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Interview w/ Trevor Hinesley (Part 2)

Published 10/10/2018

Today we have an awesome guest that I met outside of his profession. Today's guest is Trevor Hinesley, who is the CTO of Soundstripe, and in part 2 of this two-part interview with Trevor, we talk about some struggles that go along with being a leader at a company.

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Transcript (Generated by OpenAI Whisper)
In today's episode, we continue our discussion with Trevor Hinesley. We've been talking about things like mental health and purpose in these episodes. I encourage you, if you haven't listened to the first episode, go back and listen to it. Before you get into this episode, it's really important that you understand Trevor's back story and some of the things that we discussed in that episode before you get into this one. And while you're at it, go ahead and subscribe in whatever podcasting up you're currently listening to this episode with, so you don't miss out on future episodes like this one. Let's go ahead and jump straight into the episode with Trevor Hinesley. Yeah, absolutely. Okay, so I do want to take a step back, though, because this is a success story in every sense of the word, but it doesn't mean that every step of the way was easy. It doesn't mean that you've only had smooth sailing, right? And so I'd love to take a moment to talk about a moment of failure, maybe a moment where things were really uncertain for you, maybe a dark moment, where you didn't really know what the next step would be, and eventually how you got out of that. Yeah, don't let me overstate or I guess understate the challenges that can't be done. So I came with getting to this point and still having a long way to go. But when I can think of a specific example that really directly answers your question, I think it was in 2000, it would have been end of 2016. I had decided that touring was no longer for me, and we had already launched Soundstripe in February of 2016, and I think it was September. Yeah, I think it was September. We were on the road. I was on a six week tour, and my mental state had declined dramatically. We probably had, I think there were four or five other people on staff with Soundstripe at that point, but I was still touring, and I had made the decision that I was going to leave the band. But at the same time, I was actually engaged, and I had a wedding that was a little over a month away that I was helping plan from the road. I was on retainer with an app agency working 30 hours a week for them while touring and running Soundstripe with my two business partners. I was extremely overextended, and as I mentioned, my mental state was declining rapidly, and while I was on the road. For the first time in my life, I googled some of the struggles I was having mentally, and I found an article that said, how OCD people think, and it came up based on my search terms. I didn't even look up anything to do with OCD. I just put in something I was thinking about. I clicked it, and I read the bullet points, and bullet point after bullet point, it was like my mental process since the time I could remember, really, to a T. I mean, I was like in tears and called my mom and my fiance at the time, and I was like, I think I have this. So, the long story short, it turns out I very much did have OCD in the same month in 2016, September or October. I quit my band, prior to what would have been the biggest tour of our career. The company I was with was going through a restructuring, so I essentially lost my retainer job, which was paying the bills since music didn't, and since soundtrack wasn't big enough to pay us yet, we were bootstrapping. I got a dog. I also ended my engagement three weeks prior to the wedding. We were about to have, and there were just a lot of other, the two or three others that I'm forgetting right now, other life situations that came up. It was a lot, and I mean, I remember going into our office a couple of times, if we didn't have an office at that point, it was the bedroom of my business partners where we were working out of. They were like, are you okay? I was like, yeah, I'm fine. They were like, no, really okay. A lot has happened, and it didn't hit me until a few months later, I think, when I really started to analyze, my life looks a lot different than it did just a few months ago. It was tough. I obviously thought that was the one when I was engaged, and that was rough on both of us, and that on top of OCD, I was in therapy with someone who was certified by the International OCD Foundation, because I wanted to get it under control, and I was doing that two or three times a week, so I had, you know, not necessarily intensive therapy. People have it way worse than I do, and I don't, by all means, I want to be sensitive to that. But that on top of the business, trying to, we were, I had just started a rebuild of our entire application, and I was the only developer, so I was working on that, and there was just a lot of stressors and a lot of anxieties that were heightened by my life situations. It was tough. I mean, that was probably one of the darkest, if not the darkest, time in my life. And so I just want to take a moment and identify that even one of those of that list, especially for someone who deals with OCD or general anxiety or, or a similar mental state, even one small change like that can be extremely stressful. And so that, I can only imagine the level of stress that, you know, just building, rebuilding the application, or just losing that retainer, or just choosing to come off of the road. Those are, those change your life dramatically. Yeah. Right. And so to increase that by adding on, and those things are not just linear, you