Revenue vs. Support: The Fatal Flaw in Team Building with Barrett Brooks

[00:00:00] Barrett: I'm of the opinion that when you're beginning to build a team, ideally you're hiring for revenue generating roles. The biggest pitfall I see people make is they end up with a team full of people who are supporting revenue, which creates more and more pressure on the founder to generate more revenue because there's no one else doing it.
So that's the failure mode here is when you hire a bunch of people who cost you money and don't generate any. So what you need to understand is either you need to make revenue generating hires or you are the revenue generator that supports the hires you're making that are supporting roles.
Dustin: Welcome back to the seven figure leap. another amazing guest today and maybe the first guest that I've kind of officially met [00:01:00] in the airport. so it predates that a little bit. I was in Boise, as you guys know, in June at craft and commerce. And I made my way into this really cool room, for this mastermind experience.
Pre dated the conference itself. And I was a little intimidated if I'm being honest, there's some cool people in there that I knew some people I didn't know, and I have to just kind of follow my own sword and say, I actually didn't know a Barrett who I'm going to introduce you to today, And then I immediately realized that I'm the only one in the room that know Barrett and that Barrett's like, everyone knows Barrett and Barrett's like at the front of the room speaking, I'm like, okay, who is this guy?
And then turned out he's like the most kind, approachable, humble guy. And he was very welcoming to me and did not get to run into him very much during the conference. Then we're both headed home, me to St. Louis, him to Portland and the airport. And we stopped for a few minutes and exchanged text messages.
We've had another conversation since. we found that we're really kindred spirits. And what's cool is that Barrett is definitely a few steps down the road in his entrepreneurial journey, and he's done some really amazing things for [00:02:00] himself and other companies, which is really going to enlighten you all in this whole topic of like team building and scaling.
So Barrett Brooks, welcome to the seven figure elite podcast. And yeah, please take a moment to introduce yourself a little deeper than I just did.
Barrett: Yeah, thanks so much for having me. it's not an uncommon experience that I have that I might walk into a room and a few people might know who I am. But many people are like, Who the hell is this guy? and that's largely because I spent a lot of my career kind of behind the scenes building companies.
I haven't always been the front man, but I've been the person kind of working to build systems that allow for scale. And so if we kind of track my career journey, I started out as a management consultant, left that to start my first business back in 2011. It was called Living for Monday. My goal is to help young
professionals find meaningful jobs out there in the world.
that led me to intern for, Little author that some people may have heard of named Seth Godin, and really learned from him and kind of got permission from him almost to shut that business down after realizing that it wasn't working [00:03:00] financially. And, kind of went behind the scenes from there, worked at a company called fizzle, which I like to describe as kind of like the lynda.
com for the creator economy before there was such thing as the creator economy, quote unquote. and I led growth there kind of behind the scenes, building the systems to drive. New revenue, and then made the leap from fizzle to convert kit, which is an email marketing or started as an email marketing platform.
Now it's really more of a full stack marketing platform for creators led growth there. And then went on to be COO where I had responsibility basically for the whole company, other than product and design, which reported into my best friend or one of my best friends, Nathan Berry. The founder and I was there for five years.
Always scaled from 3 million to 30 million in revenue and from about 20 people to 75. And I'd say that's been the core of my career to this point. That's where I learned a lot of what I know or rather where I got to practice a lot of what I thought I knew and see what worked and what didn't.
And now I'm an executive coach to creators doing a million dollars plus in their [00:04:00] business. And at this point of deciding whether to stabilize and systematize their business or scale and grow from where they are. And, I also have a podcast called good work where I interview founders, artists, authors, adventures about how they found their lever to change the world with.
And, it's been really fun. So that's a little bit about me.
Dustin: That's awesome. Yeah. You tell you're a polished pro behind the mic. You went through that in a very succinct, but following are easy to follow it. And yeah, so good work. I'll just kind of start off with that. So you now kind of have the freedom, the space I would say to be creative for your own. Right. but I think something.
It seems to me to be a, both a passion project and something that you put in an inordinate amount of effort and time into is this new, it's not new anymore, but this podcast you launched this year called good work. I have to admit, again, I was not aware of it. I'm in the room. And I think, maybe John Mies, who, who,
is a comma is a, is a.
Friend between us mentioned something [00:05:00] about the podcast and you had this like simulcast with Nathan Barry. And so to give people context, we're talking a little inside baseball. So convert kit hosted the conference I was at called crafting commerce, convert kits, CEO is Nathan Barry and Barrett who just introduced himself as a COO for five years, as they scaled from three to 30 million.
So obviously. instrumental in their, their massive growth, good friends with Nathan, they parted on, great terms. and so they did the simulcast. So on the flight back after I talked to Barrett in the airport, I listened to that episode and I was like, this is really cool. So I've, become a huge fan of good work.
And I just want to kind of give you the props for going deep with people, doing a lot of research, asking people that get interviewed a lot,you're, you have a kind of an a list, roster of guests and some of these people, I've heard interviewed many times. And so really cool to kind of hear the story behind the story, questions that maybe challenged them in new ways.
And I know that's not easy to do as someone who gets behind the mic myself. first of all, great job. I think it's an amazing [00:06:00] show. Hope everyone that's listening to this. If you like this and you want like deeper. business leaders, but, kind of in a different light and people that are just honestly doing good work in the world and people who have kind of reached their potential, but they're using that in a really altruistic way to make a great difference in the world.
, pause this, go subscribe to good work and then come back and let's, , let's hear about the man behind it. So anyway, Barrett, kudos to you for the, podcast and.
All that you've achieved in your own business and for these other businesses. So the way I've heard the story, and maybe I'm oversimplifying, it's like you had your initial business and then you, to use your words, went behind the scenes and you're basically became this, the scaling secret to some of these businesses, including convert kit.
