Our Risky Branding Strategy Changed Everything

A brand is a funny thing. It's not really what you say it is. It's the impression you leave in someone else's mind.

Today I'm sitting down with Charlie Prangley, who is the creative director here at Kit, and we're breaking down the ConvertKit to Kit rebrand 3 months later.

Rebranding isn't just about what you're putting out there publicly, what people are seeing of you. It's also about how we operate internally. Having the right assets there gives you that confidence to like have conviction in what you're selling.

If someone's listening and they're like, okay, brand strategy, I've heard those two words put together, but like, what does that actually mean in practice?

Yeah, the brand strategy is your like vision for the reputation you want to build, the like personality you're trying to craft. Yes, creators care about earning more money. They also care about a lot of other things. Ultimately, they have this deep connection with their audience. If we understand that, we want our brand to resonate with that audience.

What's been fascinating to me is watching people react to the Kit brand versus the ConvertKit brand. The talent is excited. Hearing Matthew McConaughey being excited about launching on Kit. Tom Brady's manager talking about why they selected Kit. Brand matters so much.

And I think what enabled us to do that was—

Well, we're back 6 months later.

Mm-hmm.

You're on the podcast.

Yes.

A lot has happened in the last 6 months.

Yeah.

When we last recorded, we'd basically just finished announcing that we were going to rebrand to Kit.

Yep.

At Craft and Commerce. That was wild. And we talked through all of that, but then really all the work came and we worked on it a bunch beforehand, but so much work came to launch the rebrand. And I want to dive into that in this episode.

Yeah. It's so funny to think that the last time we recorded a podcast, we didn't know what the kit logo was gonna be, what our color was gonna be. I think we might have been in the middle of color discussions. It's wild to think how fast that all happened and how far we've come since.

Yeah, so we wanna go through 4 lessons that we've learned in that process. But first, I feel like you and I have changed a lot as leaders over the last 12 months in particular.

I am a completely different creative director now to what I was like this time last year. It's wild. I think that going through the rebrand, like, I had to make so many decisions every single day almost about this rebrand, and there was just no choice but to have confidence in those decisions, right? Like, I could not sit there and like worry, oh, should it be this one or this one? I'm gonna be honest, I did do that for some things, like the color. Yep. But mostly you just have to like commit and move forward. And I feel like that has now led into the general way that I work at Kit, the way I manage the brand studio team is just like, okay, trusting in my gut, having conviction and moving forward with it.

Yeah, I think often in life, especially if you work as your own, you're able to delay or defer. And in this process, you couldn't do that at all.

Nope.

Right? It was like everything has to fall into place.

Yeah.

And everyone is looking to you like, you know, Charlie, I'm trying to rebrand, you know, an app. What, what color are we—

should these buttons be?

Yeah, yeah, all of those things. And if you're like, I don't know yet, yeah, then there's a lot of people saying, I'm sorry, but that doesn't work.

Mhm. And also the decisions that I made had to be good, right? Right. Like there was a lot riding on this. We were picking the color that's going to be our brand color you know, for a very long time, for a long time, our logo for a very long time. It's not like I could use the excuse of, oh, we can pick now and then maybe we can change later if it doesn't work out. And so that, that was a challenge also. But I think that also was entrusting my gut and, and learning how to give really good critical feedback to the agency so that we would reach that result that we needed.

Yeah. So I want to dive into the 4 lessons that we talked about last night, and the first one is really about the process of the rebrand. I thought it was like, okay, we start from scratch and now we have to build up from zero of this new brand. But because you led the team in doing this whole thing in public, we carried over so much. And then we got to, you know, we got to start to build this new brand on like day minus 90, right? Because we brought people through this whole journey and we talked about it a little bit in the last episode when you were on about how important it is or like how happy we were with our decision to rebrand in public.

Yeah.

And now, like, I could not imagine doing it any other way, right?

I think that your impression is that when you rebrand, you're starting from scratch, because that's what a lot of brands do, right? Right. Is they're like, we are completely new now, like, we need you to see us in this new light. And they don't bring you along on the journey or like tell the story of what they're trying to keep from their old brand, because there's a lot that we wanted to keep from ConvertKit, right? Like, we got where we were for a reason. There was a lot of things that were successful in that, and there was a lot of new things that we needed to bring in to get to the next level. And we got to make that choice of what we're bringing along and tell people the story of that along the way.

Yeah, something that we had is like ConvertKit was a very sincere brand. You know, a lot of the way that we told stories, you know, it was about the emotional arc of someone's life as they, you know, learn to earn a living as a creator and accomplish these things and all of that. And that's still a big part of Kit.

Yeah. So I think the lesson is if you bring people along in the process of your rebranding, one, you don't have to start from scratch, and two, you can keep the things that worked for your previous brand as you build on top of them for your new brand.

