Techies: Rob Cascella

Original Interview: http://www.techiesproject.com/rob-cascella/

Tell me about your early years and where you come from.

Early years, okay, so I was born into an Italian family in Connecticut. I am the oldest of three kids, and the oldest cousin of nine. Had I gone to college, I would have been the first person in my family to have done so. As I dropped out (for reasons which I’m sure we’ll cover later), I think my sister claimed that title some years later.

We moved to central New Jersey, in between New Brunswick and Princeton, when I was eight. That’s where I grew up. I have had a computer since I was four, so typing is easily one of my earliest learned skills. I think, of learned skills, I’ve only been walking, talking, running, and whistling longer than I have been typing.

“I was born into an Italian family in Connecticut. I am the oldest of three kids, and the oldest cousin of nine. Had I gone to college, I would have been the first person in my family to have done so.”

I did not have very many friends as a kid. I got picked on a lot, and so I kinda went out of my way to avoid unnecessary social interactions where I might be alone, like lunchtime. I would eat my lunch quickly, and then escape to the library where, one day in my freshman year, I found a Mac SE, sat down, and started playing with it. It was my first exposure to a real personal computer — until then, everything had been glorified video game systems with BASIC programming interfaces (like C-64 or TI-99/4a)! It just worked for me. By the end of my freshman year, I was teaching the art teachers how to use the scanner and brand new system I had set up for them!

“I did not have very many friends as a kid. I got picked on a lot, and so I kinda went out of my way to avoid unnecessary social interactions where I might be alone, like lunchtime. I would eat my lunch quickly, and then escape to the library where, one day in my freshman year, I found a Mac SE, sat down, and started playing with it. It was my first exposure to a real personal computer. It just worked for me. By the end of my freshman year, I was teaching the art teachers how to use the scanner and brand new system I had set up for them!”

I tried to do a semester of college after I graduated high school, but it did not go as well as I would have wanted. Yanno, growing up, everyone told me I was smart. But I made a very stupid decision about college. I ended up going to Purdue University, in Indiana. Of the schools that accepted me, it was the best option, at least from a recognizable name perspective. But it was a terrible choice if I wanted to finally come out as gay in college. My roommates, and even the resident advisor for our dorm, were all exceptionally straight small-town Indiana boys. I recall learning three important things during our brief interactions: 1) abortion should not be even a word, let alone an allowable action, 2) women are essentially property of their mans, and 3) being queer should be illegal, but, since it is not, it should be taken into the hands of (let’s kindly refer to them as) vigilantes.

“I ended up going to Purdue University, in Indiana. Of the schools that accepted me, it was the best option, at least from a recognizable name perspective. But it was a terrible choice if I wanted to finally come out as gay in college.”

So that wasn’t too great for me. It definitely encouraged my continued avoidance of social situations that I couldn’t control, which, ironically, continued to have the effect of exposing me to new technologies. In order to avoid my roommates, I spent all of my free time in the computer labs where I got to play with UNIX in the forms of early BSD and very early Linux, and where I was introduced some very early forms of online chat.

I should back up here, because, at that point in my life, I imagined myself in a creative role. Given that so much of my exposure to systems in high school related in some way to art, I was targeting creative and graphic design as my career. My first job, in between high school and college, was running the desktop publishing department at my local Kinko’s (where I networked all the self-serve computers “just for the fun of it”). So, Purdue would have been amazing if I had my sights set on CS. But, yanno.. I’m a little slow on the uptake for some things. [laughter] So, at the time, all I consciously took from it was a way to access this world of online chat that I had been shown.

Anyway, so I dropped out. I went back home, and looked for temp work — because what the hell else was I going to do? I had that experience in desktop publishing at Kinko’s, so I went in search of some entry level design jobs. I figured I could typeset ads or something. It was during an interactive interview for one such job that things changed for me.

