Nathan Barry, Founder of ConvertKit

All right. Hello, everybody. We are here today with Nathan Berry, the author of Authority and the founder of ConvertKit. Welcome, Nathan. Thanks for coming. Yeah. Thanks for having me on. Can you give a little quick overview of ConvertKit, how it came about, and where you are now? Yeah. So, ConvertKit's an email marketing platform for professional bloggers. So you could think of it as the power of infusion soft, but easy to use in MailChimp. So kind of having that hybrid world of great automation and sophisticated features, but paired down to exactly what, you know, bloggers and content creators need. So as far as where we're at now, we're at 25 full-time employees, but not at for almost four years now. And hopefully this week we'll cross 500,000 in monthly recurring revenue. So I'm trying to get that in right before the end of the year. So, and then as far as the early days, you know, my background isn't blogging and, and then writing books. So, or and even before that, my background is a user experience design. And so I wrote a couple of books and was surprised to learn the email marketing was the most powerful way to sell those books. And so those books were self-published, sold on my site. And, you know, they did great. And I expected Twitter and Facebook and Instagram and all these hot, sexy new platforms to drive the revenue. And it just wasn't the case. Like, email was where the sales happened. And I told that to friends who were, you know, had been in marketing for a long time. And they're like, "Uh-huh." Like, we've known this since 2002. Like, good job. Welcome to the party. I thought you were said you knew what you're doing with marketing. And so I just kind of became obsessed with the email marketing and all the best practices. But I was using my elephant at the time and every time I went to implement a best practice, it was just frustrating. Like, I felt like I was fighting against the tool rather than someone saying, you know, "Hey, we know the best practices and we built a tool with those in mind." And so like best practices by default. And so I'd spend all this time writing books and I wanted to get back into software because that's what my roots are. And so I thought, "Okay, I'm going to start a SaaS application. Let's dive into that world." And that ended up being ConvertKit. And that was started in January 1, 2013. Right on. So obviously you've had some great success lately. ConvertKit's really taken off, but it wasn't like that all of the time. When it first launched, it was more of a struggle and it took some time for it to really get traction. Can you, I guess, talk a little bit about those early days and kind of the stepping stones that got you to the point where it took off? Yeah. So I actually didn't start with the idea of I want to start an email marketing company. I started with the idea of I want to start a SaaS company. Who cares what it is? You know, I just want to make this switch from eBooks and, you know, the category of digital products to software. And mainly for the recurring revenue. Call it 70 percent because I wanted recurring revenue and 30 percent because I wanted a new challenge. And so I actually started something that I called the Web App Challenge. And I did it publicly on my blog and you can still go back and read the blog posts. And I just said, "Hey, my goal is to go from, you know, today," which was actually December 31, 2012. I gave myself a day early to start the challenge. And my goal is to go from today of not having an idea or even knowing what I'm going to build to six months from now, having a SaaS app making 5,000 a month in a recurring revenue. And I knew it would be hard, but I'd just come off some really successful ebook launches. And so I seriously underestimated the difficulty of pulling that off because in a book launch, I could do $25,000 in a day, you know, in like $50,000 in a month. And so I thought, like, how hard could it be to get 5,000 in recurring revenue? It turns out very hard. And so, you know, but I was naive and I embarked on this challenge and partway through, you know, like in the first week or so, I decided that can, you know, convert it. An email marketing platform was what it was going to build. And the other requirement was that I could only put in $5,000 of my own money. And the reason for that was I'd seen lots of people come off one success and have money and then pour all of that into the next thing. And they didn't actually have to talk to customers because they didn't need money in the short term. And I didn't want to take $50,000 or potentially more that I'd just made over here and squander it all in like experimenting with software, especially because it's so easy to do. So my rule was that other than that 5 grand, it had to be customer-funded through pre-sales. Because I figured, then I have to talk to people. I have to get customers. And I have to, like, hopefully that'll help me find product market fit faster. And to fast forward a little bit over those six months, we got to about $2,100 in MRR. So, I mean, I think a reasonable goal would have been like $2,500, maybe to get to over that time period with my knowledge and expertise and capabilities. And I tend to set decently big goals for myself and I usually hit them by about, like, hit it right about the 50% mark. So that was par for the course for me. But then after that, like after that initial six months, we didn't, we basically just maintained that $2,100 a month. And I would work on it, but it wasn't really