🎙️ The Diary of a $30M COO with Barrett Brooks

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:

💡 Unexpected lessons of business failure

⚖️ The struggle of balancing ambition with reality

❌ The power of rejection

🧭 The moral cost of career advancement

🏆 The balance between success and failure

🤝 The cost of friendship in leadership roles

This is just one part of a longer conversation, and it's the second part. You can listen to the earlier episode here:

Part 1: 🎙️Purpose, Passion, and Perseverance with Barrett Brooks (Episode 109)

🎙 Listen to your favourite podcast player

🎧 Listen on Spotify:

📹 Watch on Youtube:

📄 Show notes:

[00:00] Introduction

[02:33] Life-changing advice from Seth Godin

[07:11] How Barrett struggles with a $50K debt

[08:58] How meeting Corbett Barr changed his career path

[10:19] The double-edged sword of ambition

[11:39] Overcoming conflicts with the boss and self-doubt

[13:19] Rejection is redirection

[15:16] The struggle of being friends with the CEO

[16:18] The high price of career decisions

[19:23] Lessons learned from the COO role

[22:06] The challenges of scaling and growing as a COO

[25:04] The hidden costs of career advancement

[27:16] Handling peer resentment and team growth limits as COO

[30:25] The impact of personal relationships on professional roles

[33:30] Building a startup with a friend

🗣 Mentioned in the show:

Seth Godin | https://theknowledge.io/freestyle/

Wes Kao | http://www.theknowledge.io/weskao/

The ShipIt | https://amzn.to/3WLxvsj

Living for Monday | https://barrettbrooks.com/portfolio/living-for-monday/

The Dip | https://amzn.to/3Ma4cup

Ernst and Young | https://www.ey.com/en_gl

World Domination Summit | https://worlddominationsummit.com/

Chris Guillebeau | https://chrisguillebeau.com/

Corbett Barr | https://www.corbettbarr.com/

LinkedIn Learning | https://www.linkedin.com/learning

Nathan Barry: Everything We Learned Growing ConvertKit to $40M | https://www.goodworkshow.com/guests/nathan-barry/

Nathan Barry | https://nathanbarry.com/

Convertkit | https://bit.ly/convertkit-de

Acumen | https://acumen.org/jobs/

Jacqueline Novogratz | https://acumen.org/jacqueline-novogratz/

Adam Grant | https://adamgrant.net/

Kim Scott | https://kimmalonescott.com/

Substack | https://substack.com/

Beehiiv | https://www.beehiiv.com/

👤 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.

🐣 Twitter: @Delikwu / @itstheknowledge

🌐 Website: https://www.davidelikwu.com

📽️ Youtube: https://www.youtube.com/davidelikwu

📸 Instagram: https://www.instagram.com/delikwu/

🕺 TikTok: https://www.tiktok.com/@delikwu

🎙️ Podcast: http://plnk.to/theknowledge

📖 Free Book: https://pro.theknowledge.io/frames

My Online Course

🖥️ Decision Hacker: http://www.decisionhacker.io/

Decision Hacker will help you hack your default patterns and become an intentional architect of your life. You’ll learn everything you need to transform your decisions, your habits, and your outcomes.

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The Knowledge is a weekly newsletter for people who want to get more out of life. It's full of insights from psychology, philosophy, productivity, and business, all designed to make you more productive, creative, and decisive.

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🎞️ Descript: https://bit.ly/descript-de

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📜 Full transcript:

Barrett Brooks: Hey, what if you didn't leave? What if you stayed and you became the COO here?

And so now I have this conundrum, right? I have this person that I respect and adore. He's the number one person I've ever worked for that I felt like, inspired me and helped me really grow.

And I've got this other opportunity over here, that's worth a lot of money potentially to my family. What do I do?

I did what I always try and do. And I was open. I went back to Seth and I said, look, here's the situation. I need your advice.

And to his great credit, he gave me great advice. And he just said, look, I think you should do what you think is best for your family.