Picture it: New York City, 1996. A young peasant boy is seated at a computer taking a timed QuarkXPress typesetting test. Suddenly, the computer? It crashes! Oh no, what will the boy do?! He takes it all in stride, that’s what he does! He fixes the damn computer, and finishes the test, JUST IN TIME! Returning to the test administrators, he tells them of his troubles with the test taking apparatus, and how he remedied them — just in case it happens again! Intrigued, the administrators escort him to another desk, holding another computer, which displays a different test: a technical skills test! “Would you mind?” they ask him. The boy complies. He flies through the test at record speed. When he returns to the administrators, at first, they are crestfallen: he’s back too fast, he must be bailing on the test, buh buh buh… but then they check the results, and their expressions noticeably change. “That’s the best score we’ve ever seen anyone get on this test. Have you ever considered a job in desktop support?”

Unfortunately, they didn’t have one to offer me. But, it planted the right seed. And, by virtue of the connections I had made via IRC — the early form of online chat I previously mentioned — I ended up with a job doing desktop support for American Express.

I jumped around through a number of different jobs in New York City, ultimately landing at an ad agency where, at 22 years old, I held the very fancy sounding role “Manager of IT Services” — which really meant that I was the only person in the company who knew anything at all about tech. They were an all Mac shop, but it was mine to run as I wanted, so I used the available hardware to teach myself Linux. The first time I installed Linux myself was LinuxPPC, installed onto a Jaz cartridge connected to a Powerbook 5300. There’s some serious geek cred in that, I’m just sayin’.

Once I had taught myself Linux, I was able to apply for actual sysadmin jobs, and so I eventually did that, and landed with the SciFi Channel’s “new media” division (remember when it was called “new media?”) as a Junior Linux System Administrator. This was really cool. It was the end of 1999, beginning of 2000, when, if you recall, the VC money was flowing like the Nile — I mean, it was just pouring out of the walls! I actually remember them telling us that we HAD to spend money, so we went out and bought an Aibo. Do you remember the Aibo?

Nope.

It was this robot dog that Sony made.

Wait I do remember!

Yea. It was $3,000, okay? At a time when my rent was $600. At a time when a NICE apartment on the Upper West Side would have been like $2,000. We had an Aibo. Because we had to spend our money. It was fucking insane.

“It was the end of 1999, beginning of 2000, when, if you recall, the VC money was flowing like the Nile — I mean, it was just pouring out of the walls! I actually remember them telling us that we HAD to spend money.”

Anyway, I kinda saw the writing on the wall that that was unsustainable. And I had been circulating my resume, and it ended up with this company in San Mateo. Here I am — it was 2000, so I was about to turn 25 — I’m 24 years old, I’m talking to a company in California. I’m a grunt. I’m a peon. I figure these people are never going to hire me, anyway. And even if they do, I can’t afford to move myself to no California! So I just treated the interviews super super casual. And, after a few rounds on the phone, they were like, “Yea, so do you want to come out and meet us?” Do I want you to pay for me to fly to San Francisco and put me in a hotel for the weekend? Um, fuck yea I want that! I figure that’s all I’m ever gonna GET out of it, so YES I definitely want that! [laughter]

So I fly out, they tour me through the office, tell me all about their stuff, this and that. And then, real casual like, the director of engineering says to me, “So, what do you think? You want a job?” I mean, yea, I want a job, but I mean, I live in New Jersey. “Yea yea yea, we’ll get you here. Don’t worry about that. Do you want to work here?” I mean, yea. Yea, I guess. Yea. “Ok, great! How much do you want?” Wait, what? What are you talking about? Aren’t you supposed to tell me how much I’m getting? What do you mean how much do I want? Am I on camera? C’mon, this isn’t funny.

And so that’s how I come to live in California.

The week I arrived, the guy who hired me — the guy who I KNOW was my advocate to get me in there — got fired. He was replaced by a VP of Engineering and Operations who brought only political in-fighting to the organization. Basically all progress was stalled for five months. It got so bad, that the board had to intervene. The CEO was forced to resign. And the VP, and almost everyone within the organizations below the VP, was laid off. They kept their administrative, sales, and marketing departments, the CTO, the head DBA, and one engineer. Everybody else, it was: “See you later.” I’ve just moved to California six months ago. It’s March, 2001. I have six more months on a $1,600/month lease.

Uh oh.

Holy shit [laughter]. On the upside, at least I don’t have to pay back the relocation costs! [laughter] And, again, I think I knew this VP was screwing things up, and so, again, I already had the resume out. I was really lucky: I got a job within two days. I didn’t have to leave. And, yanno, that was a really intense time. It took my peers who were laid off at the same time over a year to find another gig. Some of them DID have to go back to whatever was home for them. And these were people with more demonstrable experience than I had. So, yea, I count myself really lucky.