know, I think in terms of, like algorithmic analysis and the growth over time, that if you add more than one situation to that same list, they're not linear. They're going to multiply each other. And so one change is going to kind of play off of another change and kind of amplify all of them together. And so I can only imagine that the state that you found yourself in eventually, in perhaps when you can tell maybe how you ended up evaluating and climbing your way out of that difficult state to be in, but finding yourself there, I can only imagine felt really debilitating. It definitely did. There were times where I mean, I remember to be vulnerable for a second, I remember laying on my couch, I'd just cried for a couple hours from what I remember in the dark on my couch. And like I had, I just never gotten to a point where, where I felt like, you know, my situation was so out of control. And at the same time, it was like a weird, there was an element of freedom to it because what I realized was being on the road was extremely unhealthy for me because there was no routine. And that, that I think is what caused my mental decline while I was on the road was it, I mean, those OCD and touring in a white van, which is essentially a eight hour a day torture box when you're just driving for a mental state, right? So those things don't go together. And so I think had I been on the road and still been maintaining the same thing, I think, the same pace I was going at and all that other stuff still happening. Who knows, man, it could have been a much more emotional basket case than I was, but, sure. Yeah. But I will say that what really got me out of it was I had some incredible friends and support system. My therapist is, as I mentioned, I, at the time, got on meds. I just wanted to, since I'd had it my whole life and didn't know it, I wanted to feel what it was like to be, you know, what you outside of it. Yeah, what you'd think of as normal, I guess. And so I did that for a while. Eventually got off of meds. You know, I felt like without meds, once I got on them and knew what it was like, I felt like that was like, that was like being 80 or 90% okay. And then without meds, I was like 20 or 30% and now that I've done therapy, I know what it feels like to be on the meds. So I can kind of replicate that almost. Yeah. I feel like I'm, you know, if I'm between 60 and 70%, even 80% without meds, then I'm trying to avoid them. But that was kind of my transition. It was just a lot of, it was time. And everybody says time heals all wounds. I think that that goes further than just relationship or, you know, losing a loved one or something. That plays to into major self healing. Absolutely. Absolutely. Yeah, I think, man, that's such an interesting story. And I think your discussion on meds is really important for people who are dealing with something like OCD. You know, everybody has their own journey on that. Everybody has their own way of handling it, their own way of choosing their path. And, you know, I think your example is a perfect way of describing like, nobody's at 100%, especially if you deal with it. That's right. Right. In some way, probably, there are, I would say there are very few people who are at that, you know, normal, truly normal state. But even beyond for those who deal with something like OCD. So, but it's really encouraging though, simultaneously, because there are people who are listening to this show and perhaps more than even know, right? I would think, you know, you went quite a long time in life, presumably presenting, you know, signs of OCD without ever knowing. Yeah. Yep. Like a really long time. Yeah. Like 26 years. And this isn't a mental health podcast. It is a thinking podcast. You know, there are things that developers do, especially I think developers have this kind of cerebral, you know, job. And because of that, I think we're particularly, I won't say at risk. I would say that our jobs are particularly affected in a perhaps a deeper way than maybe like manual labor would be, right? Because there are some things, even the anxiety, general anxiety disorder, one of the most effective treatments for general anxiety disorder happens to be exercise. Well, if you're sitting at a desk all day, staring at a screen, we're probably not exercising throughout the day, right? And so there's this kind of this interesting relationship between software development, which can be, if you're not careful, really isolating. And I love that the ending of the story is that you actually had support and you had people and you had friends and you had community. And that's so important. If you're a developer, do not forsake those friendships, those relationships, community, the people around you and absolutely consider whether therapy is a use, personally, and this is my personal opinion, don't take it and run with it. But, you know, I think everybody can probably benefit from there. A thousand percent. Yeah, I totally agree. After going myself and after listening to anybody who has gone, it's kind of amazing. Well, really, the best time to go to therapy is when you don't need it because you're just trying to put a bandaid on it when you're already kind of in the hole. But if you can prevent it or even learn how to work with it, any life in general before you're, you know, losing your mind in a situation that can't thank straight, that's the way to do it. My OCD in general for me has been a blessing and a curse. It, you know, it's funny that it, people throw this around a lot and it's not offensive to me at all because I totally get it. But they're like, you know, they'll say something like, sorry, I'm OCD when they're like, you know, editing some grammar or something. And the truth is though, that is kind of the thing that