Yeah, I think that's very true. I knew we had a lot of brand equity in ConvertKit, but seeing it play through, through this whole process has just been absolutely amazing, like watching people be like desperate for next episodes of the rebrand and all of those things that made a huge difference.

Yeah, yeah, it really did. And we had a lot of feedback when we first announced this, right, that people were saying, oh, but you've been doing this for like 10 years now, why are you throwing that all away? Right. And we're like, we're not.

Yeah, I didn't feel like we threw any of that away.

No, no.

The only thing that I miss from ConvertKit as a brand.

I'm like, where are you going with this?

I don't think I've told you this before. The only thing I miss is being able to search the web for mentions of ConvertKit and know that when those characters show up in that order, they're talking about us.

Yes.

Whereas now with Kit, someone's talking about their soccer jersey or—

A sewing kit.

A sewing kit or any of these things. And we have to be, you have to, No, based on context.

Yeah.

Or if we're actually tagged @Kit.

Yeah. Yeah.

Or something like that. But that's the only thing. Everything else that was great about the ConvertKit brand, we were able to carry forward very, very smoothly and we didn't throw anything away that we cared about.

Yeah. Yeah, exactly. We did get the feedback from people as well that Kit was too generic as a name. And I think that searching it comes into play there. But I think already, I mean, we've only been Kit for like what? 3, 4 months at this point.

Right.

And already it means something to people, right? Like already we're seeing people talk about us in a new way and it's like, yeah, we, we're putting meaning onto the word.

Right. And so another thing that people said would happen a lot is, you know, we'd lose our search rankings.

Mm-hmm.

Right. Because we didn't just do a rebrand, we did a domain migration.

Yes.

And everyone's like, don't do that. And they had all these examples of like WooCommerce going to woo.com.

Yeah.

And then changing back. And so there was like the whole SEO industry was watching to be like, how is this going to go? And I was just talking to Colin who leads our SEO, and we're now at 105% of our search traffic from before, which is pretty wild. Like, I don't want this to come off as bragging because that's not what we're trying to do. But in a few different cases, we did things that you should not do as a company where you're like, oh, there, there's too much at stake. And so don't mess with those things. Don't switch domain names. It can't be done effectively. Don't change the name of your company 10 years in. 10 years in, you throw away all this brand equity, all those things. And I think that we have left a case study behind of you can do these like wild, ambitious things and do it in a way that it's hard, but it's not long-term costly. Like, you don't lose something.

Yeah, and if you care about it enough to like go into the details of making sure you're bringing with you what you wanna bring with you, it can happen. And I think what enabled us to do that was the time we spent with Koto on developing our brand strategy, which is something that, I mean, we had as ConvertKit, but it was fuzzier. It was never as intentionally crafted as what we've put together for Kit. And that has given us something that we can use to, like a filter to make decisions through.

Right.

For, yeah, all the decisions we're making, what we wanna keep, what we wanna leave, it all comes back to the brand strategy, which is what we're trying to build.

If someone's listening and they're like, okay, brand strategy, I've heard those two words put together, but like what does that actually mean in practice?

Yeah. The brand strategy is your, like, vision for the reputation you want to build, the, like, personality you're trying to craft with your brand. Because a brand is a funny thing. It's not really what you say it is. It's the impression you leave in someone else's mind. And so you have to make decisions to try and, like, leave that impression with them when they interact with your brand. And it's not really up to you at the end of the day what it ends up being, but you can make choices to try help. Get there. And so that's what we've done with our brand strategy. Um, and I keep coming back to these three words because you want to have something easy to remember. So the personality traits is bold, expert, sincere. And so everything we do, we can run it through those three words, and that's really helped us make the right decisions along the way.

Yeah. So how would you describe, I don't know, bringing that to life or other aspects of the brand strategy? Let's say you hired a new designer to your team or someone whose job is to live and breathe this this brand, what would you be telling them?

Yeah, well, first we have like a brand strategy deck that Koto made for us that really walks you through it and walks you through what it's based in as well, because they did a bunch of research and came to this key insight that yes, creators care about earning more money, but they also care about a lot of other things. And ultimately they have this like deep connection with their audience and they want to provide value to them, right? And so that's what it's based in, is it's like, it's more than making money. It's about true value, connection, getting your time back, the freedom, and all those other things that come along with it. And so if we understand that, we're understanding our audience, and that's what our brand is based on, is we want our brand to resonate with that audience, with people who care about that. We care about it too. That's what we're trying to showcase.

Yeah, that makes sense. One thing that's that's different is that Kit is much bolder of a brand than ConvertKit. What are some ways that you brought like that boldness through?