Dustin: And I would turn that sort of intrapreneur. I know you had ownership stakes in some of these businesses and had, obviously a very prominent leadership role, but it wasn't your business, right? You weren't the owner, the CEO. Now you're back into a seat where you are, but you're sort of starting back in [00:07:00] some sense to square one, right?
You're, is it true that you're now a solopreneur again?
Barrett: Yeah. In many ways, I feel like I've kind of returned back to where I began my entrepreneurial journey. It's, like I'm picking up a little bit where I left off, but with a decade plus of legitimate experience about how business really works. I used to talk about that first business is kind of being like a real world punch in the face slash MBA, where I got to learn what it really takes to build a business.
And in the process that one failed because I didn't know everything I needed to know getting into it. And so a lot of the themes that were present then are present now in this business, but they're from a more mature and informed place. And so like back then, the company was called living for Monday.
And it was about this combination of things that I felt like added up to meaning at work. And I would say talk about a lot of the same things now, but having been through the struggle of trying to figure out how that works in practice, not only how do I find meaning, but how do I help create it for [00:08:00] others?
Like, how do I create a container that is the company where people can come to work and realize their potential and experience meaning and live better lives because of it? And so that's kind of the basis for what I do now. But the podcast and my coaching work is how do I help other people put those principles to work and help reveal the ways in which they already have?
So that other people can learn from it.
Dustin: Yeah, that's awesome. And a lot of times I'll spend, considerable time on this podcast, sort of digging back through someone's history. And, one of my,
I guess. Abilities is extracting like. Man, I'm hearing this as like your values or your purpose. So do you feel like this is your calling or your mission?
And whatever the word that someone resonates with, I don't feel like I need to do that with Barry, because this is like his jam too. So I'll just let you express it. And when you look back at your own career, I know you went through a period of introspection after leaving convert kit,had suffered from some burnout, which is something I actually want to talk about a little bit, and my own experiences with that too, because I think it's part of the scaling story for so many of us, but.
, in [00:09:00] now in this current position, having the space to do creative work, have the podcast and do the things you're doing, like, Why do you do it? I know you're a family man, you've got a great wife and kids. And so when you think, why am I doing this at this time? And what do I want to be doing in the future?
what's really driving that? Do you feel there's a mission behind it?
Barrett: Yeah. I mean, my core mission as I see it is a little bit meta in the sense that I think it I'm uniquely skilled at helping people see potential that they might not see in themselves, unlock that potential. And then point it at something that matters, not just to them, but more broadly to the community that they serve.
And it could be literally their neighborhood, it could be their city, their country, the world, or it could be an online community. And I'm not highly prescriptive in what I consider to be good enough. What matters more to me is that people convince themselves and then pursue authentically something that is bigger than them, to be of service to people around them.[00:10:00]
And, That's kind of this response to what I see in the world is every mission is in response to some kind of enemy. The enemy is apathy. The enemy is disengagement. The enemy is giving up. The enemy is saying, well, I can't do anything anyways.
And so I'll just show up, get my paycheck and go home and watch Netflix. And I just think we're meant for more than that. I think basically every Person has the potential to achieve excellence in some area, and I view it as the goal of everything that I do, whether it's running a company, making my podcast, coaching entrepreneurs to highlight that for people and really just pour into them in a way that says, Look, I want you to know that you are loved and you matter just as you are.
I'm not saying you should be something more because you're not worthy. I'm saying because you are worthy and because you are capable, you are capable. I want to see what that can turn into. And so that's kind of what I view as my organizing force.
Dustin: I love that. And do you see that specifically applying maybe at least in your professional [00:11:00] life to entrepreneurship, because everything you said there could be true of a doctor, the garbage man, someone who's volunteering at church. there's a lot of applications, right. Of what you, what you described, but at least in your professional life, Is entrepreneurship a common thread that you see continuing on?
Barrett: I might describe it actually as like high agency people. Many times high agency people are entrepreneurs, but for example, an unreleased episode of the show that'll be out in a few weeks is with Tamara Winter and Tamara is, Tammy leads or is the commissioning editor for Stripe Press, which is the publishing imprint of Stripe, this bigger company.
And Tamara for sure is an employee, right? She gets a salary from Stripe, but the way she leads the way she shows up is in a very high agency kind of way, and she behaves like an entrepreneur, even though she's an employee, and that's true across a few different ways of how I look at this. Another example of this is Hannah Richie.
She was the guest in the second episode of the show, [00:12:00] and she is one of the editors at Our World in Data, and Our World in Data's mission is to help lay people, I'll call us. people who aren't data scientists to look at what is true about the world in a new way. And fundamentally, I think that their mission is really about creating hope.
It's helping people see that the world is actually getting better, even if the narrative is that it's getting worse. And so it's both, it does often get expressed as entrepreneurship, but there are other ways that this plays out as well.
Dustin: That's awesome. Cool. Well,again, not to dwell on it, but I think it's something that people have either experienced either professionally that like in their career that drove them to entrepreneurship, or they've been deep enough in the entrepreneurship and this or a previous business that this whole idea of burnout, they like is, I think something that we don't talk enough about.
And I think you've had, I mean, you've been very open that you've experienced it. You took quite a hiatus, from work in response to it. So I would assume
you've thought a lot about it, talked to a [00:13:00] lot of people about it, got coached on it, and I want to let you share your own experience. I want to share my mini version of it that I feel like I experienced earlier this year and the wake up call it provided me and some of the realizations it's driven me to, that actually helped get me in that room that, that we met in.
So Barrett, if you don't mind, again, share as much as you feel comfortable, but. What would you describe in your own experience as burnout? What did it feel like? What did you do in response to it? Like, how have you helped other people that are dealing with the same issues?
