where they sugarcoat their feedback or don't give it because they're afraid of upsetting people. Really, you're just hurting them if you do that.

AI assessment note: “Fundamentally, there are two steps, and I recommend reading a book called Radical Candor”

Q I love that in terms of the focus on management. I guess the question there is, I've seen too, kind of how poor onboarding can be. How do you think about structuring your onboarding to be as optimal as possible?

A You know, I actually got the feedback last week that our onboarding was pretty bad too, which is kind of sad, but now I know, which is great. So I can fix it. My approach to onboarding in the current system is that we just get people to read. So the first couple of days, it's just reading. And there's like an Asana checklist and people go through and read. And it is a very efficient form of data transfer. But what I've just realized is that it's great for Alex McCaw, not so good for everyone else, because not everyone learns that way. And so we're going to mix things up. We're going to have a Some more videos in there. We're going to have some in-person talks, but I'm not sure I've nailed onboarding yet at Clever.

AI assessment note: “My approach to onboarding in the current system is that we just get people to read.”

Q I'm totally with you in terms of the heaviness and weight of references. But if we stay on the element of the company is a vehicle for growth. When we chatted before, you said to me, when you hit product market fit, it's time to move into the company making phase. So I guess, what does company making really mean to you? And does this not happen from day one?

A At its essence, company building is building the machine that builds the machine. So it's scaling up the company while ensuring that communication and culture is Doesn't go to shit. It's a real art and a rare one, and I think that's why you see founders who've demonstrated they've done it before, they've just come on such huge valuations in the next company they build, because it's such a rare talent. And for first-time founders, it's a really tricky transition. You have to change how you think about your time, how you think about hiring, you have to start dealing with human problems rather than bits and bytes. And I actually think it's really difficult, especially for technical founders. Well, it certainly was for me. You've had your head down this whole time building, building, building, and now you stick your head up, and you realize the company needs a real CEO, but you, you have no idea where to start, and I was exceptionally lucky to have coaching from this guy called Matt Mashari, and he came in, and he held us early on when we were about 25 people or so, and now we're about a hundred, but he taught me the love of company building, and the love of management, and operations and management are the unglamorous side of company building, sure, but after product-market They are the difference between success and failure.

AI assessment note: “company building is building the machine that builds the machine.”

Q Well, I mean, listen, thank you so much for being honest. It's not a trade that's always so prominent on the show, but I do want to ask one specific element in particular of management, which is the kind of rise of conscious leadership. What does conscious leadership mean to you, and how do you look to imbue it today with the team?

A Honestly, conscious leadership is the best way I've found of living life. So I think the easiest way to explain it is to talk about the simple model. So there's this line, and at any moment in time, you're either above the line or below the line. And when you're above the line, you're open, curious, you're committed to learning. You're actually in a sense of trust, able to trust yourself, able to trust the environment, able to trust your relationships, and be able to trust the universe. You can trust wherever you're placing your trust. And when you're below the line, you're contracted. You're in a state of threat. Your literal body posture could be closed. Your heart is closed. You're defensive. And the big idea is that you're attached to proving that you're right. So we're simply saying is that the first key skill of conscious leaders is self-awareness. And the first act of self-awareness is can I locate myself in this now moment? Am I open or closed? Am I in the state of trust or the state of threat? Because we believe the ability to locate yourself really does start this powerful conversation inside of yourself and with anybody else you're doing this work with.

AI assessment note: “the first key skill of conscious leaders is self-awareness”

Q Well, I mean, listen, thank you so much for being honest. It's not a trade that's always so prominent on the show, but I do want to ask one specific element in particular of management, which is the kind of rise of conscious leadership. What does conscious leadership mean to you, and how do you look to imbue it today with the team?

