In this vlog, Matt Ragland recounts his unconventional path into the startup world, beginning with a Twitter DM from Noah Kagan that led to a job at Sumo. He describes his early attempts at webinars, including a disastrous live session that highlighted his lack of preparation and honesty during the interview process. After a brief full‑time stint at Sumo, Matt transitioned to contract work, juggling responsibilities for both Sumo and ConvertKit. Through networking with Brian Harris and Nathan Barry, he secured a part‑time role at ConvertKit, eventually moving to full‑time remote work there. He contrasts Sumo’s Austin‑centric culture with ConvertKit’s fully remote environment, noting the company’s rapid growth from under 500 to over 14,000 customers and a jump from roughly $20k MRR to $700k MRR. Matt closes with two key lessons: be transparent in interviews, and consistently deliver high‑quality work regardless of employment status, as this reputation will open future opportunities. He teases the next video, which will cover how to position and demonstrate skills to become a top candidate for startup or freelance roles.
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Hey, welcome to this week's vlog. If I was able to do like the Casey Neistat setting up a desk in the middle of the street sort of thing, this is totally where I would do it in Chattanooga. It's totally blocked off, so it's cool. I'm safe. Let's talk about what happened at SumoMe. Hey everyone, feels like it's been a while. It has been a little bit of a time since I did the last startup video, and I'll tell you why. I feel stuck, a little afraid. Hate that. What do you do with it? Yeah, that's why. The reason— I've just been super nervous about this video. I was talking with my mastermind group about it this week, and I was just kind of lamenting the frustration that I feel over my lack of ability to get going on what is really the last video for now. What's tough is that it's a, it's a tough story. Maybe one of my biggest failures and frustrations, but also led to what was now probably the best thing that has happened. So let's back up. You know this is about Sumo. What happened was 2 years ago during the summer, I started messaging back and forth with Noah Kagan. You know I like to do sketchnotes. That's my side hustle. That's my thing. I had done a sketchnote of a webinar with Ankur from Teachable and Noah, and I posted it on Twitter, and both Noah and Ankur said, "This is awesome," and then Noah sent me a DM. And said, "Hey, do you do stuff like this for work?" And so that continued what was basically almost a Twitter DM job interview. I don't know if that's happened to anyone else, but it was pretty crazy and pretty great. So I had a few phone conversations with Noah and they went well, they progressed. This went over 2, 3, 4 weeks. It took a while. I did some more spec work just to get a feel of working with each other. And what Noah wanted, what Sumo wanted, was someone to handle their education, some of their videos, and especially like their webinars. So webinars were and still are a really big thing. Like LeadPages was blowing it up with Tim Page, who's awesome at this. And you know me, especially I hope you know me a little bit better, that I do put a really high premium on my ability to learn and develop in new things. And so when Noah started asking me about like doing webinars, doing workshops. I hadn't done a whole lot of those. Like, I'd only done 2. I'd done lots of live presentations, and so that's what I felt good about, but like the whole webinar thing still kind of freaked me out. But I did like 2 or 3 demo webinars with him and Chad, who is the co-founder of Sumo. As it turned out, he offered me the job. As you know, I'd been so close. So many times. And I even— Noah even asked me during the interview, he's like, you're great, why, why has this not happened for you yet? I said, I don't know, you know, I've been really close. I had this feeling, and sometimes I still do, that I would always say something late in the game that was like stupid, or like I— it would, it would be revealed that like there was something important that I had no idea about, like the technical side of backcountry, them saying like, hey, how would you run this roadmap in Scrum? I know Scrum's a thing, but it's not my thing. Whoops. Or like, this was the worst. I don't even think I included this in the Help Scout video, but they're like, hey, what's your favorite CRM and why? I was like, can you remind me what a CRM is? Oh my gosh, scratch you off the list right there. But like, I didn't really care about CRMs, still don't. So it was stuff like that. And but Noah offered me the job. We were gonna do 3 months of just testing everything out. I quit the job. I had a full-time job with the school that I had been working at. Like, I was getting ready to start the school year. I quit that. I joined Sumo. And it was such a ride. Like, let me tell you a little bit more. So I did the videos. That was something that I was really good at, was putting together these videos, sketches, different things that were going to show people how to use Sumo, so working in their knowledge base, their help center, all these different things. I worked with Jamie a lot, I worked with Anton. It was a great team. I was one of the only remote ones. There was a guy over in Australia, but most of the team, I think there were 12 of us at the time, and most of the team was in Austin, Texas. So a guy in Florida, a guy in Australia, me in Nashville. That did make it a little tough. Noah was upfront about that at the time. I was also upfront that I had no interest in moving to Austin. We had just had a baby. We were, we didn't want to move to Austin. I went through a few weeks and really, and I had done a co-workshop with Nat Eliason when he was working at Sumo. We had both, he had started a little bit before me, but we did a co-webinar together and that went pretty well. But this was really the first time that Noah was giving over webinar privileges to someone else in the company. And so I did my first webinar. And you want to talk about a bad webinar. I don't know, I hope this thing is no longer like on— I'm sure it's somewhere on the internet, but I tried to use like Noah's slides and make them my own, which didn't go well because they weren't mine. Like, it was, it was bad. It was bad. And I was super frustrated. And this is— you're so terrible. If you ever think that you are— and there were probably like 400 people on this webinar and I was talking about Sumo. And first time I had ever like done it live, I was incredibly nervous, maybe more nervous than I've ever been. And it just didn't go well, which added to the anxiety while it was happening, which compounds on itself. It was bad. The worst thing though was at the end, always, always, always, if