Barrett: yeah. Well, the first thing I'll say is that I think, Burnout is most often an emotional problem, not a too much work problem. It's sometimes is too much work, but I'd say that's less common than it being an emotional problem. And so for me, it was an emotional problem and I did not realize I was burnt out until, the like inciting incident of this whole story and arc of my growth was my wife sat me down one day or one evening, actually,kind of like forced me to put my [00:14:00] phone down, which was.
Constantly in my hand at the time, and I'm like irritated, I'm trying to get something done. And she says, no, I need to talk to you. And she just walks through what she's seeing in me. She says, look, you get home every day. You're frustrated with me. You're not present with your son, with me, with our family, with our friends, you're working constantly.
And you just seem like you're not yourself. And. What I want you to know is it has gotten worse and worse and worse. And I need you to do one of three things either. I need you to change your relationship to work so that this can resolve itself and you can show up differently. I need you to quit your job or we can get divorced.
Those are basically the three options. And it was in that moment when I realized, Oh, Wow, there really is a problem here. This has become serious enough that she felt the need to not give me an ultimatum. It was actually to say, these are your options. And I'm finally putting my foot down that this isn't working [00:15:00] anymore.
And what I knew in that moment was changing my relationship to my work was not going to be possible. I just don't have that dial or switch in me. And so it was quit or get divorced. And I knew obviously of those two options what mattered more to me. And yeah. That began the long process of examining what
was going on there, and how did I end up in this spot where I, as a very self aware individual, didn't even realize how bad it had gotten.
And there were many factors, this was about a year into the pandemic, so obviously that's a huge factor in how people ended up there during that period of time. But I think there was more at play there, and so if I get into the emotional piece of it, What I realized now looking back that maybe I couldn't see as clearly was that Nathan and I just fundamentally had different visions for where we wanted to take the company and what we thought we needed to do to continue to grow and acknowledging that would have required us to admit that we weren't going to be able to work together anymore.[00:16:00]
And so there was this kind of like invisible barrier to admitting to myself what was going on, which is. Oh, I won't get to have this job that I value so much. I won't get to have this identity that I care about. I won't get to work with my best friend. What will happen to that relationship if I admit this?
And it was once I owned that it wasn't working for me, that like the way we were organizing our work, the way that my role was playing out, The goals that we had set at the company that they weren't working for me, not that they were wrong, but that they weren't working for me. That was the beginning of me being able to reclaim my sense of agency, actually.
And what I had done was I think I had given up, my sense of like where I think we should go. And the crux of that was I view it basically to the degree that I have been successful at all in my career. It's by trusting in other people. It's by coming back to this mission that I believe that people have more potential than they realize.
And if you can unlock it, you can do incredible things. [00:17:00] And so it actually wasn't me that built ConvertKit or the systems behind it or anything else. It was me that helped go find the people that could do it.
Dustin: Yeah.
Barrett: my magic thing, right? Is I have the ability to find the people and see what they have inside of them and say, here, go. And Nathan has a different skill set. He's a product person. He's a growth person. He's a like strategist and we're both visionaries, I think, but in different ways. And so where he might rely on something like software automation, I say, let's go get people to solve this for us. And those things were just in conflict in the way that we wanted wanted to run the company.
So if I were operating from my defaults, I would scale the team. I would build team. I would give them autonomy. I would have a high trust environment. And honestly, I would probably fire people when they couldn't perform and then bring new people in who can do the job. And I think Nathan had different defaults.
And so once we were able to identify that, a lot of things unlocked in terms of why it was felt so hard for [00:18:00] us to figure out where to go. So that's kind of like how I got to the place of burnout and I'll kind of leave it there for a minute and we can come back to whatever parts of it are interesting.
Dustin: I'd love to, cause I love the precipitating event. I love the, it takes. In many cases, an external person, oftentimes our spouse, right? So I reflect back that something's not right here. so I interviewed Ryan Dice on this podcast maybe a month ago. And we also talked about scaling in a very different way.
We were talking more about like operating systems and playbooks and, the sort of that side, whereas I really value Barrett's introspection here on these sort of interpersonal. Inner and sometimes inner personal, things that happened as well as the team building, which we're really going to focus on towards the end of the episode.
But something Ryan shared, which is quite similar to what you just said is came home late one night, 12 hour days at the office. And his wife was still up and he's Oh, it's, it's one in the morning. My wife's got the bedroom light on what's going on. And he said she was very calm and there wasn't any ultimatum.
It was kind of like what you [00:19:00] just said, Barrett. And she said, Ryan, I know who you are. I know who I married. You're an entrepreneur. You're crazy. Like, I get it. I'm not asking you to change. You can keep doing exactly what you're doing. What I require, though, is if you're going to continue to do that, quit saying it's for your family. I was like, Oh, man, quit using us as the reason you're doing it, because it's not like we've got plenty of money. We don't need you to do this. And that was his gut check and his ego check and where, where he just kind of slapped him in the face that he was burning The candle on both ends.
And for me, I think in a very, in a less extreme version, January of this year, and I also love that you said it's an emotional problem because from externally, my business was taken off, solopreneur I'd spoken at story brand and, and in this moment that I'm, This, this week that happened in January, I just left Las Vegas.
I spoke at trafficking and conversion summit. I was the two weeks later going to be in Orlando speaking at podfest. I was home for a week in between. And of course, [00:20:00] solopreneur, I'd lost a new cohort of my group coaching program and all this stuff. And. It was like the week I was home, I was not home.
it was like I was working 14, 16 hour days. I had, I was working all night. Cause I was trying to catch up and I'm trying to still prepare for my talk. And I was, I was hosting my first in person mastermind dinner in Orlando. So I had all this stuff, all this pressure that I'd put on myself, of course.
