Started from the bottom now we're here

On surprisingly linear career trajectories, and lifelong logarithmic learnings

There’s this 30 Rock episode (which, not to have an aside so early on here but, is one of the greatest television shows ever) where Alec Baldwin’s character, Jack Donaghy (Vice President of East Coast Television and Microwave Oven Programming for General Electric) has to get his old job back by working his way up through the ranks of NBC employment. He starts in the mailroom and throughout the episode, is seen rapidly being promoted throughout the organization in his quest to make it back to the top (I’d post a clip but NBC has decided to either take down everything online or paywall it behind their “Peacock” offering, which I’m never paying for, NBC - sorry).

And I’ve always loved the ethos behind this idea that one can start in the mailroom and work their way up to running the company. There is something very “American Dream-y” about this potential, and I think in prior generations - where you’d walk into random light bulb factories or tire warehouses fresh faced from graduation with a paper resume, wearing your dad’s suit after seeing a “help wanted” sign on the window and get hired on the spot - that this dream was rooted in some shred of reality. 

Today? 

Well those dreams are few and far between.

In fact many find themselves in the unfortunate position where the only way UP is OUT. 

There is a known path out here in the valley, where engineers will cycle between the FAANG companies, upleveling as they go, only to arrive back to their original company at a higher level and better compensated than their more loyal colleagues that stayed behind. 

The “climbing by leaving” mentality (where the only way to get people to recognize your worth is to take it away from them) is a seemingly newer phenomenon, and one that more and more workers are finding themselves subscribed to (usually, out of necessity).

My grandfather spent his entire life working the railroad, my father, his entire career in academics at the same institution. Me? Three jobs in the last ten years. But you know what? Upleveled dramatically each time I moved. 

Despite wanting each “current job” to be my last (with a view to running the place one day, regardless of where I’m at, candidly) it never seems to be. And like many of my peers, find exits to be my greatest career accelerator - despite wishing they weren’t. 

Although I’d love to say there are opportunities for us to still be both loyal AND successful, externalities make these opportunities few and very far between - and even when presented with these opportunities, seem even less likely to pan out in the long run - which is why when it ACTUALLY HAPPENS to someone, its worth taking note. 

Enter the rare, and Jack Donaghy-esque Neatworking’s connection for this week: Andy Stark (Chief Technology Officer, EasyRx).

Andy and I knew each other from the Florida tech and startup scene (hey don’t laugh - there IS a Florida tech scene outside of uncomfortably vacant NFT conferences of South Beach) - more specifically the NORTH Florida tech and startup scene (seriously, stop laughing, there IS even a North Florida tech scene, believe it or not West Coasters) - but I had never fully appreciated his journey, how much it paralleled this idealized version of career growth, and how exceedingly rare it is to find someone these days who started from the bottom, and now they’re here. (hey, that’s the title of this article! no way!) 

I loved talking to Andy, not just because of this beautifully linear path he’s enjoyed in his career, but because despite the linear nature of his career growth, his personal growth has been not only non-linear, its been downright logarithmic - at least it has recently - and I deeply align with this idea of continuing to push yourself, continuing to grow, and continuing to learn - absent (1) all other success and frankly, (2) the lack of need for it.

My Mom has always told me education, even for its own sake, is never a waste (she phrased it much more eloquently than I), but effectively that it doesn’t matter what or why you’re learning, what matters is that you (are always) learn(ing).

Well, Andy’s learning. And he’s achieving. And whether its linear, logarithmic, (or some other scale that my high school calculus math knowledge has long since forgotten), its worth our attention…so, lets dive in and do a bit of learning ourselves!

Andy Stark, Chief Technology Officer, EasyRx

Well, the protracted preamble to this Neatworking article likely gave it away, but here’s the punchline:

Andy has effectively spent his entire working career at one company.

Yea. ONE.

Having recently gotten out of the Navy and while studying at the University of Florida, he answered an ad in the newspaper (for those of us that have never seen a newspaper, imagine if CNN, craigslist, and linkedin all got together and printed their content on really terrible grey paper and it got delivered to you everyday on a truck or some kid on a bicycle. Yep. That’s a newspaper) looking for a customer service rep at a small dental software company (yes, there’s an app for everything) in the bustling tech hub of Gainesville Florida (okay okay you can laugh at that one - especially since this was a few decades ago - when Gainesville was barely a bustling hub of ANYTHING let alone tech) and despite an outfit mismatch he should have expected (he arrived in a classic interview suit, and the owner, in classic florida formal wear: shorts and flip flops) - he was hired on the spot.

Already - lots of cool things about this story (outside of me picturing this business owner in a tommy bahama style jimmy buffet shirt and for some reason likely sporting a wilford brimley-looking mustache) but what I really like about it is Andy took a customer service job as his entry point into this company.

So many of my friends and peers I graduated with were so over-rotated on what their job title would be.