One of my favorite ways is with our custom typeface. It's like, yeah, we got to design it from scratch with Koto and a hot type, like type foundry. And it was really fun to just make every little decision about the letters. And it's such a great typeface. It's got personality, but not too much. Because you can still like read it. We want everything to be legible that we write. But you can literally just take our, our brand color blue, put Kitsands on top of it, right? And it looks like Kit. It's our brand, which is not something we had as ConvertKit. We did really feel like we had to put our logo on things for it to feel like us. And I think that's because our brand was kind of fragmented where we weren't making decisions based on a clear brand strategy. It was more about gut feel and maybe some personal taste thrown in there as well. And yeah, that just leads to, I don't know, some inconsistencies and something that isn't got a lot of conviction behind it, whereas Kit has more conviction behind it.

You mentioned that the ConvertKit brand was fragmented. I think part of that is from where it started. Yeah, fragmented because we made the Seva brand.

Yes. It was never meant to be a ConvertKit brand. Right.

And then we actually just wrote ConvertKit in that same font. And, you know, it had to be— yeah, a lot of things had to be designed.

The creative director I am now would never do that, right? I'd be like, no, no, no, we have to start from scratch.

You have to start from scratch, you know, based around the company name.

Yeah.

Is there anything else in brand strategy that has been impactful?

I think that maybe brand strategy feels like something that is difficult for folks who aren't brand agencies to put together. But I think what I learned from working with Coto on it is like Really, it's just your vision clearly documented in a way that's easy to remember for you and anyone on the team to come back to and use as that filter for decision making. And so it doesn't have to be a fancy process. You just have to describe like how it is you want people to see you and keep coming back to that.

What about the messaging and positioning? Because we spend a lot of time on that.

Yes, we do.

And there's different parts of it.

Yep.

You know, we talk about how Kit is the email-first operating system for creators who mean business. Early on in the process is when we came to that creators who mean business line. And that just resonates because there's a— there's, you know, we have a level of sincerity, but so do the creators. So the creators we serve, like, you know, and mean business, it has multiple levels to it. I mean, you know, like we're here to build a business. We're not just messing around on social media for the fun of it. And then we also, you know, we mean business like Yeah, it's sincere, it's intentional. It's, you know, it's like, okay, if I'm— if someone means business, then they're very good at what they do.

Yeah.

And they're going to approach it with this drive and resilience that other people don't have.

And they're building a business with meaning as well, right? Yeah. For their audience.

Yeah. So another thing that we say is, you know, we exist to help creators build valuable businesses and we have— it means very similar things. But valuable means, you know, where you want to build equity or enterprise value or like the tax revenue. But then businesses that deliver value, like that's something that we've always had with ConvertKit where we would say like, hey, we're here to help you earn a living, not make money. Like one, make money sounds kind of cheap. Yeah. Living is like, hey, there's a lot of work that goes into this.

Yeah.

But then we've also always centered around the audience, right? The creators who we've worked with are the ones who are delivering value and they're saying, I am here to serve my audience and my business will grow as a result of that. Compared to— there's a lot of people in the make money online world who are saying my audience is an ATM that I go and just withdraw cash from whenever I want and they're there for me.

Yeah.

And a Kit creator or a ConvertKit creator is totally different. And we've carried that through, I think, really well.

Yeah.

And now we have the short phrases.

Yes.

To articulate that.

Yes. Yes. And that's where, like, we've made a change recently actually on the Brand Studio team is that we've moved Isa, who was previously our senior storyteller, into a senior writer role. And she's bringing with her the, like, depth of understanding of creators and the ability to write really sincere words that like, honestly, I mean, she makes us cry all the time, right, with her stories. But that is now being applied to like our product messaging and in how we talk about our product. And we didn't have someone on the team before whose role was to write the copy that expresses our product. It was kind of like pulled together from a bunch of different members of the team. And I think this is another way that Kidd is operating, is investing in the words. And knowing from that process with Codo how important it was to go back and forth on every little detail of the words, and now we're going to get to do that more often.

Yeah, exactly.

And I think that that's another thing we've learned, is that rebranding isn't just about what you're putting out there publicly, what people are seeing of you. It's also about how we operate internally and the shifts that we've made in, I guess, our mindset as a company. That before, we didn't have a writer on the team. Now we know that's something we need. And ConvertKit didn't have a senior writer, Kit does.

Yeah, what are some of those other shifts that you've seen in the transformation?

Yeah, I think that we've all leveled up our expectations for ourselves in a way. Like we're aiming for a higher bar of quality and we're not afraid to use the resources to help us get there.

Yeah.