But then that company then failed again about a year later. So now I was really stuck. I was kinda dating (but mostly just living with) a guy at the time whose parents are, basically, rich. His dad was something like the sixth employee, and the primary hardware engineer, for some networking company in the south bay. And they were sending him, literally, $2,000 a month to go to school and live in San Francisco. I can’t even conceive of somebody giving me $2,000 every month, just to exist, but here we were. So that money paid our rent, and I got some contract work through friends to bring in money for food, and I enrolled in City College of San Francisco so that I could get financial aid to cover the rest.

Now, at the time, we had a friend who was in the hospital battling leukemia, an eighteen year old kid. Since I was out of formal work, I got to spend — on reflection not nearly enough — time with him. It was while visiting with him one day that I got the idea maybe I should be a nurse. I thought it would be a really great way to use my empathy to help people in a really vulnerable time and blah, blah, blah.

I think in some ways that would have been a right path for me. But since I’ve been back in tech, when I look at some of the careless errors that I make, I go, “Oh, nooooooo.” Yanno, nobody dies if I fuck up in tech. [laughter] But, if I give the wrong person the wrong injection, they’re gonna die. So on reflection, nursing seemed a little scary.

Maybe nursing wasn’t the right choice, but aiming for it kept me in San Francisco. I didn’t have to go back to New Jersey, and that was really important. For 2002 to 2005, I battled with the CCSF student population for the precious little available space in required classes. Since I never did college after high school, I had to start from, yanno, start. So I was doing English and Psychology and all that crap. Through that whole time, my former manager had been on my ass to come back and work with him again. It took him like 16 months, but as soon as he landed, he was like, “I need you, I need you, I need you,” and I’m like, “You want me full-time, I can’t give you full-time, I’m going to school!”

But then I got to the point where I was like, “Okay, I can apply to nursing school now,” and I knew that I had at least a semester of lag between applying and when I would begin (assuming best case scenario that I was accepted on my first try, which was almost inconceivable). I also knew that the clinical part of my education was going to be more time demanding than the classroom portion had been for these last several years. I knew that meant that I would soon lose that extra money I had been making with my contract work. Oh, and that boyfriend with the rich parents? Yea, we broke up about eight months into me being at school. So I had been really struggling to hold shit together for a while there. And so, I knew I was gonna need at least a cushion. So I gave in, and went back to work. I figured: I’ve been living on almost nothing, and he’s talking about six figures. I should have no trouble banking cash! I’ll just sink everything I can into savings, and in a couple years I’ll have a whole bunch of money, and I’ll go to nursing school!

That was 2006. What… what year is this?

And here we are. I never went to nursing school. [chuckles] But I have had a lot of fun in the interim! So that’s from the beginning — that’s to now.

Once you committed to a life of tech, what have been the highlights and the things that have been the most exciting to you? What are the things that make you so pumped about your work?

Having somebody move me across the country was really fucking pumping. [chuckles] That kind of stuff has been exciting. I got to move out to Vegas and manage a data center installation there. That was really wonderful for me because it was a lot of things that I loved: I got to work from home, I got to live in the desert, and I got to manage this data center installation. I really love the anal retentiveness of managing a data center, and just keeping it really immaculate. That was a lot of fun for me.

In the last couple of years, tho, I’ve got to admit, I’ve really lost my excitement on tech. I’ve kind of been getting to the point of — this is 22 years in, now — I’m starting to go what the fuck do I do next? Like, I have no other marketable skills. What do I do?

And it’s also getting a lot harder. In 1999, when I first started really learning Linux, it felt entirely within reason to think that I would get to a point where I understood it all, and that it would be good. I still feel like, back then, that was possible, and I know I’m not alone on that, because I’ve had this conversation with one of my current coworkers. But there’s just been so much advancement in the last fifteen years, the last ten years, the last five years, the last two years, that there’s just too much so keep up with, and I don’t know how to do it anymore. I read a blog post this week about how they’re changing something about the way that you define functions in python, and my immediate response was aggravation. One more fucking thing that I need to remember. God damnit!

