The Exchanges

Q dig in more on that because you mentioned that kind of the more scrappy generalist versus that kind of more domain expert with years and years of experience. Super interesting element for me is the element of jack of all trades versus that very specific specialist. Did you really see the transition from jack of all trades to specialized functions and execs? And where do you think that transition is?

A I think that transition comes in kind of all of the points I mentioned. If you're a SaaS company and a decent economics and you're north of a million dollar ARR, that's That's probably one way of looking at it. If you have more than eight direct reports, it's probably, you know, attempt to make the move from a generalist hire to a more specialized hire. In my own experience, I think we've been guilty of swinging between the two extremes, and I think that's really easy to do in hiring. So it's really easy, for example, whatever function, you start with a generalist who totally knows how startups work, is super scrappy, able to contribute to, you know, five other functions out of their area of direct domain expertise. And the issue with that candidate or that person in your company is they're very unlikely to be able to build processes and scale an org. And on the other side, when you hire, you know, the senior VP, LinkedIn, et cetera, is everything they're going to do or going to want to do is going to set you back 30 to 50 K because they're used to having huge budgets and, you know, running really big processes and perhaps they're not really adapted the size of company or app. So. These are the swing between those two extremes. Once you've done the generalist, you want to go super senior, only to discover that that wasn't the right answer either.

AI assessment note: “If you have more than eight direct reports, it's probably... make the move”

Q we chatted before the show, Olof, about what we should focus on today, we agreed it'd be great to discuss the stage post-product market fit, which no one really talks about in terms of scaling the leadership team and scaling the company, and you said there's three elements of denial for the founder, potentially. I'd love to start with, what are those three elements of denial, do you think, Olof?

A Yeah, this has definitely been a hallmark of 2018 for myself, and I think for us at MixMax is starting to scale the business. And so as you say, what's really fun, there's all, they're like libraries written about product market fit and very little written about scaling and in particular building out a senior team. And so just, if I look at my own 20 18, I think as a founder, I definitely went through kind of three stages of denial in terms of hiring senior folks on the team. And so the first thing I think you say as a founder is, you know, Hey, I don't think we need this role right now. You know, you think it's too early. It's going to cost too much, et cetera. And then once you realize that you actually do need the senior role and You tell yourself, I can find the right person on my own. I'm used to doing things on my own. I don't need help to find the role. And of course, once you realize that you can't, or that you're hiring for the wrong level, or that you've, you know, erroneously put people in stretch roles, then you kind of tell yourself, well, whoever I hire, they're going to grow into the role. And in many cases they can't. So those are kind of the three stages of denial and happy to chat more about them and my own personal experience with them.

AI assessment note: “those are kind of the three stages of denial”

Q dig in more on that because you mentioned that kind of the more scrappy generalist versus that kind of more domain expert with years and years of experience. Super interesting element for me is the element of jack of all trades versus that very specific specialist. Did you really see the transition from jack of all trades to specialized functions and execs? And where do you think that transition is?

A I think that transition comes in kind of all of the points I mentioned. If you're a SaaS company and a decent economics and you're north of a million dollar ARR, that's That's probably one way of looking at it. If you have more than eight direct reports, it's probably, you know, attempt to make the move from a generalist hire to a more specialized hire. In my own experience, I think we've been guilty of swinging between the two extremes, and I think that's really easy to do in hiring. So it's really easy, for example, whatever function, you start with a generalist who totally knows how startups work, is super scrappy, able to contribute to, you know, five other functions out of their area of direct domain expertise. And the issue with that candidate or that person in your company is they're very unlikely to be able to build processes and scale an org. And on the other side, when you hire, you know, the senior VP, LinkedIn, et cetera, is everything they're going to do or going to want to do is going to set you back 30 to 50 K because they're used to having huge budgets and, you know, running really big processes and perhaps they're not really adapted the size of company or app. So. These are the swing between those two extremes. Once you've done the generalist, you want to go super senior, only to discover that that wasn't the right answer either.

