From Pixel Pusher to Product Leader
My unorthodox journey to product management
What do you want to be when you grow up?
When asked the timeless childhood question "What do you want to be when you grow up?" I never once replied "product manager" - shocking, I know. Instead, I declared I'd be an artist, spending countless hours sketching away in that long forgotten era known as "pre-smartphone."
Academics came easily to me as my memory could've put an elephant to shame coupled with an almost supernatural ability to decode teacher expectations. I delivered on time and under budget, they loved me.
High school saw me juggling three full-time jobs: student, aspiring artist, and actual employment (because sleep is overrated, right?). But when graduation loomed, I committed what some considered academic heresy - I looked at my 4.2 GPA, stack of scholarship offers, and said, "Thanks, but no thanks" to the traditional university path.
You'd think I'd announced I was running away to join the circus. The school office practically needed smelling salts. Well-meaning adults warned me about "throwing away my future" - as if knowledge came with an expiration date. But here's the thing: I'd mastered the art of academic performance, turning it into a game where A's were just high scores, not necessarily learning. Besides, university wasn't going anywhere. It would still be there, like an always-open arcade, waiting for me to insert my quarter whenever I felt like playing.
The Road Less Credentialed
With traditional academia off the table, I found myself at The Art Institute of Phoenix - where I thrived within the project-based curriculum. Unfortunately my shoebox of blue ribbons carried the same artistic weight as a macaroni necklace at the Louvre. Turns out being the best artist in your high school is like being the best surfer in Arizona - perspective is everything.
My artistic dreams underwent their first strategic pivot faster than you can say "multimedia" - a term I understood about as well as quantum physics at the time. But hey, it was 1998, right as the world-wide web was entering its consumer infancy. Back then the internet arrived in mailboxes and "You've Got Mail" was both a movie and the highlight of everyone's day.
Armed with nothing but optimism and a questionably financed Compaq Presario (sporting a built-in zip drive - that’s like 100 floppies on one disk 🤯), I embarked on my journey into the digital frontier. And that 21% interest rate? Just consider it an investment in the future, I told myself, while eating yet another pack of ramen noodles.
There I was, happily learning to push pixels, when Macromedia Flash 4.0 sauntered into my life during the final quarter of my program. Oh sweet, innocent me - I had no idea this software would be my gateway drug into the world of interactive animation and web programming. Thanks to some generous early tutorials and a mysteriously long-lasting “trial” version of Flash (ahem), I dove headfirst into this brave new world.
Eleven weeks later, I emerged as a 19-year-old armed with an associate degree in multimedia and just enough knowledge to be dangerous - or employable, depending on who you asked. My understanding of this cutting-edge technology was about as deep as a puddle, but in the wild west of late '90s web development, that practically made me a sheriff.
When Stock Options Became Paper Airplanes
Over the next seven years, I became a professional pivot artist - less ballet, more career acrobatics. My first gig was at an agency creating CD-ROMs and websites so animated they could induce seizures. (For younger readers: a CD-ROM was a rainbow-reflecting frisbee that made your computer do things).
Just as I was growing tired of making browsers sparkle like a disco ball, I leaped to join one of those early-2000s startups where money flowed like water and business plans were optional. There, I expanded my repertoire beyond just making things move to actually making things work. But alas, the dot-com bubble burst with 9/11 delivering the final blow to our digital utopia.
In the aftermath, while full-time jobs became as rare as a bug-free software release, I was thrust into freelancing. That "foolish" decision to skip a four year university had accidentally turned me into an experienced professional while my BS-toting peers were just entering the workforce. (Somewhere, a guidance counselor was choking on their coffee.) I was a twenty-something kid explaining technical concepts to seasoned executives. It was like teaching your grandparents how to program a VCR, except with higher stakes and better pay. Terrifying? Yes. Character-building? Absolutely.
When the market finally sobered up from its dot-com hangover, I landed at an e-learning company, bringing technical certification training to life. For a time, it was engaging enough. But try as you might, there are only so many ways to jazz up the thrilling adventure of data packets playing digital hopscotch through router networks. It turns out that even the most creative mind can only generate so many ways to make students excited about subnet masks and network topology before questioning their life choices.
The next stop on my career carnival ride was as creative director at a computer service franchise. Working with three co-founders, who aligned like mismatched socks in a laundry basket, taught me the fine art of stakeholder management. I climbed the ladder to Director of Marketing, helping the company expand from 10 local stores to over 100 sold nationally. Then, in a plot twist worthy of a corporate drama, my ego began writing checks my position couldn't cash, and I got fired. Deservedly so - turns out being good at your job doesn't make you immune to getting a little too big for your britches.
Getting fired was like a cold shower for my ego - uncomfortable, but surprisingly clarifying. It provided some much-needed time to reflect, sort of like a corporate timeout, but with more late night infomercials and existential questioning.