“In the last couple of years, tho, I’ve got to admit, I’ve really lost my excitement on tech. I’ve kind of been getting to the point of — this is 22 years in, now — I’m starting to go what the fuck do I do next? Like, I have no other marketable skills. What do I do?There’s just been so much advancement in the last fifteen years, the last ten years, the last five years, the last two years, that there’s just too much so keep up with, and I don’t know how to do it anymore.”

I mean, honestly, it wasn’t exactly passion that brought me here in the first place. It was that this landed in my lap, and it’s a fucking great salary for somebody with only a high school degree. I mean, that’s why I’m doing it. I don’t know if that’s the answer that you’re looking for. [laughter] I think about this sometimes: the only other skill that I know that I have is cooking and baking. Food. Well, that or drugs, but really only one of those is sustainable! [laughter] And food is really hard to succeed in! So I really don’t know what I would be doing if I didn’t have tech. I don’t know what I’d be doing with myself.

Honestly, this might sound weird to you, but it sounds a little bit different and refreshing to me, to finally meet someone willing to admit that it is work to them. It is a job. Because we live in a place where everybody puts on a face of, “I’m doing what I love, and I’m so lucky to like work on my ultimate passion.” And it’s not 100% true for everyone. It is work, and I think it makes people who don’t totally know what their passions are, or they don’t totally know what the thing they’re destined to do, feel bad about themselves. I think this is a town where people love that myth of, “I just had a passion for this, and I’m so lucky to be doing exactly the thing that I’m so passionate about with this app that does this thing.” I feel like it’s a bit of a myth, but everybody feels pressured to —

To maintain the bullshit. Yeah. Because, I think, it’s like, if we break that down, then we have to reevaluate everything. Then it becomes: how much else are we lying to ourselves about? [laughs] Ya know, in order to keep doing this, in order to keep spending $3,000, $4,000 every month on just our rent, to keep being away from our families, accepting that we can’t afford to travel or go on the vacations that we want to go on, because we’re spending all of this money just to be here. I get it. I totally understand why people have to maintain the myth that everything’s perfect.

“In order to keep doing this, in order to keep spending $3,000, $4,000 every month on just our rent, to keep being away from our families, accepting that we can’t afford to travel or go on the vacations that we want to go on, because we’re spending all of this money just to be here. I get it. I totally understand why people have to maintain the myth that everything’s perfect.”

Yeah. It is a thing that you can still do a really good job at, even if it’s not your ultimate passion. You can still be smart and proficient and do good work, even if it’s not your dream product, which I think people also worry about here. They have to be working on the perfect product or the exact company that they’ve always been dreaming of, and anything else is a failure. You know?

I wonder if that’s kind of a byproduct of what a youthful group it is that’s going into these organizations now. Ya know? Like I wonder how much of that passion is fueled by youth. Take where I am now. This is the first time in my career that I’ve looked around and gone, “Oh. I’m the old guy in the room.” Among my immediate group of about 25, I beat everyone but the director by easily more than a decade, and even the director only has me beat by less than a year. And these guys are passionate about tech. And it’s a little reminiscent of how it used to be when I was younger. I definitely remember being really excited to do the work. It definitely was fun for me, I think because it was easy, and I think because I knew it so well. It was just like, “Okay, yeah, we can do that. Here you go.” It was easy. It feels like it has that same level of ease for these younger kids, and now it’s kind of hard, and so it’s lost a lot of the fun, for me. Now it really is a means to an end. That’s over the last couple of year that’s happened.

“This is the first time in my career that I’ve looked around and gone, ‘Oh. I’m the old guy in the room.’ Among my immediate group of about 25, I beat everyone but the director by easily more than a decade, and even the director only has me beat by less than a year. And these guys are passionate about tech. And it’s a little reminiscent of how it used to be when I was younger. I definitely remember being really excited to do the work. It definitely was fun for me, I think because it was easy, and I think because I knew it so well. It feels like it has that same level of ease for these younger kids, and now it’s kind of hard, and so it’s lost a lot of the fun, for me. Now it really is a means to an end.”

What else have been struggles for you?