growing. It's really hard to sell recurring versus selling like a one-off payment, especially when you're not, you know, like, hey, buy an e-book and someone's like, cool, I can own an unlimited number of e-books. Whereas with an email marketing product, they're like, okay, is yours good enough that I should close down my Mailchimp account? Because I'm going to use one and I might try out another at the same time, but there's no way I'm going to be using more than, yeah, more than two for sure. And so you're, it's really about you're getting someone to switch. So that was a lot harder. And then when it didn't grow further, I had a hard time continuing to pour a lot of time and effort into it. Because the, you know, the books and courses that I was selling were still doing well. I'd pull in about 250,000 a year total from those. And so with, like, the same fixed amount of effort, like, say whatever effort it took to make $1,000 with books and courses, like that same amount of effort applied to convert it would, like, increase MRR by $50 or something, you know. And so it was so hard to focus on the hard long-term revenue when there was easy, short-term revenue. And so we effectively just stayed flat for, after that, for the next year and a half or so, after that for six months. Through all of that, and did you ever consider just giving up on convert kit or just kind of letting it flounder on the side and focusing on the books? Or was it always, at some point I'll figure it out kind of optimism there? It was the at some point I figured out, but it was really probably more of like a head in the sand, not make a decision, you know, this could still work, rather than there being an actual plan or how I'm going to make it work. You know, it's like sitting there and waiting for your software product to take off and to go viral or something like that, like something will happen. There will be some tipping point, though. And if I just hold on long enough, working on it 10 hours a week or something, well, doing other things, then at some point it'll work out. And at some point never came. How many different things would you say you tried and kind of what different things did you try during that time? Yeah. It was probably like four or five different marketing strategies that I tried going after different audiences that tried making, and I should give a talk about this one. I tried making the way I sold convert kit more like the way you would sell an info product. So like info products are often sold with an open and closed launch or a discount period for a certain time. So there's urgency. They're often sold more up front. So it's not a small recurring amount. It's more of a commitment. And so I tried that with ConvertKit, where I launched something called the ConvertKit Academy, where I'd open up 10 slots a month. And it was $300. You're paying for a year of convert kit up front. And then it included all this training and all this help. And so I could do that launch. And it worked okay. But I mean, the 10 slots a month, I set the number that low because that's all I thought I could sell. And there were months that I didn't even sell those 10s. And then with the churn from other accounts dropping out, and it's just not being enough money put into it to make the product better. Like it was just in this awkward place where you couldn't really put more time into selling it because the product was mediocre and didn't have the features needed. But also because there weren't customers, then you couldn't really, there wasn't money to build out more functionality. So just sat in this really awkward place. So I mean, how hard is it to not just Give up either Not by necessarily shutting it down, but just saying okay at what point you know when you try that many different things And none of them are significantly changing the situation for you After each one was there a point where you were a little closer to just saying all right I picked the wrong thing. I'm chasing the wrong rabbits here like How did that play out? Yeah, I don't think I had that much clarity with it Think I I was looking really short-term and saying Obama season working and I didn't really look at it holistically And say like wow I've worked on this for 18 months and this is where we're at yeah, like I didn't have that approach to it and maybe that's good Well, no, it's not good actually because Like that's how you can just coast on a project and be like yeah, I'm working on this and we're making traction But if you don't step back and look like Okay, this is where we're at and like and then really look at the amount of effort that you're putting in So for me, yeah, I didn't get that clarity until a conversation with heat and shot from Kiss metrics and crazy egg and a you know a bunch of other great SaaS companies And he and I were at a conference walking back from dinner, and he just stopped and said like look Nathan You should shut down convert kit And I was like Excuse me, what I just said yeah, you know, you're going to be successful at something you've proved that with the books and you can build an audience and you can sell But you're you know, you're in a half-end with convert kit. It's not working Like it's time to call it shut it down Move on to the next thing because you're you're crippling yourself effectively and You know having this project here. It's not going anywhere And it's time you place the bet and you put put work in it's time to call it, you know And then he just like started walking again And so I was like okay, you know as I'm