Note: This is part 2 of a 5 part essay series. If you missed part 1 (The Call), you can find it here.
Part 2 - Crossing the Threshold
“Give up all questions except one: ’Who am l?’” - Nisargadatta Maharaj
As we set off from the safe harbor of ideation and entered the open seas of business-building, we honed in on the exact problem we would try to solve: make developing and financing solar projects easier with software. Responsible for raising capital for large portfolios of residential solar projects at our previous company, Graham and I had lived the pain of the duct-taped, manual processes currently in use in the industry, so we had a good sense of what we should build (or so we thought). With our product raison d’etre in place, we began to write code at a furious pace, and given there weren’t really enough “business” activities to fill a day or even an afternoon (you can’t run demos until you have a demo), I pitched in to help.
Thus, I found myself writing code right next to my two extremely gifted, highly technical co-founders, which, for me, kind of felt like showing up to a gunfight with a butterknife each day. 75% Irish and 25% German by heritage, I remember trying to channel the German precision and tamp down on the Irish charm when I sat down each morning, staring at my text editor, before inevitably moving to Google and then Stack Overflow to seek out assistance, aka code that I could copy and paste. Espn.com was often my ultimate destination, when I said fuck it and admitted defeat.
I did experience those magical moments when your code comes to life, when everything just works, seemingly against all odds, and you feel like a sourcerer, albeit a very nerdy one, conjuring form from the void via spells / functions. But those moments were overshadowed by hours, sometimes days, of painstakingly hunting down mysterious and stubborn bugs, literally and figuratively banging my head against our picnic table. I preferred the intellectual side of coding. My favorite activity was doing tutorials of different coding languages or frameworks, which felt like encountering a new philosophy or philosopher in computer-form, a novel way of parsing up the digital world.
But consistently producing clean, production-ready code is less philosophy and more bringing a hard hat and lunchpail to your desk and grinding it out. In that regard, I quickly realized I lacked the attention-to-detail and wherewithal to ever be a good engineer. I also found I missed other beings. I came to eagerly anticipate even the most mundane calls with our lawyers or advisors or really anyone with a pulse, desperate for any human-to-human interaction to break the monotony of machine world. Needless to say, my career as a developer was short-lived, more (dim) shooting star than sun.
But even the faintest of shooting stars have their moments of glory. Graham was always someone who wanted to be as close to the machine as possible; if he could, I think he would write code in ones and zeroes. To this end, he abhorred all things frontend (“can’t people just use the API?”), the “web-appy” part of our web application, which left me, much to the detriment of Sighten enterprise value, nominally in charge of all Javascript, HTML, and CSS code, at least for the six months before Dave joined Sighten full-time (he was initially a consultant).
One glorious day, I found the Twitter Bootstrap CSS library, an incredible open-source codebase of sleek website stylings that could be implemented with just a few lines of code. I did this one day, no doubt aided by Stack Overflow, and voila—the Sighten platform came to life with a vibrancy and sleekness befitting a much more mature application (and a much better frontend engineer). I could barely contain myself as I turned to Graham and, trying to be as low-key as possible, said, “hey, I’ve been working on something, what do you think?”
“Holy shit, dude!” Graham exclaimed. “This looks amazing…you’re a fucking frontend savant!” His unbridled enthusiasm was amplified by his absolute shock; I wore an ear-to-ear grin. The Twitter Bootstrap “implementation” turned out to be my technical apex; a few months later I retired as a full-time engineer, much to the benefit of the Sighten codebase and my co-founders, who were doubtlessly weary of my constant entreaties for assistance. But while I lacked meaningful production code to my name, my engineering side quest paid dividends by making me a CEO who could (somewhat) understand our codebase, which gave me (some) credibility with our technical team. I also did eventually confess the full truth to Graham, and he wore an expression that said one of the most inexplicable riddles of his life had finally been solved. His world made sense again.
We kept pushing, and within our first year we had a software demo that turned heads. Based on this progress, we raised a seed investment round from friends, family, and angel investors, which was surprisingly easy to do. We started hiring, which eventually prompted a move from our shared office space in a very grim part of San Francisco (6th and Mission) to our own converted condo “office” in a slightly less grim (but still pretty grim) part of San Francisco (7th and Natoma). It was a lot of work, but it was exciting, and most importantly, we were having fun. The Sighten ship may have been puny, but it was ours and we were setting the course.
These were heady times in Silicon Valley, as investment dollars flowed like mana from heaven to anyone with a reasonable pitch deck (and to some with unreasonable pitch decks). It was difficult to tell how much of our early momentum we had created ourselves and thus was unique to Sighten, versus how much was just the good fortune of experiencing a rapidly rising tide that lifted even the humblest of boats. Only time would tell, but we continued building, and by 2014, we had our first paying customers—real companies who had decided that our software was worth real money. Not only did Sighten software exist in the world, but it had been determined to have substantial value.
