Career Crashers Episode 22: Dave Wasmer on Crashing a Career in Tech

On episode 22 of the Career Crashers podcast, Dave Wasmer, Crash's Head of Engineering, shares the story of how he crashed his career in tech by leaving a corporate job and working at startups. He also shares his advice for people ready to make a career change. Here are the show notes.

When Dave graduated from college with a degree in economics, he wasn’t sure where he wanted his career to go. He used his self-taught programming skills to get an opportunity at a large corporation. But he soon realized the corporate environment wasn’t the place for him to flourish. So Dave decided to crash his career in tech..

No one expects you to be perfect when you’re at the entry-level end of your career. But if you just show execution and show up consistently and do good work, that sets you apart so much.

Then a serendipitous blog post connected him with a startup. And everything starting falling into place.

Writing that blog post won’t guarantee you get a job. But it increases the odds that something will happen somewhere. If you get enough activity out there, the odds multiply. It becomes almost inevitable that something will happen.

Now Dave is Crash’s own Head of Engineering. In this episode, he shares the stories of how he crashed his career and built his way to great opportunities.

Related: Increase Your Luck on the Job Hunt with this Advice

Also Related: Career Crashers Podcast: Finding Work that Matters to You with Julia Wuench

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Show notes – Crashing a Career in Tech

  • How Dave crashed his career in tech to get his first job in engineering for a software startup
  • How blogging an idea led to a unique job opportunity
  • Increasing your Luck Surface Area—you can’t replicate someone else’s luck, but you do things that help you create your own
  • How Dave decided to take a corporate job after college and how it helped him learn that working in startups was more in line with his personality
  • The uncertainty in moving from working at a big company to a startup, but also the decrease in opportunity risk when you work at startups
  • Dave’s advice for people feeling the itch to make a career change:
    1. Learn out loud. Don’t just consume content while you’re learning—find ways to contribute to projects.
    2. Focus on people. Invest your relationships. Get to know the people you’re working with. Through your career, those relationships will matter more than almost anything else.

Connect with Dave

Full Transcript: – Crashing a Career in Tech

Welcome to Career Crashers, where we tell the stories of those who are not content to wait around following rules and hoping for good things to happen. Great careers aren’t found. They’re forged.

It’s time to crash the party.

All right, I am joined by my very own colleague, Dave Wasmer today. Dave, thanks for jumping on Career Crashers.

Thanks for having me on, man.

Hey, you bet. So you’ve got a great story about crashing a career in tech. When we were first looking to hire our very first engineer. And coming from a non technical background, you know, I was relying on other people to sort of vouch for the technical chops, that I was really looking for some of those intangibles soft skills, culture fit, and you told me a story right away that was like, Oh, this guy, he’s, he’s one of us. So how did you crash your career in tech and engineering for a software startup?

Yeah, it’s a it’s a fun story. So straight out of college, I was working at Whirlpool Corporation, you know, appliance manufacturer. And it was it was sort of corporate drudgery to be honest, did not enjoy the job. I was looking for a way out. But didn’t really know sort of how I was going to do that, how I was going to transition. And I always liked startups and programming. But yeah, I’ve done some freelance programming, but I never had a full time programming job before.

So I was kind of struggling and not really sure where to turn. And I was actually home visiting my folks for Christmas one year. My brother was there as well. And we were, we were just hanging out. We’re gonna go see some movie, and I don’t remember the movie was now. But he bailed on me last minute. And I was I was bummed. I’m just sitting around. Like, I don’t even have a car with me, I just flew in and didn’t even rent a car. So I’m kind of stranded at the house and bored.

So I thought, you know what, maybe I’ll try writing a blog post. You know, because I’ve been meaning to start writing a blog for a long time. One of the things I always I always put off and didn’t really know what to write about. And so I wrote about this concept that had just been kicking around in my head for a while. It’s kind of both a technical like programming concept, as well as like a potential idea for a business and sort of ended up being called the Back End as a Service space for anybody who’s familiar with that some companies in their in our like Firebase, Parse, well Parse has gone under but and one of the companies is within that space is Convey.

So anyway, I wrote this blog post describing the the business model how I thought, be cool. And just on a whim, I posted it to Hacker News. Which is, you know, for anybody who hasn’t encountered it, is super popular news aggregator or website in the startup community. And it ended up hitting the front page, like very quickly, which is, which was awesome.