And I look back at that decision now. And what I realized was I made a money driven decision at the time.

I said, I think that this role is COO of ConvertKit with this equity package is more likely to generate generational wealth for my family. And I think that would unlock the path for me to be able to do whatever I want for the next 30 years of my career afterwards.

This week I'm sharing the second part of my conversation with Barrett Brooks, who is currently a writer and executive coach, but in a previous life, he had been a chief operating officer for companies like ConvertKit and Good Coffee. So he's worked both with bootstrap companies and venture backed companies.

And in this episode you're going to hear us continuing our conversation. We talk about the things that we can learn about our purpose from business failures. We talk about how success can complicate your sense of self and the secret burden that actually comes with achieving a sense of financial freedom.

We talk about the power of rejection and the nuances of success and the extent to which it's more based on opportunity or based on skill.

And we also talk about leadership teams and how to build them how to cultivate the right kind of relationships and the extent to which the relationships that you have on your leadership team within a startup can influence your success in the longterm.

So this was a really engaging episode. You're going to hear a lot about what it takes to run a business at scale, not just from an operational level, but also on a personal level.

So you can get the full show notes, the transcripts and read my newsletter at theknowledge.Io.

You can find Barrett online on Twitter @BarrettABrooks and we'll have links to his website barrettbrooks.com and check out his podcast Good Work with Barrett Brooks.

Where he speaks with a ton of incredibly interesting business leaders and people that are led by passion to create change in the world.

So if you love this episode, please do share it with a friend and don't forget to leave a review wherever you listen to podcasts because it helps us tremendously to find other listeners just like you.

David Elikwu: I want to come back and ask you a bit more about your relationship with Seth and also some of your other relationships, but just to follow up on, What you just mentioned and funnily enough, you're not the first person that I've spoken to on this podcast that has worked with Seth. I spoke with Wes Kao, maybe last year.

Yeah. So, but I wanted to ask just based on what you were saying now, is there anything that is intrinsic to Seth and who he is and what makes him successful in the ways that you might frame that, that doesn't specifically come across, like, it's not just, Oh, something that he's written about or something that he said, but when you see him, like you can see why it works and you can see why these things happen.

Barrett Brooks: The thing that I would say about it, that has most resonated with me that might not be abundantly obvious just from reading his work, is that Seth is very clear about creating a container for every project he works on. And he talks about this and some of his like, I'm looking over at my shelf at his books. He's got different like workbooks and project planning methods.

So ShipIt was this little workbook that I'll, I'll hold up here like just tiny little thin workbook, right? On defining a project in the terms of a project and so he has written this, right? And it's it's here like you can order them and write in them. He actually does this he actually creates the boundaries for his projects, this is his process. And i think the thing that will be that's most important to hammer home about that is like not the process because here it is in a book, right? He said it. It's that he sticks to it. If he sets a boundary on a project. He sticks to it. He doesn't overextend himself. He doesn't over invest in something. He's at times almost like, annoyingly logical about whether a thing is working or not. He doesn't get overly emotionally invested. And I don't know where that comes from. Like what I think probably happened is he probably had experiences early in his career, much like mine, starting living for Monday, where it was like, wow, I got overly invested in that thing. And I got overextended. That was not great. He's never said that to me. I don't know that for sure. I intend to ask him when I have him on my podcast eventually. But I really admire his ability to separate from his emotional commitment to a mission and say, this particular project is no longer the best way to achieve that mission. And I see that now that we've tried it. And being a person working for him at times, I have been disappointed by that because it's like, well, I wanted to work on this for longer, but now years removed from that, I can look at it and be like, wow, that was really responsible because if you had kept going when you knew it wasn't going to work. And this is the whole, the dip concept, right? That's what that book is about is knowing when to quit. He actually would have disappointed a lot more people. Because more people would have gotten involved. More people would have been customers or audience for the thing. And if he knew six months ago, this isn't going to work, but he let that extend to a bigger team, a bigger audience. He's actually saying, in some ways I'm going to be selfish and keep going because I don't want to do the hard thing now. So later I'm going to do the hard thing that's even bigger and more impactful in a negative way to more people.