Amidst these calm seas and friendly tailwinds, one rogue wave did appear on the horizon, in the form of a suspiciously heavy, ominous-looking manilla envelope sitting in our mailbox one summer morning. No one sent us mail in those days, almost no one even had our address, so I had the sense that whoever had ensured that this hefty correspondence made its way to our door did not mean us well. When I saw the return address of possibly the most prominent startup law firm in the world, I felt nauseous. After a few deep breaths, I opened the envelope and started reading. Over 15 pages of painful legalise, our former employer was accusing us of “misappropriation of confidential information” in the founding of Sighten, and as is the case in legal letters, politely but really not so politely, telling us to immediately cease what we were doing, aka building Sighten.
The existential implications of this extremely well-written letter were unspooling in my mind, each thread entailing unmitigated catastrophe, when I decided to call our attorney to confirm the details of our demise. After taking in my breathless rant about how the accusations were completely unfounded, insulting, and absurd, he calmly responded: “Look, this is actually a good thing because the length of the letter and the law firm that wrote it means it probably cost around $15,000 to put together. That means that your former employer is scared, which means that Sighten is onto something legit.” The logic made sense to me on a certain level and I appreciated the optimism, but I still wondered what would happen if they actually did decide to sue us?
“Oh, well that wouldn’t be good at all, but I put the chance of that actually happening at 5% or so," he replied. Progress served with a side of existential risk, I would come to learn, was the bedrock of any startup diet. Thankfully, as predicted, the letter was just an intimidation tactic, and we never heard from them again. But my trust in large manilla envelopes, honed during the college admissions process, had been irreparably shattered. I stopped checking the mail.
As Sighten continued its descent from the ethereal to the existent, a funny, appropriate, and/or tragic thing began to happen, depending on your perspective, something I would only fully comprehend years later. I began to focus so intently on being CEO that slowly, imperceptibly, like a frog in warming water, I began to lose sight of Conlan. An obsessive, all-or-nothing commitment seemed to be the rule, really table stakes, if one aspired to be a successful entrepreneur in Silicon Valley, and I desperately wanted to be successful. But like most single-minded pursuits, there were unintended consequences. The spiritual practice I had developed during college began to wane in San Francisco, and it had disappeared almost entirely by the time I became a CEO. A treasure found and then lost. For better or worse, I was going to embody my initials to the exclusion of everything else.
Carl Jung coined the term “persona”—“mask” in Latin—to describe externally-oriented identities—ways of being, sets of behaviors, mini-personalities—that allow us to effectively interact with the world. Personas are the visible tip of the psychic iceberg, a way to map the vast expanse of the psyche onto a specific environment in an intelligible way. Like an actor on stage, these masks simultaneously reveal and obscure, communicating a very particular aspect of ourselves to the world while hiding the rest.
For most of my life, I had been skilled at adopting the right persona, at finding the mask that allowed me to source core psychological needs like approval, control, and security, whatever the context. At my extremely academic high school, I had become a deeply philosophical intellectual; at party-centric Dartmouth, I had become captain of the rugby team and social chair of my fraternity. And now, within a few short years of landing in Silicon Valley, I had become a startup founder and CEO, the ultimate mask on the stage of tech.
In software terms, personas are application programming interfaces (APIs)—standardized, easily understandable snippets of programming that allow for exchange with other computer programs. APIs often come with user interfaces (UIs), which enable users (humans), instead of just other machines, to effectively connect with a program. Without this layer, meaningful interaction becomes almost impossible, akin to asking a user to pour through the source code of a program just to log in.
For a highly social and tribal mammal like homo sapiens, this is a matter of survival, as our ability to modulate ourselves to facilitate effective connection goes a long way in determining whether we prosper and eventually pass on our genes, the only test that evolution cares about. My own shapeshifting / UI creation certainly reflected flexibility and adaptation, and there was no doubt that my masks had made me successful, at least in terms of acquiring influence and power in a variety of environments. I suppose that made successful reproduction more likely, though I was hoping to avoid literally proving that.
While necessary and natural, Jung also cautioned against becoming “identical with [our] personas—the professor with his textbook, the tenor with his voice,” lest we develop a “shallow, brittle, conformist kind of personality…with its excessive concern for 'what people think.'" For me, each mask initially felt invigorating, an expression of some real part of me or at least a chance to learn through a novel way of being in the world. But over time, I couldn’t shake the feeling that I was increasingly reading from a script, an actor lost in an effective yet stale performance, or a chameleon slowly disappearing into the background. The UI may be what the world sees, but the core code of any program always lies deeper.
