Episode 826 | How to Find, Hire, and Work with Owner-Level Thinkers

Rob Walling (00:00): When I first started my career, I was a task level thinker. I just couldn’t do multiple things at once. I couldn’t prioritize. I couldn’t manage it. I couldn’t keep all the plates spinning. And then over the course of the first five-ish, six-ish years, I remember getting to the point where I was really comfortable running projects and I think I became a solid project level thinker at that point. And then as I dipped my toe into becoming an entrepreneur, I wasn’t an owner-level thinker because I needed too much certainty. I couldn’t make hard decisions with incomplete information. I didn’t know how to do that. And then it took me another five to eight years to really feel into it and to be confident in my own ability to trust my founder gut and to develop my founder gut to the point where I was making good decisions because that’s what being an owner level thinker requires. 

Rob Walling (00:58): Welcome back to another episode, Startups for the Rest of Us. I’m your host, Rob Walling. And in this episode, I’m going to dive into themed listener questions. So if you don’t know, I’ve recently started writing again, publishing essays for the first time really since about 2011. And I’m doing that over at robwalling.com. If you enter your name and email in any of the forms on that site, you can start receiving a weekly thought from me. And some of these are mental models, they’re frameworks, they’re questions that I’m often asked by founders, whether that’s from TinySeed on this podcast, in the MicroConf community direct via email. And most of these are concepts that I have not covered in a prior book. Some of them are concepts that I’ve developed here on this podcast or am developing on the podcast. And I realized that I’m putting out a ton of audio content every year, a ton of video content on youtube.com/robwalling, but I haven’t really done serialized written content in quite a long time. 

Rob Walling (02:05): And I decided that I wanted to double down on that modality this year because I feel like there are a lot of folks who maybe don’t want to listen to audio or video and the way they learn best is through written content. So if you head to robwalling.com, you’ll hear a new thought from me every week. As I’ve been doing this though, it’s been this great feedback loop because I’m sending out these emails and receiving a lot of questions about them. And when it’s as easy as just hitting reply to an email and shooting me a question, I feel like I get a lot more questions about the topics. I’m also getting a lot of thanks and I’m glad you’re writing again, which makes me feel really motivated and makes me feel grateful to have such an awesome community. But recently I sent out an email about task level, project level, and owner level thinkers. 

Rob Walling (02:53): And in response to that, I received a lot of questions about how to find them and how expensive are they and how do you identify them and so on. And so I wanted to spend a good chunk of this episode talking about how to do just that. And if you’re not on the list yet and you missed that email, don’t worry, my friend. I’m putting all of these emails into a sequence such that if you sign up today, you will receive the emails that I sent a few weeks ago. But if you aren’t already on my email list, you should head to robwalling.com. Just look for any email opt-in. There’s one in the footer, there’s one in the sidebar of the blog. And I’m also publishing some of those emails as new essays at robwalling.com/essays. And finally, if you are on YouTube and you’re not watching me, youtube.com/robwalling, I’m putting out a video every other week and it’s completely new content that is not done on this podcast and not sent out via email to my list. 

Rob Walling (03:53): So you get just a lot more of my thinking by hitting all three of those avenues. And with that, let’s dive into my first reader question. Since I didn’t get permission in advance from everyone who responded to me, I’m going to leave folks anonymous, but my first question asker responded to, again, to this email about task level, owner level, and project level thinkers. And actually, let me do a quick definition of those three levels in case you haven’t read the book or you missed the podcast episode. So I have a mental framework about different levels of ability with folks who you work with. Most people, especially when they start out earlier in their career are task level thinkers, meaning you hand them a task and usually you have to give them some guidance around it. And sometimes you don’t and they can figure it out, but they work on that task, then they return the results to you and then they move on to the next task that you’ve assigned them. 

Rob Walling (04:50): Project level thinkers are a level above that. And those are folks who can manage an entire project with potentially conflicting priorities, a lot more going on, and they can keep it driving forward. Sometimes they’re managing task level thinkers or at least driving, even if they’re not directly managing, they’re driving one or more task level thinkers to help deliver the project. There’s obviously a lot more complexity and a lot more skills needed to manage projects. And I think most people, again, when they first start out on their career and they’re an IC or an individual contributor, they are there to do tasks and at a certain point you get good enough that you can start managing projects. A lot of people though, I don’t think they make it to this next level, the third level, which is owner level thinkers. You could call this a founder level thinker. 