So I've really taken that away from him to make the appropriate decision, the appropriate hard decision at the appropriate time and not to delay it because it causes more harm if you delay it when you already know it needs to happen.

David Elikwu: I love that. And I think there's a decent chance that if Seth Godin doesn't tell you to quit the business that you're working on, you don't end up going on to become the COO of a business that makes 30 plus million a year in annual revenue, which is an incredible journey.

So I'd love to hear more about that. Like, how do you go from the person that you're trying to build something? It's not working. You'd quit your job at Ernst and Young to now, not just being in the right position, because very often you can just be in the right place at the right time. You made the right friends. You were surrounded by the right people. I think you went to a convention where you met a group of people and everyone's trajectory from there seemed to go fantastic. But I think simultaneously, you also need to be prepared to be in the right place at the right time and have the right skills to enable you to actually be successful. I think there's tons of people that you have not got to hear their story. They might not end up on this podcast. I might not get to speak with them because they may have had an idea that could have been equally successful, but they themselves were not ready at that point in time. They didn't have the skills to be able to execute on it. They weren't able to build the right culture. They weren't able to nurture the right team. They weren't able to get to that point.

So I'd love to hear more about like your personal journey as an individual going from A to B.

Barrett Brooks: I'm going to fast forward to where I am today and then go back and grab the story on, on how we ended up here. So one way of telling the story is that I've been working for the 10 years since I shut down my business, I think it's been 10 years, to get back to a version of it that would work. Or back to a version of that mission that would work, which is now I view kind of the mission of probably my working life, not just this iteration of it as helping people realize their full potential and apply it to solving important problems in the world. There's these two halves to it, helping people realize potential and applying it to things worth working on that serve society, that serve the people in the world.

And It really took me a long time to be able to get back here, to get back to where I can be an entrepreneur again, to embrace the risks and the downsides that I knew very, very personally at that point. And to reclaim that mission because it would have been easy and it was easy for a time to like, write the whole thing off. Well, that whole thing was broken. The mission, the business model, all of it, me as an entrepreneur.

And so in that context, I give that first as that's the end of the journey, right? Almost as like a preface is coming back home to a lot of those core ideas and finding a new way to make them sustainable for myself. At the time I shut down the business, we were multiple tens of thousands of dollars in credit card debt, my girlfriend and I at the time. It was my credit card debt, but we were, we had shared financial lives at the time. I had no job lined up and the investor that I had in the business at the time was obviously not going to continue paying me if I wasn't going to keep working on the business. So I had an income problem that was very real and felt very pressing. It was the number one stress in my life and in my, my relationship at the time.

So I was looking for jobs. So I applied someone that I met at the conference that you mentioned, it was called world domination summit, which is a ridiculous name to say out of context, uh, run by a author named Chris Guillebeau. I'd say it was like creative entrepreneurs kind of service and mission oriented folks, all kind of like online misfit type people before the creator economy was a thing. I met many people there. One of them though, it was a guy named Corbett Barr. He was running a business called Fizzle at the time. And Fizzle was like education for creators before anyone knew that that was a thing. It was if like lynda.com, which has become LinkedIn learning was for creators, that's what it was. We produced all of our own courses in house. We had a whole curriculum and community built around helping people understand everything from coming up with a business idea to hiring people and scaling a team. And I interviewed with them to join as a customer, basically a customer support person was the role they had open, answering customer emails. And they broadened that into a director of customer success, since I had a lot of experience at that point in this world, and I was bringing essentially all of the lessons of failure that I had just experienced of failure of the business model, but also entrepreneurial ambition to a community of people going through the exact same thing.