Had to be a director level role.

Had to have SENIOR in the title. Etc.

(Uhhh ya’ll know you dont have any years of experience right?)

But sometimes (most of the time) its just about getting your foot in the door, regardless of the title, regardless of the comp. Taking a job that’s going to move you closer to your goal, or heck - even one that’s just going to pay the bills next month. Progress is progress - it doesn’t need a “senior” title in front of it.

(note: I took a VERY non-sexy title after law school graduation, despite some mocking by my peers. And it turned out to be one of the best decisions I’ve ever made)

The other thing I really like about it? Andy remembers truly CARING about his job, the customers he spoke with. That he would stay up at night thinking about how he handled certain calls, what kind of service he provided, and if he could have done anything to make their day better. How cool is that? Imagine if we all put that kind of care into our jobs, regardless of our title, or level.

(note to self: always care, then care MORE.)

And, other than a quick stint outside of the company, Andy stuck around. Months turned into years. Years turned into…a decade (or so)? And before he knew it (I’m sure time didn’t move as quickly as I’m making it out to be, but sounds cooler that way), he was no longer a customer service rep. He was the President of the entire company (hopefully wearing his own pair of flip flops and tommy bahama shirt at this point).

And as all good stories need good conclusions - finally sold that company, and is now the Chief Technology Officer at EasyRx (the acquiring company).

Yep, that same customer service rep from years and years ago who answered a random newspaper ad - was part of a successful exit of the company he now ran.

What a story.

Now - one may expect this to be the end of the story. And it’d be a great one.

Customer service rep ends up leading company to exit as president? That’s a good enough tagline for any feel good Hallmark movie (needs to be set in small mountain town, and instead of a software company its some kind of boutique jam canning company that has to fight against the distribution of BIG JELLY into their local grocers or something) but Andy’s story doesn’t stop there.

Despite being a corp dev-legal-M&A-whatever focused guy that I am - Andy and I actually spent a surprisingly little amount of time talking about his journey in growing and selling his company, and instead - we spoke of our own personal growth. What we were doing to keep ourselves learning, to push ourselves, to get out of our own comfort zones.

A practice we both agreed is universally scary, yet universally necessary - especially as we advance in our careers (and our years).

It can be incredibly easy for us to hit a moment in our professional and personal lives where we could say “yep, this is fine.” and we continue on the path of our own mortality never to venture out of the lanes we (either explicitly or implicitly) set for ourselves. And perhaps there is some comfort in that.

But is that really what we’re here to do? Be comfortable?

Not according to Andy. Not according to me.

And so Andy continues to write his story.

Recently venturing out into his own uncomfortable pursuits - including taking up playing music - a hobby he notes has been universally hated by his dog, as well as any of his house guests that happen to be crashing during a practice session - but one you can tell he truly loves.

He laughs, noting that people have told him plenty of times “would you just stop playing this thing and go do something else?” - but where’s the fun in that?

Andy is now in Austin - playing the banjo, the fiddle - and with any jam band that will have him as a (sometimes temporary) member.

Separating what could be a really interesting discussion into the benefits of working both your right and left brain out at the same time via music AND software/business pursuits - which I’ll leave to people that actually understand the brain (I barely understand mine, let alone anyone else’s) - what is important here is that he’s out doing it. He’s learning. He’s uncomfortable. And in that continuous learning is an immense amount of joy.

And when I step back and think about it - his journeys as a customer service rep and a musician have one striking similarity - he started both from the bottom.

Welp, now he’s here.

And without layering my admiration of his journey on too thick, he’s also taking time to learn how to sail, with an eye to sail around Cape Horn in the future (this guy is basically living my dream - he’s selling software companies, playing music, and sailing around the world - if I were to draw a blueprint for my future it would just be a picture of him).

Andy notes, of his enjoyment of sailing:

“I want to point my bow in a direction and have the confidence to get there”

And he certainly does. And he certainly will.

Such is the journey of the life long learner.

You can start any journey from nowhere. Without land in sight. Without the ability to play music. Without the ability to reef a sail. Without any knowledge of what you’re doing other than the newspaper ad in your hand and the ill-fitting suit you wore to the interview - and you can still achieve greatness.

You can continue to learn, you can continue to grow, you can continue to succeed.

Whether you’re Jack Donaghy, Andy Stark, heck hopefully even if you’re Evan Ferl (that’s me, btw).

As Andy and I wrapped our conversation, we waxed philosophic on the beauty of sailing, how freeing it is once the wind fills your sails and you’re no longer dependent on anything but yourself. And with the right amount of work, right amount of learning, and right amount of belief - you can head in whatever direction you want - reach whatever point you hope to reach.

And our lives are a lot like that.

We are our own boats.

Plot your course.

Point your bow.

And as long as you learn on the journey, there’s smooth water ahead for us all.