David speaks with Barrett Brooks, a writer and executive coach specialising in guiding mission-driven founders and creators through emotional and strategic barriers to business growth. His writing focuses on leaders and companies tackling critical societal issues such as climate change, biodiversity, education, food systems, healthcare, and circular products. Previously, he was the managing editor of The Carbon Almanac (a bestselling book on climate change led by Seth Godin), COO at Good Coffee, and COO at ConvertKit.
They talked about:
🔍 The role of agency in personal education
🔥 The power of self-determination
⚖️ The struggle of balancing practicality and passion in career choices
✨ The story of ‘Living for Monday’
🎢 The emotional rollercoaster of entrepreneurship
👥 What Barrett learned from working with Seth Godin
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📄 Show notes:
[00:00] Introduction
[03:38] The limits of traditional education
[05:35] Promotion should be based on merit, not time
[08:06] The camp that made Barrett realize his true calling
[10:31] The unemployable mindset
[12:29] How to overcome an educational bias
[15:13] The impact of misunderstood achievement on personal growth
[17:56] How Barrett's childhood jobs shaped his business mindset
[19:50] The dilemma of career change
[21:42] Lessons from immigrant families
[23:23] The reality of pursuing passion
[25:58] Lessons from building a business
[31:21] The fine line between persistence and letting go in a business
[34:09] Lessons from a New York internship
[38:00] Seth Godin’s influence on Barrett
🗣 Mentioned in the show:
Ernst & Young | https://www.ey.com/en_uk
Fortune | https://fortune.com/ranking/global500/
ERPS | https://en.wikipedia.org/wiki/Enterprise_resource_planning
International Baccalaureate | https://www.ibo.org/about-the-ib/
Wikipedia | https://www.wikipedia.org/
The Sunk Cost Fallacy | https://theknowledge.io/sunk-cost-fallacy/
Coca-Cola | https://www.coca-cola.com/gb/en
General Electric | http://www.ge.com/
The Living for Monday Show | https://barrettbrooks.com/portfolio/the-living-for-monday-show/
Seth Godin | https://theknowledge.io/freestyle/
👤 Connect with Barrett:
Website: https://barrettbrooks.com/
Twitter: https://twitter.com/BarrettABrooks
Good Work with Barrett Brooks: https://www.goodworkshow.com/
👨🏾💻 About David Elikwu:
David Elikwu FRSA is a serial entrepreneur, strategist, and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.
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📜 Full transcript:
[00:00:00]
Introduction
Barrett Brooks: My mom's expectation of me must go to college. First of all, you need to study a major that is productive and employable, so don't get a liberal arts major, don't, you know, study philosophy or history or, she really pushed me towards the business majors that were technical, if we can call them that you know, accounting and finance, or maybe as technical as business skills get.
I probably knew three years into my college career that I did not actually believe that message. I was just acting on it.
So by the time I left that job, I was terrified to tell my parents. Terrified. And it did not go well. It was like, I'm sorry, you're doing what? My dad, I think said something to the effect of like, you're making more money than I ever made in my career and you're leaving it? This seems grossly irresponsible.
My mom was maybe more open, but definitely like, wow, you are really throwing away this opportunity that you have in front of you.
And I'm very proud of myself, honestly, for sticking to it. I mean, the courage to continue to pursue the path, despite that kind of response from the people that you've looked to for your decisions throughout your life is like, wow, I'm surprised I had the wherewithal for that, but the thing that I lacked at that [00:01:00] time that I have now, I did not fully embrace the costs and consequences of that decision.
David Elikwu: This week, I'm sharing the first part of my conversation with Barrett Brooks, who is currently an executive coach and writer, helping mission driven founders, typically at Series A and above. A lot of his experience comes from his time as the chief operating officer at ConvertKit, which he helped grow from three to over 30 million in ARR. I also happened to be a customer of ConvertKit, so this was a particularly interesting conversation. And Barrett has extensive background, both as a chief operating officer and also as a growth director and we talk a lot about everything that it took to get there.
So in this part of our conversation, you're going to hear us talking about the education system and the extent to which it can help or harm. We talk about the importance of agency in education and the power of self determination, what it means to have an immigrant mindset, and the impact that being an immigrant can [00:02:00] have on your trajectory.
We talk about Barrett's early journey in becoming an entrepreneur, starting some of his first businesses and knowing when to start and to stop in entrepreneurship, and navigating some of the ups and downs of entrepreneurship, including learning what failure looks like, and when to make that decision to shut down a business.