thinking like take a few quick steps to catch up with him again And then as we're walking he just says or You can give it the time money and attention it deserves and build it into something real But there's in between state where you're like yeah, it's a side project It might work. It might not I'm trying these things and putting you know like clearly that's not working so you need to change something And so that was really the shut it down or double down Conversation and so I think a lot of people with their side projects are probably in a similar place where maybe it gets to 500 a month of Recurring revenue and you're like well, it's not worth focusing on yet, you know It's been and if it's 500 a month quickly, then you're like wow, it's exciting But if you get to 500 a month over the course of a year Then you're actually in this really bad place where it's not a failure because you got customers and they're happy You know, but it's certainly not a success and I think that's the worst thing that can happen It's a really really tough spot to be in and that's For me like with CIFTRA it was those two years where I was still working and doing other stuff and CIFTRA wasn't Making enough to support me and I was constantly like where can I cut costs so that I can afford to be on CIFTRA full-time without needing to make other income and That was probably the most stressful period But then at the same time if you quit too early and you don't have the runway or the savings and it's not making enough money You could end up in a spot where you run up against a wall and you have to go get a job or do something else So there's that it is you're constantly towing the line about when do I make the leap am I close enough is it and I think that's probably one of the most difficult decisions for anybody to make on that So once you did commit how long did it take? For you to realize okay, this was the right decision Yeah, so first I didn't commit right away I was joke that I did what everyone does when they hear really good advice and that's to wait six months to do anything with it And it looks like I kind of thought about pondering it for quite a while and then And then it could work as revenue, you know as recurring revenue does I find a lot of people don't know this But if left alone it does not continue to occur perfectly it declines at a pretty steady pace Which is really depressing But you know, so it declined down to 1300 a month and at this point You know, it wasn't even covering basic costs to maintain it, you know let alone development if anything and to probably at a point where There was more reason to give up on it than to double down on it. Yeah, so Hell on earth at that point did you make the decision to double down versus quit? So I decided that I needed a framework to make this decision because I needed to actually make a decision and I was tired of you know for the last year and a half. I've been like yeah, maybe this will work really not and I hadn't made a decision as to whether or not I was going to make it work and Really put the effort into it as as he said by the time money and attention basically So the little framework that I came up with was to ask two simple questions One do I still want this as much today as the day that I started? Right because a lot can change in your life in two years or more and just because you wanted something a couple years ago It doesn't mean you still want it now and if you don't still want it like that just makes the decision easy You know and especially Anyone probably getting into building software they they have talent Hopefully either on the development side or on the marketing side or products, you know in some way So there's lots of good things you can do with your time And so if you don't still want this like move on to something else For me I was like, yeah, I You know have these books and courses that's all going just fine I can go down that road But I still wanted to run a software company and I wanted that new challenge and I really wanted to take the next level so the answer that question was yes I want it just as much as the day I started So I moved on to question two which was have I given convert kit every possible chance to succeed? Because of the answer to that is yes, then like it's not the right product It's not the right the right market. You're not the right person to do it, you know like you've given it You're all it didn't work And it's time to call it move on And when I look back over my last couple years, I don't know I can't in like I can't honestly say that yeah I've given this my all and it didn't work. I can say that I've there's a lot of weeks where I've given it like 20% of the possible effort And so now there's a big disconnect between how much I say I want something and Then my actions yeah, and so looking at that I was like I saw that disconnect and there's still opportunity there And so that's when I decided okay, it's time to double down and so what doubling down looked like for me was I took all of our savings Which we still had more money invested in like a wealthfront account for stocks and that kind of thing But all of our savings which was $50,000 and Put that into the company and then I'd been hiring contractors just to work on things part-time and so there wasn't since I'm not a developer You know, I can write a bunch of front-end code and I can do design, but since I'm not a developer There wasn't like that dedicated product focus and someone really working hard to carry it through who really owned that whole