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Taking a Shortcut: Zach Ozer


Welcome back to Taking a Shortcut, a series where we interview our colleagues. The order in which we run these interviews is random, but that randomization is based on a process in which our Director of Content writes everyone’s name down on a slip of paper, puts each slip into its own bottle alongside a self-addressed-stamped-envelope, throws each and every bottle into the ocean, and then interviews co-workers in the order their names are sent back to him by people who find the bottles at beaches around the world. Because of how long this process takes, it’s also necessary to throw the bottles through a wormhole that dumps them into the Pacific in the year 2015.

These interviews are meant to provide a glimpse into what it's like to work at a remote first company, while also exploring the topics of oscilloscopes, reluctant jogging, recipes for breakfast tacos, and building an engineering career in NY. For this week’s edition, we spoke with Zach.

Welcome Zach!

What is that behind you? Is that an Apple II? Or an oscillis –

Oh, that’s a projector. 

Oh, man, I thought that you had an oscilloscope. I'm going to be honest with you, something I've always wanted was one of the original Macs. I don't know if they sold the kit or what it was, but someone turned the original Mac into a fish tank.

That's cool!

It’s pretty sweet because it's both that you had an original Mac and you modded it because it was not worth enough to you to just keep it the way it was, pristine for collector's value, you were like, "No, I'm going to turn it to a fish tank."

I feel like Steve Wozniak would appreciate that, but Steve Jobs would be mad at you for in any way altering his brilliant creation.

I guess the ultimate, ultimate version of this would be someone who made a classic Mac that was a fish tank that actually continued to function in every other way, shape, and form as a classic Mac.

That would be very impressive. Tell us, Zach, what do you do around here?

I am VP of Engineering here at Shortcut, which means that I'm responsible for everything related to engineering from figuring out what we're going to be doing 18 to 24 months from now with our technology stack, all the way down to what we're going to be doing in the next couple of weeks tactically to actually get feature X or Y or Z out the door.

How did you come to be the VP of Engineering at Shortcut?

I think like many engineering managers, my career started as an engineer working on building features and building products. As time went on, I started taking on more and more responsibility around project planning, team processes, things like that, in addition to the work that I was doing as an engineer.

Prior to being at Shortcut, I had been running several teams of engineers elsewhere, but I'd known Kurt and the team here for a very, very long time. I was looking for new things to do, I was out consulting and doing a bunch of different types of work for different people, but talking to the team here reminded me of some of the best experiences I've ever had working as an engineer and why I loved working on engineering: which is working on tools for developers.

I'm not going to cure cancer, I'm not going to go out and put a person on the moon, but I can help empower the people that do that and I get to work with a great team. My career progression, in many ways, happened prior to Shortcut, but I decided to come work on it here because it was just such a great team to work with and such a great problem to solve for the kind of audience that I want to spend my effort trying to help.

You want to help people build things that help people.

I think that's how I would put it. I think that's right, I want to help. I help you help me help you. Help you, help me, help you. I don't remember what – Is it Jerry Maguire?

There's something more to it. Help me help you, help me help you. We’ll get the exact quote. (Note: it is “Help me... help you. Help me, help you.” This sounds a lot more memorable when Tom Cruise is saying it.)

You went to MIT?

I did, yes.

So it seems like this is something that always interested you if you went to MIT for engineering. Tell me about your past and how you even got into software engineering at all.

I'll have to go talk to my mom and try to dig up the photo of me. Literally, there's a photo of me when I'm five wearing an MIT t-shirt. I knew forever that I wanted to be an engineer. When I went off to college, I actually thought I was going to do something very different. I thought I wanted to do material sciences and specifically in the context of chip design and manufacturing - a real low-level system chip designer basically. It turns out I'm really bad at that. The long and short of it is that I almost flunked out of signals and systems more than once.