And my wife, kind of saying, didn't say much. And, I was definitely starting to feel the tinges of burnout and, and this emotional. And as I left to go to Orlando at the same moment, like, honey, I have a great trip. Be safe. we'll miss you. And also we can't have any more weeks like this. And I'm like, okay, yeah, I get it.
You don't have to, you don't have to explain what I get it. And, I made, I've made a lot of changes since then. I started hiring team members. It was really kind of a culminating moment for me. Again, not really confrontational. It wasn't emotionally charged. It was very like. I love you. I get who you are, but this isn't working anymore.
[00:21:00] And so I, I think between me, you and Ryan, we've got different kind of stages of that. So I love that we were able to unpack what this, how this came about, how you realized it. And yeah, from there, Barrett, if you don't mind sharing, what'd you do about it? what followed,did you get sick?
what did burnout do to you once you realized that you had, you had reached it?
Barrett: yeah. I mean, there's so much there. I, I think one of the, one of the things that I didn't mention that I felt permission to engage with after my wife. In front of me about this was I felt like I owed it to my family to continue earning the money. I was earning that there was this like invisible force, which was what will we do if I don't keep this job? And of course, there's many answers to that from a state of like logical understanding, which is well, you can get another job. You could start a business like there's many ways to go about it. but really what unlocked it for me was we had always had the ambition to create a secondary stock sales as an option for teammates to cash in on the [00:22:00] value of their stock over time.
And we had gotten an offer from an entrepreneur to buy about a million dollars of stock of secondary stock from people on the team. And at first we're like, Oh, no, we don't want to handle that right now. Like we're, we know that's in the future, but now is not the time. And as I realized I was ready to leave and Nathan and I identified this, divergence of vision, he really wanted to settle into the team size we had.
And I was like, Oh, we got to hit the gas and hire. there was this moment where I said, if you want to hit pause on. team growth. I think it's time for me to leave. And so I just want you to sit with that for a couple weeks and decide, Hey, is this really what matters to you? Because if it does, then we really have reached the point of divergence.
And before we go down the hill and devolve our relationship from all of this, I'd rather be very proactive and thoughtful and just like make a plan for me to exit. And that was the first time that I said out loud and felt the freedom to say out loud, [00:23:00] Okay, this isn't working for me. And yeah. Because I have permission now and I know that we'll be okay, or we'll figure it out together on the money.
And now I can start paving a path forward. Well, fast forward. That was the inciting incident to then decide to start doing the secondary sales. that fall, right before I left, we offered the first secondary sale to investors and teammates were allowed to sell stock that they had acquired through, options. And so I sold a portion of my stock and that gave us the financial freedom for me to then say okay, what is going on for me? And what do I need to do to recover from this? The way it was showing up in, in me and in my body and in my mind was tons of anxiety, lots of rumination. I think the combination of getting to that point at work and the pandemic just meant it was like, I had this reel of moments from my life.
That were negative moments just playing on repeated my head, just like all the bad things that had ever happened to me. Weirdly, it was [00:24:00] like every athletic injury that had ever happened to me. Every like early relationship I was in that I had lost. And it was just this very odd experience of I've never been in that kind of place in my life.
I've had anxiety in my life, but never this kind of like backwards looking, how did I get so screwed up kind of thing. And I'm not exactly sure why that was happening, but the meaning I make of that from where I am now is I think I was trying to figure out how did I end up here?what were all the series of events that could lead me to what felt like a place of, peak success in my career?
I mean, we had built a 30 million annual revenue company, and I felt the worst I had ever felt about my work. That makes no logical sense. So that was one way it was playing out. In my body, it was like, It was this constant feeling of something's wrong with me, and they're almost this like hypochondria of trying to figure out, am I sick?
Am I ill? Is there something wrong with me? [00:25:00] And what was wrong with me was I was out of alignment with myself. And I was trying to find any reason for that other than I had made choices that got me there and so much of the recovery was like, I left the company and I was just exhausted, like
mentally, physically, emotionally, I had nothing to give and I think looking back, I was probably in a state of depression for a period of time leading up to and then after my departure and I just couldn't quite see it then, you know, I was functional.
It's like I got out of bed every day, but I did not want to get out of bed every day. Dustin: Yeah, that's a huge distinction. Yep.
Barrett: right. Exactly. And so much of the kind of year and a half after that was trying to really find my way back to myself. It was like asking myself the question sometimes ad nauseum in an unhelpful way. who really am I and who am I trying to become from here?
And what do I need to do to get back to that? And it was [00:26:00] just a hard meandering path of like banging my head against the wall, basically trying to find the answers and find my way back to, where did this all begin? And how can I get back to being me?
Dustin: That's awesome. I mean, not awesome, but also the way you've articulated it. I think there's people can relate to different parts of that. And I think, again, I'm just throwing in my 2 cents because I think this is a spectrum. And I think people, hit different versions of in burnouts, obviously kind of a generic term.
These are all different points of exhaustion, mentally, emotionally, anxiety, depression. There's lots of different things in play. for me, there's kind of 2 real quick points. I'd say a couple of years back when I was leaving engineering, I was basically working two full time jobs, running a new business and engineering.
And I put all this pressure on myself to launch this program. And I stupidly tried to launch it in July when no one wanted it. And I was trying to go on vacation. It's like the culmination of all this stress, completely self imposed. I literally, my chin went numb. Like I, I, And do not Google numb, numb chin.
Cause [00:27:00] it's pretty much a telltale sign. You have a brain tumor on your brainstem. it turns out luckily I did not have that, but, I was on the vacation with the numb chin, like freaking out, waiting to get back to get to a doctor. And it turned out it was basically stress. It was like, I clenched my jaw, pinched nerves in my neck or whatever.