AI assessment note: “north of a million dollar ARR... more than eight direct reports”

Q that, you know, we should hire six months out, and I'm just thinking in terms of, if you're a small company and hiring from a big company, how do you think about the past Plasticity of the individual to move from big company to small company. Is that a big consideration? And should we always go for that kind of logo candidate from the LinkedIn sales force of the world?

A I think that is just one dimension of many, and I think depends on the culture you have and the type of business you're building. This sounds a little bit to me potentially like the third stage of denial, which is they will grow into the role. And so it's worth emphasizing that growing into the role is not just Scaling upwards. It's also molding themselves to the culture and uniqueness of your company, and so we've definitely been guilty of this at Mixmax, but it's really easy to swing between two extremes. On the one hand, you have the version of, hey, let's hire the super senior director VP from Salesforce or LinkedIn or Facebook or whatever it might be. That's kind of the one end of the extreme, and the other end of the extreme is we're going to hire this super scrappy startup generalist who can do everything and who will grow into the role, and in both cases, you're making a huge bet On their ability to grow into the role.

AI assessment note: “I think that is just one dimension of many, and I think depends on the culture”

Q Well, I mean, you've teed me up perfectly for the entire interview there, because I want to break each one down. And let's start with the, we don't need that role now. So talk to me, Olaf. How do you think about this constant question of when is the right time to add certain roles?

A Well, first of all, I would say once you have product market fit, which is an entirely different topic, probably worth its own episode, assuming you do, the answer is it's probably too late already, and you should have hired them yesterday. And I think as Founders. Well, we have a couple of hesitations around it, and I'm happy to share where I think all of these retrospectively are wrong or false. Typically what we as founders say is we hesitate to hire senior roles because either we think it's too expensive or we think it's too early. And so when we say it's too early, what do we really mean as founders? And I think it's a couple of things. One is we're actually insecure about whether we have product market fit. We're not sure whether the senior hire will even have headcount to build out a team. So we're nervous about that. Or we're insecure about not having, you know, proven out thing X or thing Y and marketing or sales or whatever the function might be, and we think it's too early to bring them on. And perhaps you worry, even if you have product market fit, you're not sure what the right go-to-market strategy is, and so you're worried about hiring the wrong person.

AI assessment note: “the answer is it's probably too late already, and you should have hired them yesterday.”

Q Gosh, this is an episode of first. I've never had that one either. Okay, and so what would you most like to change about Silicon Valley and VC?

A I wonder if this will be a first or not. This might not be. What's wonderful about Silicon Valley is how much we adore entrepreneurship above everything else. And entrepreneurship is fundamentally about creating something for nothing, creating new futures that other people couldn't imagine. And what strikes me here is while we have this adoration of entrepreneurship, the way we're supposed to build companies is like a monoculture. There's traditionally like one way to build a company, one way to fund your company, One way to do things X, Y, and Z as you grow. And so I'm really interested in more models for how to structure companies. The remote work trend I think is a little bit part of this. I think it's very interesting at distributed companies overall. I think there's a ton of innovation to be made in terms of various different funding models and how the types of companies you might be building outside of the traditional like VC wonder model. So I'd love to see more innovation among, I guess, VC funding models and company models.

AI assessment note: “I'd love to see more innovation among, I guess, VC funding models”

Q we chatted before the show, Olof, about what we should focus on today, we agreed it'd be great to discuss the stage post-product market fit, which no one really talks about in terms of scaling the leadership team and scaling the company, and you said there's three elements of denial for the founder, potentially. I'd love to start with, what are those three elements of denial, do you think, Olof?