Like when we rebranded, well, Sever, ultimately ConvertKit, we didn't use like a big agency. We worked with a studio and that was the help, the design for us. Yes, just the design. Yep. And that was how ConvertKit approached things. Whereas for Kit, we worked with like a large agency who had that strategic expertise in-house as well. We spent a lot more money on it as well, and we weren't afraid to do that because we knew it was an investment in getting to the quality that we needed to have for this like long-lasting We're doing that more and more as well. Like right now we're working with a dev agency called Square Black on our website. We previously just had Corey, our senior front-end developer, working by himself on it. And now we're making sure that we have extra resources to like create more, create more at higher quality.

Right.

And we're investing in that type of thing.

I think that the Kit team really brings out bold so much more. Like we take a bold action. Some of these ideas of how we're going to build functionality or announce it or some of these moves, we're just like, we're doing— I mean, we should, but okay, that feels a little scary.

Yeah.

And as ConvertKit, we deliberate on it for a long time. Maybe we choose the safer option. And as Kit, we're like, let's do it.

We're—

it's— there's much more of a trust your gut because I think with the brand strategy and the principles and all of these things, all the work that we put in, We have the same shared understanding.

Mm-hmm. Mm-hmm.

And so then we can say, I think we should do this. And the, you know, someone else on the team is like, well, yeah, it's right in line.

Yes.

And, and so the, the shared understanding allows us to take bold action.

Yeah.

One example would be, uh, ConvertKit as a company was scared to launch a, uh, an app store or platform because it's such a huge undertaking. Like to do it well, this is a decade-long commitment. And that's not playing it safe. That is as hard as it gets in software development. And Kit is like, yeah, of course, of course we would do that. We're in it for the next decade. We know it's going to be really, really hard. And then actually bringing in experts, that's another thing that instead of trying to do that with who we had on the team, we brought in Katie, our new VP of product, who— where she led product for Square eCommerce before, right? So she has a ton of amazing expertise. We brought in Dan as the director of design who knows activation and, you know, all of these things very, very well. And we brought in Rohan who built out so much, so much of Shopify's app store strategy. And I was like, well, who does the absolute best? Shopify. Great.

Let's bring him.

And so I think another difference at ConvertKit, we would have said, hey, let's do it homegrown.

We'll learn, we'll interview people.

Who know how to do this. And at Kit, we're like, no, we're bringing it straight to the source. Yeah, who's done this before? Yeah, that makes a huge difference.

Yeah, it almost feels like Kit has more self-belief than ConvertKit did as well. Yeah, and I think that that is showing up in us as leaders too. Like, we've got more belief in ourselves now as Kit.

Yeah, we do for sure.

Another example of ConvertKit versus Kit is the way we've run this retreat that we're on right now. We're coming to the tail end of Previously, we would have a bunch of sessions and they would all be focused on different topics and we'd be strategizing and we'd end up coming out of the retreat with a long list of stuff we wanted to do when we got back to work. Whereas this week we've had what we've called Create Week, which is like hackathon where we took a problem we wanted to solve and worked in small groups to try solve it this week. Let's not make the plan and then do the work later. Let's do the work together now while we're here. And it's been so much fun.

I wanna go back to that in, in just a second, but I'm realizing that ConvertKit was very, the strategy was maybe very clearly articulated all the way down.

Mm-hmm.

And with Kit, what we've done is we've articulated a more high-level strategy and then had people be more self-directed underneath that, right? So as an executive team, we, as ConvertKit, we'd be like, here's what we're doing, Here's what everybody, each team is doing underneath that. And our 2025 strategy for Kit was actually not even one page long. And then the team said like, okay, here's how I'm going to—

We're gonna get there.

To build up underneath it. And the tie into Crit Week is that it's very self-directed. Where we didn't say, here's the projects. We put it out there and said, who would like to lead a project? What's your pitch? And everyone knows the strategy and where we're going. So the pitch is, were all really good, but then we ended up with 14 individual leaders from all levels of the company. Most were individual contributors, some were managers, some were execs, and you got this wide, wide range of projects. And then everybody just said, oh, this seems interesting. I want to join it. And then everyone just dove in and built things. I worked on a project where We used AI to develop apps and we ended up taking two non-developers on our team and they built apps that they knew would be either be very meaningful for themselves in their role or for, uh, their coworkers. So Shiv, who's our creator educator, he used AI to build a, a tag management app that his creator growth counterparts, uh, would really, really value. And then Maggie leads our agency partnerships. And she wants an agency dashboard where she built it. So she built it. And that was like this bold, ambitious thing that, you know, you just needed to bring to life. And, and so, yeah, this week we just dove in, you know, did a hackathon and it was amazing. I don't know if it's in the shot, but there's stickies and things behind us from some of the stuff that we built. But that like that fast-paced.

Yeah.

You know, hey, how's it going?