So there was like a physical manifestation, which was important because it made me, Changed a lot of stuff about how I was approaching my business. It actually made me cut off the engineering job. It was actually like the final straw. That was like, look, I'm, I'm going one way or the other. I can't do both.
let's see what happens. And then much more recently in that whole January episode, through a series of events, including what I talked about with my wife and meeting some new people and seeing new opportunities, I have been running all these cohorts myself. And so I, I've, I'm. With everything into business, sales, marketing, fulfillment, customer service, the Dustin show.
I thought solopreneur wearing this badge of honor, like this is awesome. and I distinctly remember being in a hotel room in [00:28:00] Orlando. The highest of highs in my business. I just had this mastermind meeting. All these people that I love were there. I'd spoken on stage and all these clients, and I had to show up for a zoom meeting to lead my flagship program.
It was the very first time in two years of doing that. I'm like, I don't want to be on this meeting. this feels boring. Like this is feels redundant. Or why am I doing this? And that was the trigger. I'm like, okay, it's, it's no more like. I have to scale. I have to burn this thing down or scale it.
I can't stay here because I'm starting to feel this like tinge of burnout, this emotional distress. I'm starting to resent the thing I built. And so in that phase, this is not that long ago. I was like, you know what? I want to build a 10 million company. I want to be a CEO. I need to build a team.
And I unlocked all these new creative challenges that I've wrestled with ever since. , and that bear is going to help us through anyone who's kind of in that phase here as we talk about team building. But anyway, for me, that was like the
second manifestation. I felt like I nipped it a little earlier and I made a positive reaction to it.
Where it's I just want a new challenge. It's [00:29:00] not like I'm, I wasn't physically tired. Like to your point, financially perfect. It was just like this emotional, Almost like I was bored to burnout. Like I lost the creative juice that really made me excited about my business. so anyway, yeah, I just, I kind of throw in that commentary of my experience.
Barrett: I think it's super common. And so just one comment on that, and then we'll, we'll keep rolling is, I think the positive loop here or the, the way it can result in a positive feedback loop is you start to be able to catch it earlier and earlier to your point. And so anytime I notice myself,having a physical symptom of stress or whatever tends to show up as back pain or like muscle tightness for me, or I wake up and my jaw hurts.
What I used to do was, yeah, I'd go down the Google rabbit hole. Oh, what's wrong with me? Right? Something's wrong with me. And now what I do instead is I've made a hard rule for myself. I never Google symptoms. If I need to do that, I outsource to my doctor always because they are a professional with an objective viewpoint.
Right? and there are limitations to that, but that's [00:30:00] not what we're here for. So that's the first rule I set for myself. And then I go back to when did this begin? When did I start experiencing this stuff? And usually there was a, setting off point, it's like I agreed to do something I don't actually want to do or overbooked myself for a given week or whatever it might be.
And it's like, ah, okay. So I'm actually having an emotional reaction to that. That's manifesting itself because I haven't processed that yet. And so these are the kinds of positive feedback loops that can come from this stuff. Nothing like that happens if you're not intentional, right? And if you don't actually say, Okay, so what are my patterns when I get into these times of stress or emotional misalignment or whatever it is?
And if you don't do that work, then you actually just end up in this cycle where you're repeating the same thing over and over and it never really ends.
Dustin: that's super useful. I didn't mean to spend almost the entire interview talking about burnout, but I think, as I said, there's a spectrum of it. I think anyone who's growing a business, which is our entire listening audience, anyone [00:31:00] who's specially would identify as they're scaling something.
it's kind of inevitable that you're going to start experiencing some of these things. And I think there's a ton of wisdom in what Barrett just shared. I hope in, His story, my story, what Ryan had shared previously, people will at least be more aware of it and be willing to seek the help, seek the resources before, hurts them.
And then it hurts their their progress in their business. So I want to get to kind of one of the antidotes to that, which is building a healthy team and scaling in a smart way, which which I'm going to kind of give Barrett the microphone here in a few minutes to do that. Before we do that, though, I don't want to miss the opportunity to Open up a little bit more about what you're doing now.
So we talked a lot about this journey from convert kit into, this burnout and, and, the things you, you address there, but I'm really excited about what you're doing now. I've talked about your podcast. I know you're doing executive coaching. You're doing some writing. I know you gave a, an amazing workshop at craft and commerce, which we're going to get a mini version of today on the podcast, but yeah, just, take a few minutes here, what you're doing right now, [00:32:00] what you're excited about, Maybe a little bit of your vision for what you're going to do with this, this new business that you're find yourself in today.
Barrett: Yeah. So I mentioned that I had this meandering path after I left ConvertKit and I now look at it as like I did a series of career experiments and I made a book about climate change, partnering with Seth Godin again, went to work at a coffee company as COO here locally. I went to, yeah. Back to a startup, actually, the shirt I'm wearing for watching the video is called pant the Lassa and, was in an executive role there.
And it was in that role where I started feeling all the same stuff again, but it came back a lot quicker to your point. and I was able to catch it earlier. It was like, huh, this is a completely different company, completely different role, all new people. And I'm feeling the exact same way I was. What's up with that?
And what I realized out of that was I was actually still neglecting myself. I was like looking all over for someone I could go to work for. That would be the kind of leader that I would learn from, that I could be inspired by, that I would follow. [00:33:00] And what I was avoiding was admitting that it was actually time for me to come back to being an entrepreneur again, that I was the leader I was actually looking for.
And I just wasn't ready to own the cost of that, which is now I'm responsible for all my income again. And because I had failed before, there was like all these
barriers I had to overcome. So in talking to my coach about that, I said, I need to prove to myself that I can make it as an entrepreneur at first, which is ironic because I, at this point I've built companies way bigger than worrying about where's the next dollar going to come
from.
Dustin: You're not really needing 30 million in annual referring revenue for your family in Portland, but I guess you'd make it.
All Right.
But no, I get it. So you kind of. This distant past version of Barrett did your first company, I fail, I think is a subjective word, but you know, it didn't, it didn't last.