A Yeah, this has definitely been a hallmark of 2018 for myself, and I think for us at MixMax is starting to scale the business. And so as you say, what's really fun, there's all, they're like libraries written about product market fit and very little written about scaling and in particular building out a senior team. And so just, if I look at my own 20 18, I think as a founder, I definitely went through kind of three stages of denial in terms of hiring senior folks on the team. And so the first thing I think you say as a founder is, you know, Hey, I don't think we need this role right now. You know, you think it's too early. It's going to cost too much, et cetera. And then once you realize that you actually do need the senior role and You tell yourself, I can find the right person on my own. I'm used to doing things on my own. I don't need help to find the role. And of course, once you realize that you can't, or that you're hiring for the wrong level, or that you've, you know, erroneously put people in stretch roles, then you kind of tell yourself, well, whoever I hire, they're going to grow into the role. And in many cases they can't. So those are kind of the three stages of denial and happy to chat more about them and my own personal experience with them.

AI assessment note: “those are kind of the three stages of denial”

Q we've got more than eight direct reports. The next stage of denial that you mentioned was, I can find the right person on my own. Often we hear that the majority of hiring goes to kind of found a network. So I have to ask, What did you mean by that? I can find the right person on my own. And what are the challenges with this stage of denial?

A Yeah, I think, as you mentioned, this is kind of the second stage. So you finally got convinced that, oh, you need someone to own this particular function and that person's not you and you're willing to invest. And so I think this stage of denial expresses itself in a couple of different ways. One is you tell yourself as a founder and like very reasonably so, because as founders, we're typically pretty well connected and We know a bunch of other founders. A lot of us have worked at some potentially worked at some big prior successful startup. We have investors, et cetera. They have really big Rolodexes. So we tell ourselves we can do this through our own network. And we tell ourselves that, Hey, it's going to go way faster because that way I, as a founder, I'm going to be running the process. I can really sell the vision. I don't have to do this through the intermediary of someone else. And, you know, I have great back channel because it's through my network. And of course, for a gazillion reasons, it almost never works out that way, although it can. And once that doesn't work out, you kind of tell yourself another version of same stage of denial, which is, okay, I realized I can't find a candidate through my own network. I think I know the right recruiter to help me fill this role. And invariably, you actually don't, and you really need professional help.

AI assessment note: “this stage of denial expresses itself in a couple of different ways”

Q In terms of kind of you mentioned, obviously, it's been a core element for you in 2018. In terms of kind of your learnings on timing, have there been some big learnings now kind of year in review and the benefit of hindsight when it comes to timing of adding that role?

A I would say a couple of rules of thumb, and I'll talk about it kind of generally and then specifically as a founder CEO. So I think for any founder who might not be CEO, I would almost say the rule of thumb is as soon as you have more than eight direct reports, you need to hire someone to replace yourself or at least take over most of the work. And ideally they become an entire functional leader, not just a director of function X, but literally an owner of the entire function. And for any function, I'd say where no one on the founding team has direct domain expertise and Once you're past perhaps one or two IC hires, if you know that this function is going to grow, then you might just as well hire a senior leader to actually build out that team, no matter how small it might end up. And then last is being as founder CEO, and that's perhaps the most difficult one because it's really hard as CEO to let go. I'd say figure out what area you want to own, own it for perhaps top six months, and then find someone else out to do it. And I think as founders, particularly in areas where we have Domain expertise. We're, like, very susceptible to postponing this hire, and so, kind of, what happens if you do a domain expert hire who literally has tenx the knowledge and experience in a field than you do?

AI assessment note: “as soon as you have more than eight direct reports, you need to hire”

Q we've got more than eight direct reports. The next stage of denial that you mentioned was, I can find the right person on my own. Often we hear that the majority of hiring goes to kind of found a network. So I have to ask, What did you mean by that? I can find the right person on my own. And what are the challenges with this stage of denial?

A Yeah, I think, as you mentioned, this is kind of the second stage. So you finally got convinced that, oh, you need someone to own this particular function and that person's not you and you're willing to invest. And so I think this stage of denial expresses itself in a couple of different ways. One is you tell yourself as a founder and like very reasonably so, because as founders, we're typically pretty well connected and We know a bunch of other founders. A lot of us have worked at some potentially worked at some big prior successful startup. We have investors, et cetera. They have really big Rolodexes. So we tell ourselves we can do this through our own network. And we tell ourselves that, Hey, it's going to go way faster because that way I, as a founder, I'm going to be running the process. I can really sell the vision. I don't have to do this through the intermediary of someone else. And, you know, I have great back channel because it's through my network. And of course, for a gazillion reasons, it almost never works out that way, although it can. And once that doesn't work out, you kind of tell yourself another version of same stage of denial, which is, okay, I realized I can't find a candidate through my own network. I think I know the right recruiter to help me fill this role. And invariably, you actually don't, and you really need professional help.