I remember sitting there, like, in the bedroom I grew up in as a kid. And I have my laptop out, and it was like, 1 in the morning. I was just hitting refresh on Google Analytics constantly, you know? And, and seeing like, yeah, I think it was something like a few 1000 people read the article, which just blew my mind, right. Because I had never done anything like that before. A bunch of people followed me on Twitter as a result. And so I stalked all of them, like anybody who interacted with me in any way, I was just like, Oh, this is so cool, you know. So I did track them down.

One of the guys who followed me on Twitter was this guy named Travis. And I saw that he was the CEO of this company called Convey. And they were based out of Boston, and I was visiting my family in Connecticut at the time. So I just pinged him and almost on a whim, I just said, like, Hey, man, can I can I like, buy you a coffee and just kind of pick your brain about the startup world, you know? And I figured, you know, maybe he’ll be generous with his time, and he’ll he’ll let you know, let me buy him a coffee and just like, ask him some questions.

I didn’t have any agenda. I was just sort of like, I want to learn more about this space. And, and so he replied, yeah, sure. You know, why don’t you come on up. And so I actually, I had to have my mom drive me up to Boston, from Connecticut. And my flight was like, out of Providence, Rhode Island later that day. It was just this crazy schedule, whatever.

But we drove up in the morning, and I had breakfast with him. And we just kind of got to chatting about like the company, the business idea and all this stuff. The conversation was going really well. And it’s at some point, he’s like, Well, why don’t you come back to the office and meet the team? You know, because we’re just down the street. So like this? Sure. Of course, I’d love to, you know, and we’re walking down the street and I have to kind of like, hey, like, Just give me one second, you know, and have to get like, call my mom in the car a block away. And just like whispering into the phone, like I don’t know where this is leading yet. Just circle the block. Give me a few more minutes here.

Yeah, so so went back to the office and met the team. And they were sort of impressed, I guess. I think with the sort of thinking I had around the space that they were in. You know, I ended up flying back, but continued the conversation and turned into interviews, and then on site and a job offer. And that’s how I learned that in startups.

That’s such a great story. I mean, just illustrates so many things that we see consistently coming up. You know, as we talk to people who have crashed their career in tech, especially, I guess what I like to call learning out loud, or just sharing your interests, you don’t have to be an expert, you don’t have to have started a company doing back end as a service or whatever.

But to say, hey, I’ve got an idea. Like, I’ll share a blog about it. I’m always amazed at how effective that is. Because otherwise, you’re sitting there as this talent with these ideas. And you really don’t even know your market value, because nobody else knows that you’re out there. Then also, I love how, when he followed you, you followed up and said, hey, let’s grab coffee. And I know a lot of people heard you say, let’s grab coffee, can I pick your brain? They’re like, oh, aren’t those like the big no no’s to ask somebody open ended?

Here’s why I think I mean, you can do that, totally cold. And it occasionally works, but it often doesn’t. But you were in a position where you had created some sort of goodwill with him some social capital. You wrote this article, and you saw that that caused him to follow you. So you had done something to make yourself interesting to him, which I think makes that possible.

I one time did a a Medium post, that was just the same thing. But way less advanced, it was like you know what I would love to see. And I use this app called Voxer all the time, this two way walkie talkie. I was like, I would love to see Voxer make this change and do bla bla bla bla bla, and I just posted it to Medium. And this is in the early days of Medium where it was like disproportionately like startup type people. And it only got maybe a half a dozen clicks and likes.

But it got like three different people messaged me from three different companies saying, oh, we’re working on that, I’d love to show you a prototype. And one guy, the Vice President of Voxer was like, Hey, I saw your article. I’d love to get on a phone call with you. And I wasn’t looking for a job or anything. But I got on the phone with the Vice President of Voxer to give him my ideas on his product, just because yeah, took the time to do that. So I think it’s amazing how like, companies are people too. And when they hear people talking about them, that opens up a lot of opportunity. You know?