So I had just been through three years of kind of like the trial by fire, now stepping into a business serving people going through that exact journey. And that was a great benefit, right? I could say, here's all the things that I think I messed up that I would really love you not to mess up. So I stepped into that role as director of customer support. And just said, okay, I'm going to dedicate myself to something that is very well defined. I understand what the metrics for success are. The pay isn't like what I hope for one day, but it's better than what I was making running my own thing. And I know I can be successful at this, like I just needed a win. And so that's why I took that job. And he hired me because I had met him at that conference and he knew me pretty well at that point. And we were off to the races, but pretty quickly I got started getting that drive back and I had ambition for the business. It's like, I want this thing to grow. Because of this business grows, I can grow. And only if the business grows, can I grow. And so I'm kind of dependent on it. So let's create an engine here. And it felt like we weren't really going at the speed. You know, we come back to being this feeling of being held back, weren't growing at the speed that I wanted us to. And so I actually went and interviewed, got recruited for a role to lead growth for a financial tech startup in Atlanta at the time, and got the job to lead growth, making 50 percent more than what I was making at fizzle and with an equity stake.

And so I went to Corbett, the founder, and I said, look, you're my, my mentor. Like, I trust you. I want you to know I've got this offer and I want, I want to know what you think I should do. And he's also my boss, right? So this is a weird conversation I'm sure for him to be having, but I wanted to be open with him about it. And he said, well, look, is it just the money? Is it just the money and the equity? Because, like we have a business here that we want to grow. Why don't you be director of growth here? And we'll give you equity over the course of seven years. And I was like, well, I mean, if I can have that here, all right, let's keep going.

So I became director of growth and over the course of, I don't know, 18 months, like we really built an engine. We really built an engine of growth. We were growing consistently month over month. And increasingly I was in conflict with the other co founder in the business who was more of a creative person and wanted to wake up every day and kind of like, go where the wind blew him creatively. And so I was trying to build systems for growth that were predictable, repeatable, and scalable. And he's rejecting this over and he's like, this is really cramping my style. I feel like I've got a little like boss, like a little boss down here telling me what to do, but he works for me. I don't like this. And we were just not compatible for the phases of life that we were in, what we wanted from the business. And eventually it got to the point where I was so unhappy. I'll never forget. I was sitting in the window of little gluten free restaurant here in town in Portland called Harlow two, three times a week. And I had this list of mantras I would read to myself every morning while I was sitting there. I am a good person. I am good at my job. Like just the most basic stuff. Never in my life before that, never in my life since have I sat and read mantras in the morning to convince myself that I am not broken, but that's how bad it got for me.

And so eventually, Corbett called me to his house one day for a meeting, which never happened. And he said, look, we're letting you go. And I remember being so caught off guard by that, I have built an engine for this business to grow. We have a vision for where we're going and you're firing me? And now I can look back and see that he had a business partner. They were equal partners in the business. And I was in conflict with that person. Like there's only one answer to that equation, you know, 50 percent owner. Someday might be a partial owner in a very small way. Like this person's going to go every time. So I don't blame him for that decision at all. And we're very close today, but again, here I was out in the wilderness still wasn't out of debt at this point, didn't have a clear path to income. So, this was when I really started coaching entrepreneurs one on one. It was like, that was the clearest path to revenue immediately. And I knew that could sustain me while I figured out what was next.

I had this little period where, I went and built a coaching business for probably three or four months where I had enough clients to kind of like pay our rent, pay the basic bills for my girlfriend and I, who's now my wife. And meantime, I was talking to my friend, Nathan Barry, who's the CEO of convert kit, also who I had met at the world domination summit. And he and I had been mastermind group members for a number of years. At this point, every Friday we would gather with a group of people and hold each other accountable to our entrepreneurial goals. And that started back when I was at living for Monday, running my own business, and we just kept meeting and they were all running their businesses. And I was working for fizzle and kind of like looking at it through the eyes of as if I owned fizzle, you know, how do I continue to grow this thing? And Nathan had come to me a couple of months before I got fired and said, Hey, why don't you come work at convert kit and lead customer success here? Like we need someone like you right now. And I was like, no, no, I got a good thing going. We're growing this business. Like I'm committed. So I get fired and I'm like, Hey, Nathan, I'm available. And he says, well, you know, it's rather inconvenient because I tried to hire you not that long ago, but I don't have any roles now I filled all those roles that I needed you to fill.