AI assessment note: “we tell ourselves we can do this through our own network”

Q I would love to dive into that. How, as founders, do you approach external recruiters? Is that the role of actually the VC and the board member, so to speak? Is that the role of the founder? And what steps should they take to ensure that they have the right recruiter?

A Yeah. I think as founders, we kind of through our hubris, again, we kind of neglect the deep nuance and complexity of any other function than the one that we own are really familiar with. And so unless you're a founder recruiter, you like don't realize this. So it's great to have some guidance from your board there. A couple of obvious key differences, like recruiting firms for senior talent are often kind of like very boutique and specialize exactly in that their price bounds are entirely different and you have to be very comfortable paying up for that. Of course. The other thing is I think it's really easy as a founder, especially early in your founder career, to have a somewhat transactional relationship with your recruiters, and probably you do that with kind of anyone who's a contractor, and obviously, ideally, you shouldn't. You should treat these folks as just core members of their team, because they will add more, if not, well, as much, if not more value as any of the ICs on your team in terms of finding this role, and I mean, from a candidate perspective, I think the thing you don't realize as a founder is, This recruiter is pitching your company to them, and so they need to feel incredibly jazzed about your company in a much deeper way, and there's actually a fair amount at stake for the recruiter themselves, because they have their own folk Rolodexes with high-qualit…

AI assessment note: “You should treat these folks as just core members of their team”

Q Well, I mean, you've teed me up perfectly for the entire interview there, because I want to break each one down. And let's start with the, we don't need that role now. So talk to me, Olaf. How do you think about this constant question of when is the right time to add certain roles?

A Well, first of all, I would say once you have product market fit, which is an entirely different topic, probably worth its own episode, assuming you do, the answer is it's probably too late already, and you should have hired them yesterday. And I think as Founders. Well, we have a couple of hesitations around it, and I'm happy to share where I think all of these retrospectively are wrong or false. Typically what we as founders say is we hesitate to hire senior roles because either we think it's too expensive or we think it's too early. And so when we say it's too early, what do we really mean as founders? And I think it's a couple of things. One is we're actually insecure about whether we have product market fit. We're not sure whether the senior hire will even have headcount to build out a team. So we're nervous about that. Or we're insecure about not having, you know, proven out thing X or thing Y and marketing or sales or whatever the function might be, and we think it's too early to bring them on. And perhaps you worry, even if you have product market fit, you're not sure what the right go-to-market strategy is, and so you're worried about hiring the wrong person.

AI assessment note: “once you have product market fit... it's probably too late already”

Q Gosh, this is an episode of first. I've never had that one either. Okay, and so what would you most like to change about Silicon Valley and VC?

A I wonder if this will be a first or not. This might not be. What's wonderful about Silicon Valley is how much we adore entrepreneurship above everything else. And entrepreneurship is fundamentally about creating something for nothing, creating new futures that other people couldn't imagine. And what strikes me here is while we have this adoration of entrepreneurship, the way we're supposed to build companies is like a monoculture. There's traditionally like one way to build a company, one way to fund your company, One way to do things X, Y, and Z as you grow. And so I'm really interested in more models for how to structure companies. The remote work trend I think is a little bit part of this. I think it's very interesting at distributed companies overall. I think there's a ton of innovation to be made in terms of various different funding models and how the types of companies you might be building outside of the traditional like VC wonder model. So I'd love to see more innovation among, I guess, VC funding models and company models.

AI assessment note: “I'd love to see more innovation among, I guess, VC funding models and company models.”

