In this segment of his "Get a Startup Job" series, Matt Ragland recounts his near‑hiring experience with Help Scout, a content writer role he was eliminated from after a strong interview and a well‑received writing sample. He describes how the draft he submitted was heavily edited by Greg Ciotti, which became a pivotal learning moment for his writing. Matt emphasizes two core takeaways: (1) the necessity of crystal‑clear, long‑term career goals and the ability to articulate them during the hiring process, and (2) the danger of survivorship bias and the false belief that a job is secured before an official offer. He stresses that even the best interview, portfolio, or network connections do not guarantee employment, and urges listeners to avoid premature narratives about future outcomes. The segment ends with a promise to share two more job‑search stories in subsequent videos.
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Another reason that I want to share this in such vivid detail: I'm at a great place now, and a great company, great team, and it'd be really easy for me to kind of say, oh, you know, this, this is all you have to do, it's simple and straightforward as this is how you get the job. And I do have like some really specific tips that I'm going to share in the next video. When you think about a survivorship bias, it would be kind of easy for me to say like, oh, I did it and so can you. You just got to keep, you know, hustling after it. That's not always the case. I want to, I want to shed some light on that for you. Let me tell you about Help Scout and I'll Tarantino it a bit for you. With Help Scout, I was working at UPS, not like brown shorts UPS, retail store UPS. It was a year after Buffer. Got the call. Actually, I got an email and it said we're not going to hire you. And I really— again, I get too ahead of myself— I really thought I was gonna get that job. Just remember sitting down in the pack room, just, there's like this little nook behind the foam panels where you could kind of have some semblance of privacy for, you know, a few minutes. I just I sat there, and I'm not really a crier, and I didn't cry, but I was really close. That job was for a content position, so writer. So I had gone from happiness hero/writer, I wasn't clear, to being really clear that I wanted to do content marketing. I had had a pretty good interview process. I mean, I was one of their final 2 or 3, and they had even said that my article we wrote, that one was probably the best of the bunch, and that was probably what This led to my overexcited about things, but I wrote an article and it was really good and it just got ripped apart in editing. Greg Ciotti, who did the editing and was with Help Scout at the time, he just ripped my initial draft apart and it was one of the best things in terms of my writing that could have ever happened. It was just so many good lessons and I've got a post about that that I'll link. The article that we finished with, they said was excellent and so, you know, mindset-wise, I start skipping ahead. Thankfully, I wrote back to them and said, hey, can you give me some specific feedback? And at this point, no one who's ever doing hiring is ever under any kind of obligation to share feedback on why they didn't hire a particular person. They wrote back and she said again, Matt, I just couldn't really tell if you were really clear on what you wanted, on the role that you wanted to play. And There was some back and forth on that, like, well, I wanted to be a writer. Obviously, they're like, in the interview, there was some ambiguity to them. Again, a bit of a lack of clarity, maybe a big lack of clarity on what I could bring, what my goals were. And that's probably the biggest takeaway from Help Scout for me. Don't conform your goals to what you think will pay off for you in the short term. Build your goals based on what you really want to happen in your life 5 years from now, about 10 years from now. And don't get all worked up about like, this is the job, this is the place, this is the time, it has to be this. It doesn't always necessarily have to be that. So two quick lessons from Help Scout. I'm losing light here. One, know your goals. Know what you want. Get really clear on that and communicate that really clearly. Even if it doesn't lead to you getting the job, then it will lead to you just being really honest, which is what we'll talk about in the next couple of roles that, again, I got really close on but ultimately didn't work out. The second part of Help Scout is do the best you can to not let your mind roll forward in a story that you're telling yourself about the future that has not come to fruition yet. The job is not yours until the job has been offered. Doesn't matter if you wrote the best article, doesn't matter if you had the best interview, it doesn't matter if you have the best contacts. None of that matters. Doesn't matter if you have the best experience. The job is not yours until the job has been offered to you. I'm gonna do more of this tomorrow. I've got 2 more, 2 more jobs to tell you about. 2 more. And I get better at this, I promise. And I want you to learn from it.