So anyways, he created a role for me. It was leading special projects. He had all of this list of stuff he wanted to do, start a conference for creators that became craft and commerce, do a documentary series about bloggers at the time to basically tell the story of how people are in a living this way and show that it's legitimate that became I am a blogger, and now I am a creator, which is this long running documentary series. I want to run an annual survey to do like a state of the industry report about bloggers. We started that, that's now an annual report that still runs to this day.

So I took on this, this role and that just eventually grew into leading growth there as someone left that role, and then the twist in the story is I decided I wanted to leave there too. I noticed some of the same patterns. It was not going as fast as I want it to. I felt like, there was just a lot of internal conflict. People didn't love my relationship with Nathan. They were threatened by it. I said, you know, I don't want this in my life. Like I don't need the negativity. I don't want the conflict. I don't want to be looked at as a bad person because I have a friendship with the CEO.

And I found this job at a job listing at a nonprofit called Acumen and they're based in New York. They're a not for profit led by Jacqueline Novogratz, who's an author and founder. And she was using the tools of finance to fund local entrepreneurs on the ground and developing nations to solve local problems through entrepreneurship. And was so inspired, it was like entrepreneurialism, deeply mission driven work. It felt perfect for me. Well, Seth Godin happens to be on the board. So I emailed Seth Godin and I say, Hey, I'm applying for this job. I wonder if there's anything, you know, that I should know as I go into the interview process. And he said, yeah, call me. I'll be a reference for you as well. But as long as you're coming to New York to interview, I'd love you to interview with me. Cause I'd love you to come to work for me. And I'm like, what in the world? No way. So I've got two great opportunities. I ended up taking that job with Seth and told Nathan, Hey, I'm leaving. And we had this long discussion about why, two days went by, we told the team I was leaving, like there was lots of tears and emotional departure type stuff. Nathan came back about two days later and he said, Hey, what if you didn't leave? What if you stayed and you became the COO here? And you're kind of my number two running the whole business. And so now I have this conundrum, right? I have this person that I respect and adore. He's the number one person I've ever worked for that I felt like, led me in a way that inspired me and helped me really grow in Seth. And I've got this other opportunity over here, that's worth a lot of money potentially to my family. What do I do? So I did what I always try and do. And I was open. I went back to Seth and I said, look, here's the situation. I need your advice. I know it's hard for you to be objective, but like, I don't know what to do, honestly. And to his great credit, he gave me great advice. And he just said, look, I think you should do what you think is best for your family.

And I look back at that decision now. And what I realized was I made a money driven decision at the time. I said, I think that this role is COO of ConvertKit with this equity package is more likely to generate generational wealth for my family. And I think that would unlock the path for me to be able to do whatever I want for the next 30 years of my career afterwards. You know, let's say I have to invest a decade and from there I might be able to do anything and be free of the financial burden.

Barrett Brooks: I don't know if that was the right decision, but what I realized now from the end point that I told you at the beginning of all of this is, I was trying to solve the problem that I created when I went into debt. And my business failed, which is that I didn't figure out the financial piece. And the story I was telling myself is if I permanently figure out the financial piece, I can finally do the work that I was trying to do back then. I can finally be mission driven. I can finally serve people. And I think that was a false dichotomy. I think that was a story that I told myself that led to a lot of disappointment over time but nonetheless, it did lead me to being CEO of the company. I think that it was a role that use a lot of my skills. It used the consulting type skills that I built in my first job. It leveraged all of the entrepreneurial skills I built in founding my first business, it leveraged all of the knowledge about growth and operations that I had built at fizzle. And then also in my first couple of years at convert kit, it brought it all together in this role where, and then there was this other vein of like studying, how do you build great cultures, studying social psychology, people like Adam Grant and Kim Scott, and a lot of writers who talk about how to build great companies. And this was like a test ground, Hey, are your ideas any good? Can you actually implement them in a way that makes a company grow?