process And so I hired One of my favorite developers I've ever worked with over the years at different software companies like I named David Wheeler to come on as our you know kind of founding engineer and And then I started selling so I'd always tried to find scalable ways to grow so You know content marketing or partnerships or all these other things and This time I just said like I'm gonna sell and so I made lists of Well, I met we also picked the niche of At the time it was email marketing for authors and then we'd later pivoted a little bit to be email marketing for professional bloggers But by going after a niche I was able to make lists of potential customers and then just email them and say hey Can I get on Skype call and demo this for you and just be relentless about selling So I didn't know Well Our expense is pretty quickly went up significantly You know to about I think they went up to about 10,000 a month right away and then gradually climbed to 13,000 a month, you know on 1300 a month in revenue. Yeah And so I was doing the math of You know 50,000 declining like this, but revenue, you know, where where does that match you and so I didn't have an exact number of when I was going to call it Of like this isn't working I guess it was going to be when I ran on money. Yeah, I was going to make that decision But you know, I sold like $300 worth of MRR from direct sales that first month and so we went from 1300 to 1600 and then the month after that I sold 400 and so we went up to 2,000 And so I was October 2014 and by March 2015 we're at 5,000 a month in revenue, which is my original goal It just took a year and a half longer than expected And then, and we actually did run out of money and there was a couple months later in May, 2015, and we're at about 8,000 a month in revenue, 9,000 a month in revenue. And ran out of money. I considered a bunch of different options. I ended up laying off one person on the team. Who is doing customer support and a lot of the other work in there, helping with a lot of administrative work. And we ended up being able to bring it back on three months later. But, you know, that was the thing. I had to cut the expenses from 13,000 down to 9,000 so that we could not go broke. Because during that time, I'd sold off all of my investments and all that kind of thing just to live on. But so we went, we got down pretty low on financially, but never like went really far in the negative. And it just kind of kept climbing from there and then later things took off. So we probably relied entirely on direct sales up to 15,000 MRR. And then like affiliates and referrals started to kick in after that. But even today, we still do a lot of direct sales. So on direct sales, because that's something that so many of us just hate the idea of. But the reality is too, I'm guessing it wasn't pure sales, right? When you're on the phone call, you're getting feedback, you're learning where to focus on what features. Can you kind of talk about how those calls balance in terms of actual sales effort versus actual research effort? I think, I don't think they're two different things. Because that conversation, it always starts with, hey, what are your frustrations? Yeah. Right? You use MailChimp, use Campaign Monitor, whatever it is. What bothers you about them? And you're telling me, and I'm writing it all down. I'm taking notes. And then when someone says they list off all this stuff, oh, I'm sick of paying for duplicate subscribers with MailChimp. It's really a pain to set up automations, there's no tags. You know, in that case, I'm saying, those are all the same frustrations I had with MailChimp. That's why I built Converkit. And so, and people will throw out other things. And I'm like, oh, I hadn't thought about that. Oh, that's a good point. So it's product research. But then also, you know, I don't come in saying, you should sign up for Converkit. Here's why, you know, it said you let them talk about frustrations and then you answer that. So I think research and sales are the same thing. Well, and that's a really good point too. Because I think so many people think of sales. And they think of it as, I'm going to call this person up. And I'm going to tell them to buy my product when the best sales you can possibly do is to call somebody up and say, what sucks for you right now? Listen to them and then say, okay, that's great. I think I can help you solve those problems. It's not here by my product. Here's how my product can maybe help you after you've listened to them. And that makes all the difference in the world and sales. And obviously research bonus is there too. And then whenever you're selling purely online, people are rejecting you every single day and not telling you why. So if I put up a blog post that says, this is why Converkit's amazing or here's how to solve your seven greatest email marketing problems. Oh, and it happens to pitch Converkit, you know, someone reads to that and goes, oh, that's interesting. They click through to learn more or to buy. And then for whatever reason they hit the back button. And that's the equivalent of me saying, hey, will you buy Converkit and you like staring at me awkwardly? And then slowly backing away without saying anything and then like turning and leaving, which is entirely socially unacceptable. Like, you're not allowed to do that. If I say, hey, you should buy this thing, you have to say, like, ask a couple clarifying questions. And then you have to say, like, well, here's why I'm not going to buy like you have to give a reason. And