Billion Dollar Creator

Barrett Brooks: [00:00:00] We got divorced.

Nathan Barry: We did.

Barrett Brooks: At the time, you were the CEO of ConvertKit, and I was leading marketing. Little did you know, I'm leaving the company.

Nathan Barry: First thing, I thought the timing was really interesting of when you told me.

Barrett Brooks: And then within probably two minutes, we were both crying.

Nathan Barry: Also true.

When I look back, things I wish I'd done differently.

Embrace that role as CEO and decision maker. I was listening to so many people trying to make a collective decision.

Barrett Brooks: We should have fired more people for lack of performance. This is what we need from you. If it doesn't change, I will fire you.

Nathan Barry: I still feel like we could do our marketing so much better.

Barrett Brooks: Creators look to creators they look up to for what tools they should use. And how they should run their business.

Nathan Barry: We didn't tell the right stories loudly enough to the right people.

Barrett Brooks: If we rattled off top 25 most well known people using ConvertKit, people would be like, wait, what? Where did y'all come from?

Like, we've been here, b****.

[00:01:00] Welcome to my show.

Nathan Barry: And welcome to my show.

Barrett Brooks: We're running this on, on both podcasts. The place I always try and start with my show, and that I think will be fun for everyone to hear, is Kind of like right before you got eaten by the bear, as they say in writing, you and I were taking a walk down the boardwalk in beautiful San Diego, uh, at sunset at sunset, holding hands, uh, on a team retreat.

At the time you were the CEO of ConvertKit. You can wait for the news on that one here at the end of this show.

Nathan Barry: Look at that clickbait that's happening right now.

Barrett Brooks: Uh, he's still the CEO and uh, and I was leading marketing. And I asked you to go on a walk and you're like, yeah, that sounds great.

Walk with my friend.

What could be better?

Nathan Barry: I think we had just gotten through like a strategy announcements with the team, like saying the mission and vision for the next five years, those typical things.

Barrett Brooks: Little did you know,

Nathan Barry: yes,

Barrett Brooks: that in the background I had been, uh, I had been scheming on my own career that makes it sound [00:02:00] so I had kind of like pushed you at the time to name a number two ish kind of leader in the company.

And, uh, there was a guy at the company at the time that seemed like the obvious choice. He had more experience in. In tech than me. And so you had made that call. I felt like, okay, this is a good time for me to exit basically. And so I asked you to go on a walk. And, uh, at the peak of this, we get down to a pier and I'm probably sweating bullets at this point.

Like, all right, when's the right time to tell him? I think I literally said the first line was I'm leaving the company. And you were like, what? I think literally your jaw dropped. Um, and then within probably two minutes, we were both crying.

And I thought, all right, feel some equanimity. We've got transparency now. This is good. We let the team know the next day, like half them started crying at the time. It was traumatic for everyone. So what happened from your point of view at that time?

Nathan Barry: Yeah. So first we, we [00:03:00] were going through a lot of changes.

We were gearing up to change the name of the company.

Barrett Brooks: We were,

Nathan Barry: that was a big moment in time, but the first thing I thought the timing was really interesting of when you told me, because it would have been easy to let me know before the retreat. And so we had a good size team. And I remember you talking about how important that like moment was to set the mission and strategy for the next, you know, five years of ConvertKit and how you wanted to make sure that like, I totally nailed that.

And there wasn't anything in the back of my mind like distracting from that. And so that was the reason to like tell me a few hours after.

Barrett Brooks: Right.

Nathan Barry: After that. Like it was interesting going, playing through the rest of that week as we like led in the company together, had all those conversations and kind of planned your exit.

And I just kept having that feeling of like, no, I think Barrett's the right person for like this next phase of the company.

Barrett Brooks: I mean, it created chaos for sure for a little while, and then we kind of settled into [00:04:00] it, but it was one of the early decisions, I think, where you really asserted yourself, um, number one on my behalf, which I was very grateful for, but number two, just generally as a leader in the company saying, I'm actually not really going to ask anyone's opinion on this.

I'm just going to kind of do it.

Nathan Barry: Right.

Barrett Brooks: And, and I think over time you've shown more and more of a capacity to do that and the company to like really take on that. I'm the leader. This is my company and I'm going to be a benevolent dictator. You know, I think that's the way Matt Mullenweg puts it. I think he put that on Tim Ferriss's podcast is like,

Nathan Barry: well, there's a lot of growth that happened through that time.

You and I both are huge fans of reboot and something that they always say is they have this phrase of take your seat as the leader. Yeah. One thing that they observed early on is that I was so like listening to so many people and trying to. Um, make a collective decision that it would end up leaving everyone [00:05:00] really, really unsettled.

And so what they were really pushing me to do is to embrace that role as CEO and decision maker. Right. And they're basically noticing like when you did that, when you made clear decisions, like took your seat as leader, because I had this idea in my head that like, Oh, if I make a decision counter to what.

executive or leader at the company is saying, then I didn't hear them, which is not at all good leadership,

Barrett Brooks: right? Okay. So fast forward, right? So where we are today. So we led the company together, me as CEO for three and a half years. So it's been almost three years now since I've been out of the company, but we built it for three and a half years together.

So we, in my time there, I think I got there like right around 3 million in revenue. And when I left, it was like 28 and a half or something like that. I always round up to 30 cause it's close enough. And now you're at 40 ish low forties. Um, so you know, the company has been, it was fine before me. It was been fine after me.

Uh, which is always both humbling and awesome. And so we're kind of like [00:06:00] looking back at that journey a little bit and we learned a ton of stuff. I was going to. I. I do cuss on my show, but I try not to do it as much as I would normally. Uh,

Nathan Barry: we learned a f- ton..

Barrett Brooks: We learned a f*** ton during our time together.

I thought we could get into some of what we learned together. Um, and then how we think about kind of our creator efforts. Cause you also, you know, you make this show, um, you write. I write, I make my show, I'm doing my coaching now. And just kind of how we think strategically about those things at this point.

Nathan Barry: The blend of personal brand and building companies. Yeah, exactly. Yeah. I love it. One thing, one story I was thinking about, cause we both struggled with this and I bet a lot of founders and creators struggle with it as well, is that it's basically when you, when you're the person who figures it all out as you go along and you have no expertise or credentials to back up what you're doing, how do you actually build the confidence?

[00:07:00] To Using that phrase take your seat as a leader right and make decisions and like lead with authority and there's an example Elizabeth who's my executive assistant. She's not on the team for six years now

Barrett Brooks: incredible human being.

Nathan Barry: She's she's amazing She was executive assistant to the president of Columbia sportswear I think we iterations of an executive team and all of that.

We're trying to figure out Like how to lead, what decisions to make. We had one leader on the team in particular who I won't single out, but they would often bring up like, well, this is the industry standard way to do it. Like that was kind of one of their go to lines. And Elizabeth would say, she would tell a story that the gist of it was basically like at Columbia Sportswear, which was this multi billion dollar publicly traded company.

They did it differently, you know? And her point was like, there's not an industry standard way of doing it. Like take the information in front of you and make your decision. And she was like, Quietly always trying to build me up as a leader and as a decision maker. When I look back, like things that I wish I'd done differently.

And we were talking last [00:08:00] night about, um, what would we have done differently? One of the things is to make decisions much faster. We would agonize over decisions for, you know, sometimes months or multiple months when they really should have been 24 hour decisions, maybe a week at most.

Barrett Brooks: Right. There's this interesting kind of like spectrum there of, Sometimes the way things are done in companies is for a good reason.

It's like people really have figured things out that work really well. And then there's other times where things are done a certain way for completely idiotic reasons that no one knows. I do think we, we gave ourselves the freedom to operate differently. I mean, I always talk about my, my time at ConvertKit as, It was like my chance to test a lot of the things that I understood theoretically to be true about building company culture, creating psychological safety, getting performance out of people.

You know, you read enough books on this stuff, whether it's like Adam Grant or Kim Scott, or, [00:09:00] but if you don't have a place to apply it, it's just vaporware, you know, who cares? It's like the ideas. So I always felt like ConvertKit was a little bit of our kind of lab to see, you know, could we make these things work?

These ideas that we had about. How companies could or should work if they were done properly. You know, we always laugh because people are like, Oh yeah, remote was the thing. And now of course, like post pandemic, who knows? But we had been remote forever since the company started. I mean, you started it remote.

Uh, you know, people were like 2020, 2021 creator economy is everything. It's finally exists. And we're like, what do you mean?

Nathan Barry: It's been around for a long time.

Mark Andreessen did not invent the creator economy. Okay. If anything, YouTube could maybe take credit for that whole trend. But ConvertKit got started not that many years after YouTube did, and it's been around forever.

Um, so anyways, all of that to come back to say. I do think we did a good job of letting ourselves try [00:10:00] things that were not always proven. We didn't always see a model in the world for. Let's run through a few of those of the ones, maybe the list of what worked and what didn't just off the top of our heads.

Great. I agree with the decision making thing. I mean, you and I, we were talking about this last night too. I think that there was a little bit between you and I where it was like. Kind of trying to like make sure we were on the same page. And then there was like the executive layer of the company. And then we were like pinging off of them.

Like, well, how do you feel about all this? And then there was the team and aligning at every layer of that was so much work. And that's part of the job. So I'm not complaining

about that. But I also think the more effort we put into. Checking with every layer to be like, do you agree with this? Are you good?

All that like telegraphed a lack of confidence and ended up making it harder to implement these decisions or bring it through. Cause it's like, no, I'm good. But do you actually think that's a good decision? Your body language and your tone and everything tells me that like the fact that [00:11:00] you're asking me makes me think that you don't believe in this, which makes me believe in it less.

You know, it also opens

Barrett Brooks: this window where if you're on a team, it's And an executive comes to you to discuss a potential decision. You feel like you have agency in that. If I weigh in, this could change what direction we go. And if in fact, what we were saying is this is what we're going to do. And we're letting you know, that's totally different.

That's like clear of where we're at in the decision process, right? and I think that we we probably aired way too much on the side of consensus building and Making sure everybody was on the same page and not enough on having the confidence To use the reboot language of like taking our seats and saying look we don't know everything But based on what we know this is where we're going and there was even that between you and I I think at times where?