We also talk about the struggle of balancing practicality and passion in your career, and everything that Barrett learned from working with Seth Godin, who is a little bit of a mentor to us both, me from a far greater distance than Barrett, who actually got to work directly with him, specifically on the carbon almanac and also a little bit earlier on in his career.
So I won't spoil anything, this was a really great conversation for anyone who thinks of themselves as a potential operator, someone that wants to work within businesses, someone who wants to help scale businesses, someone who wants to start something of their own, or even just wanting to navigate your career and figuring out how to grow and scale and [00:03:00] develop.
I think everything that Barrett shares is going to help you a ton.
So you can get the full show notes, the transcript and read my newsletter at theknowledge.io and you can find Barrett online on Twitter @BarrettABrooks. You can also find Barrett on his website at barrettbrooks.com, we'll have all the links to his stuff below including his awesome podcast Good Work.
And if you love this episode, please do share it with at least one friend, make sure to subscribe and follow to get the following parts of this conversation, because you won't want to miss them.
And don't forget to leave a review wherever you listen to podcasts, because it helps us a ton to find other listeners just like you.
The limits of traditional education
David Elikwu: So where I wanted to start is that I think for a lot of people, maybe they get into entrepreneurship and sometimes you hear people say it's because, you know, they weren't that great at school, they were trying to do certain things, it wasn't really working, but you actually seemed to be good at school, you know, you went to a good school, you got a good first job, and then you ended up quitting after about nine months.
So I'd love to [00:04:00] hear you unpack that part of your journey.
Barrett Brooks: Yeah. really interesting question. So while I might not have been similar in, in that way, particularly, like I got degrees in accounting and finance. I did fairly well in college. I've always been a good student, but the thing that is a little bit like many people who will say that is I hated school.
I hated how hemmed in I felt by the curriculum design in many cases, before college. So high school, middle school, I felt like I was going at about 30 percent of the speed that I could go in my classes of like, what I was capable of learning versus what the pace allowed me to learn. Every day in high school, certainly late middle school and early high school.
Maybe it was a little bit, not this way later in high school as I got into more challenging like college level classes, but I would rather than pay attention to class. So long as the teacher would allow me, and usually they would allow me because if I didn't do this, I would be very [00:05:00] annoying. So usually they would allow me, I would do my homework instead of the classwork. And that way, when I got home, I could go play sports, roller hockey or baseball or whatever, and enjoy my time that way. And so I just figured out this game where I didn't need the teacher to teach me, mostly, what we needed to learn to do the homework. And if I did the homework now, I wouldn't have to do anything after school, and that was the system that worked for me.
And so in that way, It's very much the same. I absolutely hated school because it didn't cater to me. The speed was the average of everyone in the class and I wanted to go faster.
Promotion should be based on merit, not time
Barrett Brooks: And once I got out and I went to work at Ernst and Young, which is a big accounting and consultancy firm. I was on the consulting side and there was this conversation. There were two key things that happened. One was a conversation with my boss. One was I went to volunteer as a counselor at a summer camp. So I want to tell you both stories.
The conversation with my boss, I sat down, I think it was about six months into working there. And there was a review, a review cycle that was happening. So I, I had only [00:06:00] had a half year of experience and a review is supposed to be for a full year. And I submitted one anyways, just to go through the practice of like reviewing what I had done so far. And in that time already, I had uncovered a problem for the client I was working on, which is a fortune 10 company and outside of Atlanta.
I was working on an international tax preparedness project. I wasn't in tax as a practice, but, I had uncovered this problem where they had acquired all these companies and they had ERPs enterprise resource planning, tools that were all reporting the same information, but with different format.
And what I realized is. If we just change the format of the report, basically the entire project that me and like five other people were working on would be irrelevant. And so they went and sold this and I'm sure it was like many millions of dollars worth of work. They gave me two people to come work for me, both of whom were obviously more experienced since I was right out of school.
And so I'm like, Well, shit, I should get promoted. So I go and do this [00:07:00] performance review, right. And I fill it out. And while we're waiting to hear back from it, I have this lunch with my boss and I say, Hey, what would have to happen for me to get promoted faster? And he says, well, you actually probably are going to get bumped up a level, like from staff one to staff two, but that never happens first of all. And the only thing that you can do to get promoted fully from like staff to staff, whatever, like the next level up is wait two years. And I said, well, that doesn't make any sense. What are the requirements? And he said, wait two years. And I was like, well, that's stupid.
