A Requiem for Forty Years in Tech

I have spent the past year gradually transitioning from my long tech career to one in coaching, which I intend to continue? into retirement. In this blog post, I look back at some of my career highlights and how it shaped some of my philosophy and led to coaching.?

As I went through my career, I didn’t always appreciate the grand historical sweep of the times: web 1, 2, and 3, open source, cloud, AI, but looking back on the timing of when I started, the big picture is hard to ignore. I’ll save personal anecdotes for another time in favor of this grander arc and my own personal development.

Hallucinogens and Forty Years

In the late seventies, when I was in my teens, I was fascinated with a blend of math, physics, and philosophy that, when combined with my immaturity, led me to the notion that there was one underlying true reality. I believed an altered state of consciousness could lead me to discover this underlying truth: Aldous Huxley’s Doors of Perception. I began a Quixotic quest to reach these doors. This seeking was quite cold - I was not inspired by any notion of a shared consciousness or idea that would tie me to other people. I lived in my head.

In early 1983, I was a second year student at Antioch College in Yellow Springs, Ohio, with an unidentified major - I bounced from philosophy to math to physics - and access to good drugs. As was more generally true back then, I didn’t worry too much about my future career.. That is, until on one LSD trip, I stumbled into the computer lab, and saw my friend Dan plotting some curves on an Apple II. At that moment, I understood what I wanted to study and practice.? I packed my bags and headed back home to NYU, where they had a full-fledged computer science department that had recently sprouted from the math department - unlike the many programs that spun off from electrical engineering. I was enthralled by complexity theory, algorithms (which meant something different then), and the simple properties of numbers when looked at in different bases. I was a typical geek, and not too good with people, which makes my journey all the more surprising.

Bell Labs, AI, and Unix, and a Lesson in Stress Management

My search for an underlying order to the universe morphed from a focus on altered states of consciousness - my LSD trips were anxiety-ridden at best, horrifying at worst, and my days of serious drug taking ended in my early twenties - to a dream of artificial intelligence. I studied languages like Prolog, which promised to build expert systems out of rules and inference engines. But my true foundational belief about AI was that it would emerge from stacking lots of small computer programs that linked up in unexpected ways. This led me to the fundamental beauty of the Unix Operating System, who’s elegant design was predicated on the notion that every piece of code should do one thing well, and have a “contract” that defined the input and output of that piece of code. This made it easy to connect different pieces of code, and is a paradigm that has survived the test of time. (That things evolved in this manner should not be taken for granted: systems prior to Unix were not built this way.)??

Some aspects of that dream proved prescient, and the ways in which layers of simple code transformed the world went well beyond what I could have imagined. (Even cloud services are built on this principle, and without the cloud and its highly scalable compute resources, the growth of AI would have been greatly retarded. However, I’m more inclined to think the pure stacking model helped us get to web 2, but not directly to AI, though it's a fine line.)

Bell Labs, the birthplace of Unix, was the only place I wanted to be. It had a purer reputation - I wanted to wear jeans and focus on programming and creating something new, and not on wearing a suit at IBM and making some corporation lots of money. I accepted interviews nowhere else, and on the second attempt, in 1987, I landed a position as a software developer at the site where Unix was being commercialized.

I loved being a developer, and had little sense of the business around it. I had no dreams other than to keep on developing excellent software, treating my code as an architect treats the balance of form and function. I spent hours whittling down solutions to their most elegant form, and, although I can’t prove it, I believe that both the process itself, which required an immaculate understanding of the core of the problem, and the elegance resulted in much higher quality solutions.

In 1995, I was given my first real leadership role, leading a cross-department SWAT team of twenty people to deliver a key feature, a new device driver interface for Unix. Although I still had no sense of why this delivery was important from a business perspective, I felt the pressure to deliver. The project was already six months late and wildly more expensive than we had budgeted. And one day, with a young daughter at home, and the stress building, I landed in a hospital with stroke-level blood pressure. I was back at work in no time, but I learned a valuable lesson in self-care that day. Over the ensuing thirty years, I have been a staunch advocate of work-life balance and stress management. I must have looked weird when I started removing my shoes in the office as a reminder to myself to stay grounded.?

By this point, though, Bell Labs was in its last true days, and my organization was spun out (Unix System Labs), bought (Novell), and chopped up (HP and Santa Cruz Operations, or SCO).

Irreverence, SCO, and the False Award

In the days leading up to our merger into SCO, my group needed a new manager. My manager, the venerable Ed Whelan, went to HP, leaving my team rudderless. My director, Lisa Ozimek, offered the position to me. My first reaction was utter shock. I had expected to be a programmer forever, and, in those days, managers were not hands-on - they were first and foremost people managers. But I accepted the challenge after a good night’s sleep.

My first day as manager was February 1, 1996. On that day, I was in Santa Cruz meeting my new peers for the first time. We all had to introduce ourselves, and walked into the meeting with vugraphs. All my peers introduced themselves cautiously, in a way that didn’t seem to reveal too much about? themselves: a little choir practice here, some little league or boy scout management there. Not the loose Santa Cruz spirit I would come to love.? It didn’t strike true to me, and I decided to rip up the script. I let my humanity show through. And afterward, my peers took me out to show me their real side. I’ve never stopped believing in being real at work, and always bring my whole self to the workplace. This does not mean being unfiltered! It means being authentic: speaking your mind respectfully, showing up as you are, and bringing your full self to bear on problems in the workplace, be they technical or people oriented.

That first year of management, I took my responsibilities quite seriously, but was still very close to the technology, which was a double-edged sword. By the end of the year, I had received an Employee of the Year Award, presented to me at the amphitheater at the University of Santa Cruz.?