We wanted to be in lockstep For good reason, right? Like you want your most senior leaders to be in lockstep, but there were probably some times even where We disagreed [00:12:00] and at the end of the day It was your company and you were the CEO and you probably just needed to tell me sorry This is what we're doing, you know And I was not very good at accepting that all the time, right?

so I would have needed to kind of like Get okay, actually being number two and not like trying to be the co decision maker on all of it

Nathan Barry: We built a company culture that I'm really really proud of and there's so many things in there that we shaped along the way from Crafting like our feedback culture to profit sharing to all of these things You know what happens how we do retreats and so there's a lot of huge wins there.

I think we struggled to find the balance between building a culture where everyone felt safe and heard and, and cared for in building a high performance culture. And we held those things in conflict and tension with each other when in hindsight, I don't think they actually are. And I think that we created a lot of strife between [00:13:00] us and the team because we, on one hand would be like really emphasizing the softer sides And then like more quietly between us, we're like, but we're here to win and we want people who are here to win.

Barrett Brooks: Right. Because we're both very ambitious and we can have a little bit of a competitive streak as well. Um, not necessarily between us, but just as human beings and between us when,

Nathan Barry: you know, there's some like viable to be played basketball or volleyball or something like that.

Barrett Brooks: And so I think that we had this sense of like, And we're not just saying we want to build a hundred million dollar revenue company.

Like that's where we're going. I love every person that worked for us. And, uh, and that's still at the company that I got to work with. And so I don't direct this at any one person, but one of the ways that I put this and talking about it just internally to myself, but also with peers is we should have fired more people for lack of performance, because ultimately in reflecting on [00:14:00] my own, it's like.

Whatever median performance you tolerate becomes the expectation of the company. And so if you have very, very highly talented and driven people sitting next to someone who, for whatever combination of reasons, whether it's we demotivated them or didn't lead, well, they don't want to be there. They're in the wrong job for their career progression.

They're having a hard time in their personal life. Whatever is happening, that's driving the lack of performance for them. people are sitting next to each other and we tolerate this level of performance for this person. And we're, but we're saying we want high performance from everyone. And then these two people get basically the same profit sharing check as an example.

What does that say? It says your extra 20 hours you're putting in a week just to use time as a proxy for effort, even though that's not how we thought are useless. You're getting paid 50 percent less for those hours than this person who's mailing it in. That's just not a good [00:15:00] way to encourage people to operate at a high level.

And I think there were times probably where we, where I know I feel like I erred on the side of kindness and believing in people's potential and trying to build them up beyond the point at which they needed to take their seat. Yeah. And say, okay, I'm going to step up and be a part of building this thing into a juggernaut basically, which is what we wanted.

Nathan Barry: Yeah. And so we, we kept those ideas in tension and I think probably really confused the team in the process. Like I bet it was pretty confusing to work for us where the, like there's this gap between what we're saying and like the standards that we're holding.

Barrett Brooks: Yeah. In my coach training, one of the concepts that we learned about was, um, was polarities.

And the idea of a polarity is that. Sometimes it can feel like something is on either end of a spectrum that they are opposite to one another and that in a polarity In fact that things can be intention in a balanced way that they are [00:16:00] forces that belong together. And so a simple example of this would be how committed you are to your family and how committed you are to your work.

And you can kind of think of it as like an infinity symbol of how you kind of vibe back and forth between them. And at any given moment in time, you might be erring on one side or the other. And there are probably signs of that. If you're too committed to work and not enough to family, uh, you might be experiencing tension in your marriage.

Your kids might be acting out. Um, you might be feeling lonely inside, you know, any number of symbols, right? Tendency is to think like, oh, well, I better go way back over here and focus on family since I'm focusing too much on work. One of the key concepts that I learned was that actually when one side is out out of balance, you have to stay there and fix that first.

It's to like, in this example, right size, the work commitment first, and then bring it back into balance with the family thing. And so I think if we could have thought of it more as a. Uh, kind of fluid back and forth between those things that we can both care for people [00:17:00] and expect high, high performance from them.

Or even if we could have held it as expecting the best from people is a way to care for them, right? Help them reach their potential. That probably would have been healthier for us in leading and the team and their experience of it.

Nathan Barry: I think we would have also done, done a service for people in their careers, where if they'd been getting specific feedback over time and not acting on it,

Barrett Brooks: yeah,

Nathan Barry: then.

In letting them go, that might be the thing that they need to truly internalize that feedback and actually act on it and then get that sub function in their career. Like, I think there are multiple people, people that only after leaving ConvertKit, did they have a level of growth, you know, as individuals and professionals, because, you know, we held them back.

The other thing that I thought about a lot is like, as you build the team, being proactive and curating the team. So I was having breakfast with the founder. Who built a team to 30 people, um, and scaled pretty quickly. And we were talking about how to scale from there and, and [00:18:00] what was most important, you know, he just said like, Hey, at least five people on that team, if not more are not the right fit for this next stage.

He's like, I don't know. I think they're great. And I just came to brought back a question, which I think we got from the software 15, five, which it has in performance reviews. It's if this person were to leave, how would you feel? How hard would you upset? Would you be or something? And it's like all the way from distressed to a neutral and then you get relieved.

Yeah. You know, all, all the way. Happy. Yeah. When I like brought that question up at the founder, you know, it's like, okay, well like go through your team. Like if you rated them on this question, how would you feel? And he was like, oh no, I immediately can think of five people where I would be somewhere between.

Accepting and relieved right if they left and I think that You have to act on that.

Barrett Brooks: Yeah,

Nathan Barry: and

Barrett Brooks: well, here's what's crazy is we did that exercise, right? Regularly because it's a good exercise as a leadership team. I don't believe in the stack ranking thing. I think that's [00:19:00] totally toxic No

Nathan Barry: treat everyone individually exactly then it's not

Barrett Brooks: relative to each other.

It's just Relative to this person's potential contribution or the role, the role's potential, potential contribution, which is what do we need from this role? Is this person delivering on that? That's really the question to ask, right? And if it is maybe average at best, you should be thinking about, okay, two options, one, is there something I can unlock in this person to help them get into this like top bucket of totally delivering over delivering, like on a great path and trajectory.

Or do they need to leave? One of the experiments we didn't get to run because lawyers hate this idea That's a great

Nathan Barry: tagline.

Barrett Brooks: Lawyers hate this idea. Lawyers hate this idea because of just the litigiousness of society is I really wish that we could have Run experiments on basically like conscious uncoupling for firing people because a conscious uncoupling is this idea and [00:20:00] like Divorce basically where it's like what if it didn't have to devolve into this like toxic mud slinging thing?

And we could be a little more thoughtful about this. So the typical Letting go of someone is a meeting. There's an HR person to make sure you don't say anything stupid And you say, today is your last day, you've been fired, here's your, like, NDA and, uh, and severance package. You can sign it and take the package, or you don't have to sign it, you get nothing.

And they go home, and they're in shock, and they talk to their partner, their spouse, or their kids, or whatever, and it's like, what do I do now? And so one of the big things I'm curious about is, Why don't we do it more like what, like we did with me when I left, which was very intentional, you know, it was driven by me.

Um, well it was mutual, but I mean more like I was quitting, I guess we were, it was time to move on. It wasn't like, get out of here. It was over six months, right? What if you gave people 45 [00:21:00] days and said, look, we're going to wrap up. We want you to finish out your role strong, have time to say goodbye.

That's kind of like your severance. We want to actively help refer you to jobs that you could take so that you're in a good spot when you leave. Why is that not the standard that we operate with? And the reason is you don't want to get sued and this and that. You don't want somebody to sabotage your systems and all of these nefarious reasons, right?

And I

Nathan Barry: know someone, like, I want this so much. Yeah. I would say nine times out of ten, when someone leaves the company, either on their own or they're let go, it's a surprise for one party. Yes. Either you're on a boardwalk in Oceanside and it's a total surprise for the company being left, right? Or it's a total surprise for the individual where it's like, Hey, today's your last day.

And I like deeply believe that it could be different and that it should, especially with people who have been on the team for a year, five years, like an extended period of time. It usually doesn't work out that way. This is one of those things where it's like how I want the world to work and how the world actually works.

And I've heard of people getting sued in situations like this where they try to. [00:22:00] give someone a, a good transition plan. Right. Um, and we've actually done it. I, I won't share on the podcast with, uh, you know, who, who it was because I'm sure team members will listen to the podcast and hopefully get some good things out of it.

Yeah. But you know, you and I together did this with someone, we're like, Hey, you know, this isn't working out. We need you to transition off the team. But it, like, it could be over the next 30 days or, or more and all that. And you know, we'd like to talk about when your last day would be and all that. And they just said today, today will be my last day.

I had forgot

Barrett Brooks: about that. That is true. We did try and do it. That's right. So another piece on this though, is that I do wish I had said more often to people. We have reached the point where you are not performing. Right. I want to help you over the next 60 days, 30 days, whatever the plan is. Basically they're on a PEP, a performance improvement plan.

Like, yeah, this is what we need from you. I'm going to do everything I can to help you. I'm not going to do your job for you, but I will do everything I can to support you. And if it doesn't change, I will [00:23:00] fire you. I really wish more people would say that to people because that's what makes it clear. When it's explicit, you will not be here anymore.

If we can't change this, right? That people are like, Oh wow, this is serious now. Like I got to really get in shape or You know what? You're right. I got opt out. So I do wish I had

Nathan Barry: said that more often. I think so. We run into this, we're talking to a manager and they're like, yeah, I had that conversation with the individual.

And you're like, great. And we kind of assume what the manager said and what was heard are the same. Right. And there's really probably four stages. There's what the manager intended to communicate, what the words that they actually said, and there's usually a pretty big gap there. Yeah. What the person heard and then what the person actually internalized.

And so when you go from what they intended to communicate to what was internalized, it's often a giant gap. Yeah. Like you might've lost 75, 80 percent of the communication. The manager is probably like, [00:24:00] if you don't fix this, I'm going to fire you. They say some watered down version of that. It's a watered down version that it's heard.

And then what's finally internalized is like. Hey, there's some, you're doing a good job, but there's some things you need to work on to do a great job. Yeah. My

Barrett Brooks: boss is

Nathan Barry: pretty nitpicky, you know, they really,

Barrett Brooks: they're like

Nathan Barry: picking on me over here. And most of the time, I think the problem in that lies with the manager and that feedback, because there's such a big gap, like they don't want to hurt feelings or whatever else.

