Understanding Your Weaknesses (Get a Startup Job, Part 3)

Matt Ragland shares lessons from his two-plus-year startup job search, including how a standout article about Backcountry.com landed him a product-manager interview. He emphasizes brutal honesty about your weaknesses and a clear plan to fix them, and describes reconnecting with the startup scene through Noah Kagan at SumoMe.
Chapters
Happy Monday to each of you. I've been going through this series on how to get a job in tech and some some of the first things that you should consider, things that you should think about, mistakes that I made in the past, because it took me 2 solid years, 2 and a half years of making mistakes, of not being clear, and that's what I've talked a lot about in the last 2 videos, going through with Buffer, not really being clear, and then number 2 with Help Scout, not really knowing what my professional goals were. And it's just an iterative process for me. That's what it's been. And so I want to break that down for you. I don't want to have this survivorship bias of all you have to do is keep grinding and keep pumping away and you're going to be able to knock it out of the park and like that perfect job will come, come along. I could tell a version of that story. My current role and position sound that way because all of us tend to romanticize process that we've been through because maybe or maybe not it's worked out so far. But I don't want to completely romanticize everything that's happened because some of it was really difficult, some of it I didn't have to necessarily experience, but that was just some of the mistakes that I made. So I want to shed a light on some of those for you and give you some really clear actions that you can take. Once I'm done telling these stories, a whole video on what you can do to make yourself more valuable, to make yourself more attractive in the job market, specifically around tech and startups. Next thing that happened to me, so I just told the story about Help Scout and, you know, sitting at UPS on the verge of tears thinking like, this is, this is it, it's over, I'm done. Obviously that wasn't the case, but I, I thought that I had it. I didn't. But I wrote an article. The article that I wrote for Help Scout that they still went ahead and published, thank God, was about Backcountry.com because we were supposed to tell a story of a company that was delivering an exceptional customer experience. And so I wrote mine on Backcountry.com. I love the outdoors. I love, I love the marriage of outdoor and tech, and it's not something you find very often, but I think Backcountry still does it as well as any company can do. They're almost a tech company that just happens to focus on outdoor products and retail. What I did was I wrote about their— basically they have gear concierge, and they call them gearheads. I can't even remember, but you have your own gearhead when you sign up with Backcountry, and you can tell them a little about, this is what I like to do outside. Side, and they, you know, they basically curate an experience for you. It's fantastic. And you, like, you have someone— like, my guy's name was Jeff, Jeff with the G, Geoff, uh, probably hates being called that. I, if I want to, I can just email Jeff and say, hey Jeff, I've got this, I've got an ultra race coming up, I've got a Spartan race coming up, whatever it might be, what are some of the things that people are using in terms of gear? What kind of fuel are people using for these kind of events? And he would give me some— he would give me some pieces of feedback and of course some products that I could purchase through Backcountry. And I thought that was an amazing experience, so that's what I focused my article on. And I also noticed some other things I kind of curated and put together, like pieced some things together. Like, I see how Backcountry is doing this, this, and this, and this is what it looks like to Now I grabbed some of that and I put that together myself, and Backcountry got wind of the article, read it, and reached out to me and said, this is one of the best articles about our company that we've ever seen. What are you doing these days? Why would you write something like this? I was like, well, I was applying for a job. They're like, oh yeah, how did that go? I was like, oh, I didn't get it. They're like, huh. Well, are you actively looking for jobs? I was like, well, yes, I am actively looking for jobs because I did not get the one that I was applying for. And they're like, oh, well, we have some roles open that we would like to talk with you about. I was like, oh, well, okay. And so that began the process of me learning about the role of product manager and beginning to go down that road. A road that, you know, in some ways I'm still on because the way that I've learned about product management was first at Backcountry, and I've continued to kind of grow and try and develop myself along the lines of that role. Because what I see product management as, and just a quick aside on this, is the ability to bring together different parts of a product or a company and different areas of marketing and engineering and customer success and sales and take a product or a project and gonna lead, lead that team to reach a desired outcome, whether that's a new feature in the product and then a new entire product by itself or just a new pro— a project within the company. I continued to talk to Backcountry about that. We had a couple of phone interviews And it became clear to me that this was not a role that I was ready for. That I did not have the experience that they would normally require for a role like this. And this is where I was getting better because I was very honest with them. I think the guy that, yeah, the guy that was interviewing me, his name was Mark. The interviews kept going well enough though, and I think they were, I know because they told me, like, we, we love a lot of what you do, you just lack some of this experience. I was like, yes, I agree, I do lack some of this experience. I'm not trying to like bullshit my way through this. What I found really interesting is that while I was being really honest, I didn't have all the experience that they required for a role like this, and they're like, well, why don't you come out to Park City anyway and do a full day of interviews? I was like, okay. So they flew me out to Park City. Fun, fun aside story: I missed my connecting flight because my flight from Nashville to Denver was delayed, and so I missed my connecting flight in Denver. I slept that night in the Denver airport before flying to Park City. Was 2 hours late to my interviews because I was flying. Had like 3 hours of sleep, slept on chairs, and then did 8 hours of interviews. Um, they went fine, but it did— it was more like, for me, it was more of the same. Like, me being honest, like, I remember