I don't think I said that to him because he's a partner and I work for him, right. But in my head, I'm like, that's idiotic. That sounds a lot like what they used to tell me in school. There's nothing you can do to go faster. You just have to wait. And it's like, well, if I'm more capable and I can go faster, why there should be no time requirement. There should be merit requirements. There should be things I have to achieve. So anyways, that landed with me. And I remember leaving that lunch and I thought, I can't do this. I cannot be in a [00:08:00] place where the answer is sit there. It just like broke my brain in a way that I could not appreciate.
The camp that made Barrett realize his true calling
Barrett Brooks: And so shortly after this, I go to volunteer at this summer camp, a mentor from college had recruited me. It's a nonprofit organization outside of it or in Atlanta. And they host a week long summer camp program for eight to 11 year olds who are in the foster care system in the state of Georgia, and have been abused or neglected. So that's why they're in foster care.
And the camp is meant to give them a place where they can be unconditionally loved and safe for a week in their year, where they know nothing's going to happen to them. They are focused on, they can experience joy and play and obviously the outdoors. And the magical part of this camp is that they match one counselor with one camper. And so it's a one to one ratio for an entire week. So I went and I got to be counselor for this kid. And halfway through the week, they had just hired a program [00:09:00] director for the camp. They came into our staff meeting one afternoon, and this is the only hour every day where we weren't with our campers. They came into the staff meeting. The president of the board said, Hey, this person we hired is a horrible cultural fit. We've received your feedback. Long time counselors had been saying, we'll never volunteer again. If this is how this is going to be now. And she had just, she just didn't understand the like nature of the organization that she was joining. So they fired her midweek and they said, we're going to be recruiting a new program director. And we'd like you to be someone who's been a counselor before. So if you're interested, please let me know.
And so I had just had this conversation with my boss. I'm in this system that just wants to like, grind me up and spit me out. And here is this person saying, you can come make half of what you're making right now, probably. But your clarity of purpose, the mission that you're working on, the people you serve is like, so, so viscerally important. And I could tell that based on the experience that I had been having with my camper that week, and just the degree to which he had become reliant on me [00:10:00] emotionally in three days.
And as I heard that, I thought, I can't do this work. I cannot do what I'm doing for work, knowing that work like this, that this camp exists. I just can't hold those two things in my brain. And so within 30 or 45 days, I quit my job and I said, I got to go do something more important than this work.
And I think that was the beginning of me slowly, but surely, or maybe I was already there, but slowly, but surely realizing that I was just unemployable because I must have control over the pace at which I go and I must have control over the degree to which the mission I'm working on matters.
The unemployable mindset
David Elikwu: The phrase you use, unemployable, is a really interesting one. It's one I've wrestled with a little bit in some context, in terms of the, the extent to which it applies to me. And I think it probably does to a significant extent. And it's funny, I wasn't even expecting some of our stories to align so much, cause a lot of what you shared is something I can empathize with, but there's something specific, I want to ask you about this idea of agency and, you know, a lot of the things that you described seem extremely agentic.
And when I think about, so, [00:11:00] you know, even for me to explain some of the things that mirrored my story that made me think of this question.
So for example, when I was in, I think it was sixth form, I had English class. In fact, actually for most of my classes at some point during the year. So I was doing the international baccalaureate. So the IB it's, I think a bit like AP, you do over two years, but what it means is that you don't have exams like final exams in the first year. You have final exams at the end of the second year and after the first year you just have, maybe you do some coursework, like you do get tested on stuff, but really you're preparing for the end of the second year. And I think at some point, I think it was when we started doing elective classes. So there's some things that are pre prescribed and then the elective course is usually actually your school picks for you. But they were elective and I wanted to pick my own stuff. So there was a few classes that I just stopped going to. And on the top floor of the school, I pulled a desk out of one of the classrooms and I just pushed it right to the back of the hallway and I would just come to school every day and I would just go and sit there like just at the end of this hallway. And I would just study by myself.
So in [00:12:00] some classes, it works very well. In some classes, it did not work as well because, you know, there's probably a lot that I'm missing by not going to class at all, but I'm interested in like you mentioning that story, where that came from, because I think for me, I think it might be similar, but I know that at least in that context, I had come from a school, like a previous school that I went to where I had got some decent grades and I did have some teachers that encouraged me. And so I did feel like, oh, you know, I might actually be good at some things.