And that's where like the followup in writing is so important because you're like, we talked about this. Cause

Barrett Brooks: you have to think about it, right? When you're receiving feedback, anyone, even if you're great at it, You have a stress response to that. It's very rare not to, and a stress response shuts down part of your brain.

And so anytime you're getting feedback, it is not processing in real time, all of the words and all of the detail. And you know, so many people say like, well, but if you put it in writing, then it's serious, you know, then I like I'm in trouble and it's like, well, I mean, you were in [00:25:00] trouble regardless if you want to frame it that way.

Whether it was in writing or not is just, are we clear? You know, we had an exec at one point, anytime I had critical feedback, I really tried to write it down because I wanted to be clear, you know, and I wanted to know that I had fully communicated and this exec would be like, why did you write that down?

Now it's on paper and I have to like, worry about that. And I'm like, whoa, that's the point. Like, I do want you to worry. I want you to work on these things. That is the reason. And if I write it. Now you can process it in your own time. And I know I, we can refer back to the same document and say, Hey, on this date, we talked about this thing.

How's it going? Yeah. And support them in that. Right. Whereas if it's just spoken, you might not even remember what you said.

Nathan Barry: It goes back to Brené Brown's clear as kind. Yeah. And the number of times where you're saying like, I could say this, but it wouldn't be nice or, you know, it's like, we're not going for nice.

We're going for kind and clear communication is kind. Yeah. And it's such a hard skill to [00:26:00] build and at whatever level of business you're building, whether it's as a solo creator working with freelancers or the three person team or the 30 person team or the 300 person team. If you can build those feedback skills, everyone is going to thank you for it.

Barrett Brooks: Yep, for sure. And honestly, 80 percent of my coaching work is that, uh, there's the inner game of the entrepreneur and what's going on for them and what they want and getting clear on that. And then it's the relational game. And so much of that is driven by an entrepreneur knowing what they need from someone and then being clear about it repeatedly.

Yeah.

Here's what I need. Here's what I need. Here's my expectation. Here's my expectation. Okay. So we've harped on this a little bit, so I want to go to, to a couple of things. So one is we did a lot right in the culture and I think there's probably some things there that we can get into. And then also, I mean, obviously the company is huge.

Like we've done some things right on growth that would be helpful to reflect on. And then [00:27:00] also kind of where we probably made some mistakes. I don't want to bum people out, but honestly, performance management and like making sure that you're setting the standard is such a massive topic for leaders. And it really is one of the most important things.

And. You know, to right size it. It's not like I think we needed to let go of 80 percent of the team at any point. It was probably like consistently every year, maybe we needed to let a few people go to just keep the standard. And, and honestly, just to keep the momentum of the company going forward. So that everyone there, and we're going to get into the positive aspects of what we built, for example, profit sharing, massive benefit at ConvertKit, it's the kind of thing that can make you really comfortable to the point that you don't want to leave in a variety of other things.

I think we did well. And so I think what you gain on the positive aspects is they really get focused on the people who are driving the benefits, right? Who are driving the growth of the company and therefore creating the Profit and the ability to [00:28:00] do things like great team retreats and other stuff like this.

So what do you look at as the cornerstones of the very kind of congenial, like a friendly culture that we built at convert kit?

Nathan Barry: Yeah. I think one of the biggest ones is feedback and we worked on this a lot and still have to continually work on it. Cause it's like fighting against human nature and one of the biggest things, I'm not sure where this actually came in, but it's the idea of when someone comes to you with a problem.

About someone else. Yes. You know, they're like, Oh, Barrett is blah, blah, blah. Right. Yeah.

Barrett Brooks: A jerk.

Nathan Barry: Yeah. You know, he did all of this and to like, first really listen, ask questions and then to say, okay, first, thank you so much for bringing this to me. It shows that you really care about the culture of the team performance, whatever it's related to.

Second, this sounds like great things that you need to tell Barrett. And so, you know, I just have a couple of questions. One. When are you going to talk to him? And two, [00:29:00] would you like me to be there? Because it's basically like, are you bringing this to me so that you can talk through it and get clear on the feedback before you deliver it to the individual that it relates to?

Or maybe you're worried that that conversation won't go well and you'd like a third party to be there to facilitate.

Barrett Brooks: You know, kind of like a counselor between two married people or something like that. It's like a little bit of a mediating force.

Nathan Barry: And so what's interesting is this, when I started implementing this, it was Like a complete game changer in my like management relationship.

Cause what I would do before is someone would bring in a problem and I'd be like, Oh, you're right. That is a problem. Okay. And I would take it on and like, I will go talk to this individual. And then, you know, you end that zoom call, go to your next one and you have another problem and you get to the end of the day and you're like, wait, I've got five problems that I have internalized and I need to then go deal with.

And so not only are you making a worse culture, but you're also making this really long to do list for yourself. And so like that redirection back of everyone. Of like helping someone clarify their thinking and then go have the conversation. Absolutely [00:30:00] huge. But I think we played out that feedback culture so much and it really, really worked.

And I even like today find myself working with team members on that exact thing. Cause it's so easy to slip back into the world of like, you know, Oh, this person isn't performing or, you know, if they would do their job, I could do mine. It's like, great. Well, Sounds like a conversation you need to go have with, you know, this engineer, this product person or whatever.

Barrett Brooks: It's also that so much of that dynamic of telephone is what drives toxicity in cultures and politicking, you know, as kind of this like backdoor conversation type thing that doesn't involve the person that could change or change the situation. Um, Julia DeWall on my podcast. She's the co founder and president of Antares.

Um, she talked about working at Starlink at SpaceX and Quinn Shotwell is the person who actually runs that company day to day. Elon is obviously the founder. Um, they would be an executive [00:31:00] team meetings. And one of the things Gwyn would do is she would really hold Julia's feet to the fire on like, what's your metric?

Are you hitting it? If you're responsible, get it done. And Julia realized, Oh, I'm actually very reliant on this other team. Because my ability To deliver on my go to market metrics is based on production's ability to get satellites out the door. I've got to go nail that person down on the timeline. I need to know when I can have 10, 000 satellites ready to go so that I can ship them or whatever the situation was.

It would be so easy for that to become this toxic triangle thing going on where it's like, Julie is complaining to Gwen about, uh, this person not doing their job and then Gwen trying to run around and solve it. And what's really interesting is Gwen's thing was just like, you're in charge, you get it done.

If you need something, tell me fine. I don't want to hear excuses. And so she had to go have the conversation with the people she was dependent on, right? That is healthy. [00:32:00] And that conflict happening between the actual people that can solve it is how companies actually create momentum. It's when you start going in the circle.

That it slows everyone down. People get bummed out. The vibe gets all off and shit starts getting toxic. And now you're wasting time on these toxic relational dynamics instead of driving progress. It's like we have a business to run. I can't be dealing with the telephone

Nathan Barry: thing. You know what? I think the, the hard thing is as a leader, if.

You know, we were in Gwen's position, the like kind, helpful, the behaviors that we would commonly attribute to those words would be, Oh, let me jump in with you and try to resolve this problem. And you think like gut feeling is that that would result in a better culture, a healthy culture. And it's just not true.

And it's fascinating because you're like, this goes against everything that I learned about, like sharing my toys on the playground, [00:33:00] being helpful, like pitching in that, you know, in a family, on a team and all of that. And it just, in management structures, it makes things worse.

Barrett Brooks: One of the biggest lessons that I probably learned after I left ConvertKit that I now reflect back on that I would do way differently is Uh, I have learned to trust people, trust adults to be adults, to act in their agency, to tell me what they need to receive requests that I make and say yes or no, based on what they can do or can't do.

Right. And for a long time in my life, not just at work, but at work was one example of it. I, to your point, would take on the burdens of others and say, let me go fix that for you. Or let me be the person to carry that burden because it feels like a servant's thing to do, right? And there are times when that's helpful, but when you do it automatically, without someone specifically asking you, that is an act of taking away their agency and making them dependent on you.[00:34:00]

That is a fatal flaw of mine in terms of just like, it seems wonderful and people come to count on it and appreciate it. But what I would do differently now is I would trust people that they can handle what I need from them and that they'll tell me if they don't, or if they need help, and I would encourage that kind of relationship between us where it's like, I'm not going to hold back on what I need from you.

Cause I need what I need from your role, you know, to separate it from the individual. Um, and I trust that if you need extra help resource or you're like burning down, you're going to come tell me and ask for what you need in return. I didn't do enough of that. Um, and I think that's a totally different skill because you can still help, but you're relying on that person to let you know when they need it.

Nathan Barry: An example I can give is with Brendan, who's our engineering leader now at We're talking about building up, uh, we need more engineering help. And so we're building up a contract team to help. And so we were running this [00:35:00] project together. We're working on it and going from there. And I realized that I wasn't setting clear expectations and we were doing it together and we weren't making the progress that I need, that we needed.

And so I came back to him and said, Hey, I need you to get three engineers on this team by June 15th. And you should have 10 by December 15th. You let me know if there's any help you need in that process. And he went, okay. That is very clear. I can execute towards that. I'll come back to you if I have any questions to clarify that, or if there's anything that I need from you in that process.

And it completely changed the dynamic. Yep. And I could feel both of us like go from this Shared responsibility, this, this tension, this confusion, like, and just like settle back into our seats and like roles were clear. Look at that. And like everybody just kind of settles down.

Barrett Brooks: Yeah. So the flip side of this is, uh, and in Kim Scott's framework of radical candor, she talks about directness and basically personal care, the two factors.

I think when I reflect [00:36:00] back that really the cornerstone of many different practices that we had. Of our culture was building strong relationships by knowing each other's story, knowing who these people are as human beings, why they're at ConvertKit, what matters to them, um, even things that they struggle with in life, not to overstep boundaries, but.

To build that ability to care for one another. I think if you don't know one another, you can't really care for one another in that way. And so when I think about things like team retreats, listening walks, even unsolicited feedback at times. Uh, I don't know if y'all are still doing the internal team podcast thing that we did for a while.

So much of that centers on, can we know each other's stories? What has shaped us, who we are, what we care about, why we're here. I wonder if that resonates with you about kind of the driving force. I think

Nathan Barry: we should explain what some of those things are. Because when we say listening walks and right, unsolicited feedback, I think people are like, [00:37:00] what's your favorite?