There’s a great concept I’ve heard, I forget who, I won’t be able to attribute it, but I didn’t come up with it. But there’s a great concept I’ve heard called Luck Surface Area. And, and I remember thinking, you know, back to before I got into startups and sort of went in this career in tech, being super frustrated at reading all these stories of people who had ultimately ended up ended up being a similar experience to my own, which was like, just this crazy set of coincidences and things that stars aligned. And it’s just, I looked at it, and I was like, that’s so frustrating to read, because I can’t reproduce any of that. Right? Like, it’s just, it would they got lucky, you know?

But but thinking back over it, you know, I realized and this is true, more have more instances in my life than just this one story. This is a good example of it. But these are all examples of like Luck Surface Area where Yes, you know, writing that blog post is not necessarily going to guarantee that you get a job or even, you know, have a really high probability. But it increases the odds that something serendipitous will happen somewhere, right? And it’s extremely difficult to predict those things. But if you do enough, if you get enough activity out there, those odds multiply to the point where it becomes almost inevitable that something will happen.

I love that Luck Surface Area idea. It’s like there’s, there’s like luck bullets flying through the atmosphere. And the bigger the surface area you put out there, the more likely.

So let’s back up a little bit. How did you end up in a corporate job that was kind of making you feel a little, meh, in the first place?

Yeah, so I graduated college with an economics degree, which is kind of funny. You know, the, the, sort of the economics that I enjoy studying is somewhat self defeating. Where I, you know, I don’t really, I wouldn’t really enjoy most jobs that economists go into. And so while I really enjoyed studying it, it was sort of like a, it was a fun intellectual exercise. But career wise, it was kind of a bummer. Because the only options for me after college with my degree were really academia. Or, you know, doing a job that I just sort of didn’t philosophically agree with.

So I ended up pursuing a career in tech in the IT space, something programming, right. Because I taught myself programming for many years. And, and Whirlpool was just, it was a combination. You know, I like to sort of reframe the narrative in retrospect, sort of retell the story to make it sound much more intelligent then I was but at the time, you know, Whirlpool was an opportunity they paid decently. And, you know, it was potentially good experience.

There was certainly a part of me that that I knew I love startups, but I also knew startups were risky. And, and the corporate drop, at least from everything I had heard up until that point was the sort of the safer option. And so I knew that I wanted to at least try the corporate route, the big company route, because I wanted to know for sure whether or not I could, I could hack it, whether or not I could handle it.

Because if I didn’t like it, and then I went off to do startups and I failed at startups too, then at the very least, I’d know, like, well, at least this is better than the corporate life. Right. But if I had never done that route, then I think I would have been afraid. I would have had a much greater fear of failure and startups and much less risk tolerance. I guess you could say. Because I would have thought like, Well, you know, I’ve got to succeed at this, because, you know, I don’t know whether or not I can hack it in the startup or the corporate world or something like that.

I think that’s kind of one of the reasons why I went into that, that role in my career in tech. And that turned out to be, I think, a very good lesson. Both in terms of, of what I what I like and what I don’t like, in a work environment, you know, in a professional working environment. But also, it turned out to be a handy bit of experience over the years where just like having some amount of experience in a Fortune 500 company, you know, that the that Convey company actually ended up sort of pivoting into enterprise software. And I ended up doing some sales engineering, where I was on calls with Fortune 500 companies.

And so having that little taste of first hand experience of like, what is it like to work in this kind of environment is actually really helpful to broaden your horizons and make you able to operate in a lot of different settings.

Yeah, there’s sometimes a, having experienced different types of work, helps you put the kind of work that you end up in, in perspective, and like, like, I know, for example, some really young people who have come into a startup as their first ever job, which I think is a great job. Sometimes what they struggle with is appreciating just how good it is compared to the rest of the market. And so they might be like, Oh, well, you know, a startup job, but it doesn’t pay as much. And sometimes they have like a, an inflated idea. Like, I think a lot of people think, Oh, well, if I wanted to just make a ton of money and have an easy job, I just go into the corporate world and like, not necessarily, it’s good to sort of know.

So when you made the switch to a career in tech. When you got the opportunity at Convey, you know, started by this blog post. Was that a, did that feel like a scary decision to say I’m going to going from something really stable, a corporation that has been around for a long time, and it’s not going to disappear in a quarter or a year to something that is a fast moving startup that could go bust? Did that feel scary? And what went into that decision? And you had to move? Several states away as well?