I found, though, that I actually really liked working on software itself, building things where I could feel the impact immediately. I could go and write a few lines of code, run it and see, “Oh my gosh, that's on the screen. That’s doing what I expected, or more likely, "Oh, nothing is on the screen. I have a horrible stack trace and I've broken something terribly."

Even as I say that, I think back to my earliest days of really working in software in any way which was as a kid, I used to break my parent’s computer pretty regularly. I'd install some random thing that I downloaded from the internet. Try and get some custom driver for some piece of hardware I didn't actually have. The number of times I just had to wipe my parent’s computer and reinstall Windows from scratch I can't even count because I just would mess things up so badly and so regularly.

It taught me really good skills in terms of debugging and fixing things. There is nothing like the pressure of a parent bearing down on you, saying, “Oh my gosh, the family computer is totally broken. I can't do anything. You need to fix it right now!” to really get you to develop those debugging and repair skills for computers.

Did you grow up in Massachusetts? Where did you grow up? Why MIT?

I grew up in San Antonio, Texas.

Far away from Massachusetts.

Far away from Massachusetts. Why did I want to go to MIT? I think it was one of those things that was just a pipe dream realistically. From my perspective at the time, it was the best engineering school in the world. I'm always someone who says, "Okay, what's the absolute best that you could do?" You work backward from there in terms of, "Well, what can we realistically achieve here? In a week, what can we realistically achieve in a month, in a year?"

I'm always someone who just tries to shoot for the stars and go for the most extreme version of whatever you can do. For me, that was, "If I want to go be an engineer, I might as well try and go be an engineer at MIT. If I can't do that, there's lots of other good options available to me," but that, to me, was the best I could do.

You live in New York, how long have you been in New York?

I've lived in New York since I graduated from college. It's been 13, almost 14 years now. I did a brief stint in Austin at someplace around the time of the great recession. I thought I might move back to Texas, it turned out I'm too much of a New Yorker at this point. Moving back, it didn't feel right. I was still young and fresh out of college and I wanted to go out a lot. Austin is a quieter town than New York is. So, 13 years.

What was it like to get into software engineering and be in New York instead of somewhere that’s visible from a really tall hill in San Francisco?

When I first moved to New York, most of the tech there was really finance-oriented. It was interesting being in New York because, basically, everyone I knew went to go work for a bank. Even as an engineer, I went and worked for a bank. I did it for a year and decided that it was soul-sucking and it was terrible and I was working towards nothing that was contributing anything to society. I pretty much immediately quit. That's actually why I went to Austin.

I took a month off. I backpacked around Southeast Asia, Thailand, Vietnam, Cambodia. It was like, "I'm out of here, man. I'm just not working in finance." That's when I went to go work for a startup in Austin. Working at that startup, I felt like, "This is why I like doing software engineering.” I can do something that has an impact. It means something to people.

Because it was the Great Recession, that startup went out of business not long after I joined. I decided to come back to New York because I felt like my network was there and I'd have a better shot, especially compared to Austin at the time.

Even beyond that, I think it was also a really special time to be in New York because if you look at the track record of VC investment here, it was dramatically changing at the time. There just were more startups in New York that were doing interesting things. It's obviously not like San Francisco where literally every person that you talk to is just working on a startup, entrepreneurial. I always really, really valued the fact that New York had that balance.

At the end of the day, I could go and talk and nerd out with a bunch of people about engineering and tech stuff, but most of my friends were – for better or worse, they were like doctors and lawyers and bankers and reporters and artists and stuff like that. People were doing other things, and it wasn't like everything was about a startup. People could make a living doing something that was not in tech. I really love that about being in New York.

When you're not engineering software, what do you like to do?

I don't know how much engineering of software I do these days, so much as talking to people about the engineering of software. When I'm not doing this, I have a lot of things that I'm passionate about. I have a two-year-old daughter who I love. I have a dog, Bart. I spend time with them, that's number one. Both of them like to go outside, so we try and do a bunch of walks.