How to overcome an educational bias
David Elikwu: And for additional clarity, there's one class in particular that I'm thinking about, which was my English class, where at this new school that I've moved to, to take the IB. There was a teacher who from the very first thing that I submitted, she wrote me an email saying, this feels a bit too professory and she didn't mark it. She did not grade it and she just thought that it was plagiarized. And it's funny because, so I was shocked receiving this and I showed it to some of my friends. One of my friends burst out laughing and he pulled up his homework that he submitted and [00:13:00] he pulled up Wikipedia and he'd literally just copied word for word the entire like first few paragraphs of this Wikipedia post, so he had 100 percent plagiarized without even masking it that hadn't been picked up. He got an A, the equivalent of an A on that piece of homework and mine was ungraded and then after that there was quite a few times I would submit things and she would just not grade it because she thought I'd plagiarized or something like that she wouldn't even mark it or if she did mark it she'd give me a B.
And that was just burning me because in my previous school I've been predicted like you know, the best grade for English. So, there was definitely this incompatibility there where I was like, I definitely feel like I'm better than you are assuming that I'm going to be. And so I would rather just not come to class at all and just do it myself.
And it worked out to an extent in the end, because I think, yeah, on my final grades, I got, I did both English language and English literature. And I got, I think I dropped one mark across both exams. So I got a hundred percent on one and I dropped one mark on the other one. But again, it was just this idea that, I was just adamant that [00:14:00] there's no way she could tell me that, you know, she's not accepting my work.
However, the caveat to that is there's also some subjects where I did the same thing and it didn't work out to the same extent, so there's a balance there.
But yeah, so I'd love to know both in the school context and then later on in the work context, like what got you to a point where you had that confidence that actually, Hey, you know, there is a path that I'm supposed to be on, but I actually think it's better to go my own way.
[00:15:00]
The impact of misunderstood achievement on personal growth
Barrett Brooks: I know you're the interviewer, so I won't ask you a bunch of questions, but I'll just note that it's really interesting to me that you reached the limits of her imagination. She could not conceive of the possibility that you, at that age, could produce that quality of work.
And so rather than conceive of something that broke her mental model, either of you or of generally people that age, she chose to ignore it and assume that you had cheated. And that's fascinating to me. I think we do this to each other all the time in the world. I think it's very sad that, that's the case because there's another experience that would have encouraged that drive in you that like natural inclination towards it and developed it and blossomed it, you know? And so, you know, all of these [00:16:00] things have consequences and rewards to them, and obviously here we are today. So like, maybe we wouldn't change it.
So I think there's kind of two roots for me. One is my mom is two generations removed from immigrants from Mexico, also like enough down the chain where I think she was at the stage where they very, her and her sisters very much were not part of the culture that they came from. Like their family made the habit of kind of rejecting it almost not, not explicitly, but implicitly in order to assimilate and become part of the predominant culture and then to then succeed, right. To like, go through the progression of moving up the economic ladder and yada, yada.
And so despite the fact that there was no language or cultural knowledge being passed down at her point, there was still this, like, I think immigrants work ethic to what she embraced in her life. Her mother was a nurse, her dad was really in the military and then ended up being an entrepreneur [00:17:00] himself and like, made all of his own wealth through that, but they were poor growing up.
And so, my mom responded by becoming a high agency individual. That was her solution was I will take control of my destiny. And I know that I can dictate my outcomes. That was the message that she internalized and that she lived her life by. And that was the one that she passed down to me, still lives her life by.
And so I'm very grateful for that because she, I like to joke that she was more like a coach on many occasions than a mom. She just instilled in me this belief that if you want something, you go get it. You go make it happen. You earn the right to have it, and that's the way of the world. Now, I've had to like adjust a little bit to learn that that's not actually always the way of the world as an adult, but it was a helpful internalized idea throughout my life that if I take my agency and go apply it to something that yields good results.
How Barrett's childhood jobs shaped his business mindset
Barrett Brooks: And the second thing is, there would have been some of this, but it [00:18:00] began early enough in my life that it wasn't entirely messaging from my mom. There's just something built into me where I was constantly seeking new stuff. And so like with many entrepreneurs, I've just got those early roots of like, I would walk around the neighborhood asking people if I could wash their cars, blow off their leaves, mow their lawn, clean their driveway, pressure wash something. I just wanted to like, earn money so that I could do things with it. Probably starting around the age of, I don't know, 10, nine, maybe.
