the Webb blog

A decade in tech: a retrospective

11 minute read

The Beginning

I got my start in the web/tech space over a decade ago, during the economic recession of 2008.

Two years prior I was in college for a couple months until Johnson & Wales' campus police called to let me know I'd need to leave by the end of the week. Unbeknownst to me the college fund that was allegedly prepared for me never existed (!!) and the funny thing about bounced checks is, no one likes them; especially an institution that needs to pay its faculty. Anyhoo, in 2008 I was tasked with "getting myself back into school" somehow and was sent to the next town over from JWU to start.

My landlord, a portly self-deprecating guy with a glass eye and a heart of friggin' gold, allowed me stay rent free as long as I kept him up to date with my job search progress. In my downtime I perused online communities like deviantART and Pixelfuckers (defunct) and attempted to emulate what I saw in the awesome desktop modding scene. That led to attempting vector art and boy, this was frustrating as hell to learn. Photoshop's pen tool just did not make sense at all and Illustrator was too strange. One clicked. I could do it!

2nd Vector

Yes, revel in this monstrosity. Admire it. Fear it (the later version of this looks way better).

At some point I was designing so much that I decided I needed a website, naturally. I mocked something in Photoshop and emailed a PSD to HTML service to see how much it would cost to convert my "super awesome" design to a website and I was quoted either $100 or $500. Whichever amount it was, I was incensed. Furious, even. Couldn't they see I was trying to start something? Why would they charge me so much? The audacity of these people!

In my anger, I learned how to code my first website[1].

Yes. I was petulant and figured it out because I was misguided in my anger at someone/some people trying to run a business in a recession. It sounds quite silly in hindsight but, there you have it.

At that point I also understood that web design and development is not something easily done correctly. Doesn't it make sense why someone would charge to do it for you? Armed with this newfound knowledge I dove into the Internet head first and scoured it for web development tips. Often, these tips came from horribly designed websites 🥴. Indeed there was a time before Envato and their Tuts+ tutorial sites burst onto the scene.

I Made It

Sometime in 2012 I was working retail and applying for web design/development roles I was definitely not suited for but YOLO (pretty sure YOLO wasn't said then but y'know, same energy)! Just fire and forget, leave for work, come back home and check email. One day I got a response back from thoughtbot, a design/development agency in Downtown Crossing (Boston)! One of the co-founders wanted me to come in and interview for their apprenticeship program. Elated, I made the trek downtown with my heavy laptop and couldn't wait to show off my work.

My elation disappated when Chad Mazolla said (paraphrasing, too long ago):

Your code is terrible...but your design is good. Great, even! We need more stuff like this on the Internet.

And with that, I was in! The program lasted a few short months and while I was the only one who wasn't offered a job through thoughtbot or their partner companies afterward, I will say that it was the best experience I could have had at that point in my life. If nothing else, I finally had something I could put on my non-retail resume!

Over the next couple years I would go on to do contract jobs and later work for startup after startup after startup. I've worked for a "regular" company here and there but end up going back to startups. Even though they come with uncertainty[2], they are often working on challenging ideas and projects that can change some aspect of the world in interesting ways. I'm drawn to that. I also love learning how to do things I either don't feel like learning on my own time or never thought about learning. The best teacher is experience so why not get paid to do it? This allows you to initiate ambitious side projects solo instead of waiting/relying on someone else to get an MVP running.

Perhaps more important than the technical skills acquired, I learned how not to treat people. Sometimes this was an analysis of my own behavior but more often than not the actions of leadership exemplified this.


The following scenarios are situations I've been on the receiving end of.

  • You're an apprentice and a developer mentoring someone else in the program regularly talks over you and pumps up his apprentice whenever he can. Maybe his disdain for you is because you're self-taught or was personally invited by the co-CEO to join the program. Or maybe the developer didn't like you having regular conversation with the (female) office manager. You're new, you just want to absorb information from everywhere.

    • You learn many years later that this same developer also treated prospective clients quite rudely.
  • CEO picks his nose and makes eye contact with you. This happens enough that you learn how to have a blind spot whenever you turn your head and see him in your peripheral vision.

  • As a contractor, you end up doing the job of the guy you're reporting under while he browses Joystiq for gaming news. You are later fired and realize he threw you under the bus for his work not getting done. Many years later you see him in a Target department store and after recognizing you he discovers a sudden interest in ceiling architecture.

  • As you're dealing with the excrutiating sorrow of miscarriage, the CEO puts you on a dubious "project" for his father's company. A week or two later you're in a firing meeting, sans CEO. In the minutes following the firing you look around for the CEO to have a conversation with him but he's nowhere to be found, even though you just saw him five minutes prior.

  • CEO constantly lies to you and your coworkers about the health of the company and surprises y'all a week or so from Christmas on pay day with "Hey, sorry, we can't pay you" phone call. Money eventually shows up but this happens at least once more before the company folds.

  • CEO loves your work and mindset and tasks you with unleashing your creativity on core properties. Then come caveats. You create something cool, you guess, with caveats because core users would be "confused" by drastic changes. A month or so later, CEO okays a developer not hired for their design sensibilities to drastically redesign the core product. CEO reiterates your importance while restricting your expression.

  • You notice there's someone on the platform you are helping develop who has advocated for harm and negative energy towards people who share your creed/likeness/ethnicity. You get on a call with the CEO and he not only downplays the matter but he disregards how you feel about it. He also claims organizations like SPLC are disengenous and blow things out of proportion.