so when you're selling online, all you know is that 25 people visited your sales page and zero purchased. But if you have 25 individual conversations made up or not, all 25 of those people have to give you a reason that they're not going to buy your product. Yeah, well, and that's powerful. I would say it even goes a step further because in hindsight, I think one of my biggest mistakes was sifter was I had plenty of feedback coming in via email. Lots of suggestions and we had just enough traction that people cared enough to make feature requests and that sort of thing. And it was one thing to hear those via email, but every time I got on the phone with somebody, I would get a dozen other things that were just small enough and just annoying enough that by themselves weren't a big deal. But in a phone call, it was, well, this bothers me. This bothers me. This bothers me. And they were all easy to fix, but they weren't big enough for people to mention via email. And so that face to face conversation just solves so many problems and helps you see things that you otherwise would never know about or never notice or nobody would just take the time to tell you. Yeah, that that's absolutely true. And then the other thing is whenever we build these products, we are at least for me and I think this would be perfect for so and so. You know, like you have all these people out there who think like they would be perfect for this product if only they knew about it or would buy it or would come stumble across Google ad about it or something like that. And it's like, if you know who those people are or you have that avatar in your head, then go call them up and say, hey, I built something that I think is perfect for you and here's why. Well, and to be fair, I think in your case, too, having a little bit of credibility from your books and your previous work made it easier to get those conversations because I certainly, you know, I remember getting a lot of outreach and I'm sure plenty of people who read people trying outreach. They're like, nobody responds to me. Nobody gives me the time of day. And so it's not quite that easy and it certainly helps to build an audience and build some credibility ahead of time. And then it makes those much easier. The big just makes the emails easier. You're going to get more of a response and you'll be able to have those conversations in the first place. So it's not super easy, but it's worth it. Yeah. And then so I have posters behind me on the wall that are some of the. I don't even know what to tell them. So they can work at core values. Maybe they are. But one of them is teach everything you know. And that's how you build that credibility. And so it's one thing to say, like, I'm going to build a software company and, you know, I set off in my own quiet world and go do that. It's another thing to be public about all of it to let everyone know what your goal and your mission is and your progress along the way. Because when I published that article saying, I'm launching the web app challenge. I'm my goal is go from zero to 5,000 a month in revenue in six months. I'm going to blog about the entire thing. The number of people that came on alongside and said, great, if you need anything, let me know. I mean, I had emails from like Ryan Carson at treehouse. I mean, that's how I met heat and Shaw was he. I think either emailed me or posted a comment on that article and said, cool. I like to help people who are in motion. So if there's ever anything you need, let me know. And so that was so much easier. I got a lot of help from Amy Hoey in the early days. And she said something about. She was referring to how frustrating it is to help someone who's not going to do anything with that. And so she said something like, I have all the time in the world to help people who are in motion. You know, because then a little bit of guidance, you just change that and they're going to execute on it. Really, you have to publicly prove that you're going to make this happen. And then other people will say, like, I will happily give you 30 minutes or this introduction or that kind of thing in order to make it happen. I never thought about it that way, but the in motion thing is just a great way to look at it because I had like with sifter, I was fascinated with bug trackers and talked to people about them for years. But until I started creating mockups and sharing them with no observable goal, just beyond sharing it, that's when people started coming out of the woodwork with suggestions and encouragement and like you're going to do something with this right. And it makes a lot of sense. And I think that's probably a great way to overcome if you don't necessarily have the credibility yet, but you put forth some effort and you put something out there that shows you're making progress and working towards a goal. And then people see that they're like, Oh, yeah, I'll have a call with this person. They're clearly doing interesting things. And so that that could be a great way to overcome that challenge. And to do it all publicly, like in the early days, I was fascinated by how I could write about like the first article I ever wrote that was popular was about how I made $19,000 on the App Store. Well, while learning to code was the full title, so a little little clickbait in there. And that one took off like crazy. And I had, I was having conversations with all these people who were running businesses doing half a million or a couple million dollars a year on the App Store. And they were in some way not looking