you're on a webinar, always make sure that you are really not live anymore. Because I got to the end and they're like, "Thanks, Matt, glad you're here." And way to beat, way to beat, way to beat. Oh, I said, I said, and we were still live, we were still live at the time. I think I said like, Thank God that's over. And the host came back and was like, well, we're really glad to have you lead the webinar and tell us about how to grow your list. I was like, oh no, oh no. And like, people are messaging me on Slack like, you didn't just do that. I did just do that. So after that, not long after that, Noah and I had had a discussion and, you know, It just wasn't, it wasn't working out. They needed me to do a lot more workshop webinar stuff than I was ready to do at the time, and they needed me to do it. They needed someone to do it sooner than I was able to do without like patience, coaching, practice. Like I needed to do 10 of those, and for me, like I practice, but for me doing like the live practice, that's when I really learn and iterate and get better. So we agreed to, for me to go to basically contract, and it was pretty, yeah, I was frustrated about a lot of different things with it and also frustrated with myself. I've talked to y'all about, you know, my ability to not just build myself up in a good way, and my, the thing was like I probably wasn't as honest with Noah during the interview process as like maybe I was in the past because I wanted this so bad. Like, I don't, I don't think I told him that I'd literally only done like 2 or 3 webinars before. Probably would have taken a step back and maybe that would have made everything a little bit better all the way around. It was a mess. I remember like us having that discussion And I was thinking, what, what am I gonna do? We have— how old? He was 4 months, Kanan, who you've seen, 4 months old at the time. My wife was working nights. Golly, it was rough. Yeah, I talk about my faith a little bit. This is one of the This was one of the times that— I don't know how you feel about faith and God. I went to Jeff Goins' Tribewriters Conference literally the day after this happened, and I'm just in turmoil. You know, what am I going to do? What have I done? And I talked to Brian Harris there. He's like, "Hey, how's it going with Noah?" And like, this had just happened. I was like, "Well, you know, I'm actually just doing contract work right now. We decided we decided it wasn't a great fit. And I could have moved to Austin, like that would have helped. Again, we didn't want to move to Austin. And so I told him that and he was like, oh, you know, gave me some advice. Yeah, I kind of went back to the drawing board. And here's the thing, like, I'm not a quitter and I'm not— I don't half-ass things. And so like the contract work I was doing, still wanted to kill it. Well, I was gonna make it happen. I was gonna do good work no matter what. Not even a week after that, I did another SketchNote webinar with Brian and Nathan Barry. And after that, Brian introduced me to Nathan through email. I had a conversation with Nathan. Nathan's like, hey, ConvertKit's starting to grow, starting to grow a little bit. We're hitting some momentum. We could use some extra help. Would you be willing, would you be open to picking up like 15, 20 hours a week? And I was like, yeah, I would. So right now, literally a week, literally a week, maybe 10 days, making full-time money just between 2 different companies. I do really want ConvertKit to work out at this point because like I want to be, you know, full-time on a team. I did think that maybe I could, you know, reposition myself with Sumo again. So I dedicated myself to crushing it for both of them. About a month after that, Nathan and Noah both asked, I think within the same week, if I would— Noah asked me if I would come back full-time and Nathan asked me if I would just start full-time with ConvertKit. And I learned later that Nathan waited the time that he did just so they had enough money to pay pay me more full-time. So I decided to go with ConvertKit at that point. It was a great decision. Yeah, I just think with Sumo, they were really good to give me like that first foot in the door and that first opportunity to get, you know, just my name, my work into tech a little bit. But I felt a little bit more comfortable with the culture and the team at ConvertKit. And the other big part of that is ConvertKit's a fully remote, dedicated, you know, remote company, whereas, like I said, with Sumo, they are almost all in Austin. And so the difference between being like the remote guy or part of a remote team is pretty significant. I went full-time at ConvertKit in November 2015, so it's been a year and a half, year and a half now at the time this has come out. And at the time that I joined as a contractor, we had under 500 customers. And about the time— I'm not looking at the numbers right now, but we have over 14,000 customers now. So incredible. I think we were doing like $20,000 in MRR, maybe less, I don't know, but maybe $20,000 in MRR. We just crossed $700,000 a month. Amazing ride. It's been fantastic. It still is. Glad, glad I got that off my, off my chest. This has been a little bit longer episode, so I'm gonna go ahead and cut it here. But thank you for listening to this. Thank you for paying attention and encouraging me during all these series. I hope that you're getting some really good takeaways from these. Yeah, I didn't do the big takeaways from this one. Number 1, I wasn't— again, be honest— I wasn't as upfront with Noah as I was like for some others, and that came back that came back to bite me. The other part is that even if you go like from full-time down to contractor part-time, that doesn't get— as long as you're doing the work, there is no excuse not to do incredible work, to do your best work, because that will come back, that will benefit you, that will show no matter what, no matter what your role is, no matter what you've been given, people know you're going to deliver something great. And that's what I hope that you take away from this. Doesn't matter what happens, doesn't give you an excuse not to deliver great work, and I think you're all capable of it. So the next video in this series is probably going to be the last one for now, and what I'm going to talk about is how you can position yourself, how you can demonstrate your skills to make yourself a really viable candidate, make yourself a top candidate before you even get the job. Okay, there's a little secret, and I've seen it work in ConvertKit. I've seen it work at other companies, and it can even be great if you're a freelancer. So pay attention to the next video that's going to be coming out on this series. I can't wait to share it with you, and I hope you have a great week. I'll talk to you soon. Peace.