In school, the like gifted program would get to, you know, gifted program. You'd get to join teams and start little businesses and have this like market on the stage within the cafeteria that would happen for a two day period. And it was a entrepreneurial unit of teaching within the class where the goal was to come up with an idea where you would make the most money amongst any of the other, you know, entrepreneurial ventures in the class. And it was meant to teach understanding your market, building a product people [00:19:00] want, selling it. And of course the things that worked were like cotton candy and other shit like this. And so I, I didn't fully get, and sometimes I still don't fully get the degree to which people just want things that they want, you know, it's like, I want to make things that I want them to want sometimes.
But I loved that and I ended up making these little like bead animals, you know, you could like make these little woven bead animals and trying to sell that in school. And so I just had all these roots of being very drawn towards the agentic experience of making something or doing something and making money from it directly and all of the things that would unlock for me.
So I had many experiences like that, so I think that joint kind of path of like, I was naturally inclined towards it and I liked the natural reward cycles of it. And then my mother's messaging of high agency, you're in control, you're in control, work hard enough, do the right thing, and you'll be rewarded for it. I think those are the two roots of it.
The dilemma of career change
David Elikwu: How do you balance that yearning for agency with also the sacrifice? Because in the example that you mentioned of even quitting your job, you're potentially [00:20:00] quitting your job to earn half as much to go off and do something which might give you some purpose, but there is a risk.
And I think, you know, funnily enough, you mentioned that your mom having that immigrant mindset, I'm technically a first generation immigrant. My dad came to the UK during, there was a civil war in Nigeria. So his family kind of one by one slowly came here. And so he studied here, but then went back to Nigeria where he met my mom, so we came back. So for me, it was the first time and for my mom, also the first time.
But I think there was a strange balance for me in that on one hand, having immigrant parents is basically like agency boot camp because they have done something incredible, which is moved to an entirely different country to get a whole new opportunity set. And I think just witnessing that, or just having that idea in the back of your mind fundamentally changes the way that you approach the world. I genuinely believe that. However, at the same time, there is then also this mentality of kind of protecting this thing that you've now got. And actually, now that I have this opportunity, maybe I should play it safe and just become a [00:21:00] doctor or a lawyer. I mean, I did go off to become a lawyer, but I actually wanted to do it. But still, you know, there is this idea that actually now we don't want to rock the boat too much. And maybe we should just get the best job, play it safe, make as much money as possible.
So I'm interested for you being in that position, was that something that played in your mind at all? Like, okay, I definitely want to accelerate, I want to go faster, I want to go further, but I'm leaving, you know, working at Ernst Young, there's a lot of prestige in that. There's a lot of, you know, privilege, there's a lot of money. There's a lot of things that come attached to that. If I leave this thing to go work at this summer camp, how does that change maybe how my friends see me or how my parents see me or how I see myself, you know, there's a big world change that goes beyond just the purpose that I feel at work.
Lessons from immigrant families
Barrett Brooks: Yeah, there's so much there. First of all, the number of people who I have interviewed on my podcast who are either immigrants or children of immigrants that I did not know that before I invited them on is fascinating to me. And it's become a big theme of what we ended up talking about across episodes of the [00:22:00] show.
And ironically, actually, so I'm being interviewed by you this morning and this afternoon, my time, I'm interviewing the child of Nigerian immigrants, which I just find fascinating have happened on the same day.
Yes, I felt the consequences, I felt the weight of the consequences or potential consequences quite a bit.
So I kind of think like there's this income ladder that generations move up when families are upwardly mobile. So my Grandfather on my mom's side. Well, both my grandpa, all four of my grandparents grew up extremely poor. My grandfather on my mom's side used entrepreneurialism to move up the wealth ladder and then lost most of his wealth in the 2008 financial crisis. And so he returned kind of to more like where he began. But my mom followed in his footsteps and she moved from like lower middle income, maybe upper working class to high middle income, high earner over the course of her career. And so that was kind of the foundation from which I was starting was like, by the time I went to [00:23:00] college, we were middle, mid high income family. Although that's not how we had lived. Whereas my parents both grew up extremely poor. My dad grew up in a, lived part of his childhood in a cottage by a Lake in Wisconsin with no running water and no electricity. And that, I can barely fathom like in from the place that I am in my world and life today. I just cannot fathom that that was my father's reality.