up to me, but like their business was at a high level. Mine was at a very small level, but because I wrote about it, I got to play on their level. Yeah. And the same way that like with ConvertKit, you know, in those early days, I mean, I gave a talk at MicroCon when ConvertKit had gotten to $2500 a month. And it's just an attendee talk. Um, but there are so many people there who were, you know, at 10,000, 50,000 a month in revenue. And all of a sudden, because you're sharing, and I was like, why am I the one talking with like, you've done so much more than I ever have. Um, but it like elevates the level to get out there and be willing to talk about it publicly. And so I've always had that mindset of whatever I'm learning, whatever, uh, whatever I'm working on, just teach that, share it publicly. One of the other posters says work in public. And that's just, hey, I learned this thing. Hey, I built this thing. Here's how I built it. Um, also this is where where I'm going. And anytime you read an article and someone saying, this is where I'm going. These are the steps to make it happen. Uh, then you just, you just want that person to succeed. Yeah, like there, there are Kickstarter projects that like I don't care about the project at all, but when someone spells it out of this is what I'm trying to accomplish. This is the story behind it, et cetera. You're just like, cool. There's a $50 contribution. You know, and it's the ones where you're selecting like no reward, you know, because you don't care about whatever they're making, but you want to help people who are in motions. Yeah. There was a thought on the tip of my tongue and I've lost it. All right, well, I'll skip that one. Um, so one of the other things I want to talk about is when convert kit was getting started. And drip because they were born around the same time, serving very similar audiences. Uh, how did that unfold in terms of, um, and, you know, so many people were scared of, oh, there's a competitor, there's a big player or whatever. And drip kind of took off faster, but you're ultimately kind of able to catch up. And when you're going through a trough like that and there's a very similar product, that's very solid, uh, that's taking it off like all the more reason to give up. Like, oh, why don't just go use their product instead of dragging myself through all this? How did that go? Yeah. I always thought it was interesting in the early days that people compared convert kit and drip so much from a competition perspective because they would say like, oh, you're getting into a competitive market like drips in that market. And I was like, no, I'm getting a competitive market because mailchimp is in that market. You know, and campaign monitor and fusion stops in a lover and eye contact and constant contact. You know, um, and so people looked at like our two little tiny boot shop companies, you know, I'm doing like a couple grand a month and maybe drip at the time, like six months after launch, I think it was doing like 10 or 12 grand a month. And then there's like mailchimp doing 250 million a year. Uh, and so then it's like, there's a ton of room for everyone, um, but also the two products didn't start as competition. And so I drip was email marketing process companies when it started. And so drips, I believe started four weeks before a convert kit. Um, at least the first mention of it publicly. Um, and I actually, I didn't understand what what drip was for, um, because if I probably would have used it if, uh, the marketing had made sense to me, there's actually a Twitter conversation somewhere between Robin, I where I'm asking questions of like, Hey, does it do this? And he's like, no, it doesn't know, you know, cause I'm trying to find a tool to switch from for mailchimp. But if someone's building it, then like great, I'll do that. Um, and I walked away from that conversation going, Oh, okay, this isn't for me. And it's not going to solve my problems. And then a month later, I decided to build something that was for me and would solve my problems. Um, so convert it started in like the info product space. Um, and then, uh, and drip started in the SaaS product space. We went after two totally different markets. And then later drip pivoted into marketing animation and, and like, broad to like, SaaS in for products, whoever. And we just stayed in like, we switched from talking about info products to, uh, like professional bloggers, stayed in the same space, but I don't mean deeper and then added all that automation functionality. And so it probably wasn't until a year, a year and a half in that we actually started going after the same customer base. Um, but yeah, I mean, it was definitely frustrating. I think, I think we're at the end of that six months when we'd hit 2000 a month in revenue. I think other time drip was at like 12,000 a month, but what's interesting is you can go back and listen to the startups for the rest of us podcast. And they hit a trough at the same time. Um, uh, they had this initial success and I think it was a nine or 12,000 a month somewhere in there. And then found that the market what they weren't good for that they didn't have product market fit. And so then that's when they made the pivot into like more true automation rather than just email marketing for SaaS. And so they had this spike and then this, you know, flatline or very slow growth. And then they, they started taking off again. Yeah. Um, yeah, it's, it's interesting. Uh, and because then later, you know, like I think April, 2015, so that's like, come