These scenarios are situations I've witnessed and/or stepped in to defend/protect.

  • Designers wrack their brains over new features and present to UX lead for her expert opinion. Idea gets shut down due to claim by lead over "impossible"[3] claims.

    • I walk by and overhear the designers speaking amongst themselves, bummed about yet another idea that seems feasible but apparently "isn't".
    • I create a branch and implement their idea in ~10 minutes. Designers are happy, UX lead is not.
    • To be clear, this doesn't add extra work for anyone but me.
  • Back-end engineers who want something done on the front-end approach UX lead. "Too much work", "not worth it", "impossible", and so on is claimed.

    • I'm present during this conversation and rattle off similar experiences I've had in my personal projects that relate.
    • Developers are happy, UX lead is not.
    • No extra work for anyone but me and it's not an obscene amount.
  • At an annual all-hands event, CTO speaks about how he learned the importance of listening from a leadership course he's been taking. 10 minutes later, CEO blames entire company (and himself but not really) for our lack of innovation leading to the then-(still?)negative status of the company while the CTO stares at the ground in deep thought.

    • A developer protests accusation and mentions several instances where he tried to provide input, only to be shut down by CEO.
    • Conversation turns into a shouting match.
    • Other developers jump in to co-sign the initial protest.
    • You later learn that some developers at the company ignore the CEO and pursue things they know they need to work on.
  • Marketing team repeatedly express frustration with lack of non-developer-friendly tooling for things like updating the company blog, sending email blasts, and so on. CEO is a technical developer and regularly dismisses them, starting sentences with things like "It's so easy" and "All you have to do is...c'mon, it's not so bad."

    • I don't have much to do so I offer to improve some aspects of their job. After initial pushback I'm begrungingly allowed to do so.
    • Two days later, I'm tasked with going about this process with caveats (and throwing away substantial work in the process).
  • CEO has something negative to say about anyone who quits. "He wasn't that great anyway" and things like that, often on conference calls.

These are all the scenarios I could list off the top of my head. I'm a positive person by nature so this was an uncomfortable walk down Memory Lane.

For people in the web/tech space, the aforementioned scenarios are quite common. Heck, I'm quite sure they echo what happened today somewhere...and you witnessed it. A common thread that links the leadership mentioned (aside from the CTO) is apathy; a complete lack of empathy, social understanding/awareness, or just care. In the comment about my self analysis earlier, I linked a blog post where I realized I put my ego before the team I was hired to work with. I was, quite frankly, a jackass[4] and there's no room for one unless you work at a zoo. Self-reflection is a useful tool you should pull out every now and then and as you can probably tell, most people don't utilize it.

Software is hard, relationships are easy

If you don't build your dream, someone will hire you to help build theirs.
— Tony Gaskin

I reflect upon this quote often as I help people build their dreams (startups) while also building my own. I do believe there's been a sea change in the industry around employee happiness and retention. Have a look at job postings and you will see work satisfaction and happiness as a perk.

No one wants to work in a hostile environment and after a while, people realize they don't have to put up with bullshit and they quit (or are fired before they get the chance, lol). To echo the tone of Gaskin's quote but modified for business leadership:

In order to build your dream, hire the best people and treat them like family.

Assuming you have a great family or a close cadre of friends you regard as family, would you treat them like the aforementioned leaders have? Probably not. It's really not that difficult to be a decent person.

One of my closest friends is in a coding bootcamp and shares his works in progress with me and another close friend on a regular basis. I'm the most technical of us but what sense would it make for me to downplay his efforts? What would I gain from that? It's my responsibility to assist in his professional development because I have the means to and I consider him family.

A decade is a long time and software and startups come and go. Even people do. Memories, do not (I mean, aside from cognitive disorders).

You remember the developer that treated me like shit during my apprenticeship? His name came up in an interview I had two years ago via my interviewer, half a decade later! Therefore, it is imperitive that you treat people how you would like to be treated, your reputation could precede you whether it's positive or not.

No matter what life-changing product you embark on or assist with creating, you will get there a helluva lot faster surrounded by people who respect you and vice-versa. If you've forgotten about the Golden Rule, here's a handy refresher. 🕸


  1. My first domain name was (it now redirects to Back in the early 2010s, I blogged about design and redesigned my site at least three times a year. It was the hottest of messes. Back then I used Google and regularly searched for "PW Software" to check my search ranking. For a while, a company called "P+W Software" was the first result. The constant linking of my website to Facebook and deviantART improved SEO so much that I soon took the number one spot. P+W Software was later acquired by another company. When ICANN released the .page TLD I was absolutely required to obtain what's probably the nicest domain on the planet and make it my new default home on the Internet.

  2. All but two startups I've worked for no longer exist. The first one was acquired but I was seasonal help and thus was too far gone to delight in their success. The second one seems like it's not doing too well behind the scenes.

  3. A word I hate more than almost anything (the taste of asparagus will be difficult to unseat) is "impossible" and to hear professionals in the web/tech space use this word so casually is frustrating. We literally have supercomputers in our pockets to share memes but it's "impossible" to make text with a drop shadow expand across the screen before flipping into an explosion of color with emoji rain. Impossible is not a word, it's an excuse.

  4. I really wanted to underscore how much of a jackass I was prior to that post being published but was advised against it by leadership. This most likely had something to do with editorial voice of the company but few words exist to exemplify negative behavior with such conciseness.