Maybe I'll explain listening walks and then you explain unsolicited feedback. Both are really critical listening walks. Basically what it is is you pair two people together and you send them on a walk for 10 minutes, 15 minutes, something like that. And usually, so you walk one direction until a timer goes off and you turn around and walk back the other way.

You just give a question and you can get all kinds of, it could be any question and you're just walking side by side with this person and one person talks and answers the question and the other person says nothing and just listens. And you do that until the timer goes off and you turn around, you switch at pairs and then the other person talks.

And so I'm trying to remember some of the, do you remember some of the questions we went with? Things

Barrett Brooks: like, um, what experiences have shaped you as a professional? Yeah. Or what do you wish someone, uh, knew about you?

Nathan Barry: Yeah. I knew, yeah. What is one thing that you wish other people knew and understood about you?

Barrett Brooks: Yeah.

Nathan Barry: And like, [00:38:00] it's the hardest thing. You're like, uh. And you're like, start talking and you're going through it. And, and then usually about two minutes in, you say everything that you have to say, and then you're like, how much time is left? And the other person is keeping time. They're like eight minutes.

Like I have nothing else to say. The instruction that we give is when you run out of things to say, start over and say it again. And usually the second time you end up like saying so much more. And then what's really cool is when everyone comes back together, because you always try to pair people up with someone they don't know.

Yep. You kind of decide like, Hey, do we want to share? And if we do like, all right, you know, you both have to agree. And then you end up answering this question as if you're the other person. So if we did it together, right. I would get up in front of the group and say, my name is Barrett. And the thing that I wish people knew and understood about me is this.

And so you end up with this other person. Like truly listening to you because they couldn't ask what like they couldn't say anything and then fully [00:39:00] advocating for you And there will often be this level where you'll kind of beat around the bush when you're talking about yourself Like I really wish this thing and then someone else will just come out and clearly state it like I wish this That is what I think I was just too scared to say it and it's such a cool practice And we've watched people who are on totally different teams become really close friends You Um, because they feel like they're really understood because they spent 20 or 25 minutes doing this exercise 20

Barrett Brooks: or 25 minutes

Nathan Barry: I think

Barrett Brooks: that's I just want to hammer that home because it's almost absurd

Nathan Barry: Yeah,

Barrett Brooks: the amount of connection you can get from such a short amount of time a 20 minute walk And a 45 minute or hour long debrief.

Uh, now there have been times where it went into the night kind of thing. And we like, just let it flow because we saw the connections happening, but there's something about being seen on that level. It almost doesn't matter the question where it's like, wow, that person actually understands a thing about me [00:40:00] that they never would have had they not done that exercise with me.

And the amount of trust that comes from that. And then getting to kind of be in that ritualistic type circle where everyone who opts in is sharing. It's like, I have an advocate, I'm understood. Now the whole group knows this thing that I wish they knew about me. It's really powerful. Because you think about the question,

Nathan Barry: and again, it can be anything.

We've done like five different questions. Even as simple as like, how did you come to ConvertKit? Yeah. Uh, and you end up like unpacking someone's story and you realize that like they were actually in a really bad spot before this and like, you know, unlock things in their career or whatever else. But my favorite question is what is one thing that I wish other people knew and understood about me?

Like the question is, what do you wish you could get out, but you don't have the opportunity to. And we're like, we're giving you the perfect floor to get this out. And yeah, it's, uh, it's, uh, It's really powerful. Yeah.

Barrett Brooks: So let's talk about unsolicited feedback though, to, to give another

Nathan Barry: cause that started out of the [00:41:00] mastermind group that we did even before ConvertKit

Barrett Brooks: for years.

Yeah. So

we knew each other for years. We met at here in Portland. Actually, we're filming in Portland at a conference called world domination summit. Every time I go to say that in public, I'm like, uh, thanks, Chris. Founded by Chris Gillibeau. And I tell

Nathan Barry: you the, the story of, uh, Taking the max into Portland from the airport.

No. So I had this first event, it's 2012. Uh, I'm like barely in the creative world and I'm like, let's meet people. Let's see where this goes. I knew there's a thousand people coming to this event. And so I'm riding the train from the airport in, and these two other people seemed very like creator y types.

And so I start talking to them. They asked like, Oh, what are you coming in for? And I'm like, I'm at this conference. Kind of thinking like, Oh, we're for a conference too. But they didn't say that. No. Oh, what's it called? I'm like, Oh, it's the world domination summit. And they're like, The world dominatrix summit.

Like they're looking at me here. It's [00:42:00] like, I don't know what's in that bag over there, guy. And I'm like, no, no, no. It's uh, no, Dominique, it's not as weird as it sounds. I promise. Yeah. Anyway. So that was my first Portland experiences. I'm on my way to the event where they weren't

Barrett Brooks: creators. Just welcome to Portland.

Yeah. Uh, okay. So we formed this mastermind group. We met, um, whenever we like. Name drop about this. Now it seems like it was preordained, but it was like you, me, James Clear, Caleb Wozniak, uh, Baron Quadro, Krista Stryker was in it at the time. It was a group of us and we like got together, really great creators.

We started hosting, um, retreats like twice a year, I think, or once a year, whatever, I can't remember hosting retreats and we were just figuring it out. Uh, it was basically a chance where we knew everyone could do an extended hot seat session where they would talk about some strategic issue in their business.

Um, and everyone would focus on that problem [00:43:00] for 30 minutes or something like that. One time, I don't even know someone was like, Hey, what if we all sat around now for kind of a closing session and for 10 minutes, we talk about each person, like they're not in the room, like, what are all the things that we should tell them so that they can succeed in their business that maybe we just haven't had the chance to, or whatever, um, cause everyone talks about their friends when they're not in the room.

That's just the thing that happens. Right. Uh, so we tried to basically make it explicit, the things that they really should know if they're going to achieve what we think they're capable of. And it became this really awesome practice. You know, you hear that and you think, Oh, these people are going to rip into me.

And in fact, more often than not, it was like very positive stuff. Like this person's superpower is this, and I don't even think they realize how good this thing that they're doing is. And then there would of course be also critical feedback of like, here's how they could grow. Here's what I think they're missing.

Here's how I think they're playing [00:44:00] small. So going back to just kind of like convert kit is one big experience or experiment. I mean, we were kind of just like, well, what the hell, let's bring it to the company. And so we started doing it in teams at ConvertKit. And I think the most powerful version was, uh, the entire company to the executive team, where that is extremely rare, I think, where an entire company gets to sit there and collectively give, that was always the harshest, I think, of any feedback, give direct feedback.

I think they knew we

Nathan Barry: could take it too. Yeah. So they're like, All right.

Barrett Brooks: They would go, you know, it'd be nice for a few minutes. And then someone would be, would like lean in, you know, it's like, all right, let me get my notebook real quick. Um, and so it became this, this practice where the first time someone would join the team and do it, they're like, Oh my God, this is horrifying.

Before they do it. Yep. Yeah. They'd be so

Nathan Barry: nervous about, yeah.

Barrett Brooks: And then they participate in it with their team and they'd come away saying. Wow. That was awesome. I've never gotten feedback like [00:45:00] that. Ideally people would be getting this quality of feedback all the time. Right? Of course. Sure. Real time. Use it to operate on an ongoing, and it just doesn't happen.

You know. All you management gurus. I know what it's supposed to be like, I'm with you. It doesn't happen. So I don't know what to tell you. My answer is have a practice where it can come out. And I think that was another one of the touchstone things that I just think really brought people closer together and aired out stuff that needed to be said.

Sometimes that just didn't have another venue. Yeah. There

Nathan Barry: were a couple of prompts that we would give in advance. What like we encourage people that to prep for this usually two weeks in advance. And to think about each person on their team, what feedback would you give them? Go through that list and say, what have I said already on this?

And there's something like, I haven't said this yet. It's like, cool. Well, you've got the next like seven days to schedule a zoom call and like deliver that feedback. Cause saying something for the very first time, if it's really critical feedback in that setting, it's not really a cool move, you know, [00:46:00] but it ends up being that forcing function.

Then the other thing is we give a couple other questions to think about the constructive feedback to give. And it'd be like, let's imagine you're going to work with this person every day for the next 10 years. Yep. What's something that's not a big deal, but if we're 10 years, like, all right, let me tell you about like, this drives me crazy or you should do this differently or whatever.

Barrett Brooks: Yeah. It's like my wife squeezes the toothpaste from the middle of the tube. Like, come on, we got the rest of our lives together. We can't do this. We have separate toothpaste though.

Nathan Barry: There's got to be a solution to everything. Quick aside. Yeah. Then the other question is, let's say that. You know, six months from now, this person is up for the biggest performer or the biggest promotion of their career.

You know it, they don't know this is coming. What advice could you give them now to give them the best opportunity to get that promotion? And those types of things usually lead to like, you're doing a great job, but okay. Yeah. Like if I'm really in your corner hoping for you to get this promotion, then [00:47:00] here are the things that, yeah, this could hold you back.

Barrett Brooks: Yeah. Okay. So there's two directions. I think we could go from here. Um, one is There's this whole other side to how we design ConvertKit that continues to evolve around, uh, kind of comp and benefits and like how we thought about that. And then there's the growth element of like how we thought about growth, where we came up short.

I don't know which one, which one seems more interesting. Let's go comp and then, and then growth. Okay. So if I were kind of like laying out the framework for comp at ConvertKit, It's a first, a standardized salary system that has roles and levels and it tries to create an equitable way for everyone to know they're getting paid fairly as a baseline.

There's profit sharing, which is as the company grows and we're more profitable, everyone benefits. There are stock grants, which were not there for a long time, but now exist. There's kind of this like secondary process that you run now to, for people to realize value from their stock every so often. [00:48:00] Uh, and then there's kind of like the benefits package.

So none of this is like world beating brand new stuff. The combination might be unique. Um, I don't know which one seems most interesting to you to dive in on.

Nathan Barry: Well, I think the framework that surrounds all four of them is balancing short term versus longterm compensation. Yeah. and performance based versus a guaranteed compensation.

And so if you put those in a two by two matrix, um, then short term guaranteed is salary. Long term guaranteed is 401k short term variable, you know, performance based is profit sharing and then long term, uh, performance based is equity. And so I think a lot of companies really, they go like the Basecamp or Mailchimp route, and they say, we're never going to sell.