in many ways has helped me in my job because of every detail oriented person, you know, and funny. One of our core values is done is better than perfect, which is pretty much directly opposed to the idea of OCD. So it's been almost like a personal challenge for me to stick to that one. But it is. I mean, there are, there are positive things that come with, with OCD, some of them, like some of incredible people in history have been, have been OCD. I believe Albert Einstein might have been. I know Martin Luther, if you're a person of faith, he was, he was actually OCD and there's been a lot of, and that technically is what led him to do the, the thesis that he tacked on the Nine Five Theses. But there's just a lot of interesting people over time that have used what many would consider a weakness as their strengths. Yeah. Yeah. And, you know, I think a lot of people are ashamed or otherwise, you know, they don't want to acknowledge a part of who they are or a part of what has made them who they are. Yeah. You know, I don't, I don't think necessarily that, you know, people should see the name Trevor Hinesley and immediately add a tag, mentally, to your name that says OCD. I think that's, you know, that's, that underserves kind of the complexity that is OCD and, and the, the difficulties that go along with it because it really is an individual experience, you know. And, but I, at the same time, I think it's really important to remember that, you know, these, these things that we struggle with and everybody has a different struggle. And that's really why I take the time to talk through some of these things that do have a name because everyone has something in their life that they're struggling with. Everybody has some kind of frustration or, you know, something that has held them down. And some are different, you know, again, it's an individual experience, but, you know, it is so important to allow yourself the freedom to accept it, to accept whatever that struggle is and then turn around and respond to it in a useful way, right? Rather than saying, well, man, this is going to hold me down and because I have OCD and, you know, I'm a perfectionist, well, therefore I'm never going to be able to finish anything and I'm doomed. Right. That's an awful, an awful acceptance, right? But instead of you can say, yeah, you know, this is the situation and I'm going to turn around and kind of use whatever aspects I can to accomplish the things that I want to accomplish. I think it's important to that, you know, there's a distinction and I say this a lot just in general to explain to people like if it comes up, like I, you know, I'm OCD or whatever, but the reality is I have OCD. I have two feet also. So it's a thing I'm not defined by it and I think a lot of it's actually easy, especially with stigmas that we give ourselves and that society has with that kind of thing to make it a defining piece of you, just like people define themselves with their career or whatever, but the reality is is you have to treat it as an element of yourself and, you know, treat it accordingly. And today's episode is once again sponsored by Digital Ocean. Digital Ocean provides flexible configurations sized for any application. They have industry leading price to performance ratios. They have pricing that is consistent across regions at any usage volume and they have predictable and affordable pricing. Some products that you have used in the past probably have complex pricing structures, with digital ocean, you can always know what your business will pay per month. And on top of that, digital ocean is providing you as a Developer Tealistener with $100 worth of credit. Perhaps I should have led with that $100 worth of credit. That's just basically cash value that you can use on digital ocean services. Head over to dio.co slash t that's dio.co slash t a to get started with digital ocean today. Thank you again to the Dio.co for sponsoring today's episode of Developer Tea. Again, you know, if you shape everybody else's lens of you, then that, you know, of course, that's going to change the way they see what you do as well. And I absolutely agree with you that, you know, we have to remember that, you know, who we are and what we are and what we have carrying with us and the experiences that we have, that we have to keep those really in context. Agreed. Well, that's an excellent kind of moment in your life because, you know, not because it's something that you want to revisit all the time and dig up. But because it's, you know, this is just another example of adversity and how adversity is, you know, not a sentence. It's not, it's not the end of a career if you find out the above CD or if you decide that you're going to shift your entire career upside down. And, or if you lose, I mean, to that point, like in that story, you lost a job. Like that's, you know, for some people that is so debilitating and, you know, I want to encourage the people that are listening to the show that there is something on the other side of whatever that story is, whatever that moment, that dark moment is. Absolutely. And, whatever you're going through, it is always maybe an in a different measure, but always temporary. Yeah. Yeah. Yeah. And even the thing that will kill you. Right. Yeah. Yeah. Which, you know, that's kind of where my mind goes. It's like, you know, a lot of the things that I've been studying over the past year have been driven on philosophy and, and, you know, most of philosophy, if not perhaps all philosophy, is about dealing with the reality and the eventuality of death and the temporary nature of all of the things that we deal with. And so even that though, there it is, it is temporary. Absolutely. So yeah, absolutely. I think that's such a good story. Thank you