YOLO
Standing at life's crossroads, I did what any reasonable person would do: completely switched careers. Because when your artist's soul is calling, the only logical response is to leave what you know best and become a professional photographer.
This was the mid-2000s, that magical era when owning a decent camera still made you special, before everyone became Annie Leibovitz with an iPhone. I shot everything - weddings (where family drama comes free with every booking), fashion (turns out models don't actually survive on air), and product photography (making inanimate objects look sexy is a peculiar talent).
But as it turns out, turning your passion into a profession is like eating ice cream for breakfast. It can be tasty, but will likely lead to an upset stomach. The glamour of professional photography eventually faded like an overexposed Polaroid and no amount of shaking would help.
So naturally, in a moment of what I can only describe as inspired madness, a friend and I decided to become magazine publishers. Because clearly, what the world needed in the midst of a digital revolution was another print publication. We called it Provoke Magazine - catering to the creative community.
The first issue was a hit, distributed by hand like a couple modern-day newsies. Just as we were about to send our second issue to print, the economy decided to take a knee. The real estate market collapsed faster than a house of cards in a tornado, taking our publishing dreams with it. Turns out "print is dead" wasn't just a catchy phrase - it was our new reality.
But hey, at least I still had my trusty Flash skills to fall back on! Until Steve Jobs, in what I can only assume was a personal vendetta against my career choices, declared Flash persona non grata on Apple devices. It was like watching your favorite childhood toy get recalled for lead paint.
So there I was, buried under a mountain of debt, armed with two recently obsolete skill sets. If pivoting were an Olympic sport, I'd have been going for gold.
Rebooting Career.exe
In a moment of what some might call career humility (and others might call desperate pragmatism), I applied for a lower-level web design position at GoDaddy. The product was called Website Tonight - a name that suggested speedy but delivered something more akin to "Website Eventually, Maybe."
I became a master of digital duct tape, finding creative ways to make the platform's output look less like it was designed by a caffeinated toddler. But there's only so long you can polish a digital turd before you feel compelled to suggest improvements. My initial feedback was met with all the enthusiasm of a mandatory password change policy. But all was not lost as it was suggested that I meet with Barb, a c-level executive whose reputation preceded her like thunder before a storm. Everyone I worked with feared her and each practically began writing my professional obituary. But there I went, armed with a bold vision and the kind of courage that comes from having nothing left to lose.
After twenty minutes of presenting to someone with the facial expression of Mount Rushmore, she finally spoke. It was like hearing a sphinx deliver a prophecy: "I like it, but you'll never get it done on that team. Let me get you in touch with UX." Just like that, I impressed the unimpressable and was granted a shot at the big time.
Soon I was paired with a UX architect, meticulously crafting user experiences like a digital watchmaker. We hit it off immediately. When a UX Architect position opened up, I was encouraged to apply. I scrambled to repackage my past work and throw my hat in the ring. Despite my lack of formal credentials (HCI degree? More like HCI degree-adjacent), my internal networking, charm offensive, and demonstrated ability to get things done won them over.
Though I'd made it to the UX big leagues, I was still viewed as the team's exotic pet - fascinating but potentially dangerous. They kept me safely contained to internal projects, working with young Product Managers who were probably wondering why they got stuck with the new guy.
But here's where it gets interesting: being the "risky hire" turned out to be my golden ticket. As these internal projects started succeeding, word spread faster than office gossip about free donuts in the break room. Suddenly, there was a place for the unconventional UX architect.
So I Guess I Do This Now
GoDaddy's organizational structure had the consistency of a mood ring, constantly shifting between siloed teams and flat hierarchies. During one of these corporate reshuffles, I somehow ended up as the product manager of the marketing suite - because apparently, that's what happens when you're good at your job and standing in the wrong place at the right time.
Suddenly, I found myself traversing executive expectations, interacting with various product teams, and conducting performance reviews for former peers (Special shoutout to Brian Dunn, who I know is still processing that feedback session.)
My products performed well enough to catch Barb's eye again - though this time, instead of being sent to the principal's office, I was being moved to GoDaddy’s website marketing team otherwise known as Front of Site. The FOS team treated conversion rates with the precision of brain surgery, only with more ad hoc experiments and fewer medical degrees.
Initially welcomed with all the warmth of a vegetarian at a barbecue competition, I managed to prove my worth by delivering improvements to the purchase pathway that generated an extra million dollars monthly. Suddenly, I went from interloper to golden child faster than you can say "increased cart size."
After three years of the GoDaddy grind (which I'd initially accessed through what was essentially the corporate equivalent of sneaking in through the loading dock), I did what any reasonable person would do at the peak of their success: I resigned. Turning in my security badge was like trying to close a Microsoft program that's 'not responding' - it required multiple levels of force quit.