And equity doesn't have value. Surprise expand. We sold, uh,

Barrett Brooks: that's a MailChimp joke for people who didn't get it.

Nathan Barry: Yeah. [00:49:00] It turns out 12 billion is hard to turn down. Uh, I don't, I don't blame them for that one, but you know, it led to some mixed incentives. Yeah. So you end up at this, like we're never going to sell.

And so, you know, profit sharing or bonuses is entirely like short term cash is the way we were going. Or you end up with the traditional VC startups where. The exit is all that matters. We're going to be very low on, you know, short term comp for this, like moonshot exit. And it ends up with this, you know, crazy logarithmic distribution of returns basically where almost everyone gets nothing.

And then, you know, the companies that win, like the returns are incredible. And so I think really what we're trying to do with ConvertKit is map out. Could we have the best of both worlds? Could we make something that's really well rounded? I think it worked well. Like that's something. That I just think so many companies should just straight up copy, like clone the ConvertKit method into their business.

Yep.

Barrett Brooks: So I agree with you. I think baseline, it is a very well designed system. I'm very

Nathan Barry: proud of ourselves [00:50:00] about that. You know, I think it's pretty good. If we were sitting closer, I'd pat you on the back too, right?

Barrett Brooks: Uh, and it does have some shortfalls, right? So there are some costs to it. Both. Profit sharing and equity ultimately are company performance driven, not individual performance driven.

And so there is a bit of a collectivist kind of thing going on there. And this goes back to the conversation about letting people go, because if you are a very high performer and you know, profit sharing and equity value to you are driven by collective performance of the team, and you only have a slice of that, You really want everyone to be really f***ing good at their job.

So that's the leadership responsibility to the team in that, in that element, we played around with individual performance driven profit sharing for a while. And obviously stock grants can vary and things like that. But I think what we found is, or what I found from the individual performance driven [00:51:00] profit sharing formula was that the amount of stress and tension it drove, um, Between managers and individual employees was not worth the incentive it was creating for people to perform because you ended up with all this conflict over, like, did you perform?

And I was having this conversation with Laura rotor on, on Twitter the other day about what is the appropriate? Okay. R for an engineer. And it's, it will drive you mad trying to set an okay. R that is measurable for an engineer. When they don't set the roadmap. They don't control the adoption of the thing.

Their job is basically build it as well and fast as you can. It's really hard to set a metric for that. I'm not saying it's impossible. It's just hard. But if that thing is tied to performance now, it's like people only want to make sure bets that they're entirely in control of that may or may not drive company performance.

So I just found that that created too many mixed incentives [00:52:00] and it was, it was Simpler to say we all benefit when the company grows on that end. But that is a flaw there. And then on the standardized salary thing, we were getting into this last night. So what are the shortcomings on that from your point of view?

Nathan Barry: I mean, overall, I think standardized salaries are the way to go, but you have some pretty significant shortcomings in that you end up with people who are contributing at vastly different levels to the company performance, getting paid the exact same amount of money. What's interesting is. We're like ruthless capitalists and total socialists within the company.

Yeah. In these different angles that we play out. And I think this like collectivist, everyone wins equally within the company. Ideals that we have really rely on holding the bar for performance high and curating against that. It's like the thing it's the thing in every aspect of the compensation and the culture and all of that.

And so when you don't do it. Then you start to get all of these other things. [00:53:00] And so the biggest shortcoming on the standardized salaries are that you end up with people performing at very different levels or delivering value at very different levels, getting paid the same amount. And so there's oftentimes that you're bringing in someone who could perform at a really high level, could drive a ton of value for the company and you can't close them because.

You know, they're outside of your salary bands.

Barrett Brooks: Yeah. From a recruiting standpoint. Right. It's like, well, experience level, performance level, contribution level, you would be this level of this role. And they've got a, another offer from Netflix or whatever. Yeah. It's like three times the cash. I may have just lost

Nathan Barry: a candidate to Netflix.

I hate Netflix for this reason, because they're

Barrett Brooks: so absurd with just their total comp scheme because of how much money they make.

Nathan Barry: Yeah. And I mean, their revenue per employee is like, I don't know. And, you know, 2 million plus, right. And so they pay really, really well.

Barrett Brooks: And that sucks, right? Especially if it's someone you really believe is going to make a massive difference in a relatively small [00:54:00] team size company, like ConvertKit, one person can drive a lot of value.

If that gets you out of integrity with the system you've designed, now you've got a problem.

Nathan Barry: Mm-Hmm.

Barrett Brooks: Because the moment you make one decision to operate outside the system, it opens up all kinds of problems. Yep.

Nathan Barry: And then you write back to negotiating salaries individually. Exactly. You just have a, a strong baseline.

Right. Instead of one off to every situation.

Barrett Brooks: Yeah. So that's just a shortcoming, I think on balance, you know, it worked well for us.

Nathan Barry: Is there a way to solve that?

Barrett Brooks: I mean, I think the way. Um, and that gives good long term incentive for someone to help drive value. The second way is we didn't use this a lot, but you can do things like signing bonuses, spot bonuses, um, other things like that, where it's like, if someone really just knocked something out of the park, you can give [00:55:00] someone a 20, 000 check and say, look, this isn't a good thing.

You did this, therefore you're getting money. Like it wasn't, I'll give you this money. If you do this, I should say it that way. It's because you did this of your own accord and value system. And it so overshot what we thought was possible. I want to reward you for that. Uh, retrospectively, right? So Dan Pink talks a lot about this and, uh, in drive about incentive structure and carrots and sticks and things like this, and basically he says, if you dangle a carrot, it takes away all intrinsic motivation.

But if you retrospectively reward the kind of things that are reflective of the values and value to the company, that is actually net positive because it's, uh, rewarding the intent, intrinsic drive that, that Got you there versus dangling it. Like if you do this, I'll give it to you kind of thing. So I think that's another way that we never really tried, but I would be curious about

Nathan Barry: when

Barrett Brooks: it's

Nathan Barry: interesting, as you say that my default would be to focus on the, like dangling the carrot, [00:56:00] right?

And maybe that's what most managers would default to as well, which we didn't do much at ConvertKit. We did a lot more of the, um, spot bonuses or equity grants for. You know, a milestone that someone had already achieved.

Barrett Brooks: Caveat there that Dan, Dan Pink says is for highly variable and creative work. So if something is rote, you are a person building things on a manufacturing line.

Carrots worked really well. Okay. So I will caveat with that. Um, yeah.

Nathan Barry: We're like every sales leader is like, no, it works pretty well to dangle the carrot. Yeah.

Barrett Brooks: And I think that's still up for debate. You know, it's gone back and forth where there's some companies that went no variable comp or commissions for salespeople that is paying really well, and then hold them to a performance standard.

And then there's most companies are still doing the traditional commission based thing. I don't know where the research on that ended up. So

Nathan Barry: yeah,

Barrett Brooks: someone knows comment, let us know.

Nathan Barry: So that's the compensation side, like going to the growth side of the company or even growth and product, you know, overall, cause they go hand in hand.[00:57:00]

I'm curious what stands out to you in the, like what we really nailed and what we do differently.

Barrett Brooks: The single thing that I think I believed then and most believed now, continue to believe now, is at least in the creator market, people do not make rational purchasing decisions. And maybe that's true across all human behavior.

I don't know. Yeah. But I know in this market, they make social purchasing decisions. And what I mean by that is, Creators look to creators they look up to for what tools they should use and how they should run their business It is more peer to peer than any market I have seen other than maybe like vcs following each other into the hot thing And so what I took away from that is if you want to grow in a market like creators You must win The role model creators as customers you must have them and I think we proved that I think well, it's just a mod Honestly, maybe we were some [00:58:00] of the earliest to do it But you see it with substack you see it with circle you see it with teachable It's like you go through the, the creator economy tech stack, YouTube.

It's like, why does YouTube send plaques, right? They want big creators talking about how big they are and they want to gain the social reputation and value of big creators are on YouTube and you should be too. Um, so, so I think that's the biggest, biggest lesson I took away is what are all the ways that you can associate.

Big creators that are role models to a lot of other creators across verticals with your brand as active users that love the product that you make.

Nathan Barry: I think we both did that really, really well and not very well at all.

Barrett Brooks: Yep. Uh, we did it well individually at times. We did never systematized it to the point that I think we could have probably is kind of my take on that.

Nathan Barry: I agree with that. Like, I don't know that [00:59:00] we've ever. Like fully advertised to the level that. Andrew Huberman as a customer. Or, uh, I was talking to a creator yesterday at TravelCon, uh, who works for, uh, Kara and Nate, the very, very popular travel content creators. And he goes, why didn't you, why don't you promote the fact that Kara and Nate are on ConvertKit?

We should do that. Like, right. They're two of the most popular people in the entire space. They've been on ConvertKit for, I don't know, six years now. And like, we just have an endless list of creators to. Promote and showcase and we tell stories really well And that's something that like you really brought to the company in the early days is Building that muscle and and setting how we do it, but there's something about getting that out there and getting attention

Barrett Brooks: yeah

Nathan Barry: on those stories and Like really positioning as the platform that all of these professional and star creators use that I think we still haven't nailed, like the quality of the content that we put out [01:00:00] doesn't match the level of attention and views that it gets.

And I still don't understand that disconnect.

Barrett Brooks: Okay. So two things here. Um, one is for years we talked about the Nike sponsored athlete kind of model. Uh, or beats by Dre and the way that they went about like LeBron wearing beats every time he warmed up before a game gives you exposure in a way that like can, you know, people aren't walking around holding their computer open to their convert kit home screen, you know, so there is some element of like, you know, when I have a pair of Jays on, you know, it's a Nike product.

When someone sends an email, you have, I mean, you can know, but it's not like no one's looking at it. Like, Oh, look at the brand name on that email right there. And so there's some of that going on where I think we could have done a better job of figuring out. What's our version of the Nike sponsored athlete thing.

I think Substack pulled it off pretty nicely, you know, to give them credit. It really [01:01:00] pissed me off, but what they figured out was, Oh, let's just give people money and then what they have to do is talk about Substack, right? We'll just directly pay them for it, which is

Nathan Barry: what Nike did. Yes, exactly.