Feeling like the only queer in the organization has definitely been hard. It wasn’t until 2008 that I was on a team with somebody else who was queer. That was like 11 years into my career? There had been other queers in the companies — in sales, in creative, etc — but none in tech. And, I wasn’t working nowhere — this was New York City and San Francisco.

At one point, I actually ended up — how should I say this — separating from an employer after completely losing my mind about their insensitive treatment of queer issues. They had run a Red Cross blood drive, and it wasn’t getting much attention. So the director of HR came around and tried to drum up participation. When she asked me, I was like, “I guess I’ll do it, whatever.” I had been smoking a lot of weed at that point, so I messaged to a friend I was like, “Ha ha ha. Somebody’s going to get my weed laced blood! Lucky them!! Ha ha!” And he’s just like, “Dude, you can’t donate blood, what are you talking about?” I’m like, “What am I talking about? What are you talking about I can’t donate blood? Of course I can donate blood!” They’re like, “No, you’re gay.” And so I’m all, “Wait, that shit’s still real? What fucking year is this?!”

“Feeling like the only queer in the organization has definitely been hard. It wasn’t until 2008 that I was on a team with somebody else who was queer. That was like 11 years into my career?”

So, I went and researched, and, yea, okay it is still real, apparently it’s still 1985. So, I went back to the director of HR, and said — seriously, just like this, because I thought it was fucking hilarious — “Hey, listen, it turns out, because I am a man who has had sex with a man at least once since 1979, they will politely accept my blood donation and then throw it in the trash. I think that’s wasteful, and so I’m not going to do it.” She goes, “Okay,” and crosses my name off the list.

So, they do the event. I was away the day that they did it, but they sent out an e-mail afterwards, and the email was the first thing that I saw when I opened my laptop on my first day back after a really intense, very emotional weekend. I’m not making excuses, just trying to set the scene a little bit maybe. Anyway, here’s this e-mail, and it’s describing the very successful blood drive, and how they got this many units of blood and other than one person who had to be excluded due to recent travel restrictions, it was a resoundingly successful event.

I went non-fucking-linear.

I typed up this huge email, breaking down bit by bit why it was nonsense that gay men would be excluded from donating. That this is in violation of our company values which state that all employees must be included in all things.

I then went on to be very, very, VERY colorful in the illustration of how that made me feel. It was the excessively colorful last paragraph that pushed me over the edge, but I think it came out of a lot of feeling completely fucking alone in this company. Because I evidently needed to be completely galled, the HR person, on my way out, had the audacity to give me, “C’mon, Rob, he COO is gay!” Well you know what? Where the fuck was that information when I asked for it!? When I asked my manager, and his manager, and his manager: Where are the other queers in this company, so that I don’t feel so fucking alone? Why did nobody have anything to say?

So, that’s probably been the hardest thing about the work.

I had moved away from home when I was 17, so I wasn’t living at home before I moved to San Francisco anyway, so that wasn’t specifically hard for me. I have a brother who was just under a year old when I moved away, and having limited time to spend with him kinda sucked, but our relationship was pretty strong anyway.

The being alone part was hard, but that had nothing to do with tech, that was just me. The, “I’ve moved all the way across the country to this place that’s supposed to be Mecca for me, both in ways of queer and in ways of tech..” part.. that was rough, since I discovered pretty quickly within those first two years that it was neither. [laughter] I was able to be laid off and not find more work, and it was no more gay from my understanding than New York City was. I guess that’s probably been the hardest. But, again, not specifically related to tech.

Yeah, it seems like it’s kind of an extreme version of just not knowing anyone like you and how isolating that must be, and how that must affect your morale over time. Were you able to find support networks anywhere during that time?

Yeah. In the early 2000s, there was still a lot of really good underground-y online stuff, like the online chat stuff. That was somehow more nurturing, or more of a bonded experience, than chat is today. It’s so disposable today. There were definitely groups that I got to be a part of that I hold on to some legacy from that. Most of my current friends descend directly, in one way or another, from those early chat experiences.

How how do you feel about the current state of tech bubble or boom or however you want to look at it versus the last one?

I have been growing increasingly concerned. It definitely does seem like we’re at a point of being back to crazy times, like: how can these organizations be worth billions with a B? No, I don’t buy it. Even if what you’re buying is the talent in the company that built the product to add it to your portfolio, I don’t buy that it’s a billion dollars. Plus people quit. I just don’t get it.