Rob Walling (05:41): You could call this an executive level thinker, but I call it owner level. And I think of it like a task level thinker probably thinks ahead a few hours or maybe depending on the task, a day or two. I think a project level thinker is thinking ahead weeks, maybe a few months, again, depending on the size and complexity of the project, and an owner level thinker might be thinking ahead six months, 12 months, two years, thinking about everything that’s going on at a company, coming up with brand new ideas and then weighing them, not having entrepreneurial ADHD and shoving that all to their team, but actually evaluating thoughts and ideas that are coming up and opportunities and then getting the team on board to implement those. It includes not only management of people, but management of priorities, saying no to a lot of things, a lot of decision making as an owner level thinker, making a lot of hard decisions with incomplete information versus as a task level thinker, you don’t have to make hard decisions and you usually have very complete information. 

Rob Walling (06:47): And as a project level thinker, you might have to make some hard decisions, but for the most part, you have most of the information. And then as an owner level, it’s your whole job. Anything that comes up to you is a hard decision with incomplete information. And so to wrap up the definition, owner level thinkers obviously are managing a lot of priorities and a lot of people, and they are painting a vision, keeping everyone accountable and moving the whole team in a direction. But you can have an owner level thinker who doesn’t manage anyone, and you’ll still know that they are their kind of next level. They just think and execute at a level that is seriously advanced compared to the other folks you’re working with. So with that definition, my first question asker said, “This was very well framed and laid out. Would you say owner level thinkers are typically more senior and experienced or is it more of a personality type and a mindset?” And in my experience, I think it takes years to learn it. 

Rob Walling (07:51): I can’t think of someone who has just the personality type or the mindset and is in their first couple years thinking like an owner because owners think strategically, they think long term. You need a lot of information, you need really, really good founder gut, really good intuition, you need to be making good decisions. And I just think without quite a few notches on your belt, quite a bit of work, quite a bit of mistakes and successes and seeing what works and what doesn’t and all the scar tissue that comes from working your way up, it sounds like a weird way to say it, but I think it is generally more senior. Now that doesn’t mean just because someone is more senior that they’re an owner level thinker. I guarantee you, there are folks who are 15, 20, 25, 30 years into their career who are still task level or project level thinkers. 

Rob Walling (08:41): So it doesn’t mean everyone gets there, but I have a hard time imagining an owner level thinker that hasn’t been working for at least a few years. Now, I do see some startup founders that are in their mid to late 20s that are really sharp and there are some TinySeed founders that are executing like crazy, doing millions a year in ARR, and they’re like 28 years old. And so there’s something there, but I think it’s extremely rare. I think generally, and I will speak for myself in this, when I first started my career, I was a task level thinker. I just couldn’t do multiple things at once. I couldn’t prioritize. I couldn’t manage it. I couldn’t keep all the plates spinning. And then over the course of the first five-ish, six-ish years, maybe a little longer, I remember getting to the point where I was really comfortable running projects and I think I became a solid project level thinker at that point and I remember getting better at it. 

Rob Walling (09:32): And then as I dipped my toe into becoming an entrepreneur, I wasn’t an owner-level thinker because I needed too much certainty. I couldn’t make hard decisions with incomplete information. I didn’t know how to do that. And then it took me another five to, I don’t even know, five to 10, five to eight years to really feel into it and to be confident in my own ability to trust my founder gut and to develop my founder gut to the point where I was making good decisions because that’s what being an owner level thinker requires. So to recap that, I do think generally it’s more senior and experience. If I was going to hire someone, I would generally be thinking about years on the job as at least a proxy. And of course then you have to evaluate because again, someone can be 15 years in and still be a task level thinker. 

Rob Walling (10:16): Second question is, in your experience, what is the compensation range for US or North America? Because obviously in Canada, someone might be 20 or 30% cheaper. And this is the compensation range for owner level thinkers. This is really hard to answer because it depends. So you can get someone who has the raw material, who is a great project level thinker and is itching to be an owner level thinker and really run their own thing, but they’ve never been allowed to. And so they’re right on that cusp. It’s hard to tell. We’re going to talk a little bit later about how to evaluate or how to identify project and owner level thinkers, but if you get someone right on that cusp who becomes an owner level thinker within the first year or two of working for you, then obviously you can get them at a certain salary range. 