so much for being vulnerable and sharing that with the people who are listening to the course. Of course. So I'd love to talk to you for a moment, kind of zoom back up to this place that you've found yourself, which so I recently moved from a position where I was in leadership over developers. And now I'm much more like a sole contributor. But this position that you've found yourself in, which is really leading a group of developers and you've gone from, you know, being a touring musician, freelance remote developer to being a CTO and legitimately, you know, building a platform at scale with many developers who depend on you for leadership and direction and, you know, morale and all of these things. I'd love to know, first of all, how confident are you in your own ability to lead these people? And number two, you know, how drastic did you feel like that moment, that shift of going out of that, you know, building something on your own just in your own time versus leading a bunch of people? How different is that life? Very. To put it simply. No, I, you know, want to be pretty intentional about saying that like confidence is a very big shift to go from being a sole developer to having to lead people. And you know that same transition, sure. But confidence is very much a fickle mistress. And I think like the second, especially if you're in the startup world or in any kind of business context where you're either, you know, call what you think of as moving up the ranks or you're just changing positions or whatever, like, or even learning new skill sets and stuff. Like you usually, as soon as you get to a point of confidence, something pulls the rug out from under you, I feel like. Yeah. Yeah. Yeah. Yeah. I mean, a lot of people, that's the typical imposter syndrome thing, which is talked about a lot in developer circles. But it is very much a real thing. And, you know, being a sole developer, I felt extremely confident because I knew, especially the work I was doing, I knew that I could tackle any challenge that came my way really. And that was the fun part because it wouldn't be any fun if I felt like I have no idea what I'm doing, everything's crashing and burning around me. You know, I enjoyed that. But then as soon as I moved into having to lead people, it was a totally different skill set. And one that I had never really had the opportunity to grow in other capacities outside of, I mean, I had some organizational leadership things in college and high school, but that was a not to disagree. Not to disagree. Old different beast. I mean, we're talking about when you're managing people, it's not just, you know, making sure their work's good, just like you mentioned, there's morale there. Like, and since I'm one of the owners of the business, like I'm feeding these people too, like there's a lot of responsibility that comes with that. And it's not, it's not necessarily a walk in the park, even on the best days because there's just struggles that come up. Right. Yeah. But that was something that I faced more in post-Sendron with relation to, you know, I qualified to even lead people, right? Like that feeling of, you know, and this is particularly relevant for developers because a lot of the job has nothing to do. Until you get to that level, a lot of the job has nothing to do with, you know, discuss, like talking with people and understanding their feelings and learning about psychology. Like you get a little bit of that, right? But so much of the job has much more to do with this more binary representation of something working or not working. And so you get this moment of shift where, you know, suddenly people are relying on you to solve more, a soft problems like these emotional problems that people have or, and it's not about, you know, emotional frailty even. It's like, you know, I feel like as a developer, I want to be learning the right things. And you as the CTO, man, you have to foster that environment, right? And knowing what to even recommend for people that that's such a, it can be a stressful thing. But I think the best CTOs and the best leaders and the best managers, they kind of own that. They recognize that, hey, you know what? Like I'm just another person. I'm another person like anybody else. Absolutely. One of the things I think is made that's really helped me, I guess, is just kind of being able to be vulnerable about the fact that like I don't have all the answers. And I will never have all the answers. And it doesn't matter how many books or podcasts I listen to or how good of a developer I am or, you know, how good of a communicator even issues are going to happen. There's going to be problems I don't know how to solve. There's going to be answers that I don't have to question. So being very open about that thing and even open about when I make mistakes, I think is helped foster a kind of a open environment and that has helped me because there's been so many times in meetings, especially when right after we did a big hiring phase at the beginning of the year. And all but one of the Developer That are there now were hired in that round of hiring. So when they came on, I onboarded three people over the course of two weeks and it was like, I just told them, I was like, look, I don't know what I'm doing. I'm doing it. I'm doing my best. You're here to help me figure that out. Absolutely. I hired, there are people on my team with so much more, just even development experience than me, much less leadership. You know, so I just asked for patience and thankfully they've had the grace to allot me that. And it's been a really rewarding experience even in the tough times. But I think if I had one major takeaway too from the whole leadership side of well leading and managing people, it would be being open