What is a Manager Good For, Anyway?

I don’t remember what I had done to merit that award, but I know that I right away realized the award told me I had not yet succeeded in my biggest role as a manager.

What is a manager anyway? Many people don’t want to be managers - especially middle management - but these positions are the key to any growing business. If you’re starting a company, maybe you have too much work to do, so you hire some help. Or you hire an expert for an area I know little about - a lawyer, a programmer. But when do you hire a manager? I can only think of one reason to hire a manager: you’re too busy to manage people directly. Middle managers are the people that scale your capabilities.?

To be successful as a manager, you need to help your employees be as productive as possible. (Not that companies always believe this: companies will often reward managers who look more like individual contributors, but I believe this practice harms growth). They must become the leaders who will drive your team towards its goals, and develop future leaders themselves. This becomes more and more true as you climb the ladder: the more effective you make your people, the more your organization scales. I am never more proud of myself than when I see someone in my organization successfully lead a mission critical project. Delegating, empowering, communicating, and coaching are the key management pillars of scaling. If you are not effective at these skills, you will fail in your role as manager.?

Thus, I regarded my Employee of the Award as a challenge: next time, I wanted someone in my organization to win it, not for me to win it myself.?

The Internet parts 1 and 2, Open Source, and Product Management

Some time in the early nineties, I remember a conversation with my good friend Larry Feigen (who remembers everything and doesn’t remember this conversation) and his officemate Steven Pendergrast. We were debating whether Unix needed a network subsystem in its default configuration. That is, we were debating whether most people installing Unix would want to connect their computer to other computers to allow them to do things like email, or to move files by something other than a floppy disk. There was no “internet provider” at the time in the way we think of them today. Though the internet did in fact exist, it was in its pre-world wide web days, and accessible by only a minority of computers. Most people who needed “remote access” to a computer did so via very slow modems. In those days, it could take a minute or more to just download a simple file like a thumbnail picture.?

Things were about to change.

In late 2000, SCO announced it was being acquired by open source linux distributor Caldera. It was a death-knell of Unix, and a harbinger of how open source would kill traditional software business models. I was not a fan of the acquisition and the new company’s strategies. At a meeting with executives, I was invited to leave if I was unhappy. No more than two hours later, I had accepted an offer to join a spin-off of Novell, Volera.

At Volera, I was on the bleeding edge of the internet, first building proxy servers and helping to lead our involvement with the internet’s standards body, IETF. I worked on the ICAP standard (Internet Content Adaptation Protocol), a precursor to allowing websites to personalize content and ads. When that ended after 9/11, I moved to building application servers at BEA Systems. It was at this point that I realized I was ready to move away from engineering, and went back to school for an MBA. As one of my engineers had commented to me, “the internet was just moving different bits around”. I.e. It's still just engineering. I wanted to see the industry from a broader perspective, and I became a Product Manager.?

As product manager, first at BEA, then at Oracle, I learned so much about the software business, about managing people, and about what I really wanted from life. At Oracle I led a product team that was the most fun of my career, until it wasn’t. Working under my friends Cameron Purdy and Mike Lehmann, I embraced the cycle of build great product, make your customer successful, and tell the world about it. I ran a $200mm business, but that barely turned Oracle management heads, and as cloud computing got bigger, the independent software product market got less fun. I left for the startup world, and Lightbend.

Web 3 and The Real Reward, As Painful as it Was

Spring of 2020 was calamitous in New York, and for me. I returned from vacation two days before lockdown, and promptly came down with Covid symptoms. Three weeks later, Lightbend, with two of its largest customers being large cruise line operators facing a major financial crisis, killed my product and did a mass layoff. Three weeks after that, my father, in a nursing home, contracted Covid; he passed away two days later.

All this had a bracing effect on me. I shaved my head in some monkish ascetic rebellion. It was as if I had been set free from expectations and confines of my own self-imposed rules. I owned my own destiny, with no one left to blame. And when the blockchain/web3 world came knocking looking for an executive with enterprise software experience, I was ready to take my chance.?

The web 3 world is an interesting world that I’ve written about elsewhere. It is filled with charlatans - both in the more familiar realm of crypto, but also in a technical sense. I was lucky to land in a company, Digital Asset, that does not fit in that category.?

In those three years as Chief Product Officer, I got to work with an untold number of extremely talented? people, but to bring my story full circle, I got to work with my brilliant successor. Bernhard Elsner was a diamond-in-the-rough product manager when I met him, pushed and pulled with differing company visions and no real seasoned enterprise software mentor. If my earlier award at SCO was for individual contributions, my best work at Digital Asset was in coaching my eventual replacement. Bernhard was never “employee of the year,” but the irony is not lost on me: In my last full-time position in tech, after forty years, I had finally achieved my goal.

Since leaving Digital Asset, I served as Fractional Chief Product Officer at another fintech, but the days are clearly near where I am a full-time coach. I have been involved in so many important technical revolutions, from Web 1, 2 and 3, to the open source movement (mostly fighting it until the last few years!), but I have drifted quite far from the hallucinogenic dreams of my youth. I no longer consider myself a techno-optimist searching for “truth” through science (pharmaceutical or otherwise). Instead, I am a humanist, determined to raise a generation of more conscientious leaders, to improve the world and workplace for everyone, and to help people pursue dreams that align with their values. I am creating a better world one person at a time.

Author's Note: In finally deciding to post the above, I am reminded of a quote I had taped to my terminal back in the day: A work of art is never finished, only abandoned. This applies to both my tech career and the above article. I wish I had a neat bow for both, but such is life. If you want to find out more about what I do today, visit my website at craigblitzcoaching.com.