on, coming up on two years. Um, we were at 5,000 a month in revenue, you know, as we're starting to take off and they were at, I think 36,000 a month. Um, and then from then on, we just, like our worst growth month was like 18% month, they growth. And we continued that all the way up to a year later, I think we were, um, like 50,000 MRR larger than them. Um, and who knows what's happened since they've been acquired by lead pages, uh, because that's like lead pages is a big marketing machine. They have 40,000 customers or whatever and, uh, plenty of millions to put behind it. Um, but it's interesting. I think the, the audience segment plays a big role. Uh, we accidentally picked probably one of the best possible markets by going after bloggers because, you know, if I get, if I have a small business product and I get you to use it and you love it, you might tell three or four of your friends, like, hey, this thing's pretty great. But if I get a high profile blogger to use it and they love it, they'll tell 100,000 of their closest friends. Yep. Um, and so like our affiliate programs have been able to do well. Whereas in other industries, it just affiliate programs don't work. Yeah. Yeah, absolutely. So it's interesting, but I don't worry about drip. I worry about like the bigger products like, uh, the Mailchimp's, um, we're like an active campaign that's, uh, has a lot of resources. Well, and that's, I love that affiliate marketing has worked well for you when, like you said, so many people are like, oh, we'll just throw an affiliate marketing. But like, some things just aren't naturally shareable or don't have an audience that can or will share. And so it's a great example of the fact that just because an idea worked for another company doesn't mean it's going to work for you. Just because an idea didn't work for another company doesn't mean it's not going to work for you. And I think sometimes I know I always struggle with that was, oh, well, that's not going to work because so and so tried it. And it didn't work. It was like, well, how did they try it? Are they in the right industry, the same audience, the same, you know, there's so many variables that can really affect which tactics are successful. Um, one of the other questions now that you're bigger and it happened quickly, I mean, basically two years. Is there anything you miss from the days that convert kit was smaller? Oh, I don't think so. Um, let's see, things that I miss. Probably being more embedded in the product and working on that side of it because my background is in design and user experience. Though I've actually spent the last two months leading our engineering team and being very heavily involved there. And so it's been a lot of fun. But there was an in between time where I just wasn't very involved in that process. I was very heavily on the sales and marketing and growth side of things. Um, yeah. So I like being able to still, you know, write some code myself and design out a new feature or, you know, spend three or four hours and ship a pull request and, yeah, like make the product better than it was when I got up this morning. And so that doesn't happen very often anymore. Yeah. What's a lot simpler in the early days, I think. Yeah. And it's just like, look, I can kind of do whatever I want because there's 50 customers and whatever. But now like one little blog, there's 10,000 customers. And so it's, it's a big deal now on other things. I don't think there's much else that I miss. Like it's really fun to show up to a conference or something like that. And people go, oh, yeah, I use convert kit or like my mom had all my family over for dinner. Two nights ago, and my mom was saying, hey, I was reading a book the other day. And convert kit was mentioned in that I was like, what? You know, and so that kind of stuff is fun. And I just don't worry about money in the same way. And so, uh, the whole journey was a lot harder than I expected. But I don't really miss the early days. All right, fair enough. Um, so looking back, This kind of two-part question to wrap it up. What was the most painful or the lowest point in the whole process for you? Let's see. Oh, man. I mean, money out of money, that sucked. But at the same time, we had traction then. And so it wasn't so much as a money problem. I mean, it wasn't money problem. But whenever I think of problems, I always think of them in terms of, "Does this get solved with time?" So if I'm going to stress out about something, does this get better or worse with time? And so in our case with the money problem, we were growing. And yes, so our burn rate was getting lower each month. And so that problem was getting less significant with time. And so that's a problem where you're like, "Okay, I need to worry about that because it's a real problem." But it's not that big of a deal, whereas the problem was they get worse with time. Those are the ones where you're like, "Okay, I have to fix that." So that was pretty stressful. I think making the decision to put all of our savings into convert kit at the time of doubling down. That was definitely stressful. And then I think the first time that I had to fire someone. Especially with a remote team, I didn't want to hop on a Skype call or Zoom call and say, "Look, I'm letting you go." Especially for someone who had done great work and had been a big part of everything in the early days. And so I ended up. Well, and it was especially hard because not everyone on the leadership team agreed that letting this person go was the right move. So all those