Dive in and do it.

Yeah.

Yeah. And also what Nathan probably wants to tell you but won't is that his team won the Most Progress Award.

We did. We did. We have a little trophy to prove it. That's something that I really want to keep going as we build out Kit is this idea of taking bold action and saying, hey, we can build the future. And so we're going to do that instead of like, oh, we talk about what's possible for a long time or how to do it.

And then base it in reality.

Yeah.

Yeah.

And instead it's like, no, I can make that happen right now.

Yeah. That was really fun this week, actually. We dove into a, it's the most we've ever talked about AI, I think, as a company is this week. And we're all like, we're using it to help us build faster to get these proof of concepts out. Like I built something in Replit for the first time and it was really fun. And that's something where like, oh, I've never considered being able to do that. And now Oh, with AI it's possible.

Well, and that we're spending so much time on the scaffolding to make that possible.

Yes.

Like that was actually the project that, um, I was on the team that worked on was we made tutorials on how to do this. And so yes, we built two apps, which was wild that that actually worked out. And like they're production ready in there. Production ready might be a little slow. Uh, they are definitely internal team production ready. Um, but really it was about the creating tutorials along the way so that anyone else can follow along. Like I started playing with this a month or so ago and, oh, so you got a head start on Create Week. Well, so what's, yeah, exactly. So we cheated. That's it. No. So what I did is I was like, oh, I wanna try to build an app for the kid app store.

Mm-hmm.

And I think I can use AI to do it. And I hit so many roadblocks and I didn't understand this.

Mm-hmm.

And so then I pulled together a team and said, hey, let's. Figure out how to overcome all these roadblocks and then teach our community how to do that. Like for example, an OAuth authentication between the app that you make and Kit so you can display data, like total pain to do. But now we got to the point where we have one perfect prompt that you can put into an AI agent and it will do that entire first step, which would normally take you days. And you watch it do all those things and it does it in 2 minutes.

Nice.

And that's wild. But then really, I guess this is the thing that Kit's doing. Kit is thinking in scalable terms everywhere of not just how can I do this, but then how can I make the platform so that everyone else can do it?

Yeah. Yeah. Isn't it interesting to hear how we're even talking about this? Kit does this. Yeah. Yeah. Whereas I don't think we ever really said that as ConvertKit. ConvertKit does this. List. We can, we can have conviction around that now.

The next lesson, and this is something that is probably obvious to you, but I have really internalized is brand matters so much. I, I've always cared about design and I've always cared about product and, you know, and company culture and all these things which collectively, like, they come together and they make a brand. Yeah, but I've never been the brand strategist or obsessive about about these things. But what's been fascinating to me is watch the Kit brand play out the last 3 months. We have closed more star or celebrity creators in the last 60 days, 90 days than the entire rest of the company history combined. And the rate that it's happening is wild. And you know, we worked for a long time for that to happen, but just, you You know, as a quick aside, it's like Ellen, Matthew McConaughey, Lil Jon, Hasan Minhaj.

Morgan Freeman.

Morgan Freeman. Tom Brady is launching his newsletter right now as we're recording. It's like today.

Oh wow.

He's launching his newsletter on Kit. That was actually a really fun retreat moment was we got the news that he is launching, you know, like while we're all here together and we got to celebrate. But what's been fascinating to me is watching people react to the Kit brand versus the ConvertKit brand. I think as ConvertKit, everyone treated it as like, okay, cool. Yeah, it's like we have a thing that we're doing and ConvertKit is a tool that we'll use to do that.

Yeah.

And the behind the scenes managers care about tool selection, but the talent doesn't know or care. As Kit, people just accept us in all these conversations in a way that they didn't. And the talent is excited, like hearing Matthew McConaughey talk about being excited about launching on Kit, hearing Tom Brady's manager talking about why they selected Kit, all of those things, it's a different level and you see it carry through in everything. The pitch decks are a huge thing. What your team has done to set our sales and partnership up for success with these amazing pitch decks. We had a very tight timeline to pitch Tom Brady because they wanted to launch for the Super Bowl because he's calling the Super Bowl in a week, right? Super Bowl's in 8 days. He's trying to launch his newsletter, grow it in advance of the Super Bowl. And so we had the absolute tightest timelines, but we pulled all that together. And I think we did that entire pitch in 24 hours and their team was just blown away. And it is because of how the Kith brand came through all of this.

Yeah. And as creative director leading the brand studio team, our sort of like audience or like the customer we serve is our internal team really, in that we have to make sure we're providing them with the assets to do their jobs, to reach their goals. And it meant so much to me to hear Maggie on our sales team just rave about how proud she feels to present these kit slides to folks. And I honestly think that like, you know, someone getting on calls, like having the right assets there gives you that confidence to like really have conviction in what you're selling. And I think it helps. And I think that that's, that's showing up. And it means a lot that Maggie is just like proud to present them, you know?