Barrett Brooks: And maybe we could have just done that.

Maybe you should do that now, you know, just literally pay all these influential people who are users and say, go talk about us. Right. But do it in like, not a, you know, sponsored ad kind of way, but like, let's figure out a native way for you to integrate this into what you're doing. Um, I don't know. I think we could have done more of that.

Just pay people to talk about it. And then the second thing is this is a flaw of mine was for a long time. And I've had to get over this now with my own work as a creator. Uh, I was just hesitant to slam it in people's face to like, because I felt like. A great story is not one that centers on our brand name.

It centers on creator as hero. And I don't [01:02:00] think I ever figured out how to integrate those things of telling great creator stories and making sure that the brand got associated with that. I think there was, I created too much distance at times between the way we were storytelling in the actual fucking name of the company.

You know, you have to associate those things if you want people then to, yep, have it lodged in their brain.

Nathan Barry: Well, I think there's a lot in that of. Even just the hesitation that we had around the name, right? We didn't put it prominently in URLs, right? Like instead of, uh, like substack, for example, being, you know, your name dot substack.

com, we didn't do the same thing of your name. convertkit. com. Cause we got early feedback from people that are like, I'm not here to convert people, you know, whatever. And so there's a bunch of places where we subconsciously held back on that, I think, because of the name. Now. In hindsight, we should not have done that.

It's [01:03:00] like, get over yourself, move on. It's the name, you know, like people need to know it. Yeah. And so like we held off for a long time, putting powered by links on there now powered by links, drive a huge amount of traffic.

Barrett Brooks: So powered by what we mean by that is it says powered by convert kit on the bottom of all, uh, forms and emails from free accounts.

Uh, and then people can also add it like if they're an affiliate or whatever. So,

Nathan Barry: yeah, there's a bunch of things there. I still. I feel like we could do our marketing so much better. Like I think that our reach and influence as a platform or how to, I was going to say our reach and influence as a platform is so much bigger than I guess our reach and influence.

It's like a, we, we power so much more of the internet. Yes. Yes. Yes. Then, and, and businesses then I think people realize, right.

Barrett Brooks: Uh, and just have a bigger business than much more well known brands. That is the part that's wild to me is like if we rattled off, right. The top 25 most well known [01:04:00] people using ConvertKit.

People would be like, wait, what? Yeah. Where did y'all come from?

Nathan Barry: Like we've been here, bitch.

Barrett Brooks: It's just, no one knows it, you know, um, that drives me nuts. That, that definitely, you know, I still have a little bit of a chip on my shoulder about that because we joke about people saying, oh, the creator economy is the hot thing in the middle of the pandemic. There was a decade of groundwork that got laid and we were a huge part of that.

Yeah. I'm not going to say like we created the creator economy. That would not be true, but we powered a big portion of it. Right. You know, and I just don't think that that is appreciated or understood to the degree that it's true.

Nathan Barry: I think in that we didn't figure out like our press and PR aspect of it.

Yeah. I think we were dismissive of media of media and that side of it. And so it ended up being like creating this. Like perception as everyone paid attention to the creator economy. Later people behind the scenes actually running these creator [01:05:00] businesses knew our role in it, but the media, as they're showing up, I was, uh, doing an interview with Owen from the wall street journal.

Uh, just a week ago. Yeah, exactly. Thank you. Um, I love that on the, on the podcast before we're going to have, like, it'll be a shot of me and it's going to have to cut over to Barrett just enough to get the little reaction. If you're listening to the audio, this is why you should check out YouTube. I gave a great emoji reaction.

Yeah. Go to YouTube, like, and subscribe this. The story was about tick tock ending. And, you know, or the, the require from the requirement from the U S government to divest, divest what, and whatever's going to happen. And the journalist very much saw the creator economy as someone who, an individual who makes money on a social platform, and we ended up having three separate calls over the course of two days as like, you know, the first interview for 45 minutes, and then later that day, like another 20 minute call.

For them to be like, wait a [01:06:00] second. So how does this. Work and then a call the next day is like I talked to my editor We're still trying to write this other story and I'm like no Here's how it actually works right because they're like you didn't give us any stories of Creators who make all of their money on Instagram, right?

And we're like, that's because that doesn't happen. It's a bad

Barrett Brooks: business model.

Nathan Barry: Yeah. Like Instagram does not do payouts. Right. You know? Um, and so we're talking about like multi platform and how it actually works of how people have like a hub and spoke model, the hub and spoke thing. Right. Uh, that's visual for it, you know?

And, and so that's where people have platforms with distribution, usually, uh, say Instagram, Twitter, LinkedIn, YouTube, et cetera. And then they're going back to a platform where they have. Engagement connection, usually email and you know, the balance of those two things, but it was fascinating that they had a, not only a story in their head, but also an idea of how the creator economy works in our narrative just didn't match that at all.

And so like this writer was just really struggling [01:07:00] to like reconcile her idea of the world with like the data that I was sharing of how it actually works. And I think, how do we done things better? We would have. And I'm not sure how, cause it's not like a strength of mine, but getting, we would have gotten that story out there so much more and really tried to drive the narrative instead of like kind of being the proud rebels where we were like, Oh no, they, they're wrong about that.

Barrett Brooks: Right.

Nathan Barry: And like being dismissed, go

Barrett Brooks: take control of it. Yeah. And actually

Nathan Barry: just say like, no, it's kind of our fault that they're wrong about that because we didn't tell the right stories loudly enough to the right people.

Barrett Brooks: Now I got a hundred ideas for what you should do now.

Nathan Barry: Okay.

Barrett Brooks: So let's

Nathan Barry: go through a couple of them.

Barrett Brooks: So Ryan holiday probably won't appreciate me bringing this up because he writes such high quality books that are of a different genre now But his first book it's called trust me. I'm lying. I think tactically it's one of the most brilliant books. He's ever read I mean, I enjoy his current stuff for the stoicism and all of that mature Ryan.

Yeah, but the trust me. I'm lying thing I mean that is a [01:08:00] hell of a playbook for getting attention What's crazy is

Nathan Barry: he wrote that because he's like I will explain how this all works and so that it will stop working

Barrett Brooks: Right.

Nathan Barry: It a hundred percent still works.

Barrett Brooks: It still works for sure. And he basically talks about how to ladder a story from like a no name creator in the grand scheme of the world, all the way up to like top tier media.

Right.

Where you plant something down here. And then you leverage that to get something like local news coverage. And then you leverage that to do a piggyback story and a bigger publication. And then, and the thing is media feeds itself. Once someone's telling a story, it's like, how did you, some editor is saying to some columnist, how did you miss that?

Go get that story, you know, figure out another angle. Cause now they got the lead that we don't have. And so it was this playbook on how to do that. ConvertKit at best. ConvertKit at best. If it gets mentioned in a creator economy story is like, and there's this other thing over here. Yeah. It's at the end of the sentence or the right.

Yeah. [01:09:00] And mostly it doesn't even get mentioned, even though it's bigger than the brands that are getting mentioned in terms of reach of the creators using the platform money, the creators are making size of the company and revenue, you know, length of time that we've been around,

Nathan Barry: like, I don't think that people realize that Converka is larger than Substack and Beehive combined,

Barrett Brooks: combined in revenue.

And if we look at like. Emails in the database as a proxy for number of people that can be reached in the world by users of the platform. It probably dwarfs those other platforms and no disrespect. Like y'all have built great businesses. I love that. It, it makes the pie bigger. Um, but just like. You know, I love basketball and hip hop culture and all it's like, put some respect on my name, you know, it, but to your point, we should have worked harder to earn it.

We should have worked harder to make sure that we were the advocates for our own story. So I would start there. It's like, all right, so we know what we would have done now. You just [01:10:00] got more money and more people,

Nathan Barry: right?

Barrett Brooks: Let's go to work, you know, let's go make it happen. Let's go sponsor the people that should be talking about it.

Let's go plant the media stories. Let's get people like, let's go hire Ryan as a consultant and say, how do we ladder the story of this company now from where we are and take the proper place at the creator economy table? Yeah. It's like, all right, little brothers, y'all are doing a great job. We belong here too.

You know, this is actually our table.

Nathan Barry: Well, what's interesting is if you go through any other business. If I was giving advice to someone else, quick aside, usually the thing to do, if you're like, I'm really stuck on this problem, it's like, okay, well, let's say that, uh, let's cross out Nathan's problem and this is Joe's problem.

What advice would you give Joe? And it's

Barrett Brooks: like, oh, well now I know it. Like it's called a perspective shift in coaching. It's very

Nathan Barry: effective. Yeah. You know, we're talking about like awareness or closing a sale or something we would go through and we would list out the actual humans who were involved in this.[01:11:00]

So instead of being like, how do we get media to cover ConvertKit, we would just go and list the 25 individuals who write about the creator. You might get as many as 50 if you stretch it. Right. But I don't think it's more than that. Right. You know, and then you would just be like, okay, what events are they at?

Where did, you know, can we take them all to lunch? Can we just relationship? Yeah. All of those things. And then, Can you put them in a, in a, uh, retargeting audience on Facebook? 50 is a little too small. Yeah. You can't quite do it at that size, but like, there's a bunch of things that you could do. It's one of those things where like if you're losing a game and you're like, I didn't wanna play anyway.

Yeah, yeah, yeah. You know, no one even likes that game. Yeah. Who cares? Instead of coming in and saying like, no, I'm losing that game because I'm not playing it according, like, according to its rules. I don't like the rules

Barrett Brooks: or whatever. Yeah.

Nathan Barry: And so then you say, all right, well. How is the game play and I'm going to be great at it.

I was hanging out with Pat Flynn the other [01:12:00] day, and he was talking about the things that his kids are interested in. And in Pat is I don't think people realize how competitive Pat is.

Barrett Brooks: Very competitive person. So Pat's a founder of smart passive income, longtime advisor and affiliate at convert kids. So, okay.

Nathan Barry: Yeah. But he was talking about how during the pandemic, his kids got really into fortnight. And he was like, Oh, I got to beat them at everything. And so he got so good at fortnight that they were like, as fun anymore, you know, and they moved on and then they got really, really into, into Pokemon. And he was like, Oh, I want to do this with them too.