because no one can fault you for making a mistake because everyone makes mistakes. I think when people get into problems is when they hold something too close to their vest and then it's too late or they're not upfront about their shortcomings, which puts unreasonable expectations on the other end that you're not able to meet and that's unfair to them because they're left wondering why isn't it what I thought it was going to be. So yeah, yeah. I talk about this on the show a lot and it is this very simple concept of following the fear or using fear as kind of a compass, right? And wherever there's fear, there's some reason for that fear to exist. And often the reason for that fear is a problem, but something that needs to be fixed, something needs to be changed very often, you know, fear, for example, of sharing a mistake. That fear might be driven off of the misconception that other people are drastically better or they make drastically fewer mistakes than you. And that's usually not true, right? And so you have to, in response to that kind of fear, for example, you might have an intentional fostering of mistake, tolerant culture, right? And then people lose that fear and you start dealing with those problems. And so using that fear as a pointer, as a way of uncovering, you know, what are the malformed, you know, poorly designed things that we just kind of accidentally ended up with? Absolutely. So, and I think as we learn, you know, what are these kind of the symptoms of a poorly designed culture or, you know, in the same way that we have anti-patterns surrounding software, we have anti-patterns surrounding management and code smells. We have management smells, I guess you could say, culture smells, right? These things that really are, they're not a problem in and of themselves because, you know, fear is important. We can't get rid of fear. It's an important thing to have. It's not something that we want to foster, but it's not something that we want to eliminate entirely. We want to follow it. And we want to find these things that are culture smells, things that we can, you know, investigate. You know, why is it that you feel this way? Well, because X, Y, and Z, well, X, Y and Z, those are bad things. Like, we want to rip those out. We want to fix those things. That's so true. I think fear too is, you kind of alluded to this. It's just a tool like anything else. And if used properly, it can, I mean, really be a guiding star. It can kind of point out flaws. I mean, that's the whole concept of caution. Caution is a healthy version of fear. Yeah. And so, man, this is so exciting to me because these are the things that change companies and they change the way that developers look at their careers entirely. If you can, you know, if you are continuously receiving only one kind of feedback, right? If you're always getting positive feedback, then something about that feedback loop is wrong. Right. And in the same is true, if you're always getting negative feedback, something is almost certainly wrong about the way that you're dealing with feedback. And so that's another example of a culture smell. So many things that you can pay attention to that often, I think companies, they try to deal with them directly. So you're afraid, well, we're stopping afraid, it's okay. Well, that's not really the problem. We need to dig a little deeper on that. Well, excellent. This has been such a great conversation. Thank you again for being totally open and honest and vulnerable and, you know, setting this example of leadership for other people to follow of, you know, it's really all about accepting the reality that if you're not, you know, if you're not a humble, then eventually you're going to be humbled, right? Somebody who's going to humiliate you and you will be forced to be humble. So if you start out from that position, then, you know, that mistake tolerance is just naturally high. Totally. Jonathan, thanks so much for having me, man. And thank you too for having such a cool environment that you're fostering with Developer Tea. I think this is awesome. Thank you so much. And I do have two quick questions for you before we close out. Sure. And the first one is actually, both of these, I ask everybody who comes on the show. The first one is if you had 30 seconds to give advice to any developer, no matter what stage and career they're in, what would you tell them? Be kind to everyone and learn how to learn. That was quick. That was less than 30 seconds. That's excellent. That is absolutely true. And second question, what do you wish more people would ask you about? Super Nintendo and old Final Fantasy and Japanese RPGs. These are things that you spend your time with. That's right. Yeah, in my deep dark nerdy closet. That's it. Somebody can probably find Trevor Hinesley, whatever your secret screen name is on some forum somewhere. I'll be talking about this. Trevor, thank you so much for spending time with me. Yeah, thank you for having me, Jonathan. Thank you so much for listening to today's episode. I hope it was inspiring and exciting. And I hope that you'll take some time to go and check out what Soundstripe is doing and what Trevor is doing. Thank you again for listening to today's episode. Thank you to Digital Ocean for continuing to be a sponsor of Developer Tea for $100 worth of credit on Digital Ocean Services. Head over to dio.co slash t that's dio.co slash t e a to get started today. Whatever you leave your podcast behind today, I encourage you to subscribe and whatever podcasting app you are currently using. This will prevent you from missing out on future episodes of Developer Tea. And it's always easy to unsubscribe if you find this to not be that useful. Thank you again for listening. And until next time, enjoy your tea.