The reality of pursuing passion
Barrett Brooks: But my mom's expectation of me was must go to college. First of all, must go to a state school where either you will receive scholarship money, or you will pay for yourself because we are not paying for like, excess costs, you know, we can cover the basics, but not anything beyond that. You need to study a major that is productive and employable, you need to be employable when you leave. So don't get a liberal arts major, don't, you know, study philosophy or history or any of that stuff. That was a very strong message I received. And she really pushed me towards, you know, kind of the business majors that were technical, if we [00:24:00] can call them that from a business standpoint, you know, accounting and finance, or maybe as technical as business skills get, because she believed that if you are an accountant, you know, certified accountant or a certified financial person that you will always be employable. And so that was how I chose my majors because I'll always be employable.
I probably knew three years into my college career that that message did not actually res, I did not actually believe that message. I was just acting on it and that I had made a mistake, that I was not actually interested in the things I was studying, but I was already there, you know, I probably succumbed to the sunk cost fallacy and just kept going. So by the time I left that job, I was terrified to tell my parents. Terrified. And it did not go well. It was like, I'm sorry, you're doing what? You are making? My dad, I think said something to the effect of like, you're making more money than I ever made in my career and salary and you're leaving it. This seems grossly irresponsible. And He hasn't used that exact language, but that was the message. My mom was [00:25:00] maybe more open, but definitely like, wow, you are really throwing away this opportunity that you have in front of you.
And I'm very proud of myself, honestly, for sticking to it. I mean, the courage to continue to pursue the path, despite that kind of response from the people that you've looked to for your decisions throughout your life is like, wow, I'm surprised I had the wherewithal for that, but the thing that I lacked at that time that I have now, I did not fully embrace the costs and consequences of that decision. I don't think that I fully understood and was ready to take responsibility for all the potential downside. I think I was only looking at upside in terms of, yeah, the purpose in my work and what I wanted from a financial outcome standpoint, but it's very important to do the kind of like odds adjusted reality of these outcomes, right?
Because most likely outcome was that the business would fail, which is what happened. I did not factor that in enough to my decision making and I don't think I took enough responsibility for it.
Lessons from building a business
David Elikwu: So tell me a bit more about this [00:26:00] business because precisely the last thing that you mentioned is what I'm specifically interested in in the context of the story you just told, because you've now sold your parents on this dream of, hey I'm quitting this job, but I actually, you know, there's something I believe in. There's a journey that I'm about to go on. There's this thing I'm about to do, and you try and do it, you try and do it. It takes months. It might take a year or so. And it eventually ends up not working, even though I think in the interim, maybe you raised some money, like that, there were signs of things working out, but then eventually, you know, you kind of came down on the other side of that slope.
So I'm interested in one, like what that journey introductory was like, but then also how did it feel like when you're coming towards the end of that journey having gone through all of those other parts.
Barrett Brooks: So first of all, I was actually planning to apply for that camp job. And I went to the president of the board and I said, I intend to apply and he said, okay, great. And a week or two later, he called me and he said, Hey Barrett. So, here's the thing. My daughter is planning to apply for this [00:27:00] and she's got a psychology degree. And so she's likely to get the job. And I'm just wondering if you might be open to serving on the board instead. And this was another thing that later I had to go back to him, this man who I respect a lot and who was a mentor to me and we served on the board together. I had to go back to him and say, you know, that really actually made me quite angry. Now, upon reflection that you essentially shortcut the process. You didn't even let me interview. You didn't even put me in front of the people making this choice. Because your daughter was applying and maybe she would have gotten chosen, but that sent me on a whole path that I wouldn't have had to go down if I had been able to go into that job and you didn't even give me a chance. And I'm angry about it.
And it was in the context. Well, we can get there, but so, so that's the first thing, I was going to apply for that job. That was the path, and then he told me that. And it was like, well, now what do I do? I've already decided to leave this job.
What I saw in the camp opportunity was that there was this [00:28:00] class of jobs that never gets talked about to business graduates, at least where I went to school at a state school. And it was this kind of like small business, startup nonprofit, kind of that more class of things. It's like no one said, Hey, you could start a business or you could go to work at a small company where you can have a large impact. Uh, or a disproportionately large impact to your experience. They just talked about fortune 500 companies, companies that could hire a hundred kids at a time type places. And so I said, that's very interesting to me. I wonder why that's the case? It seems like there's a lot more purpose, meaning agency, like relevance in more small companies where people could go to work coming out of college.
And if we look at it from a systems perspective, it makes perfect sense, all of these incentives are aligned for a big university to partner with big companies who can hire many people at a time, because if you look at like US news and world report or whatever it is that does the college [00:29:00] rankings, the like, number one thing they rank colleges on are, what is the hiring placement rate of your graduates within X days after graduation?