Right. Yeah. And we're just winning deals left and right with those. And the momentum that comes from this is just wild. And when Maggie said that, she was like talking about the level that people are blown away by the quality of the brand and the presentations and everything else. And she's talking to these huge agencies, the big talent agencies in Hollywood. She's talking to marketing agencies and everyone else. And these are people who probably see 1,000 pitches a year. And so it's at the highest level and we're blowing them away. When we got the verbal agreement from Tom Brady to sign with Kit, his manager said, hey, I just want to say that if I could describe the kit team in one word, it'd be professional. Like the way that you guys have delivered on this, the thoughtfulness of like the full launch strategy and everything else just blew us away. And like to get that level of unsolicited feedback, you know, you know that, all right, this is working and all of that effort put into a rebrand really, really matters. And so like, I go back to those comments that we saw, you know, probably you and I were reading as we recorded last time in June where people were very positive, enthusiastic, but there's some of these other ones that are like, oh, it's gonna be a big waste of time and all of that. And it has been absolutely the best move and it helps individual creators. Cuz what happens is we're building the momentum that we have is insane to me. And it builds up this incredibly strong network that then benefits every other creator on the platform. Because now like Tom Brady is bringing in advertisers who are like, hey, what other newsletters can we sponsor? And that's cascading down to the rest of our professional creator base. And then as the brand reputation grows and the product improves and more and more creators come on, it's just absolutely wild.

Yeah, it's so cool. And I love hearing those stories because our sales team is so great at reporting back like, oh, we like closed this deal, but also why and like stories behind it and hearing the things that were mentioned as like a reason we were chosen relate back to our brand and our brand strategy and what we're trying to build, the reputation we're crafting that our sales team are clearly doing a great job of embodying. And that's really special because brand is one of those things that's hard to measure the impact of by itself. 'cause by itself it doesn't do a lot. Like, it has to be applied to other things to have the impact. So to just hear brand coming up, you know, in these— all these touch points as the reason that people are relating to us, are choosing us, I'm like, okay, now I feel like I'm doing my job right. Yeah.

And, you know, we did an exercise with all of our managers and leadership where we did a SWOT analysis. So you go through and look at our 2025 strategy and where we're at in the market. You do strengths, weaknesses, Opportunities and threats, and you break it down and everybody did research and thinking about it in advance, but then wrote a bunch of stickies down and under strengths there was a whole bunch of stickies around brand.

Yeah.

And it just shows how much we believe in it and how everyone is seeing it play out.

Yeah, it's awesome.

Oh, actually this is a good moment.

What?

My phone kept blowing up with a whole bunch of things. And it's the announcement of Tom's newsletter.

Oh, nice. I was like, why are people texting you?

Like, no, it's all the reposts and messages on social of like, we're excited to announce that Tom launched his newsletter. Look at that. Launched on Kit.

Woo-hoo.

Get access to the 7-time Super Bowl champion's thoughts on business, media, leadership, health, and of course, football. And then this is the first reply. The power of Kit. Look at that. Nice.

All right.

With that moment recorded, I'm now gonna put my phone on do not disturb so that we can record uninterrupted. And then I'm gonna go answer like the next 50 texts that I'm about to get. Cause everyone's going to be very, very pumped and excited. I think the last lesson that I wanna talk through is that the rebrand, like the work of the rebrand continues so far beyond the like, okay, here's the finished brand deck and styles and everything. Like when, you know, Coto as an agency who helped us through this whole process, when they're like, all right, we're done.

This project.

Thanks so much. Yeah, this is finished. That's like when the real work began.

Yeah. For our team especially. Like it's— yes, Coto can build this beautiful thing for us, but it's on us to implement it.

Yeah.

And to get that right in the execution.

But what are some of those things as you go through the implementation of the brand, you know, basically from in finalizing all the details to now? Yeah, that really stood out.

What stood out to me was, I guess, what we were trying to counteract of what we're doing as ConvertKit is that we wanted to keep consistency. And so I was really strict on making sure that everything we were applying the kit brand to was consistent, that we're making consistent choices in like how we use the ratio of our headings to our body text or like anything like this in the assets. So that we're starting from a good base. Because if you start from that point, it's just easier to continue it than if you put out a mess and then have to fix it later.

Right.

Because that's what we're dealing with, with ConvertKit.

I mean, the systems all the way through.

Yes. Systems.

Anyone who's listened to me knows that in the last like 3 years, I've become obsessed with systems and flywheels.

Yes.

And we have brought that through.

Yeah.