I'm a reluctant runner, and what I mean by that is I enjoy running, but I hate exercising. To do a 30-minute run takes me 30 minutes to get ready because I have to mentally prepare myself to get out and go do it. When I'm out there and just out running, it's a great way to clear my head and I like doing it. It's funny because even as a reluctant runner, I ran the New York City Marathon in 2015, which I was really excited about. It was one of those things where I ended up doing it, and I thought to myself, "What am I doing? I am not a guy who likes running. How did I end up running a marathon?"

I love to cook, I've always loved to cook, it's something that I did with my mom a lot growing up and we still love to do together. I do that a lot. Then I've got two food passions. One is barbecue, specifically Texas brisket. I also really like lamb ribs. When COVID is over, I'll send you the list, but I've got this whole barbecue tour of South Texas that I used to run. As a New Yorker, the quality of barbecue has really gone up dramatically in the past five years. That's been something awesome to see. It's gone from inedible and nonexistent to- there's actually places that if they were in Texas, I would go to, assuming they were convenient enough, I wouldn't go out of my way for them.

If they were nearby.

If they were nearby, I'd show up. The other thing is breakfast tacos, not just any Mexican food, but breakfast tacos. In California, it's a breakfast burrito. In South Texas, it's actually a breakfast taco, and the specific San Antonio breakfast taco is beans and cheese, so melted cheese with refried beans. I've been spending my time perfecting my bean and cheese taco recipe over the pandemic and I think I've got a pretty knockout bean and cheese taco thing.

The key, Richard, and this you can share with our readers, the key to a perfect bean and cheese taco is that you have to make it what I call “toasted”. What it means to toast a bean and cheese taco is that you take the tortilla and you heat it in a pan, I use a cast iron, but you can use whatever you want. You basically want to melt the cheese onto the tortilla, the normal one is you sprinkle the cheese on top afterward and the beans melt it. This is like an open face quesadilla that you then add beans into and then fold it up. If you do that, it doesn't matter how bad the tortilla is, it doesn't matter how crummy the cheese is, it just is transformative. It radically changes your perception of what these components should taste like or do taste like.

I hope that this description of this ultimate breakfast taco recipe you've given us leads to Shortcut being one of the top search results for breakfast tacos in the coming months.

That would really help business, right?

It would! What is something that you've learned or had reinforced from working at Shortcut that you would share with the world?

I don't think of myself as having been here that long. I've only been here for a little over two years, but of course, in startup age, that makes me practically ancient. One thing that's really been reinforced for me working at Shortcut is about how important and how valuable it is to spend time being thoughtful about your communication. That sounds really generic and buzzwordy; I’d call it airport non-fiction. It's something that Malcolm Gladwell would tell you. By the way, people often say I look like Malcolm Gladwell. I don't want to confuse you here, Richard.

I almost thought I had gotten on the wrong Zoom call. 

Especially having a distributed team, really spending the extra time to write everything down and be thoughtful about not only how is this useful for me, but how is this useful for all of the different people who might consume this? Really, we're trying to be empathetic in your communication. We're thinking, "Okay, I'm going to write down this process or procedure. What's the TLDR here? What's the thing that people really need to take away from it?" Because they're being inundated with all of these things that come in, so how can I filter and make sure it goes to the right people? How can I make sure that the right people are involved in discussing it in advance and how does this flow through?

I think in earlier parts of my career when I was working in offices with people, I just grabbed someone, sat down, had a coffee, and we talked through it and the information would percolate through the organization. Now because we're all behind Slack and all behind Zoom calls and all behind these other things, you really have to be a lot more intentional and thoughtful about it.

It's been so amazing to me to see the difference between when I really sat down and spent the time and really invested extra effort in that, versus just typing something quick up and firing it out. I think that that's something that's really been re-emphasized to me being at Shortcut is just how in the past I might have devalued that or thought that it was not as important and how both impactful and important it's been being here at Shortcut.

Fantastic answer. With that, we'll say the interview is done.

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