A Honestly, conscious leadership is the best way I've found of living life. So I think the easiest way to explain it is to talk about the simple model. So there's this line, and at any moment in time, you're either above the line or below the line. And when you're above the line, you're open, curious, you're committed to learning. You're actually in a sense of trust, able to trust yourself, able to trust the environment, able to trust your relationships, and be able to trust the universe. You can trust wherever you're placing your trust. And when you're below the line, you're contracted. You're in a state of threat. Your literal body posture could be closed. Your heart is closed. You're defensive. And the big idea is that you're attached to proving that you're right. So we're simply saying is that the first key skill of conscious leaders is self-awareness. And the first act of self-awareness is can I locate myself in this now moment? Am I open or closed? Am I in the state of trust or the state of threat? Because we believe the ability to locate yourself really does start this powerful conversation inside of yourself and with anybody else you're doing this work with.

AI assessment note: “the easiest way to explain it is to talk about the simple model”

Q reminds me of something you said to me before, which is really found in clear, but it was more a process of, like, self-actualization. And we actually had Mathilde at front on the show, and she said, ah, this whole mission from day one, in many ways, it's kind of BS. Organizational discipline's way more important to look for, she thinks. Would you agree with her in this thought process?

A Well, the beauty of different founders and different companies is, Is that there's so many different flavors of success, you know, it really just comes down to the founder and the motivations, a lot of motivated by external validation, like money status or having an impact in the world. And to be clear, there's absolutely valid motivations, but then just not really mine. And as you alluded to, I actually started this company as a tool to self actualize. So there are a lot of ways, maybe healthier ways of self actualizing, like meditation and therapy, but a company is a fantastic way of pushing yourself and setting up this Feedback loop that you really needed for self-growth. And I ask everyone at Clearbit to think of the company as a self-growth vehicle. And for the record, I actually totally agree with Matilde that operational excellence is key to scaling. You know, we were lucky enough to get a lot of coaching early on in the days of Clearbit to actually make Clearbit operate extremely well.

AI assessment note: “I actually totally agree with Matilde that operational excellence is key to scaling.”

Q So agreed in terms of feedback being a gift, can I ask, what do you do internally to create an environment where people feel safe enough to give Maybe raw, unvarnished feedback, which in most cases is the most constructive. Is there anything that one can do to make people feel open enough to share to that extent?

A You know, there's a real skill to giving and receiving effective feedback, and we could do a whole podcast about this. Fundamentally, there are two steps, and I recommend reading a book called Radical Candor on this. The first step is you need to have a real, genuine relationship with each other, such that the person you're giving feedback to really trusts that you have their best interests in mind. So you've got to have that real genuine relationship. The second is that you need to be absolutely candid. State the facts. State the story in your head. Don't sugarcoat things to make people feel better. You're just doing them a disservice by watering down the feedback. That's what I see the most is managers operating in what I call ruinous empathy, where they sugarcoat their feedback or don't give it because they're afraid of upsetting people. Really, you're just hurting them if you do that.

AI assessment note: “The first step is you need to have a real, genuine relationship with each other”

Q reminds me of something you said to me before, which is really found in clear, but it was more a process of, like, self-actualization. And we actually had Mathilde at front on the show, and she said, ah, this whole mission from day one, in many ways, it's kind of BS. Organizational discipline's way more important to look for, she thinks. Would you agree with her in this thought process?

A Well, the beauty of different founders and different companies is, Is that there's so many different flavors of success, you know, it really just comes down to the founder and the motivations, a lot of motivated by external validation, like money status or having an impact in the world. And to be clear, there's absolutely valid motivations, but then just not really mine. And as you alluded to, I actually started this company as a tool to self actualize. So there are a lot of ways, maybe healthier ways of self actualizing, like meditation and therapy, but a company is a fantastic way of pushing yourself and setting up this Feedback loop that you really needed for self-growth. And I ask everyone at Clearbit to think of the company as a self-growth vehicle. And for the record, I actually totally agree with Matilde that operational excellence is key to scaling. You know, we were lucky enough to get a lot of coaching early on in the days of Clearbit to actually make Clearbit operate extremely well.

AI assessment note: “I actually totally agree with Matilde that operational excellence is key to scaling.”