And so if that's the number one thing that you are getting measured on, and the number one reason people come to school at your university, which is the only way you make money, you're going to do what it takes to get people employed. And the best way to do that is to partner with Ernst Young, Coca Cola and GE and whoever else, anyone who will hire hundreds of students at a time because you've got thousands of people who need employment.
So I saw this gap between that, which was what the university was doing, the career center at the university was doing and this concrete camp job that I saw over here. And it's like, there's probably hundreds of kids who want to go to work in this camp type job, but don't even know it exists. How do we solve that?
And so I started this company called Living For Monday. And what I wanted to try to do was to plug that gap where I found the most, at the time I talked about it much more as like purpose driven or [00:30:00] passion oriented jobs and revealed them to students and then coach students to go get those jobs and basically be a matchmaker between them. And this ended up being about a three year journey where I call it my real world MBA. It's like, I got to study everything that has to do with entrepreneurship in actual, you know, my career is on the risk kind of terms and learn all the things I needed to learn that I wish I had known before I started by building a business that ended up failing.
And so there's so much in between there, but basically to summarize it, I chose a very bad market to make money in. College students are famously poor because they have no income source other than perhaps their parents or scholarship money. And if you go to a college student and say, Hey, don't go get a bad job, get a job you're going to be really interested in. They're like, I'll take any job. I don't care what the job is. I just need a job. And the people who actually feel the pain of, Oh, that job's not what I thought [00:31:00] it was going to be. Are the people three, four five years into their career who are waking up to the fact that like, how did I end up on this path again? I don't even like this work. Those are the people who needed what I was trying to sell, but I didn't have the experience to realize it.
And so the whole business model piece of that venture was broken from the beginning. It just took me a little while to figure that out and to see it for myself.
The fine line between persistence and letting go in a business
David Elikwu: So just going off what you were saying, I find it interesting because, I'd love to hear a bit more about specifically what the journey of building was like and what led to you then deciding that you needed to shut it down specifically, because I think, very often the kind of person that has the mindset actually, not just to start something, but to quit their job in order to start something, which I think is actually completely different types of people.
There are loads of people that will go along with their job secretly wanting to do something else and either never going and doing it, or maybe trying to do it in the, in the safest, most risk free way, but quitting your job and going out and saying, planting a flag in [00:32:00] the ground, this is what I'm going to do. And having your mission and orienting your entire life around that also makes you incredibly vulnerable.
And I think then being the kind of person that wants to do that can be hard to then get to a point where you're willing to give up that thing and to give in and say, actually, okay, this has not worked.
There is also this idea that there are these statistics around how many businesses fail. And I think the case that you far more often get is that the people break before the business does. And a lot of people don't even push their business to the point where they realize that the business isn't going to work or the business is breaking. Like they themselves will break long before that for a number of reasons. It could just be that maybe they didn't try hard enough. They are not actually trying to scale it enough, you know, maybe they find it more difficult than they imagined. Like all kinds of reasons that could happen where it's actually just a case of you as a person saying, Hey, it's not that this business isn't working. I just quit. I just don't want to do this anymore. This is too hard. I am putting this [00:33:00] down. I think it's entirely different to get to a point where, Hey, you have tried to build a business. You've seen signs of it working. And you're invested in it both emotionally and, you know, in terms of the wider scope of your relationships, your, cachet as a person is on the line, your CV as an operator is on the line. And you have to admit that, Hey, actually this isn't working. I have to stop. I have to go do something different.
Barrett Brooks: Yeah. It was quite the journey. I don't know that I would recommend someone go all in, you know, right up front. There's this middle ground, right? Which is, I think if you can test an idea to the point where you see that there is some validation, not like necessarily get all the way to like replacing your full income, but some validation that you have a product and there's someone willing to buy it, Or a group of people willing to buy it. You know, let's say you need to make maybe four or five sales to people you don't know before you start to have an indication that the thing is valuable, repeatable, they're not just doing it out of social obligation [00:34:00] and you can begin to see trends amongst who those people are and what their needs are. I would probably do that before I left the job next time. But that's neither here nor there.
Lessons from a New York internship
Barrett Brooks: The path to realizing that I needed to close it down was first of all, and the summer before I closed it down, author named Seth Godin put out a call for applications for an internship with him. And he would do these things where once every summer or two, he would have a group of interns come in and, you know, he called them interns, but they were people of all ages and all career stages who would come work with them for a period of time. So I had raised a little bit of money from my aunt and uncle. And $10,000 to be exact and spent it all on building a web platform for this business that I was building. Worked with designers, had it built out. And so it looked professional, it looked designed by a professional, although like the taste, you know, you could argue whether it was any good at the time. So I at least looked like I [00:35:00] was really, you know, I had taken a risk, made it my career, I had invested in it and made a web presence that looked professional and I was going for it, right. So these are the qualities I had that were positive at the time.