Q quite a big seed round and, you know, we're looking to build out the team, but we can't find the right people straight away. And we're hiring for devs. And so, we kind of need them now. Let's go for kind of short-term contractors. How do you think about that kind of plastered gap, so to speak, when hiring contractors to fill that void? How do you think about that?

A The way I think about this, and we actually had one of our senior leaders join the team this way, and this is, I think, very different from IC hiring. One of the challenges of hiring senior talent and building out a function that you know very little of is, of course, You know nothing about the function. And so what that means is there are a host of unknown unknowns that are unknown unknowns to you, but won't be to someone with more, more experience in the function. And so I see it really helpful if you're building out whatever it is, HR or sales or marketing, or perhaps product or design, whatever function it might be engineering for the first time to have a very senior consultant come in and work with you for a good couple of months. And the main advantage there is you get kind of a litmus test of what it's like working with the senior leader in this function before you even commit fully to building out the function. And in some cases, the person who's your consultant might even join your company full time. And so it's a great risk-free way in my mind to ease the transition.

AI assessment note: “it's a great risk-free way in my mind to ease the transition”

Q that, you know, we should hire six months out, and I'm just thinking in terms of, if you're a small company and hiring from a big company, how do you think about the past Plasticity of the individual to move from big company to small company. Is that a big consideration? And should we always go for that kind of logo candidate from the LinkedIn sales force of the world?

A I think that is just one dimension of many, and I think depends on the culture you have and the type of business you're building. This sounds a little bit to me potentially like the third stage of denial, which is they will grow into the role. And so it's worth emphasizing that growing into the role is not just Scaling upwards. It's also molding themselves to the culture and uniqueness of your company, and so we've definitely been guilty of this at Mixmax, but it's really easy to swing between two extremes. On the one hand, you have the version of, hey, let's hire the super senior director VP from Salesforce or LinkedIn or Facebook or whatever it might be. That's kind of the one end of the extreme, and the other end of the extreme is we're going to hire this super scrappy startup generalist who can do everything and who will grow into the role, and in both cases, you're making a huge bet On their ability to grow into the role.

AI assessment note: “I think that is just one dimension of many, and I think depends”

Q In terms of kind of you mentioned, obviously, it's been a core element for you in 2018. In terms of kind of your learnings on timing, have there been some big learnings now kind of year in review and the benefit of hindsight when it comes to timing of adding that role?

A I would say a couple of rules of thumb, and I'll talk about it kind of generally and then specifically as a founder CEO. So I think for any founder who might not be CEO, I would almost say the rule of thumb is as soon as you have more than eight direct reports, you need to hire someone to replace yourself or at least take over most of the work. And ideally they become an entire functional leader, not just a director of function X, but literally an owner of the entire function. And for any function, I'd say where no one on the founding team has direct domain expertise and Once you're past perhaps one or two IC hires, if you know that this function is going to grow, then you might just as well hire a senior leader to actually build out that team, no matter how small it might end up. And then last is being as founder CEO, and that's perhaps the most difficult one because it's really hard as CEO to let go. I'd say figure out what area you want to own, own it for perhaps top six months, and then find someone else out to do it. And I think as founders, particularly in areas where we have Domain expertise. We're, like, very susceptible to postponing this hire, and so, kind of, what happens if you do a domain expert hire who literally has tenx the knowledge and experience in a field than you do?

AI assessment note: “as soon as you have more than eight direct reports, you need to hire”

Q I would love to dive into that. How, as founders, do you approach external recruiters? Is that the role of actually the VC and the board member, so to speak? Is that the role of the founder? And what steps should they take to ensure that they have the right recruiter?