Then you were at this rate
failed, with other people's companies, but now you're back to I feel called to do this on my own, but my only experience in doing it on my own didn't end well. And yeah, I could see how that would create a lot of self doubt.[00:34:00]
Barrett: Yeah. So there was this question of, okay, so what kind of business then? Do I want to start a startup again? Go get funding. Do I want to build product based business or do I want something simpler? And where I landed was I had been coaching for seven or eight years on the side of all these other jobs, and I knew it was a skill set that people value, that I'm pretty good at, and that it was something I could train at to become world class at.
I've got this resistance to the job title of coach just because it can mean so many different things, and I think it Often means a negative thing to many people who see it. And so that was the big emotional barrier I had to get over. And I just realized that if I train as if I'm a professional athlete for coaching, then no one will be able to debate like the value that they're getting from me, as long as I treat it like a real profession.
And so I just dedicated myself to that. And the reason I picked the model was it was the clearest way to get to the most [00:35:00] definite. Yes, I have succeeded at Providing for my family financially as an entrepreneur that You just add layers and layers of complexity to that, the further away from services you get and the bigger the team and funding and all of that. So I said, all right, fundamentally, I think I'm a creative person and I've ended up in operating roles
that I'm good at, but I actually want to be the founder, the creator, like that version of it. And coaching is the best business model I can think of that requires the least number of hours, the most excellence for me and frees up the most time to do creative work.
So I designed it so that Tuesdays and Thursdays are my coaching days. I can handle a max of 16 clients. They pay me three grand a month. And Obviously, you can do the math on that on what the top potential earning is while using two days a week for coaching, handle four clients a day. so if that can get me to about 50 grand in revenue, like,that's a great model basically.
And I [00:36:00] still have three days a week to write, make a podcast and all of that. So I viewed it as. I want to be primarily a writer with coaching as my business model, and that's transformed a little bit too. I'm right now, primarily a podcaster with coaching as my business model and writing kind of happens in the background, pretty much for myself at the moment.
So that was kind of the inspiration for it, but it all comes back to this mission that we talked about, which is. I see coaching as a very effective tool for unlocking the potential and founders and allowing them to achieve their visions. And if I'm aligned in terms of the cause or the end result of the work that my clients are doing, it's actually a great lever for impact.
we come back to this lever idea. There's that Archimedes quote of, give me a lever long enough and a fulcrum on which to place it and I shall move the world. I love that quote. And that idea of creating a lever for ourselves using our career, the career is the fulcrum and the lever is where are we pointing [00:37:00] it.
so for me, I see coaching as a way for me to impact many different areas of the world that I care about through the founders. And it's a really effective lever. And so I'm kind of viewing this period of my career right now as this five year chunk, almost of a fallow period where I'm pouring into other entrepreneurs, I'm interviewing people on my podcast that I admire that have their own levers for impact.
And then all of that, I expect at some point might actually lead me to start a bigger company, something that's going to be bigger than me, more product oriented. I'm approaching that with what I call an open handed posture. I'm not pressing. I'm not trying to find it now. It might be true that I'm a forever coach that this is my true calling and best lever I can find.
But I'm also open to the fact that maybe this is an in between period where I'm just pouring into myself and moving towards something new that I can't yet see. So that's kind of where I'm at right now.
Dustin: That's a beautiful summary of. the present and like being kind of detached from the future. But [00:38:00] realizing that what you're doing now not only fuels the present and, support your family life and the things you needed to do, but you're planting many seeds of opportunity that could sprout into lots of different relationships, businesses, partnerships, all the things with the podcast and, and obviously the work that you're doing directly with founders in coaching.
one very tactical question. I do want to get into this, this, this kind of team building framework. do you have a team now? Has it just you, or do you have an executive assistant or any, anyone else supporting you?
Barrett: Yeah, so I have an executive assistant. She works about 10 hours a week. she's phenomenal. I know a lot of people use folks from around the world in that kind of role. I chose to actually hire someone that's been a career executive assistant and big professional services firms. And I pay her a pretty good hourly rate because I know that I can trust her with almost any scale of project.
so she handles my calendar, she handles all my travel, she handles my schedules. Actually, she's been pitching speaking events for me on my behalf. And so it's just really beautiful, kind of like partnership where she can handle [00:39:00] many different scales of tasks and projects. And again, it's an example of me trusting her as a professional where if she has a limit, she'll tell me.
And, my job is to give her the highest leverage things I can think of that she can help me with to build my business. She's the only person I work with, that consistently. I've got a producer who runs the kind of post production on the podcast, that I outsource that to, and then actually a developing thing is that I made a pitch to my wife, who's currently on a sabbatical, had gone through her own experience of burnout.
I said, I think I might actually be the creative person. And I don't know that I enjoy running the business side all that much. as you're looking for jobs, yeah. I want to offer you a job as the CEO of this company and maybe you could come run the company and I'll be the product basically for now.
and so she's currently considering my job offer for that. All the other opportunities.
Dustin: mean, that's where this is going. I'm still waiting on the response. No, that's awesome. I love that. And my wife and I have, I've worked together a couple of different times and we've. Figured out that that's not for us, but, I [00:40:00] really respect couples who can do that. And, that's great. And that actually segues really well.
my current status, I talked about January. I was completely solo. A few contractors doing contract y things. Very, very, fractional. Yeah. And so I literally three weeks ago, hired my first executive assistant, also us based, just a real professional pay her. Well, we're continuing to kind of find the things to take off my plate, but that's been very freeing.
I've already got a couple more positions, in mind for the second half of this year. And so finally, I've kind of teased this 10 times now,your, your workshop that you did in Boise, Was super well received and obviously we don't have time to do a full workshop, but maybe at a high level framework.