Rob Walling (11:03): And if I think US or North America, I mean maybe $80,000, $90,000. But if I think of someone who has the experience and has been allowed to stretch their legs and really drive an org and really be an owner level thinker and they were kind of paid commensurate based on their value, you were definitely looking at low to mid six figures. However, it depends on where they live. I know task level individual contributor developers living in the Bay Area who are making $500,000 a year, that includes stock grants and such. And then I know folks living in a very low cost of living city or working remotely who are doing a very similar job and making $100,000. So when we say the US, that’s a big spread in Canada as well, but you get the idea. Could some owner level thinkers be making $250,000, $350,000 a year? 

Rob Walling (11:53): Absolutely. I just know most companies listening to this podcast and most folks that I deal with, you don’t have the budget to hire folks like that. And then I think the last question is, is it possible to hire these owner level thinkers without payroll/W2 or when you say full-time is the payroll/W2 assumed? Perhaps you could do a mix of 30 hour pay plus some kind of bonus structure based on goals since W2 payroll can create additional tax liabilities depending on the state or location. I mean, it depends, maybe. I’ve never heard of this. If someone is this good and they’re this valuable, they will be full-time W2 with healthcare if you offer it, any other benefits you have. Think about it this way. How do you get someone who’s this good to come work for you? Because they can work anywhere they want if they know their value. 

Rob Walling (12:41): And so 30 hours a week plus other stuff is, I don’t know. I mean, it’s a scrappy bootstrappery way to do things and maybe you’ll get lucky, but owner level thinkers are hard enough to find in the wild anyways. They’re hard to find. And if you find them, hopefully they know their value and they can kind of go anywhere. So I can’t imagine someone wanting to come on board and work for 30 hours a week pay unless that really fit their whole lifestyle and they were like, “Oh, I only want to work 30 hours.” There are some folks who do want that lifestyle and they want that freedom of that extra 10 hours a week. And in that case, yeah, maybe it would work. Maybe you could hire them. Here’s the thing, maybe they want to work as a contractor because they do want to maintain that freedom and flexibility of their lifestyle. 

Rob Walling (13:24): And in that case, I guess it could work. It just generally, I think if you want someone in your org, this owner level thinker will likely become a pretty pivotal part of your org and potentially be managing a whole area or department, managing the whole thing. They maybe should get equity as a retention motivator. And so yeah, I think those are my thoughts there. W2 creating tax liabilities depending on state and location. Yeah, it’s just what happens. I mean, there are certain states I don’t think I would hire in because of that. So thanks for those questions. And so I think that question begs another question that you really have to ask yourself is, do you have the budget to hire a project or owner level thinker? Because back in the day when I was bootstrapping nights and weekends, I just didn’t have the budget. 

Rob Walling (14:13): And this is why I developed some bad habits of doing everything myself and only hiring virtual assistants or really inexpensive resources and really junior resources and training them up and giving them SOPs. And it was fine and it was what I needed at that time, but it came back to bite me later because it was a bad habit that I developed and it took me a long time to get to the point of like, oh no, at a certain point I need to spend more money on my team and I need to hire more mid-level and senior people so that we can move faster and that all of the decision making burden is not on me. So being realistic with yourself about budget, do you have it? And if you do, hire project if you can, project level and owner level if you can, but obviously it can be pricey. 

Rob Walling (15:01): Every founder I know dreams about what an exit might look like, but if you’re doing between two and 25 million in ARR, you’ve probably realized you’re in this weird middle zone, too big for the online marketplaces, too small for an investment bank to care. That’s exactly why my good friend Einar Vollset started Discretion Capital. Einar is my co-founder at TinySeed, and he’s helped companies you’ve heard on this podcast have life-changing exits. If you listen to the ScrapingBee or GymDesk episodes, you heard those founders talk about what Discretion did for them. Those were massive outcomes. His team has helped Segments.ai exit to Uber and SparkLoop to ConvertKit. Whether you’re just trying to understand what your company might be worth, you’ve got an offer on the table and you’re not sure if it’s any good, or you want to run a full process and get maximum value, head to discretioncapital.com and have a conversation with Einar’s team. 