A Yeah. I think as founders, we kind of through our hubris, again, we kind of neglect the deep nuance and complexity of any other function than the one that we own are really familiar with. And so unless you're a founder recruiter, you like don't realize this. So it's great to have some guidance from your board there. A couple of obvious key differences, like recruiting firms for senior talent are often kind of like very boutique and specialize exactly in that their price bounds are entirely different and you have to be very comfortable paying up for that. Of course. The other thing is I think it's really easy as a founder, especially early in your founder career, to have a somewhat transactional relationship with your recruiters, and probably you do that with kind of anyone who's a contractor, and obviously, ideally, you shouldn't. You should treat these folks as just core members of their team, because they will add more, if not, well, as much, if not more value as any of the ICs on your team in terms of finding this role, and I mean, from a candidate perspective, I think the thing you don't realize as a founder is, This recruiter is pitching your company to them, and so they need to feel incredibly jazzed about your company in a much deeper way, and there's actually a fair amount at stake for the recruiter themselves, because they have their own folk Rolodexes with high-qualit…

AI assessment note: “treat these folks as just core members of their team”

Q interesting, because I really want to tuck in on that, because that's one element where I often see founders where they go, okay, I can't do it myself. But the recruiter will help me, and it's kind of this halo of this savior recruiter. Why does, do they need professional help, so to speak, around that element, and what can kind of go wrong, and how should they approach it?

A Well, on the recruiter side specifically, and having to chat more about, like, why very often you can't do this through your own network, unless you've directly hired senior talent before, if you think to know you're right, the right recruiter, you almost certainly don't. And the reason for this is, I think, Overall, as founders, we have a lot of hubris, which is a great asset when trying to find product market fit, and it's pretty counterproductive when you're trying to build a senior team, and so we've probably worked with recruiters to help us fill IC roles in the past. We probably even have great relationships with a couple of those recruiters, and so we kind of underestimate the complexity and richness of the talent market, and so we think that someone who's a great IC recruiter is also going to be a great senior management or leadership recruiter. And the truth is, of course, vastly different. And so they're kind of an entirely different set of recruiters, which is, you know, sounds obvious when you just hear it, but you're probably not aware of, at least I wasn't, for senior roles. Much more to say about this, and I think how we as founders overall approach external recruiters.

AI assessment note: “we think that someone who's a great IC recruiter is also going to be a great senior”

Q quite a big seed round and, you know, we're looking to build out the team, but we can't find the right people straight away. And we're hiring for devs. And so, we kind of need them now. Let's go for kind of short-term contractors. How do you think about that kind of plastered gap, so to speak, when hiring contractors to fill that void? How do you think about that?

A The way I think about this, and we actually had one of our senior leaders join the team this way, and this is, I think, very different from IC hiring. One of the challenges of hiring senior talent and building out a function that you know very little of is, of course, You know nothing about the function. And so what that means is there are a host of unknown unknowns that are unknown unknowns to you, but won't be to someone with more, more experience in the function. And so I see it really helpful if you're building out whatever it is, HR or sales or marketing, or perhaps product or design, whatever function it might be engineering for the first time to have a very senior consultant come in and work with you for a good couple of months. And the main advantage there is you get kind of a litmus test of what it's like working with the senior leader in this function before you even commit fully to building out the function. And in some cases, the person who's your consultant might even join your company full time. And so it's a great risk-free way in my mind to ease the transition.

AI assessment note: “it's a great risk-free way in my mind to ease the transition”

Q No, I love that ninety-day time frame. If it's not the right person, say, I mean, I get a lot of founders ask me, a lot of first-time founders who've maybe never let people go before, how do I do it the right way? What are your thoughts on the right way to let someone go, maybe?

A Yeah, this is one of the non-fun parts of running a company. I think if it's someone who you hired into a very senior role, that conversation in some ways It's both easier and harder than letting someone in an IC role go, and in very many cases, I think that hire knows that themselves. One of the things I've discovered just on my, like, personal learning journey is it's very hard to disguise what you think of people's performance on the team, and so what you can do as a leader acknowledging that it's, you know, you probably can't hide it even though you think you can is to often both ask for feedback, From that person and also give clear action oriented observation based feedback.

AI assessment note: “give clear action oriented observation based feedback”

Q But I do want to start, and for those that maybe missed our round one episode, how did you make your way into the world of startups and really come to found the game changer of email that is Mixmax, Olaf?