In so many ways, you know, where we're just like, look, we're gonna do this over and over again. And 'cause before, like on design things, you or I or David or someone—

Someone would jump in and—

We do these one-off things.

Yeah, yeah, yeah.

And we'd get it out the door.

Yep.

You know what's interesting? We, like ConvertKit was scrappy. Kit moves with the same pace but is deliberate.

Yes.

And it's the systems that allow us to do that, right?

Yes, yep.

Like actually ConvertKit couldn't have turned around a pitch for Tom Brady in 24 hours. Kit can and can do a, you know, a pitch that wins and blows them away because we have these systems that are so built out.

Yep.

Right. Like we did tap in designers at the end, like Jackie on our design team came and helped us out, but she was like, hey, I've got tickets to something. I need to leave at 5 o'clock. And we're like, okay, that's in 47 minutes, you know? And so she helped us clean things up and all of that. But we were in a good, good place because we had such a good thing to start from. And that, yeah, we're able to deliver because everything that we've done with the Kit brand is systematized.

Yes.

And so we really put in the work upfront to set ourselves up for success, you know, over the next 5+ years.

And because we were having to apply this brand to everything, right, there was so much work to be done. We really learned very quickly that simplicity is best and we set ourselves up for this by crafting a typeface that was, had a lot of personality. Like I was saying before, you can just have a color on the typeface and it looks like Kit. And whenever we would start to get more fancy and like, oh, let's add in more elements, it like felt too much and it started to not feel like Kit. And so it was like, great, okay, we can do this faster because all we have to do is just keep things simple.

Yeah. All right, so those are the 4 lessons that we've learned, I think, doing one of the most iconic and successful rebrands of the last decade.

Not that you're biased at all.

I'm Slightly biased, but when you think about, I mean, now we're at this point, right? Like agencies and, and design sites and all this have written case studies on how we did the rebrand and all it along. Like it is something that people will, will study so much. But I wanna go back to this idea of leadership and, and personal growth. If you could go and sit down with Charlie 12 months ago, mm-hmm. Who either has, who, who has just finished announcing this to the team.

Yeah.

Like we're going to do this. What advice would you give her?

Just like, trust your gut.

Yeah.

Yeah. I honestly think that you inviting me up on stage to present the announcement to the team is like it unlocked something for me. It was like, okay, this is your seat at the table, right? Take it.

Yeah.

And so then I just like I did.

And that's the thing. It's like for any creator listening, I would just say like, you belong.

Yeah.

Take your seat as the leader of this thing and and be bold and execute in that way.

Yeah, for sure. And I think as a creator, when you're running your own business, you don't need someone else to give you that seat, right? Like, you have to give yourself that seat and start, I guess, seeing yourself at a higher level. Because I think that's what, that's what you did for me was like open up my mind to like see my position in the company as something bigger than what it was. Like I was over here in my little corner leading the brand studio team. I've always been quite like a visible person in the company just because I like to make jokes in the Zoom chat and team meetings. But this was like, yeah, it gave me the permission, I guess, that I had somehow been waiting for to step up and lead across the company. And maybe the advice I would give to myself before you asked me to present was like, don't wait for that permission. Just like, yeah, Act like you have it already. Yeah.

The other thing that has been a big theme at this retreat is this idea of dreaming.

Mm.

Uh, Isa, who we've talked about a few times, she wrote a book about dreaming.

Yeah.

You know, it's this, and like having these big dreams and pursuing them. And so many of our creators do that.

Mm.

And we did something at this retreat that we'd actually done 6 years ago.

Mm.

Which in Oceanside, California, as ConvertKit, we had we served a lot of technical marketers and authors and bloggers. And we had done this big wall of stickies and photos, magazine cutouts of dream creators that we would love to pursue. And it was a whole thing on getting the team to think bigger. Because the names up there felt ridiculous.

Yes. At the time we were like, well, we might as well put it up there, but it's not gonna happen.

Yeah. And so earlier this week, Isa referenced that wall. She was talking about how we had put this dream out there and how we'd achieved and gotten some of those names and so many more that were even bigger than people that we'd listed there. And so that was one set of dreams. And then another is I've talked about in my newsletter and annual review and something, my speech to the team to kick off the week, I talked about 4 big dreams that have come to life for me that I never thought would happen.

Yeah.

One is rebranding the company to a brand that like would carry us forward for a decade or more, like building a truly iconic brand. The next is bringing Kit Studios to life. We have the Boise location. Chicago might be open by the time we publish this. Like the next one is our free plan. Like so many people— when people recommend Kit, what I hear over and over again is, oh, you should start with Kit. They have 10,000 subscribers. Subscribers for free.

And people are like, really?

Like, they don't believe it. Yeah.

What's the catch?