Again, a lot of the people listening, maybe it's their 1st hire. Maybe they're going from 2 to 3 or they want to go from 3 to 10 employees. tell us Barrett's Barrett's best advice. you're doing that well and not, not regretting it because I think it's a huge fear for a lot of soulpreneurs. Like, man, I got another mouth to feed.
I, what am I going to, then I got a [00:41:00] meeting to attend. I got people to manage. A lot of us left the whole career cause we hated managing all the people. I'm throwing myself in that bucket. So yeah, man, I just want to turn the mic over to you and let you enlighten us a bit on that before we wrap up.
Barrett: Yeah. Yeah. And I'll just say that I think this is the area that is the greatest unmet need and the kind of creator world where you get these mature businesses, but it's not a skill set. Many people have built. And if I make a course, it will probably be on this. So we're kind of testing this out as a, as an area of focus.
But here's how I think about hiring. It is a skill just like anything else. And if you're running the kind of business that I think a lot of your audience runs, Yeah. Yeah. They've figured out everything, to your point, they've done every aspect of their business. They've done content, they've done SEO, they've done sales, they've done product delivery, and.
The number one thing I want people to understand is that hiring and managing is just another one of those skills to add to your tool belt. It's not a fundamentally different thing. It is not something that some people know and others don't. [00:42:00] It's a skill that some people choose to build. And if you approach it that way, I think it can become the biggest asset.
It becomes your lever as the CEO. One of my mentors and people I look up to is named Jerry Colonna. He was actually episode three of good work and he's an executive coach, founder of reboot. He says the job of the CEO is three things. First is to set the vision. Second is to recruit and retain the people.
And third is to allocate resources, and he added a fourth one recently that I strongly agree with, which is to create a culture of belonging or to create belonging in the organization. And you'll notice that none of those things involve product delivery, product creation, sales, any of that stuff. And so I think in a mature organization that's ready for scale, The CEO moves further and further away from the day to day work and more and more towards leadership.
And I think fundamentally everyone has the [00:43:00] capacity for it. So if we think about hiring, your business breaks down into a set of processes. Every business could be defined by these 10, 20, 50, 100 processes, whatever it is. And so the first task in building out a team is actually to understand the building blocks of your business and to break it down.
Here's every process required to run my business at its current scale. And then for my vision, that might be a year out, a three year, three years out, five years out. Here's every process that would be required in that version of the business.
As I can imagine it right now, obviously it will change over time. And as you define those processes, you start to see, Oh, some of these things go together. Like they are like minded skills that would be required in order to do these things. And magically, you start to define something that looks like a role. And, there's two things to understand about roles. First of all, the two types of roles are either revenue generating or [00:44:00] roles that support revenue.
And I'm of the opinion that when you're beginning to build a team, ideally you're hiring for revenue generating roles. The biggest pitfall I see people make is they end up with a team full of people who are supporting revenue, which creates more and more pressure on the founder to generate more revenue because there's no one else doing it.
So that's the failure mode here is when you hire a bunch of people who cost you money and don't generate any. So what you need to understand is either you need to make revenue generating hires or you are the revenue generator that supports the hires you're making that are supporting roles. So you can label each, you can imagine like a square of processes that make up, here is a role that a person could reasonably do, label each one, it's either a dollar sign or it's a hand.
A dollar sign means it generates revenue, a hand means it supports revenue. And understanding the difference is important. A job description often looks like a laundry list. That's a horrible way [00:45:00] to define a job. If you look at the average role posted online, it's probably poorly defined. No single person could handle the workload, and no one has the experience that they say is required to do it.To avoid that, I do three things in terms of roles. The first one is I decide what is the one metric that will evaluate this person's success if they join the team. Only one could be new customers, could be customer satisfaction, could be new products created, Pick a metric and that metric should layer up to the business growing underneath that.
There's probably two to three leading metrics that drive the number one metric. So what's the thing that happens before their key metric that you could measure to know ahead of time if they're likely headed in the right direction. So you have one key metric, two to three supporting metrics, and then you get just three to five.
Responsibilities. These could be run this process, run that process, run that process. It might be create processes around this thing, [00:46:00] but those processes or those key responsibilities should roll up to driving the key metric. And if all everyone did that listens to this show is said, here's the role I'm hiring for title this revenue generating or support number one metric, three supporting metrics, three to five responsibilities, you would be more successful at identifying what you're looking for.
Thank you. Then almost anyone is when they're designing roles. Dustin: That's
Barrett: So that's the design piece.
I'll give you two more quick things here.
Dustin: That's awesome. I mean, it's making me feel better about how I hired my executive assistant. And then some of them, I probably a little, verbose, but ultimately, yeah, it's in her case, it's I track my time. It's like the amount of hours I get to add to my CEO hat and take out of my operator and admin hat is.
You winning, which means you get bonuses and stuff. So that is like the metric. So I love the simplicity of that. Very, very good.
Barrett: so that's designing roles, right? And then there's the, how do you find the people? And I think fundamentally what you have to understand when you're looking for people [00:47:00] is probably you don't know them yet. You do not know the best person to fill the role. Every one of you listening to listening to this things.
No, no, I do know them. It's my sister. It's my friend. It's this. It's that. Please don't hire that person, or at least don't hire that person until you've evaluated other options. It's very unlikely that you have met or already know the person that should come to work for you. It's possible, but it's unlikely.
The most likely time that that's true is if you've managed teams in the past. Where you've had people doing this kind of role working for you before. So that's not true. You have to go find these people and there are hundreds and thousands of communities online where these kinds of people exist. So your job is to go find where that is.
If you need to hire software developer, there's places to make those hires. You need to hire an executive assistant. There's places to make those go find those places and post your role there. Ask people to apply. The other way is to look up people. LinkedIn. I know people love to [00:48:00] crap on LinkedIn. It is the single best tool for actual scaling businesses that exist in the world.