And so he ended up getting super into it. He now has a million subscriber YouTube channel about Pokemon in a couple of weeks, he's hosting a 5, 000 person Pokemon event in Orlando, you know, and he's built a, that is a 40 something year old man, just to be clear. Okay. But you know this thing of like Pat is someone when he gets into something he like Studies the game and becomes an expert in it plays it And so I think it's doing the same [01:13:00] thing with you know with media Yeah, that's what you do is study the game and play it really well.

Barrett Brooks: Yeah, everyone knows our playbook for the next 18 months Yeah, exactly.

Nathan Barry: We've shared it

Barrett Brooks: all. Okay, we got divorced. We did it's been almost three years. Yep We're good co parents. We are good co parents. Um, I am still an owner of ConvertKit, so I did not fully leave the ecosystem. And I talk to people like Haley, who's over there behind the camera, and other people at ConvertKit all the time.

So I feel like I'm still connected. Uh, but it was really painful for both of us. And I think we've, we've done our work to continue growing back together and like finding a new groove as friends. And, um, which is where we started anyways, but I think it's really interesting. I have never heard anyone really talk about a departure like mine, unless it's like, yeah, that fell apart and ended up totally horrible and everything burned down or whatever.[01:14:00]

And I think we tried really hard not to make that the case at the time of the departure. And we, it took some time for us to be able to even like get back together and figure out how to be and all of those things. And I'd say we're still in that process right now. Um, but I'm curious reflecting back, maybe let's focus first on like the process of me leaving.

Yeah. If someone else has a key exec leaving or even a co founder leaving or something like that, like what did we learn? about how to do it well, and maybe what mistakes did we make and all of that.

Nathan Barry: Usually the way these things go is like we're talking earlier, it's a complete surprise to one side or the other.

And something that we did really well in round two of your departure is that it wasn't a complete surprise. Right. We, We talked through things a lot, um, not to continually plug reboot and make this an ad for them, but they have these four questions that you and I have both come to rely on a lot [01:15:00] in any time we're, we're dealing with conflicts of any kind.

And those questions are, what am I saying? That's not being heard. What's being said that I'm not hearing. What's not being said that needs to be said. And the last one, which changes the format slightly is how am I complicit in creating the circumstances I say I don't want. And I think that I don't remember if you and I sat down and went through like those exact questions, but things like that is what we kept coming back to as we work through, you know, is this the right partnership for the stage of both of our careers?

You know, is this what we want to spend our time doing? And where's our conflict really? And I think that's so helpful. Like when I've had team members who are going through conflict and I'm playing that like facilitation coach role, I'll often have them both journal on those questions. And you can totally tell who is earnestly trying to resolve this and who is like, just mailing it in.

Yes. That just wants to be [01:16:00] stuck in the conflict. Yeah. Or who's like, you know, it's like, uh, what's being said that I'm not hearing. And they're like, uh, I don't know. Yeah. All right. Well, you didn't put any time, you didn't try. And so I think the first thing that we did really well is had a lot of open conversations and we really tried to work through those and understand it.

And we had some good frameworks and a lot of good help to do that.

Barrett Brooks: Yeah, I agree. The way I remember, it'd be interesting to see if you remember the same way was. We had been kind of openly discussing the possibility for some time. Cause I think we were, I mean, we got to also remember we were a year into a pandemic, like leading the team, a lot of the tools available to us for getting together in person were not there at that time.

So there were all the normal stresses that everyone experienced related to all of that, taking away our life force, you know, as like human beings. Um, and I don't discount that as a factor at all. I mean, on some level it's like, Oh yeah, Barrett's a cliche. He. In the middle of the great resignation, he quit his job as a COO and it was like, I'm going to [01:17:00] go find myself.

So that's one story you could tell. Um, but I remember one particular conversation where you said, Hey, you know, I was in coaching with Dan last week and I said a thing out loud to him that feels true to me, which is that I think going beyond my original goal of 50 people was one of the mistakes I've made because I'll never know.

Could we have grown this company under the original constraint that I was shooting for? And I remember hearing that and we had been having these conversations about how to continue to grow and like what matter and what Our priorities were and I just said, I don't think I got it in the tank. That's what we're doing.

Like This isn't a threat. I'm not saying like Use this as leverage. I'm just saying like sit on that for a couple weeks And if you come back and you're sure you don't want to hire. I just I gotta we gotta start talking about me leaving um, I don't know if you remember that but that was kind of like my that was like the Decision point you came back and you're like, yeah I think I want to like Really try and study the team size for a while and just stay where we are.

And that's what I want to do. And that was actually a [01:18:00] moment of you taking your seat too, because it was in the face of the knowledge that, you know, you were going to lose your partner in crime if that's what you decided in some ways, that's like a great act of courage. Uh, or in very concrete ways, not some ways.

just is. And I said, okay, let's start the process. You know? Um, and basically we took, so that was March or something like that. March or April. And, uh, we took five, six months basically. And you and I started working through the plan and what the transition plan was going to be and who was going to take over what.

And we had just introduced a benefit where every five years, a teammate could take a month off, uh, sabbatical. And I had planned to take mine that summer when I hit my five years. And we said, all right, still go do that because maybe you're just tired and let's just make sure that you don't take a few weeks off and come back like chipper Barrett, you know, cause that would be nice.

And I took the time off and I think I came back more like, nah, I got nothing, you know, I'm tired. [01:19:00] Before I left though, uh, on my sabbatical, we told the exec team and we told them fully transparently. Here's what's gone down. Here's what we're planning on. Here's the timeline. And. Barrett's taking the sabbatical partially to see, might he want to stay when he comes back?

So that is still a possibility. So we're not telling the team. Uh, and then on the other side of the sabbatical, I came back, we solidified it, set the timeline, told the team as quickly as possible after that. And then I think there was another six weeks or four weeks or something, and, and kind of wrapped up.

Um, I think that was about as good and transparent and honest and like mature as we could have been in all of that. Um, I think I started feeling a lot more of the pain when it actually ended, you know, it was like, I was trying to keep it all together and make sure everyone was taking, you know, I was doing the thing I was like, making sure everyone's taken care of.

And then I remember my last day, you know, we had a conversation, I logged out of slack and I was like, Oh my God, what am I going to [01:20:00] do tomorrow? Like, this has been my life for five years. What does one do in this situation? And that was really when the processing started for me, I think, where it was just like, how did I end up here?

Like, what did I do wrong? I felt very unfinished. And like, we had this vision, right? Get to a hundred million dollars in revenue, billion dollars driven to creators and GMV fully remote and independent. You know, we had this mission and vision we were trying to do. And we were like 30 percent of the way there.

Nathan Barry: Yeah. I remember hearing from our board basically saying, This is going to get a whole lot harder before it gets easier and be ready for that. And actually in the time period. So first, like I think the, the 18 months before you left war on us a lot on both of us because we went through, you know, leading through a pandemic where we had no idea what to do.

I mean we did all kinds of projects that we spun, like we were like, creator

Barrett Brooks: fun, like creator fun. [01:21:00]

Nathan Barry: You know, we're like, I guess a daily podcast. I guess, you know, trying to figure out how to lead through all this and then you know there's all the social justice change social justice

um, everyone's boycotting Facebook should be also boycott Facebook, you know, and it's like, go dark for a month, um, thing. So there were a lot of engineering leader left. I was in charge of engineering for six months. Like that's right. Yeah. Then in the six months after you left, we turned over almost the entire executive team because shortly after the, after you left, we our new engineering leader left and then our growth leader left.

Um, and so there was a lot of just a lot to lead through in that point. And then, you know, it was interesting is I think that I used you as a crutch in a lot of ways, both in how I showed up to lead the team, because One thing that you're really good at is bringing like a hype and energy and that community clear communication.

[01:22:00] Yeah to the team And so I was trying to figure out how to step up and do that But then also I use you as a crutch in decision making and we I think both do this with each other Yeah, we'd be like, well if I could do it my way, yeah, then I do these things And you'd be like, well, if I can do it my way to do these things, and there'd be like 50 percent overlap in the, in the list.

And for whatever reason, we wouldn't do it. Which is so weird. Looking back, we both had this idea that we would have managed differently for performance if we were fully in charge, which is ridiculous. And so afterwards we had a bunch of people leave and then we started the process, like we let quite a few people go after that too.

probably the most egregious examples.

Barrett Brooks: Yeah.

Nathan Barry: Um, that to, to this day, I don't know why, like what it was in me before, where I was like, no, no, no, we're like not going to hold a standard on performance.

Barrett Brooks: And just to kind of peg that, I mean, I think today y'all basically have about the same number of people [01:23:00] as when I left.

We've, Yeah, right at 70, 78 people. Okay. So a little bit bigger. We were in the neighborhood of 75 when I left. Yeah. So just for, to peg it, you know, that it was like, there's dip and then building back. And this

Nathan Barry: year we'll hire quite a few more. So I think we'll end the year, you know, in the nineties. Yeah.

But yeah, there was a bunch of things that I think I like to use the reboot analogy, like took my seat as a leader and made a lot of those decisions. And so a few people have said like, Oh, you know, after Barrett left, you had like the biggest spurt of, of career growth because you just had to do it, do it on your own.

But it was, that was a very, very challenging time.

Barrett Brooks: It's interesting. Cause, um, I used to say this back then, I think it kind of annoyed you sometimes, but we operated very much like a co leadership model, you know, it was like really neither one of us made independent decisions ever, basically And so we kind of had this weird.

It was like [01:24:00] see the office of the CEO, COO is almost like, yeah, you can look at it. Uh, and I get why people like Paul Graham and others will say a co CEO model is unhealthy, except for in the rarest of instances, because it's often a lack of clarity on who is driving the decisions. And I think we had some of that, you know, it's like, we really should have been more clear on which of us were driving, which decisions and just.

Trusted each other and corrected when we got out of bounds, you know, what has the process been like for you as we have now tried to kind of like find a new ground to stand on together in terms of friendship and like business and just rooting for each other and everything else.

Nathan Barry: Yeah, I think we, we did a good job of always leaving the door open on the personal relationship side.

You did a much better job of like staying, you know, in touch or following up more often. You're a little busier to be fair. I guess that's true. Yeah. Uh, but then I think it was just those gradual [01:25:00] conversations, you know, and staying in touch, you came to craft and commerce the next year, you know, and so we had more, more time together.