I don’t think about it too consciously, but probably unconsciously, it’s probably fueling a lot of my discomfort about the state of things for myself. I have been in the position before where I’ve had to compete with people I know were a lot smarter than me for work! And now I’d be competing in a much different way. Because I am even less attractive now that I’m 40 years old, right? Now I’m not this young kid that you can abuse and make do whatever the fuck you want to.

So I am a little bit concerned. I didn’t know to plan for it back then, but I’m working on it for this time. But, in any case, I think, just like back then, I’m just going to keep riding it until I can’t anymore. Hopefully, I’ll figure out a good plan B before then.

“I have been in the position before where I’ve had to compete with people I know were a lot smarter than me for work! And now I’d be competing in a much different way. Because I am even less attractive now that I’m 40 years old, right? Now I’m not this young kid that you can abuse and make do whatever the fuck you want to.”

What would ideally you like to see change in tech, culturally or technologically or economically or whatever?

I would like to see it spread. I would like to see this type of an environment exist in places that are not just San Francisco. And I don’t quite get why that hasn’t migrated yet.

Where do you see yourself five or ten years from now?

Such an interesting question. In the past, the answer to that question has always been, “exactly where I am now, just making more money?” answered just like that: as a question. [laughter] Let’s see, ten years from now, I’m going to be 50. I really don’t know that I have the capacity for any more advancement within tech. I don’t know that I want to go the route of architect. And I’m pretty confident I don’t want to go manager. I think it should be evident, from your interactions with me, that that would be a terrible terrible idea. [chuckles]

But, I don’t know. I see a couple possibilities.

In one scenario, I’m still working in tech, either for my current employer or another, but I’m living somewhere in UTC+8±2, so somewhere between New Zealand and Burma, and working 100% remotely.

In another scenario, I’m living in UTC+8±2, but giving scuba diving lessons to western tourists.

And in still a third, and I think more realistic, scenario, I’m still in California, working in the medical cannabis industry in some capacity. I’ve been fighting this impulse for the last several years, but every single time I really try to come up with something that I can actually feel passionate about, this is all I come back to. My current partner surprised me recently by proposing the idea, “What if we opened a dispensary together?” so we’ve started exploring that possibility.

So I don’t know.

“Ten years from now, I’m going to be 50. I really don’t know that I have the capacity for any more advancement within tech.”

How are you supposed to know?

I wish I knew. I’ve never known. I’ve always just kind of been doing it. I don’t know. I’ll take it as it comes. In a perfect world, if I could actually script it, I’d be doing some sort of queer rights activism. My current partner — he’s actually a student at City College right now — came home one day, and he goes, “Hey. What would you think,” he’s ethnically Cambodian, “if I wanted to move to Cambodia and do queer rights activism there?” It’s a country that’s kinda ripe for it. I thought, “That would be fucking amazing! It would be incredible to be part of that movement! Oh my god!” So, who knows? Maybe I’ll be doing that. If I could do that and fund it with — like I said — a job that I’m still getting San Francisco money from — and just not losing all of it — yanno, that would be fantastic.

Yeah [laughter].

I don’t know. I don’t know.

My last question for you is what advice would you have for someone just getting started out in tech and perhaps feeling isolated?

That’s a hard question, because I still don’t know. I mean, if I didn’t have the employee resource group where I am, I would again be in a place where most everyone immediately around me is very straight. One of our DBAs, she’s not specifically a lesbian, because she’s married, but she was right on top of me. So I would’ve had that, but I don’t know if I didn’t have her or the employee group. I wish I knew [laughs]. I guess it would just be keep waiting and eventually it happens. There’s groups. There’s these meet ups, but they’ve never felt right to me. Even our employee group has done one or two, like, social mixers with the queer groups from some other local tech companies. And I’ve gone to them, but it’s just like a bar. So, I guess, in a way, I still feel alone. I’m working with more queers, but I still feel alone. I’m not working with queer engineers, so I still struggle with trying to answer that question, I guess.

“I guess, in a way, I still feel alone. I’m working with more queers, but I still feel alone.”