Rob Walling (15:53): Another question though is, do you need owners and project level? Need is I think a difficult thing for me to define, but I would say that my life has gotten so much easier as an entrepreneur since we have hired more mid-level and senior folks who can take these big tasks off my plate and it frees me up then to think longer term and to think about new initiatives and to stay in my zone of genius, which is not day-to-day operations of a company. Of course, I can operate one. I’ve done it many times. TinySeed is my sixth company and I can operate. It’s just not my favorite thing. And day-to-day operations and management and being in the weeds is perhaps not say the best use of my time if I can find someone who can do it as good as or better than me. And that’s the thing. 

Rob Walling (16:42): There are a lot of folks who manage people and motivate people better than me and they should be doing it. And so that’s the way to think about it is, do you need and do you have the budget? Then another question I received complimented my essay, robwalling.com/essays if you want to subscribe and get those emails. And the question, well, it’s two questions. Where do you find? Where did you find is the question. Where did you find your owner level thinkers and how long did it take you to find them and integrate them into your company? So I’m going to generalize this. Where do you find folks who are thinking at this level? Obviously, if you have an incredible network, this is where you should build your network, not your audience. If you have an incredible network or an audience for that matter, you look there first because warm introductions, even second or third hand are going to be some of the best folks that you work with. 

Rob Walling (17:36): But here’s the thing, every time we’ve hired, we have created a job description and we have posted it all over the internet. We’ve hired Remote First Recruiting to help us promote the job and then to screen candidates so we’re not doing all the work. And I definitely recommend it’s Dan and Ian’s Remote First Recruiting, a bunch of TinySeed companies use them and TinySeed and MicroConf have used them for almost every hire we have ever done since they’ve existed. But that’s where we start. And the reason I’m saying we start there is we post on the job boards, we promote it through our socials and our own media. We put it through our email lists and we go to the TinySeed Slack, but then we start working our network and asking folks, “Do you know folks who might fit this description?” And the owner level thinkers that I work with now have come through a mix. 

Rob Walling (18:28): Some of them were known previously by me and folks on my team. So Tracy Osborn, who’s the head of product and does a lot of the heavy lifting at MicroConf and TinySeed, spoke at MicroConf in 2016, I believe. And she was a startup founder of Wedding Lovely and had gone through 500 Startups. And we hadn’t stayed in touch, but when we posted this job description in, I think it was what, 2019? Yeah, 2019, 2020, she was interested. And I was like, “Oh, a former startup founder interested in doing this role.” That’s instantly a good sign. No, it can be a bad sign. Take it on the flip side, some folks, startups fail because they kind of drive it into the ground and they’re not good at it. And then some folks, startups fail because most startups fail and that’s just the way it goes. But it’s not as if there’s some secret place to find these folks. 

Rob Walling (19:23): I mean, for us, it’s literally just job boards and the key is screening, right? It’s getting down to the folks who are really executing and who have a role that is similar or have the raw material, and this is where it gets tough, is you’re investing in someone to become that. Because when Tracy started working with us back in 2019, she was a really solid and exceptional project level thinker. I think that’s my evaluation these days. It’s funny, I haven’t really thought about this, but she’s developed into an owner level thinker over the years. And there’s a couple other folks on our team that have done that. And so I think there’s a certain amount of seeing the potential in people, but that can be dangerous, right? Because you can see potential that they never develop into. And of course, being able to actually evaluate project and owner level thinkers is something we’re going to talk about in a second. 

Rob Walling (20:16): But this second question of how long did it take you to find them a normal amount, whatever it is, a couple months from posting the job until they were hired and starting two months, two and a half months, whatever, until they gave notice and all that. So it was a normal amount, but then the question is how long to integrate them in the company. And that’s the big thing is I think a lot of folks become owner level thinkers when given the ability to stretch their wings and when given the responsibility, and they have to earn it, but a lot of folks have worked at other companies and they’ve potentially been constrained by management or lack of responsibility or there’s just not room for them. There’s no growth opportunity there. And so I guess what I’m saying is a lot of folks you hire like this, I think are going to be more project level, but it’s the question you’re asking yourself as you talk to them is, do I think they have the ability to become, to grow into this role as an owner level thinker? 