The catch is that we're bootstrapped and profitable and we want to invest in the community. And that's something I've always wanted to do because I admire Figma so much as a company. And they took— they made professional-level design tools that anyone in the world on like a Chromebook could use in the browser.

Yeah. And they became an industry standard because of it.

Yeah. And then the last one is building an app store. And there are so many things that now when I have an idea, I'll like call someone up and say, hey, I think this app would work really well for you and your business. You know, as you serve creative clients or all of that, like, do you wanna build it? I'll give you my sketches. And yeah, so there's a bunch of apps that have come out along those lines. And I had all of those dreams come true in the last year. Mm-hmm. All as part of this journey to become Kip. And that was really our message to the team is dream, put out these big things and then build it. That was the contrast of Create Week is, all right, you can have these ideas and these big dreams and all of that, and then you can just sit down and make them happen. And I think that there was out of 14 projects, probably 9 or 10 shipped something really like that is very useful and valuable today. And they had like 10 to 15 hours of actual working time to do it. Like not even very much.

How do you think you either grew or had to grow as a leader to make those dreams come true?

I think a couple things. First was articulating them clearly, like believing that they could happen. Because for a long time I thought that those are too big or that's for a company that had substantial funding or that's, You know, where we missed out, we rebranded once, we missed that opportunity, we lost it. Or launching a free plan that's, you know, 10 times more valuable than what we had before will cost us way too much MRR. And from this position that we have, like, oh, now we can't afford to lose that. And so believing that it's possible, articulating it really, really clearly, and then recruiting people who have the ability to bring it to life. In doing that, it just, it makes all of these things come together. And I think realizing that we, we have such a privileged position because, you know, we do $45 million a year in revenue, we're profitable, and we're not answering to investors and like on some short-term time horizon or anything like that. And so it's like we can take these risks and bets and we can do things because we're like, this is the way we believe the world should be.

Yeah.

And so we're going to make that happen. I think it's kind of interesting to watch yourself acquire new skills. And before, to get up and deliver a speech that hit all the points that I wanted to and carried the emotional arc that I wanted to and everything else was really, really challenging. And I can think of a bunch of moments where I'm like, oh, that could have been better, or all that. And last night was one where I was like, okay, I had 5 bullets of what I wanted to cover. And that was all that I wrote was just the 2 words per bullet. And I was really, really happy with how it came together and hit all the points and wrapped up everything we're doing. And I was like, ah, that is a skill that I have now that I didn't have a year or a couple years ago.

And that comes back to the articulating. Division, right? Being able to take what's in your brain and like say it in a way that resonates.

Yeah.

And the— yeah, that lands with people and expresses it clearly. Yeah. And I came up to you after that, I was like, oh man, you're such a good public speaker.

But yeah, it just comes from that practice and everything else. The other thing is to be able to touch on like really hard emotional things and to tell really hard stories and to let myself cry But then to be able to bring it back.

Yes. I don't know how you do that because when I start crying, I can't stop.

But there's only— there's two team members came up to me afterwards and they're relatively new to the team and they both said, I've never seen a man cry in public before like that.

Wow.

And like that demonstrated a level of like vulnerability and leadership that was really, really meaningful. And like that's just the— I mean, that's something we brought forward from ConvertKit to Kit is like all of us leading from a place of sincerity and vulnerability and all of that.

I think that's why I'm here 8 years later is because this time 8 years ago we were in Oceanside on a team retreat and you cried telling the story of like why it's important for you to help creators earn a living. And I think that was when you got me hooked. I was like, okay, this is different. Yeah.

And it's like, I think you can build something really special if, you know, you put everything into it. And that's when I just think about the next 10 years of Kit. It's this level of sincerity and, and effort and the boldness and, and everything else and the community that we have rallying around it. It's just I'm very, very excited for it.

Yeah. And I think creators can see it too, that everything we're doing is because we just believe so much in creators. Like, we care so much. That's why we do this.

All right. I think that's a good place to leave it. Uh, it's been amazing to go on this rebrand. Thank you to everyone watching who has followed along with this. If you haven't seen it already, go and check out the videos that we have on YouTube breaking it down, telling the story. Like, we created a documentary.

Yeah. And it's really good.

It really is. And we don't just say that because we made it. No. Lots of people on the internet say that it's really, really good. And then I would say just watch the brand, like see what we're doing and implementing it. And if you are thinking about taking bold steps in your creator business, or you're thinking about doing something where you're like, oh, I wanna let go of this and pursue this new thing, but there's too much risk in that, like be bold, take those steps. Thanks so much for watching. If you enjoyed this episode, go to YouTube and search The Nathan Barry Show, then hit subscribe and 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 just who else you think we should have on the show. Thank you so much for listening.