So that was how I ended up COO. And It did not end up creating generational wealth for my family. It generated a decent financial return, but I left that role eventually. And I still had to wake up and figure out what to do for money. And so in some ways I was better off, I had more freedom, but I still had the exact same problem. I was trying to run from, and ultimately this comes back to the thing I said earlier, I didn't take ultimate responsibility for the consequences and responsibilities that came with starting that first business. That was the thing I had to come back to was, even though I've had some financial wins now. We don't have enough money. Let's say you need $8 million in investments to live off of from the age of 35, you know, at my family's like cost of living or whatever, and all of the obligations that I have, that's just not reasonable. The odds of that happening are almost zero, like literally almost zero. One way of thinking about it is, well, if I just get $8 million or $4 million, whatever the number is, then I'll finally be free.

Another way of thinking about it is if I just design a business model that can pay for my family's like lifestyle and what we need. I can do whatever I want. And that was the thing I eventually had to arrive at so that I could come back to this mission of helping people realize their potential and apply it to important problems in the world.

So that's a very, very long story to get back to, that's how I ended up COO, but there were some important learnings and turning points along the way.

David Elikwu: Yeah, I think there's so many different strands I'd love to pull on. I'd like to start, just because I think in terms of the, the meaning and purpose stuff, there's probably a lot more we can connect that to in a bit, but I'd love to ask more questions around the, the development of competence. In that role, particularly as COO and first of all, was the weight of responsibility, did it feel dramatically different stepping up then into that role, considering the context that you'd mentioned about, Hey, some people already have concerns about your, your relationship with Nathan, et cetera. And now actually you're going to take on all of those responsibilities. You're going to have to lead some of those same people. It's not like they're all leaving, and you're going to have to help to drive the business forward. And then second of all, now, I think, you know, you have gone from level to level. You've gone from, Hey, this thing you started yourself maybe working with Seth in between working at Fizzle, working at this other place. You have gone up the steps, but now you're kind of getting to a step that you haven't necessarily been at before.

And I mentioned this just even thinking about the context of, I think the last time we spoke, I was mentioning. You know, I was previously working at a startup, which grew incredibly quickly. I think, when I joined, we were kind of, we just raised a series B. We were kind of in the process of growing from about 50 people to 150 people. And from there, within about three years, we grew to 450 or more people. And that was, first of all, a really incredible journey. It was a great journey to be part of, it was a lot of fun. It was also incredibly, there was a lot of turbulence. It was, there were so many things you learn from scratch, like what it felt like to work at a business or, you know, be part, especially, you know, a senior ish level or having some oversight over the business. So I was in two roles there first as chief of staff. So I reported directly to one of the co founders and then I wanted more product experience. I moved into the product team and kind of created a role for myself there. In so much of that, there was so much yawling for the first time. Like I have no idea, you know, I've worked at a big corporate law firm, you know, one of the biggest firms in the world, blah, blah, blah. But what it feels like working at a company that has, let's say up to 150 people is actually completely different to, I think, 150 to 350 people. And then, past 350 people, that is, well, and this is partly why I left. That's now a corporate job. Like you now work for a corporation. This isn't a startup anymore. It's a completely different thing.

And I think there's two things that I was weighing up and I'd love to hear your thoughts on that. Like on one hand, it is, you have to upskill dramatically. Like I can even imagine. I know that Convertkit was intentionally kept a lot smaller but going from, I think, 20 people to 70 people or so, I'm sure there's multiple step functions there where a lot of complexity is involved there's a lot that changes in the kind of relationships that you need to work on. There's a lot that changes in terms of how the business works and what is required to drive that forward. And then simultaneously, there is your own internal work, like you were just talking about, where there is actually something that I want from my life and at these different stages, how well aligned is this work that I'm doing.