internal people things is hard. When firing this person, what I ended up deciding to do was. They lived one state over and so I caught the 6 a.m. flight out there. You know, I texted the night before and said, "Hey, I'm going to be in your city. Tomorrow, can you meet up for coffee? Can we grab breakfast?" And I was like, "Sure, what time works?" Like, "8 a.m. Great." And I caught the 6 a.m. flight over. Met them there, you know, let them go, thank them for everything, had some good conversations, and then a couple hours later for the home. And that ended up being a really good decision because. And it's one that I don't talk about much, but. I think it's showing to that person and to the rest of the team because we're at like 10 or 11 people then. They're like, "Hey, I didn't make this decision lightly." I took it really seriously. I'm not going to say like, "You know what? You're not a good fit. You're gone." Like to let this person go, I actually got on a plane and, you know, I really only took me a day because I went there and back same day. But like, I think it showed that I valued each person on the team and if I was going to let someone go, I was going to do it right. But I stressed out about that so much. So that was probably the lowest point. Well, I talked to Josh about barometrics the other day and for him it was kind of the same thing when they financially were kind of struggling and had everybody took a pay cut and he said that was some of the hardest. It's always the personnel issues, the people that I think everybody stressed about as the company grows. Yeah, for sure. And that's the thing. I was talking to Jason Cohen from WP Engine and there are 450 employees now and I was in Austin and I, you know, went to their office to meet with Jason and just hang out and catch up because, you know, I met him years before microconfin. Like, right when convert it was starting. And he just said, like, whatever people problems you have at 10, 10 employees, the ratio stays the same. You know, problems for employee now just go up to 450 and beyond and just know that whatever problem is like the biggest edge case that you think you'd never encounter, you're going to encounter that like three times a year. And so you just have to get out probably one of the best moves I've ever made was hiring a director of operations to handle so much of that and all the business stuff. Yeah. So yeah, it's been quite the journey, but it's fun to be at the stage where we're at and have the moment. So then the one final question, which it'll oftentimes pivots off of that, this may not, if you could go back and tell yourself, you know, what is this now, almost three years ago, total. Yeah, almost four. Almost four years ago. So what would you tell yourself to do differently? Yeah, it's a double down sooner. Like, to realize that I'm in this in between state of, I haven't given up, but I'm also not serious about it. I'm not working hard to make it work and giving it my all. And you can give something you're all, even if you only have 20 hours a week. Yeah. You know, you're working full time on this and it's a side project, you know, and I just wasn't. I was like trying to, I had these projects for Converkit and I was moving them forward and, you know, whatever pain. It's not necessarily quit your job and take a leap of faith so much as if you've got free time, give it all your free time and, you know, put yourself into it. Yeah, and take it really seriously. And so I wish I would have asked that question. Those two questions of do I still want this as much today as the day that I started and have I given this every possible chance to succeed? And I think, you know, it may not be useful to ask yourself that every single day, but maybe every week and certainly every month. You know, I'm reevaluate those side projects and ask those two questions. Do I still want this? If yes, this is my effort, match my desire. Yeah. And be willing to pull the plug sooner rather than later. Well, and that was more or less the thought process I had with Sifter was after going through everything I had gone through. I was at a point where it was like, this isn't what I want right now. I can see myself wanting to do this again someday, but right now this is just not my heart's not in it anymore. Like I was in a totally different place. And it wasn't anything to do with Sifter. It was just I was so mentally and physically in a different place. And that's basically what I had to do was ask myself, like, am I really doing the right thing? Or am I just continuing this because, you know, I've been doing it for so long. I'm not going to consider anything else. And it turned out that's kind of what I was doing. Yeah, and it's not about some particular like I built a SaaS company badge of honor. And it's like, what do I want? Yeah. Because we're all skilled talented people. Well, we can all pair our mortgages through a handful of different ways. Like you have any experience in software like you could pay your rent, you know. And so it's really about what do I want? What makes me happy? What do I want to pursue and go for that? And don't base it on, you know, that someone else says that you have to run a software company or you have to have the style of business or you have to, you know, any of those things. So yeah, I like that approach. Well, that's a pretty good note to end on. Alright, thanks so much for taking the time. I really appreciate it. I'm sure lots of other people get a lot out of this as well. Absolutely. Thanks for having me. Yeah.