A So in terms of making my way into the world of startups, I think there are kind of two things for me. One was values and then kind of a specific point of inspiration. So for me, a core value and kind of motivator for me in life has always been to feel that I'm creating something for nothing and that I can empower other people either to see the world in new ways or express themselves in new ways. And so I think that actually led me after college to try out academia. And I quickly realized that that was like way too slow for my temperament. And I think I'd also hesitated a little bit about the business world. It just It felt really boring, and this was in the mid to late aughts, and so fortunately, and this is where the inspiration point comes in, I had a friend who had started a business, and he made it seem both really easy and really fun, and little did I know that it was neither. Startups are definitely not easy. They can, uh, they're also fun. Of course, startups are also one heck of a grind, so I think that's something you need to be aware of and just make sure that they're still really existentially satisfying to you.

AI assessment note: “in terms of making my way into the world of startups, I think there are kind”

Q interesting, because I really want to tuck in on that, because that's one element where I often see founders where they go, okay, I can't do it myself. But the recruiter will help me, and it's kind of this halo of this savior recruiter. Why does, do they need professional help, so to speak, around that element, and what can kind of go wrong, and how should they approach it?

A Well, on the recruiter side specifically, and having to chat more about, like, why very often you can't do this through your own network, unless you've directly hired senior talent before, if you think to know you're right, the right recruiter, you almost certainly don't. And the reason for this is, I think, Overall, as founders, we have a lot of hubris, which is a great asset when trying to find product market fit, and it's pretty counterproductive when you're trying to build a senior team, and so we've probably worked with recruiters to help us fill IC roles in the past. We probably even have great relationships with a couple of those recruiters, and so we kind of underestimate the complexity and richness of the talent market, and so we think that someone who's a great IC recruiter is also going to be a great senior management or leadership recruiter. And the truth is, of course, vastly different. And so they're kind of an entirely different set of recruiters, which is, you know, sounds obvious when you just hear it, but you're probably not aware of, at least I wasn't, for senior roles. Much more to say about this, and I think how we as founders overall approach external recruiters.

AI assessment note: “we think that someone who's a great IC recruiter is also going to be”

Q But I do want to start, and for those that maybe missed our round one episode, how did you make your way into the world of startups and really come to found the game changer of email that is Mixmax, Olaf?

A So in terms of making my way into the world of startups, I think there are kind of two things for me. One was values and then kind of a specific point of inspiration. So for me, a core value and kind of motivator for me in life has always been to feel that I'm creating something for nothing and that I can empower other people either to see the world in new ways or express themselves in new ways. And so I think that actually led me after college to try out academia. And I quickly realized that that was like way too slow for my temperament. And I think I'd also hesitated a little bit about the business world. It just It felt really boring, and this was in the mid to late aughts, and so fortunately, and this is where the inspiration point comes in, I had a friend who had started a business, and he made it seem both really easy and really fun, and little did I know that it was neither. Startups are definitely not easy. They can, uh, they're also fun. Of course, startups are also one heck of a grind, so I think that's something you need to be aware of and just make sure that they're still really existentially satisfying to you.

AI assessment note: “So in terms of making my way into the world of startups”

Q No, I love that ninety-day time frame. If it's not the right person, say, I mean, I get a lot of founders ask me, a lot of first-time founders who've maybe never let people go before, how do I do it the right way? What are your thoughts on the right way to let someone go, maybe?

A Yeah, this is one of the non-fun parts of running a company. I think if it's someone who you hired into a very senior role, that conversation in some ways It's both easier and harder than letting someone in an IC role go, and in very many cases, I think that hire knows that themselves. One of the things I've discovered just on my, like, personal learning journey is it's very hard to disguise what you think of people's performance on the team, and so what you can do as a leader acknowledging that it's, you know, you probably can't hide it even though you think you can is to often both ask for feedback, From that person and also give clear action oriented observation based feedback.

AI assessment note: “give clear action oriented observation based feedback”