Yeah, that’s a great question. And it’s funny, because I think at the time, it was very scary. But in retrospect, it was actually the least risky thing I could have done with my career in tech. At that stage. So that it was scary in the moment, obviously, because I, you know, I had a what seemed like a secure decently paying job, you know, and I was in this kind of, like, management fast track program, where they basically were trying to, and it cracks me up even saying that, because their fast track idea was like, you’ll be a manager in like, you know, five or eight years maybe, and like, I left Convey, just just over four years after joining, managing a full team.

And so anyway, their idea of a fast track career in tech has a different speed. But yeah, it was, it was scary, both for like the, you know, startups are risky type of thing. But also, you know, I was moving from Benton Harbor, Michigan, which is like small town, Michigan type of place, you know, I’d spent the past four years going to school in Michigan, very sort of comfortable environment to like living in a big city in Boston that I’d never done that before. You know, I didn’t know anybody in Boston, I was sort of like just transplanting myself so that was definitely scary.

It was also scary on the job front in the sense of like, I had done some programming freelance in the past, but I’d never sat down nine to five, five days a week, just programming all day with a career in tech, you know, and I knew I enjoyed programming as a hobby and I thought I would like it as a job but I wasn’t sure that I was going to I wasn’t going to show up there and be just burned out after two weeks of it, you know?

So it was definitely terrifying but but I think back on it now looking back and, and it’s funny because there were a bunch of guys from Whirlpool. You know, my last day there we went out to a bar to grab a drink and sort of say goodbye type of thing. There were a bunch of older guys I worked with on my team that I become, you know, loose friends with and they were all kind of patting me on the back and saying Like, yeah, this is the right time of your life because I was single at the time.

You know, I didn’t have any real obligations or anything, they’re saying, this is the right time of your life to take these kind of risks, you know, I think back on it, and I think like, if Whirlpool had a bad year and decided to downsize, that team that I was on, there was not another employer within 200 miles of that spot that could have employed me with those skills.

I looked at some of these guys who are much later in their sort of career in tech stages in their life stages, who had families and mortgages and kids. That would have been devastating, right, they would have had to uproot their entire lives and move somewhere else. And, and I look at it now. And it’s like, yes, any single startup is risky. But if you are a talented person who can contribute to startups, it’s actually in a lot of ways less risky than the big corporate job, because if this company goes under, there’s a half a dozen other ones that are starting up that are chomping at the bit to try to get you to join them. You know?

Yeah, that dynamism in startups, that churn is you could see it as, Oh, it’s less stable. It’s risky, you know, companies might go out of business in 18 months, or whatever. But it’s on the flip side, like you said, if you look at startups, as an industry, there’s just so many constantly, that saying, I’ve done product, or I’ve done engineering front end at a startup in the past, there’s a whole bunch of them lined up that just raised money that are fighting over you.

It’s I think it’s a little a lesser known fact for young people, especially coming out of college that like how big this ecosystem has gotten. And it’s still growing that like, anywhere from five person startups to 500 person startups. They’re all over, there in almost every city now. And once you’ve done work at one, it’s a lot easier than you think, to transfer to another startup. And I think, arguably much easier to go from startup to startup then from big corporation to big corporation, for sure.

So if you had, if you had a couple pieces of advice or questions or things for people to read, that you would you would recommend to someone who’s in a similar position that you were, say they graduated not long ago, and they took the first sort of safe feeling job, whether it’s in software engineering or not, it’s sort of a corporate thing. And they’re, they’re kind of not feeling it right now. And they’re thinking about trying something new, maybe startups or otherwise, what would you recommend? What would you have told yourself when you first started to feel the itch at Whirlpool? And then what would you recommend to people now, given your experience?

Yeah, that’s a great question. I think, I think I’d echo at least one of the things you mentioned earlier, which is, creating value out loud, is a big part of it. I think. So. And going back to that Luck Surface Area concept, you know, if you think that you’re trying to make a change, but you don’t necessarily know exactly which direction you want to go in. It’s super easy, I think, to fall into the trap of just reading like Hacker News, or Reddit or TechCrunch, or, or some of these stories or news outlets where you hear these awesome stories about these companies and these jobs and it all seems so distant and far away in a lot of ways, and, and unattainable.