specific— I had, uh, I had a couple of great interviews, a couple that didn't go as well, mainly with the engineering teams. They're like, how would you handle this, this roadmap with Scrum? Like, do you know how to work within the Scrum, with Scrum? I was like, no, I'm sorry, I don't. I, and I told you that. And so the, the key thing that I found with Backcountry that I would encourage you to be is be honest with your skills and with what you're able to to do. You know, don't try and, you know, don't try and build yourself up too much. I'm a confident person, and the other thing that I'm good at, and I did communicate this really well and I believe always have, is even if I don't know something, one of my biggest strengths as a person and as an employee is that I can learn really quickly. You give me, you give me the time, you give me the tools to to learn whatever it is I need to learn. I can do that really quickly and implement it quite fast. So I communicated all that. It was interesting. I drank espresso the whole day. I told them, you know, this is what I'm good at, this is what I can bring, this is what I'm gonna have to learn. So we high-fived at the end. I got to spend the night in Park City, be-bopping around. And then I went to Alta Snowbird and did a killer trail run before flying out. So I was literally there like 36 hours. 2 weeks went past, we had another interview. They called literally everyone that was on my reference sheet. I think they were the first time someone's called every single one of my references. After 2 weeks, they called me personally and said, you know, Matt, We think you're great, but you just don't have the experience that we need to put you in a product management role right now. And of course I was disappointed. I had decided that Morgan and I would move— Morgan, my wife, and I would move to Salt Lake if I had this job offer. What was crazy is at the time she was like 4 months pregnant. I would have had to have moved there before because she was still finishing up school at the time. But we had decided we were going to do all of that. It was great pay, it was the outdoors, it was tech, it was a great role. But again, they said, "You just don't have the experience." I was like, "Yes, well, Mark, we've known that for a month." And he said, "Yes, you know, did, but, you know, we just really wanted to find a a role for you. The, the tough thing is that we don't— like, if we had an, like, an associate product manager role, like, that would be perfect for you. We had availability right now for you to come and, like, learn on the job for 6 months to a year and then put you right into it. That would be perfect. I was like, well, I'm fine with that also. And he's like, yeah, uh, we just don't have that role. That was the— that was the end of Backcountry. Of course I was disappointed, but it was a different kind of disappointment. Appointment, I didn't really expect to get the job. Everything about it was just like a bonus, you know, getting to go to Park City, getting to like have more experience in a product manager interview, to learn about that role and what it does, and to be really excited about it. And still, still am. That was something that I really enjoyed and was really appreciative of in, in the process. The big takeaways from my experience with Backcountry Be really honest, maybe even to a fault, about what your current skills are. If there are things that you need to learn how to do, go into it. Now, this is something I would do differently if I was to have that kind of interview again. I would go into it knowing what kind of specific questions to do more research about the things that I wasn't 100% on. Like, if I was going into it thinking like, oh, I'm really kind of stuck on the engineering side, I'm not really sure how to how to go forward with that. I would have done more research, talked to more people in trying to figure out what kind of questions do I need to ask about the things that I need to learn about. If I know that a talent of mine is to learn and implement new skills really quickly, what are the questions that I need to ask to— in order to get those tools and teaching available to me? So I would have done that. But being able to be really honest And on top of that, not just be really honest, that's good, but then to build on top of that. That's the big lesson that I have taken away from Backcountry. Be honest about what you can do, and then the things that you know are important that you aren't as strong at yet, say, I'm not as strong at this, but here are the, here are the things that I'm going to do to improve that. And here's the timeline. Here's the goal that I have. Because at that point, they're going to say, oh, that's perfect. That's exactly what we would have recommended, or they're gonna say, oh, that doesn't really fit for our roadmap, for our framework. Here's what you should try instead. So that's the thing that I would do. That's what I would have you, have you take away from my experience, my story with Backcountry. Know what you're good at. Be clear. Know your goals. Know your strengths and weaknesses. And if your weaknesses are something that need to be become just more capable with, maybe even not a strength but just something that you have a better grasp of, know which steps you need to take and be able to vocalize them clearly, be able to communicate them clearly so that the person interviewing you or even your report, your boss at the current role that you're in knows like, oh yeah, this is, that's what I would recommend. Or they're going to say, 'that doesn't fit with our environment, you should do this instead.' Okay, next we've got another several months because I kind of took a break. I've— after backcountry, the next part of the story is me kind of taking a break from looking because I just thought, you know, it's not— maybe it's not in the cards for me. And so I actually taught as a substitute teacher for that school year, I was a coach, which I've been a coach for a number of years, and then I ran a school summer camp. Late summer, early fall 2015 is when I started to talk to Noah Kagan at SumoMe, and things started to pick back up again. All right everybody, this is a longer episode, a little bit longer story. Thanks so much for watching this. Go ahead and hit thumbs up, give me a thumbs up if you've been liking these. Leave a comment. This is a series that is, I think, going to be ongoing, but I'd really like your feedback to know, is this something that you want to learn more about? Are these stories and tips and tactics that you're interested in? So give me a thumbs up, go ahead and hit subscribe in the bottom as well, and leave a comment so I can know what you're thinking about all this. All right, thanks so much everyone. Have a great week, and I'll see you next time.
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