Rob Walling (21:11): And the interesting thing is I have no guess on timeline, could they become one in six months or maybe it’s three years? I think either is fine, as long as they can do their current role as a project level thinker and they’re kind of evolving over that time. To me, when I look at small companies especially, and I see people evolve, it’s like you’ve heard this thing about how you’re the average of the five people that you hang around with. So that’s a friend group analogy. You see it with musicians where like The Beatles or Led Zeppelin or any incredible group that develops, they lift each other up almost unintentionally. And maybe there’s a friendly rivalry or there’s certain things that they kind of rub off from one to the other and one person who’s exceptional at something, everyone else recognizes that. This person’s exceptional at sales or exceptional at decision making or exceptional at moving things forward, exceptional at management. 

Rob Walling (22:06): You see that person, you’re like, “Man, they’re really good. I’m going to kind of do a little bit of what they’re doing.” And everybody gets better if the raw material’s there and everyone’s interested in learning. And I see the same thing on these small teams. And so if you start hiring people that are exceptional and they’re getting better and they bring someone up kind of underneath them, maybe they’re managing them and they start getting better as well, the whole team, all the rising tide, it raises all the boats. And the hard part is if you hire someone who isn’t as good and it’s noticeable, it’s tough. It kind of drags the team down, drags the morale down a little bit and it can put a damper on that. I almost think of it like this exponential ascending. Another analogy is like these scenes, right? 

Rob Walling (22:49): You had the Seattle music scene in the 90s and every couple years there’s, well, there used to be like a new scene in a city and there was the punk scene in the UK in the 1970s. And it’s like, well, why does this happen? And it’s because these bands see the other bands around them and they’re influenced by them, but they’re all kind of rising up together. And there’s this momentum and there’s this interest and there’s this curiosity and maybe they’re intentionally helping each other out or maybe it’s unintentional, but whatever it is, everyone’s getting better and it’s this virtuous cycle. And so that’s also how I think about, especially small teams. And I think you could be small teams within a larger company, people really impact each other. So if you get exceptional people working for you, and if you are able to just keep feeding that, then new people who come in realize what the expectations are of this company, everyone is very, very good at what they do and none of us drop balls. 

Rob Walling (23:47): And we’re all kind people, but man, we execute and we ship and we punch way above our weight class in terms of what we get done and the impact we have on the world. Tiny team, think of MicroConf and TinySeed is nine full-time people and two part-time. And we have invested in 210 B2B SaaS companies in the last seven years. We run all the MicroConf events in addition to Mastermind matching and Connect. We push out this podcast and YouTube, we run SaaS Institute premium coaching. We run a full SaaS accelerator. We have $59 million, almost $60 million of assets under management. There are teams that are two or three times the size of us that don’t do the number of things that we do and the way that we’re able to do it is because we have a lot of exceptional folks on the team. 

Rob Walling (24:40): Another question that I got a lot was how do you identify folks? Is there a specific job title or job description? I think that’s where you start, right? If you want an owner level thinker, you don’t put a job description for an office manager, right? I mean, you may get an owner level thinker at that, but when the hierarchy of job titles, these things have meaning, right? There’s entry level, then there’s individual contributors, and then there’s supervisors, and then there’s managers, directors, vice presidents, C-level folks. And I think generally, if you want someone who’s really going to take control of an entire area, entire business unit, entire whatever, you want them to take ownership, I think you’re talking at director level or above. And typically a certain salary is equated with that as well. So identifying folks who are project or owner level thinkers really comes back to asking them questions about what have you done to drive projects in the past, right? 

Rob Walling (25:38): And what have you done to take ownership and grow something beyond what it is? Like have a vision when you’re looking ahead six months and have the incredible autonomy and decision making power and potentially budgetary power to drive things forward. You’re not just asking them, but you’re actually looking at their resume, like what have they actually done? And then digging into, oh, you were on a team of 300 people and you say that you drove these results, what did you actually do? What did you personally do versus the rest of your team? Your marketing copy and your design is amazing. Did you have a whole team doing that and you basically just project managed everything? That’s okay too because now you’re a project manager, but you get to know their skills. There’s the unspoken when you’re speaking to someone, right? It’s how much energy do they have for something? 