If you want to hire every, almost every professional that you might hire has a LinkedIn profile and they have their whole resume right there waiting for you to look at it.
That's exactly how I found my EA. So if you go and you search city role history, You can search skills is any number of things you can hone in on 50 candidates without ever even getting an application and reaching out to those people.
And we won't get into how here because we don't have time. But reaching out to people proactively extremely effective way to make hires. And so you're looking for three things in people. And this is actually what they're looking for
as well. Dan Pink defined this in the book drive. People want fundamentally three things at work, autonomy, mastery and purpose.
They want a clearly defined role with clearly defined success measures where they can shape the role to get the outcome that you want first. That's autonomy. Mastery is they want to be able to grow. [00:49:00] They want to stretch in the role that you're hiring them for. They don't want to just do the same thing they've always done.
They want to know you care about them reaching their goals, too. And purpose is about meaning. I see there's a bigger thing at play here that I'm contributing to, and that gives me meaning for the work beyond just did I do the task or not. Well, you should evaluate for those three things. Do people have examples of times when they handled autonomy?
Well, specifically, what have they done that proves that, How will this role fit into their career arc and what skills do they hope to build in this role for you that show that they're going to be continuing to grow towards mastery by working for you? And then third, what's their personal relationship to the mission that you're on or the end work that you do?
And I evaluate for those in addition to, and before I evaluate for, do you have the existing skills to do this job? Because skills can be learned, the other stuff cannot.And so the last thing I'll just say here is when you [00:50:00] bring people in, it's your job to actually deliver on that, to actually give them autonomy and to actually encourage them to grow, to remind them of the vision that you're pursuing that gives the role meaning, Two books here for hiring process.
That's really, they're really, really well structured and give you kind of the nitty gritty, both by, Brad and Jeff smart G E O F F are called who and top grading, very effective system for being able to evaluate. Do people actually have experiences doing the things that you're asking them to do?
And that could be either, do they really handle autonomy well and getting specific examples of that? Or it could be, have you been in a before and drilling down on the component skills of that. So I'll just leave those two resources there. Those are kind of the best I've found. and we could keep going, but I think that's a good basic overview.
Dustin: I think so. Yeah, no, that's, that's insane. As far as the, the value delivered in five minutes, I, for anyone watching the video, I need more posted.
So I'm like, taking all the [00:51:00] notes. I'm going to have to get a transcript of this and, and, and, and, Read it for myself. And I've actually heard, I haven't heard a top grading, but I think in the past month, four or five people have said you should read who,when that, when that starts to happen and you got to start listening, okay, I guess I really do need to read it.
that's awesome, man. well, great. I feel like, yeah, we're doing a masterclass and, Addressing, identifying and addressing burnout. And then Again, I think one of the big antidotes to that's like building a really healthy team, having people in your corner, starting, strategically with that, with the right, identifying the right rules by understanding the processes of your business, designing that role to where it's really attractive and effective, and then going out and advertising it and finding the right people to fill those roles.
And I mean, speaking from experience, the first time's kind of hard and. daunting and, and then, a lot of our people listening, no marketing,you have marketing funnels. Well, we created a hiring funnel and we use that for the EA and the beautiful thing about that is and kind of clone it.
And now for the next role in the next role, I have one selfish [00:52:00] question before I let you say, Hey, how do we get a, how do we get ahold of Barrett and listen to your podcast? You said you probably don't know the person you want to hire. I actually have the, one of the next rules I want to hire is more for I wouldn't even call it a sales closer, but more like an enrollment advisor.
I guess you could say Hey, are you a good fit for our program? And which one I was thinking all external, Hey, there's some guru who's a great at sales, and then it was pointed out to me like, Hey man, you have 120 alumni of the same program. some of them have some fractional time available.
They're all love birds. Like you and the program, like, why not go to them and say, is anyone here want to help sell this program? Because you've experienced it. And so what do you think of that? Like having alumni
Barrett: That's actually another great exception to the rule. I think if you've managed teams and you've had people who have proven to you, they can do the job or, people who have been through your programs and. Awesome source of new employees because they will be inherent advocates for what you do based on personal transformation that they've experienced.
So that's another great place to find people.
Dustin: Great. Barrett approved. All right, well, look out [00:53:00] alumni. I'm coming for you. All right, man. Well, I really appreciate it. You've been super gracious with your time. I think we like doubled the time that we had allocated. I've, I've personally really gotten a ton of, enjoyment and fulfillment from the conversation.
So to close this out, Barrett, where should we go? how should, how should we go deeper with, with Barrett Brooks and learn more from you and, and experience what you're doing over with your creative work in your podcast?
Barrett: Yeah. Well, if you're the kind of person who believes that career should be meaningful on their lever for impact in the world, you should go to a good work show dot com. All the show notes and past episodes from the podcast. love for you to subscribe wherever you get podcasts. It's available basically everywhere.
and then secondly, if you're kind of at or about the seven figures and income, revenue, I should say. And you're considering this point of, do I want to scale or stabilize where I am? that's a perfect time to engage me for coaching. And you can find that at Barrett brooks. com slash coaching.
Dustin: awesome. Well, this is again, huge pleasure. Huge blessing. Great to know you. I got to know you a lot better during this conversation. I'm glad we were able to record this one. Let [00:54:00] everyone else listen in. so obviously Barrett's, just a font of wisdom has, has been down a lot of the roads that a lot of us are currently facing and, yeah, so definitely go check out the podcast.
Highly recommend Barrett for. so thanks again, very grateful for you and your humbleness and, and getting to know me and, open it up for our show here. hope to do it again in the future or whatever your next version of your adventure is Barrett. thanks again for being here.
Barrett: Yeah. Thanks for having me.