Barrett Brooks: So one of the questions that was present in my mind throughout all of this is, this worry of failing upwards, if you've heard that term before this idea that like, I inhabit a white man's body from a middle class family and like, it's the most likely profile where you get to fail upwards. That's just the reality. That would be the worst possible outcome in my mind is that somehow I am just being afforded opportunity after opportunity, despite failing previously.

And so I tried to check myself realistically on that and make sure that there was real substance and every step of the way. You know, there's no ultimate judgment who's the arbiter of whether you are or are not failing upwards. But here's my assessment of a quick assessment of the steps along the way.

And my first business, I succeeded at growing audience, but failed to find a sustainable business model. Okay, So maybe we're 50 50. At fizzle, we built a great customer support, like engine that I hired someone in to replace me for that still works, or still work to like after I left. Okay, that seems like success. And growth we generated an engine that was working. We were growing consistently month over month. When I left, actually, this was interesting. I got happy hour with the team about 18 months after I left. And they said, you know, I was looking at the metrics the other day. And I realized that from the day you left, we have been flat as a business. And for the year prior to that, we had grown consistently. And we attribute that to the system that you were running that we didn't maintain when he left. I would say that's half a success and half a failure. It's a success in that we were growing. I think it's a failure in that it was not sustainable after I left. Now you could argue whose responsibility that is, but it's like, okay, so I don't know, maybe we'll call it 70, 30 success, failure. And then stepping into convert kit, it's like our marketing was working, but I started to question myself because one of the other leaders in the company kept saying like, why aren't you guys doing more? And I'm like, well, am I succeeding or failing? I'm not entirely sure. Now, as I look back, I think knowing everything I know now, having led that company for having a three person marketing team, we did an incredible amount of work. I've, I have never been a part of a team that did that much work per person than that one. And so I feel very good about that.

So anyways, that's a little bit of a self justification, but I think it's an honest look back at, I really wanted to make sure I wasn't just failing upwards. And that tees up my answer to your question, which is that in some ways, stepping into that COO role felt like the first role where the title responsibility and accountability matched the way I was acting in my job at work, it felt like I have been acting like an owner, being a partner on strategy with Nathan this whole time and this role finally creates a container for that to be official. It did create lots of complications with, for example, the other leader in the company who was very accusatory about our quality of work and like, were we doing the right things and all of that? Eventually that got toxic enough that we had to let him go, to be frank. And I think that that's a common thing when peers work with one another and one of them gets elevated to a core leadership role where the other is subordinate to them. Like, even if it's not positioned that way socially, like if in fact someone is subordinate, that used to be a peer, you see this at corporations all the time where you have this kind of like horse race for succession and one takes over the other one always leaves that's just how it goes. So we had some of that.

I felt like that role was the first role where I was appropriately placed for what I felt my skill level was. I thought that my skill level, my understanding of business, my understanding of team building, hiring, all of that stuff was such that I was fully prepared for that role. And Nathan and I actually just recorded a podcast for both of our, our shows that you can listen to if you'd like to about all the details of what we learned together, but one of the things that made me walk away from that role was I felt like, we were artificially limiting our growth by limiting team size. And by trying to optimize for too many metrics at once, we were trying to optimize for profitability, top line revenue growth, and keeping the team small. And I think that those things were inherently in conflict with one another. And it limited our growth in a way that was not dictated by the market. And that I think left us vulnerable to companies like Substack, Beehive and others coming in and claiming market share where we had a massive lead in the market and should have not been able to to lose any of it really based on our position. I felt like I outgrew what Nathan was willing to outsource in that role. Eventually I realized that my frustration level was so high with that, that I was burning out, that like the frustration of not being able to execute in the way I thought we should was what made me burn out, not working too hard, not being overextended, not being in a role that I felt like I wasn't competent at, it was I wanted to go 70 people to 200 people or whatever that looked like to drive growth. And as a organization, we were setting strategy that wasn't aligned to that.

So in some ways, I think I never really hit my competence edge. Like I'm still seeking that there are days when I feel maybe I'm getting there in my own business, but mostly not like I'm still seeking the competence edge, I want to find out where that's at And it makes me, that is a thing that makes me want to run a company again. There are lots of things that make me not want to run a company again, but that's one of them that makes me want to.