Rob Walling (26:24): How much interest do they have in the position? Because the more interested someone is, the more likely they’re going to love what they do and want to really drive it forward and take ownership. Here’s the other thing, project level and especially owner level thinkers, they can work anywhere. How do you convince them to work for you? That’s the other thing, right? Is to build something that’s so interesting and whether that’s just your culture, whether it’s the product you’re working on, but something that is appealing and interesting and you’re painting a picture of the vision of where’s the company going to be in two years, three years, five years or whatever. When I get asked that when I’m interviewing candidates, I mean, tell me I can’t paint the picture of where I want MicroConf and TinySeed to be in three, five years. We are impacting founders at a grand scale and I want to keep doing that. 

Rob Walling (27:13): I want to keep running these events and you’re surrounded by ambitious entrepreneurs who are executing every day like those are the people we’re dealing with. This is the best job I’ve ever had. Literally the best job I’ve ever had is working at MicroConf and TinySeed. And so our ability to recruit folks of this level becomes a little easier because we do have something interesting we’re working on. But back in the days of Drip, when it was just Derrick and I hacking away on a little email service provider and went to hire our first developers, everybody wanted to work with us because A, it was remote work and B, because it was really exciting. It was super exciting to be working on a project like that in the Central Valley of California. And then even once we hired remotely, people were interested because they saw the traction we were getting. 

Rob Walling (27:55): And the product itself was beautifully designed thanks to mostly to Derrick Reimer. And the code quality when we went to hire engineers was beautiful and it was so well maintained. And Derrick had been an amazing gatekeeper of that code base and that helped us hire really picky engineers. It was such a selling point to them. And then when we went to hire customer success, well, I was like, “You get to work directly with me. Is that interesting? I’m going to train you on everything I know about customer success,” which isn’t that much, but it’s probably more than you know right now as we were hiring, that was a selling point, right? Then we went to hire the next one. It was, by that time we had built momentum, there were five, six of us and the team was awesome. And everyone who knew people on the team were like, “I really want to be on that team.” We were the most desired employer, at least in the bootstrapped software space in our area. 

Rob Walling (28:43): And that doesn’t happen by accident. And if there were project or owner level thinkers that we could have afforded, which we couldn’t, I think they would have come and worked with us. But it’s something to think about. You have to recruit these people. Even if you’re in a conversation and they’ve applied to your job, folks who are great are going to get multiple job offers. And so you’ve got to be thinking about, how do I sell this job to them just a bit? And then I think lastly, in addition to the title of, let’s say director or VP or whatever you’re going to do, obviously you have to have bullets in there in the job description itself, right? You need the nitty gritty of what they’ll be doing that communicates the level of responsibility you’re looking for. And I’m not saying just having them in the job description means that they are going to magically have that when they apply because we all know that’s not true, but having them in there then is this great reminder of, I need to evaluate for these as I’m in the interviewing conversations. 

Rob Walling (29:38): And look, are you going to be 100% correct with hires? No. And that’s why the old adage is to hire slow and fire fast. And whatever on the hire slow, if someone’s not working out and you have misidentified them, the willingness to let them go while it sucks and it sucks for you and it sucks for them, you’re doing everyone a favor in this situation. They’re not going to be perfect. No matter how hard you try to find owner level thinkers and as much as you screen for them and as much as you offer them the right pay and you have an amazing environment and they want to come work for you, everyone you hire will not work out and you will misidentify some folks and that’s when you do have to make that change in order to keep that virtuous cycle that I talked about earlier going. 

Rob Walling (30:23): There are many things you can evaluate during job interviews and then there are certain things like long-term follow-through, ongoing communication that you just can’t measure in an interview. And you can ask about past experience doing this. You can get references and talk to folks who they worked with, which is important. But there are just certain things that are pretty much impossible to identify in a job interview. And that’s where potentially you can do just a sample project or you can bring them on for a 60 day trial and see how they really work day to day. And frankly, they get to try you out as well. So thanks to everyone who asked me questions about task level, project level, and owner level thinkers. And again, if you are not on my email list, robwalling.com/essays and there is an opt-in. On the right-hand side, I email about once a week with new thoughts, frameworks, and ideas, and it gives you an opportunity to hit reply and get directly into my inbox. 

Rob Walling (31:25): So thanks so much for listening this week and every week. This is Rob Walling signing off from episode 826.