The aftermath included multiple calls from executives trying to lure me back, but I'd already committed to my next adventure. Sometimes you have to know when to fold 'em, even when the house is begging you to stay at the table.
Product Management Bootcamp
The next six years were like a product development fever dream - the kind that deserves its own Netflix series, or at least a documentary subtitled "What Were We Thinking?" Working alongside a collection of brilliant minds (whose sanity was optional but appreciated), I embarked on the journey of startup entrepreneur.
Backed with a little seed funding, we set out to create the ultimate digital potluck of church communication tools, where every social media API brought a dish to the table. Think Facebook meets Twitter meets Sunday sermon, but with more divine intervention. We started strong, convinced we'd revolutionize how congregations connected. Turns out, we slightly underestimated the fact that APIs can be as temperamental as a choir director during Christmas season, and customer support needs might exceed our "have you tried turning it off and on again?" approach. It's amazing how quickly startup dreams can turn into painful life lessons when you're watching other people's money evaporate.
After gracefully accepting our first venture's swan dive into startup oblivion, we pivoted to plan B: building a product agency where we could transform our spectacular collection of successes and face-plants into wisdom for other digital dreamers. Because nothing says "trust us with your product" quite like a fresh failure under your belt.
Turns out, our hard-earned scars made for excellent consulting credentials. We found ourselves playing digital sherpa to everyone from wide-eyed startup founders to corporate behemoths like Panasonic and Dell - guiding them safely through the treacherous valleys of product development. Between consulting gigs, we couldn't quite shake our entrepreneurial addiction and launched a couple mobile apps into the great app store abyss. They enjoyed their 15 minutes of fame before joining the vast graveyard of "almost made it" apps from the mobile gold rush.
The karmic punchline wasn't lost on us that we finally found success by helping others avoid the very pitfalls we'd so enthusiastically discovered ourselves. Sometimes the best way to succeed is to fail upward with style.
Now I may be allergic to moments of success or just thrive on uncertainty, but a new disruptive technology beckoned like a siren song. It was time for me to say bon voyage to my agency days, set sail, and chase the next big wave - artificial intelligence (AI).
Hello A.I. Please Don’t Destroy Me
In 2016, I jumped on the AI Oregon Trail just as it was upgrading from covered wagon to rocket ship. My first product? Creating a perfectly legal digital stalker that analyzed social media posts at major live events - think of it as paparazzi, but with algorithms instead of cameras. The crowd tracking business was booming until Cambridge Analytica decided to remind everyone why privacy matters, causing social media platforms to slam their API doors shut faster than a teenager hiding their browser history.
But like any good tech way finder, keep moving forward and the path will reveal itself. Enter predictive AI, I connected with a new team attempting to build a digital crystal ball that could predict donor behavior. We created models that could tell you if someone would support a cause before they knew they wanted to - a power that proved both impressive and mildly questionable.
Despite our best efforts to convince the world that our AI fortune-telling machine was a necessary companion and not a creepy mind reader, it turned out that having an algorithm making AI guesses was a bridge too far for most folks.
On the verge of packing it in, ChatGPT burst onto the scene in late 2022 like a digital rock star, making AI suddenly seem less "Terminator" and more "texting with a friend." The AI gold rush that has followed is making the California Gold Rush look like a casual treasure hunt. Re-energized, a move from predictive AI to generative AI was inevitable.
So here I am in late 2024, wearing the Chief Product Officer hat at BoodleBox, where we're essentially running a matchmaking service for top AIs, humans, and custom knowledge. Think of it as a digital dinner party where ChatGPT, Claude, and their AI cousins mingle with humans over a shared feast of information.
And in what can only be described as the universe's idea of a practical joke, BoodleBox has found a sweet spot in higher education - an irony not lost on someone who once fled academia faster than a freshman avoiding 8 AM classes.
For the first time in my professional odyssey, I'm building something I'd actually open my wallet for - without the usual product manager's Stockholm syndrome. If that's not real career progress, I don't know what is.
The parallel between my introduction to Flash and AI in EDU is almost poetic - once again, we've got educators scrambling to teach something they're still learning themselves, students chomping at the bit to use it, and industry desperate for skilled practitioners. It's like watching history repeat itself, just with better processors and fewer animated loading screens.
This month marks the 25th anniversary of becoming a professional adult and regardless of title, I introduce myself as a Product Manager - though that's like calling a Swiss Army knife just a knife. Product management is really more of a mindset that's been marinating in decades of experience, failures, and occasional strokes of genius (or luck - I'm still not sure which).
Turns out that managing products isn't so different from being an artist after all - you're still creating something from nothing, just with more opinions and fewer paint stains. Full circle? Maybe. Or maybe just another pivot in a career that's had more turns than a mountain road.