David Elikwu: Okay, something you just said, there's a question I'm going to ask you. I'm going to take a step back and ask you the, the first question that I had in mind. The second one was something that it's funny as you were just speaking now, I was thinking, Oh, you know, this is something I want to ask you after.

And then I just thought, actually, I would just ask you right here live because why not? But going to the first question, I'm really interested to know, based on what you said, do you think things would have shaken out the same way if you and Nathan weren't friends?

Barrett Brooks: No, definitely not. There's no way that someone without experience being the COO of a company would get hired to be the COO of, I don't know what we were when I took over as COO. I don't know, 12 million, 15 million, something like that, maybe. We did something like 10 to 30 ish when I was COO. You don't get hired as COO $10 million company without having an end. No way.

David Elikwu: Yeah.

Barrett Brooks: Absolutely not.

David Elikwu: I actually also meant the other part of it, which was with you leaving specifically at a point where, and I think about this because I've also been a co founder of a business where the original founder is a good friend of mine, and I wonder the extent to which that creates its own sense of conflict, where sometimes you have conviction and you believe a particular thing, one, you're not the founder. Like you, you're not the, the original founder. And then two, this is also your friend. And I wonder how that changes the dynamic compared to if you are hired into a role just as an executive and the extent to which you not just feel like you can challenge the person, but you're not really inhibited by, Oh, my personal feelings towards this person, even if I like them, but the context of the relationship is different.

Barrett Brooks: Yeah. Oh, it definitely affected the relationship deeply. I mean, for one, we love each other deeply as friends and that will always impact the way you interact with someone in positive and negative ways. I think that there were times where we probably said things to each other that we would never say to just a coworker in negative ways. Whether it was like referencing personal life things or just what we were willing to, where we were willing to go. I don't think we ever did that in purposefully hurtful ways, but I think there were times, you know, like if you're in a, in a long term relationship with a spouse, there are times when you go way back into the past and say something about something hurtful from a long time ago now, because it's useful to you. We do things like that in the relationship. That's not helpful, you know, you don't do that to a coworker or you don't in a healthy organization. And so we had little things like that, that would happen occasionally. That was not the predominant nature of the relationship.

It was very difficult for each of us to continue to update our view of one another based on reality because we had known each other for so long, you know, it's like, when you know someone from the age of five, you might think of them as a version of them that they no longer are. Just by nature of knowing them for a long time. And this is commonly why people, when they leave organizations, they'll go get a job that's like a massive promotion somewhere else with a lot more pay. And everyone in the organization they left is like, wait, what? And then they do a great job. And it's like, Oh, they were just being underestimated, you know, because you had a view of them of where they came in.

There's this other concept that the longer, you know, someone, the harder it is to keep your view of them updated for the present. So if you knew me back when I was trying to run living for Monday and that business was failing, you might continue to think of me as the person who was not able to figure out a business model for the first business I started like, that might be your view of me even today. I don't think Nathan did that either on purpose or to that degree. But I think there was an element of that for both of us. Like we knew each other when we were nobodies doing nothing with no success under our belt.

And so updating your views to reflect an accurate picture of a person's present abilities at work is very challenging, very, very challenging. And I think that affected the relationship for sure.

And ultimately, as we talked about in our conversation on our podcast together, Nathan and I, I think that there was an element of deferring to one another too often. Like we never fully defined what decisions are yours and what are mine. And can we really, really trust each other to let go of that set of things mutually so that we can operate better.

And I think if we had been more aligned on that. And I don't know that we could have without going through it together. So let me just say that too. But if we had been more aligned on that, and if we had trusted each other to occupy our seats in the organization, and then truly said, okay, this is the North star, let's go get it. We might still be working together. And I think we both know that. So it would not have worked out that way if we weren't friends, for sure. If we hadn't had all that history, I don't think it would have worked out that way.

David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time.