So I’m a big fan of the idea of trying to balance the ratio of consumption to creation in your life. And, and I think at the time, you know, when I was at Whirlpool, I was very much skewed in the consumption mode, like I just I, I was playing around with programming, but but I really just loved reading these stories. Sort of, you know, almost like a fantasy type of thing of just imagining what it would be like.

But having that that sort of realization in my career in tech, turning that corner to realizing that, that there is a lot of opportunity out there. And then if you can show value in public that that is that Luck Surface Area starts to kick in. And I realized that super hand wavy in a lot of ways, like what does it mean to show value in public, but like, it means a lot of different things, right?

So if you’re in engineering and software development, it means like working on open source projects, or building your own little side thing, right? And don’t, don’t go crazy about worrying about Oh, is this perfect code? Or is this gonna, you know, take off on its own and make me money or whatever, just do stuff that interests you and show some passion about something and show some engagement with it. But it doesn’t have to be code, right? If you’re in marketing or something like that. There’s lots of ways that you can pick up marketing tasks and just like do them in public and show the world what you know, you know?

And again, especially if you’re at the entry level end of your career in tech, I think it’s intimidating to see some of the, you know, amazing content and work that people do out loud the experts in the field, and you get bombarded with that. Nobody’s expecting an entry level person to produce at that level, right? And that’s okay. You don’t need to shock the world with your brilliance and marketing. But if you just show execution if you just show up consistently and do good work, that sets you apart so much.

So yeah, I’d say I’d say focusing on that. And then the other big thing I’d say looking back is focusing on the network and the people. And this is something that like probably, you know, a lot of people are better at than I was being the sort of introverted engineer.

But, you know, I think back to I joined Convey, and they were just coming out of tech stars, which is this startup accelerator program. And I sort of regret that I somewhat squandered the opportunity to build a better network at that stage, it’s hard to appreciate when you first start your career in tech, how much of your long term career development is focused around your network. Because at that early stage, so little of it is, you know, you feel like, Oh, well, a good career in tech is racking up titles and applying to jobs with good resumes and everything. But in reality, every job I’ve had since Convey has come through my personal network.

And I have said, I’ve only applied to one job since Convey and I’ve had like four or five, the all the others have just been like personal conversations with people I knew through contacts or whatever. And it turned into like, yeah, you know, you seem like you’re a smart guy, how about we work together, and it’s a job offer. So I vastly underappreciated the value of a network early on, and I would say invest in that as much as you invest in your skills and your, your more sort of tangible assets.

Yeah, and you are living proof of the advice that you just gave, I know that I met you, because Chuck, who works for us knew you personally, and you guys had shared interests, and you’d met in college, and he knew that you were into coding. And so you know, I would, I would not have, you know, made that connection. And then on the show your work side, you know, not only was your story about winning that first startup job, very cool, and very in line with our mission at Crash and got me excited. But I went and spent some time Googling you, as everyone will, by the way, and you had a blog, you had a couple posts on there. And you had some things that showed some interest in philosophical things, in addition to code.

You know, it was clear that you were not just coding nine to five, but that you were involved in some various GitHub stuff, you had posts on forums about your opinions on Ember or whatever. And that kind of stuff actually means a lot. Even now, I know, when you started at Crash, you made it very clear that you wanted to be exposed to aspects of startups that you didn’t have as much exposure to like the fundraising process, they continually learn. You’re still showing your work, Chuck, I mean, Dave and Ilya, our other engineer have a podcast called Crash Log where they just talk about what they’re working on as coders as engineers.

They’re always tweeting about, Oh, I just, you know, did this new thing with, you know, this JavaScript, blah, blah, blah, I don’t even know, I screwed up. I tried to say it. And you know, and it’s like, they’re, they’re working out loud in a way that I think will only continue to benefit whether it’s recruiting more employees to work with you at Crash as we grow, whether it’s whatever your next venture is. That’s something that it continues lifelong. So, yeah.

Hey, Dave, I appreciate you taking the time to tell us your story. I’ll put any links you want me to put in the show notes here for anybody and keep keep up the good work helping us help others crash data.

It’s a blast. Thanks for having me on, man.

You bet.

All right.

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