Um, we started to fall into some of the older habits of like, The things that we'd give each other advice on, like playing to each of our strengths. It was in a different dynamic, but you know, something that you and I have always done together is like writing conference talks where I would sit down and be like, all right, so I'm going to, here's what I'm trying, you know, like talk through the arc of it.

And then you would stop and be like, okay, so what it sounds like you're trying to communicate is this. And you'd reflect back, you know, I'd give you like an eight minute, Then you reflect back like the eight sentence version of that. And I'm like, yes, as I write that down, that's the talk. And then we, you know, shape it around that.

I really liked it when you started to ramp up your personal brand and content, because it felt like that gave me like an avenue to be a cheerleader for you and to like, cause one [01:26:00] thing, you know, I've always been much more the face of ConvertKit, even as we've built it together. And so I've always known, or I feel like I didn't know your abilities As a leader and an individual much better than the general, the world knows it.

And so as you've ramped up your personal brand and content, that's given me the ability to be like, like Barrett's phenomenal at these things and like advocate for that. And with the launch of the podcast and those things,

Barrett Brooks: the podcast is my startup right now, and I want to make it sit alongside heroes of mine in the podcasting world.

Tim Ferris, Krista Tippett, Ezra Klein, you know, it was like this series of people that I think of as like their world class great, good work is going to be up there someday and all I got to do is stay in the game long enough to win. Right. I think you probably feel what I feel on some level, which is, I think I can be world class at this.

I'm not there yet, but I'm going to put myself on the path and that's the goal. [01:27:00]

Nathan Barry: I'm trying to do the same thing and take content seriously on another level. Cause. Realizing what an opportunity is to grow, convert kit and the brand and everything else. And I think it requires two things. One is the consistency for a very long time, which both you and I have struggled with where we'll start something and you know, we'll run it for months or a year and then we're pivoting or shutting it down or restarting or whatever else.

And then the other thing is. Like this relentless improvement. Yep. Like I got, um, someone I got to know, uh, in the last six months is John you shy, who's a really great YouTuber. Uh, he worked at both Instagram and YouTube and then has gone out on his own and is creating all this content about the creator economy and all of that.

And he, uh, he's coming to speak at craft and commerce this year. I mean, he just sent me a text the other day. Your content is so good. [01:28:00] And your packaging is so bad. You could actually like really go somewhere with this. If you, you know, he's like better thumbnails, like a bunch of these things to, to really like bring a lot of these, like YouTube fundamentals to, uh, to the content.

And so, you know, what I'm trying to make plenty of time to do is to be like, all right, John, like, You know, tell me what to do. Show me the way, show me the way we're going to record it. We're going to get in front of the team. I think also like hiring more of a team, getting the right people around me. Um, some, you and I are both like jack of all trades people.

Right. And I think we're both at a place in our personal brands where that'll start to hold us back because we're not hiring or investing. And then, you know, the consistency starts to be reliant on our own, You know, willpower and ability to show up for failure. Yes, it is.

Barrett Brooks: Cause if we're sitting around fiddling with like video editing and [01:29:00] audio levels and stuff like that, it's just not, that's not where we're great.

Right. You know, the crew here is world class at that. We don't need to be the ones doing that kind of thing. And so two things that, that sparked for me that you're like section there. One is when I set out to make this show, it was minimum five years in my mind must be consistent for five years. Don't get to stop no matter what.

I don't get to even evaluate it until I'm on the other side of that. And I'm going to do everything I can to speed that process up, right? Like I want it to grow faster, but I'm not going to evaluate it for five years. So 250 episodes at minimum.

Nathan Barry: Wow. Yeah.

Barrett Brooks: Um, you don't even get to think about it for at least 50.

Yeah. Cause the reality is no one cares. No one even knows it exists right now. All things considered. And the second thing is I knew up front, I got to hire someone to produce this because it will never get done,

Nathan Barry: right?

Barrett Brooks: I will quit immediately if I'm the one on the back end, like doing the editing and making the clips and all, I just can't do it.

Nathan Barry: Well, I think that like trying to understand from the [01:30:00] beginning how what you're doing with a personal brand is different from what's out there Now. Yeah, it's not a requirement. You have to be different to be successful. Yeah, but having that angle I think is really helpful. And so that's something like I'm pivoting You My podcast in a couple of ways.

Announcement, big announcement, breaking news. Uh, the first thing is I'm going to in person episodes only love that because I just found the conversations are better. The clips perform better. Okay. So I have heard

Barrett Brooks: that there is something algorithmically that video platforms can tell when it's recorded on Riverside

Nathan Barry: and

Barrett Brooks: that it gets deprioritized.

I don't know if that's true, if it's just like one of these internet lore type things. But I could totally see that being the case where if there's a common code snippet or something happening or some formatting thing that they just pick it up and they're like, ah, it's just another like talking head thing.

Nathan Barry: I don't know if I believe that, but I do think that the, that the audience engagement is different or let me back up. So I was, uh, out visiting Ryan holiday. A [01:31:00] few months ago and tumble brag. Exactly. Uh, but there's lots of Ryan holiday things that'd be actual breaks. I could say, but we'll, we'll leave those.

Uh, so at his bookstore and the next door he has, he's built out a podcast studio. Yeah. And, uh, I was asking like, Hey, are you recording a hundred percent in person now or not? It's like, ah, we're Trending that direction or most of the way there. And he said he asked his team to do an analysis on all of the clips that they do.

Cause they have for daily stoic, they have a million plus subscriber Instagram account and you know, they've grown socials really big and his team had analyzed it and they said on average, a podcast clip performs 50 percent better if it was recorded in person versus versus virtually. And the reason that I think it is, I don't think it's actually an algorithmic thing.

I think it is a perceived quality thing where when I am browsing through a clip, I can tell immediately, right? [01:32:00] The camera is slightly off at an angle, the mic position, you know, all, all of these things. I assume it's a higher quality conversation because it's a higher production quality. And so I like, then the watch time is slightly longer.

And so we go on from there.

Barrett Brooks: Well, and the rapport of the people speaking to one another is different and all of

Nathan Barry: it, it ends up being. Better in a bunch of different ways. So what I'm doing with my show is switching to two different styles of episodes. First, trying to do the conversational one like this, where we're just talking through riffing on topics much more than interviewing.

But both myself and the guests can really demonstrate expertise. Um, and hopefully get some things not shared before. And then we're going to do a second episode, which is purely a coaching episode, like in front of the whiteboard, breaking down their business, talking through things. Yep. Exactly. Cause I don't see anything like that happening, right?

And so as we record all of these in person, I think it'd be higher quality content, totally unique and targeted at [01:33:00] this like professional creators, you know, 500, 000 to a million a year or more in revenue looking to scale. And I don't care if it ever puts out big views, but you know, I'm getting these notes from a lot of creators that I respect where they're like, that episode was amazing.

And I'm like, You listen to the show. That's that's fantastic. And so then it's like, all right. So now that I have that format, I just have to show up consistently. And like you're saying, do it for five years.

Barrett Brooks: Yep. Okay. So we should wrap up here. Cause people get bored of hearing us talk probably,

Nathan Barry: even though

Barrett Brooks: we could keep going, we could do it forever.

Yeah. Um, this is like, uh, our version of the random show for Tim Ferriss. Um, suffer higher quality, uh, in terms of density of information in this particular episode. No, no, nothing but respect all of a sudden Kevin. Nothing but respect. Nothing. I can't wait for that to get clipped. Look at this bozo hating on like two of the most popular people in the world.

They think they're better than anyways. [01:34:00] Um, all right. My last question for you, uh, this is my last question I always ask on the show, which is. Through the work that you're doing and at the stage of your life, who are you becoming?

Nathan Barry: Oh man.

Barrett Brooks: To get a little existential here at the end.

Nathan Barry: There's so, that's so broad.

Perfect. You're not going to give me anything to like narrow it down slightly. No. Who do you see yourself becoming? Who do you hope you're becoming? Uh, I'm going to go with the first thing that comes to mind. I'm sure there's a much more thought out journal dancer that will come, you know, tomorrow, tomorrow, later.

Um, yeah. I think the biggest thing I've always been someone who knows what I want and what I value. And I think I'm becoming someone who is decisive and confident enough to actually act on that. Like a question that Dan, my coach will ask me, it's like, well, if you were in charge or you were the decision maker, what would you do here?

And the things I'm stuck on. And I will often list out of like, Oh, [01:35:00] I do this, this and this. And he was cool. You are in charge. You were the

Barrett Brooks: decision maker. Yeah.

Nathan Barry: And so I think I tried way too hard to be, uh, to be liked, to make people feel heard and to make sure I wasn't a burden on other people and all of these things.

And the, the person that I'm actually working on becoming is someone who is much more. Like confident collected and like steady in that and just trusting my instinct and going with that and also being like relentless in, in bringing that to life. Like, these are the things that I want. And someone's like, well, that's not reasonable.

It's like, you know, and still driving towards that. And so, yeah, it's way more fun as a way to live life. And I think it's way more like settling and comfortable for the people around me. Because similar to what you were talking about, I actually can't remember if it was earlier in the [01:36:00] show or last night or whatever, but as you know, as you're always checking in on other people and you'd be like, is this good with you?

And, and, and shifting to saying like, Oh, I'm going to trust that you're an adult who will tell me, you know, what your needs are and all of that. Like, I don't have to manage that. I think that's the big shift that I'm making as well and saying, this is where I'm going. If you want to come along for that journey, that's amazing.

If not.

And then letting people, you know, opt in or opt out on their own. I love that, man. I'm really proud of you. I'm excited to see the fruits of that. Thank you. It's a ton of fun. Well, this has been a great conversation. Uh, we have two different shows. Indeed. Good work with Bear Brooks. Yep. Follow, subscribe everywhere, write reviews.

And so whichever episode, whichever one you're listening to is on, go and download both. You don't have to listen to it twice, but download both. Yeah. And, uh, leave those ratings and subscribe and you know, you're going to see a lot more content [01:37:00] coming from both of us. It's going to be a lot of fun. For sure.

Thanks for doing it. Always. If you enjoyed this episode, go to the YouTube channel, just search BillionDollarCreator and go ahead and subscribe. Make sure to like the video and drop a comment. I'd love to hear what some of your favorite parts of the video were and also who else we should have on the show.