So I applied for this internship with Seth Godin and I'm thinking, okay, this guy's going to get thousands of applications. Like I did my job by applying, I'm not getting picked. That's for sure. I get this email one day I'm sitting on my wife's parents couch at their house. And she's like napping upstairs and I'm just sitting there watching TV or something, and I pull up my email and it says, something like Barrett, you're in. And it's from Seth Godin. And I just feel my heart start racing. And I click the subject line, and I open it. And he goes through this whole thing. It's like, I had thousands of applications and yada, yada. And I'm like, oh man, it's going to say no at the end. And then he says, you're in, would you like to come to work with me? And I'm like, absolutely. I'm in no doubt for sure.
And so anyways, I go to New York and I work in his office for two weeks with, [00:36:00] I think it was 15 other people, all career stages, incredibly talented people from education, law, design, coding, everything. And that was where I really started to learn what it looks like to be on a highly talented team with all the different skills in the room that you need to make it succeed, with direction and vision and strategy in place. And every afternoon we would take a break for a little while and Seth would kind of do these like, almost like workshop sessions where we became the audience for a little while. And it was almost like a break for him to pour into us and mentor us for a little while. And I don't remember what he was giving the session on that, that one afternoon, but he stopped and asked if anyone would give him an example. And I said, well, here's, what's going on in my business, you know? And I gave him the lowdown and he's walking me through basically like some coaching questions, some kind of like Socratic teaching method. And we're going through it. He said something to the effect of sounds like you just picked the wrong audience. And it was just so simple. So if, if anyone's ever listened to Seth Godin [00:37:00] talk or write or anything, he's just so quippy, you know? And when he said it, it was like the emotional reaction wanted to be like, no, you're wrong. And you know, all of these things, but because I had such respect and trust for him, it landed differently and it just kind of like seeped in and I was like, damn, that is what happened. And so we kept going a little bit and he said, it might be that you just need to shut it down and call it a success. Maybe you've gotten everything you needed to get out of this.
It wasn't like in that moment I decided, but in that moment, the seed was planted that allowed me a path of dignity to shut it down and acknowledge that it wasn't working, without declaring it a failure, like without declaring the effort of failure, even if the business model failed. And that gave me this out where I was like, Oh, this can be a huge success. And it just didn't work financially and that's okay.
And so that was really what allowed me to get to that point where I had the courage to say, I tried something, served its purpose in my life, and now it's time to go do something [00:38:00] else.
Seth Godin’s influence on Barrett
David Elikwu: Okay. Amazing. I think you've had the rich man's version of what a lot of people imagine or dream of, because a lot of us, me included, you know, we read Seth's work, we read his emails, we watch his content and whatever else he does, read his books. And, uh, I think very often, exactly what you're saying are things I can imagine Seth saying. And I think, even for me, there's a lot of times where I've, I've read something that Seth has said, and I'm like, Oh, wow, you know, that's true. And I can't imagine how much different it might be to be in the room while he's telling it, and he is actually saying it specifically to you. It's not like a, Oh, this might apply to my life.
No, he's actually saying it directly to you.
Barrett Brooks: Yeah, I mean he, that man has changed my life in many wonderful and positive ways, and I'm very, number one, grateful, obviously. And number two, very protective of them. Anytime I see people talking negatively about Seth, I, I really, you know, I don't like go to battle online just because I think it's not productive, but it's really important to me to advocate for him and the real impact. He [00:39:00] is, as he appears online, every experience I've had with him, he is in alignment with what he appears to be. And that's very, very rare in the world, exceedingly rare in the world. And I've been really grateful to know him because he gives me, I don't make anyone my hero. I don't make anyone my like, and I'll be all role model, cause I think that's dangerous. But he has showed me that, one can declare an identity through your work and also act that way in your life, and those things can be the same thing. And I'm sure he's out of alignment with himself, just like anyone gets out of alignment with themselves at times. But that's the kind of person I aspire to be.
I aspire to say who I am through my work, through the implication of my work and also through my words and conversations like this, and then actually to show up that way, um, I think that's the ultimate definition of success for me is to show up as I say, I intend to.
David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It [00:40:00] really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time.
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