What’s more, there were periodic psychic revolts, even full-fledged rebellions, against the constrictions of whatever mask I happened to be wearing. Code that couldn’t work within the current API started throwing errors, demanding a new interface with the world, or at least a tearing down of the old one. When high school felt too intellectual, I wallowed in a prolonged emo phase complete with hair that went over my eyes (brutal, I know). When college became too beer-soaked, I moved to a monastery and became an ascetic. After four years of the Ivy League, I set up residence in a tent in Bumblefuck, Alaska. Some of the revolts felt noble, even sacred; others had a different feel. When you find yourself 10 beers deep hacking darts outside of a dilapidated cabin on the Kenai Peninsula, many words come to mind—hedonism, alcoholism, nihilism—but sacred isn’t one of them.
I alternated between thinking there was something wrong with me—a psychic vagrancy bordering on self-destructiveness that made me reject everything I had been building towards in one fell swoop—and believing that these about-face side quests reflected a laudable curiosity, an instinct to expand beyond the known. Or maybe it was just the restlessness of youth, trying on many masks to see which fit. In my more honest moments, I could feel the twin, seemingly opposite compulsions of moving towards something while running away from something else, as if constantly seeking new waves while trying to avoid some aspect of the ocean itself.
Donning the CEO mask felt different from the outset, both because it involved creating something outside of myself and because it seemed like the culmination of a process of maturation, of finally getting real and growing out of the naive and quixotic pursuits that had defined my youth—like finding ultimate truth or experiencing God or seeing how many Keystone Lights one man can consume. I was “adulting,” and CEO seemed like the pinnacle of the adult mountain, at least within my western capitalist milieu.
Other founders told me to “budget a decade for this'' (“this” being the full life cycle of company building), which I initially dismissed with exceptionalism—maybe it was a long, hard road for them, but we have a great idea and a great team, and blah blah blah; it would be different for us. Up and to the right, all the way, no speed bumps—naïveté unbounded. But in some part of my mind, below the surface-level confidence, I could feel a low-grade, barely perceptible anxiety at the commitment I had made when I became CEO. To the itinerant mask-wearer, flitting to and fro like an inebriated butterfly, the CEO mask had a heaviness to it; once on, I had a sense it wouldn’t be so easy to take off.
Sighten continued to make rapid progress, and with each step deeper into the CEO identity I found myself increasingly existing in my mind, turning over all manner of business questions and strategies—thinking, thinking, thinking constantly—building models, writing code, putting together decks. Ones and zeros are the quanta of software, the bricks of any digital edifice, but computation was also slowly colonizing me, becoming my default way of apprehending the world, even re-shaping how I viewed myself. I think, therefore I am. There seemed to be an infinite mountain of things to analyze as we grew, and thinking had been a comfortable and safe place for me since grade school, so it was easy to let Descartes become my patron saint and set things on autopilot.
The reality is we all had SO much to learn, no one more than me. I had a business card that said I was a CEO, but in terms of substantively being a CEO, of having any fucking clue what I was doing, I was still very much in the “fake it ‘til you make it” phase of development. We were all cosplaying to some extent; but when done correctly, eventually LARPing a CEO or a CTO starts to change you, to truly transform you into what you had hitherto only been imitating. Or at least that’s what every wet-behind-the-ears founder tells themselves in Silicon Valley. Ultimately, only time would tell if our faking led to making.
There were certainly feelings of rapidly growing competency, even flow states, like when I would run a super smooth software demo, running the gauntlet from sports small talk to a technical discussion of our API capabilities. After a particularly successful call with a big prospect in western Pennsylvania, Graham turned to me and exclaimed: “how the fuck do you know how the Pittsburgh Penguins are doing this year?” He was a hipster, so my encyclopedic knowledge of sports never failed to amaze him, especially when it turned frosty finance dudes into Sighten proselytizers. His amazement always made me laugh, especially because he had recently built his own computer and seemed truly fluent in the native tongue of machines, which was objectively way more impressive and difficult than mindlessly maintaining a sports addiction. I suppose we all have our skills and what is most foreign to us, including the Pittsburgh Penguins and their up-and-down campaign of 2014-2015, is often indistinguishable from magic.
Taken as a whole, the day-to-day work felt clarifying, focusing, empowering—exactly what was needed if I was serious about building a business and learning the craft of a CEO. But as more of myself existed within the confines of thinking, the parts of me whose primary way of being was feeling began to atrophy. To be fair, this was a process that began long before I was a CEO, whenever I first realized that ideas don’t seem to be bound by mortality, but it was accelerating and reaching its crescendo now. I had no idea when I had last cried—maybe in middle school?
With less space to feel, I was losing connection to the why behind all of the thinking, which for me had always been that connection to the earth, the felt sense of oneness with the universe—the unity. This lighthouse, the reason I had set out on the climate tech path and founded Sighten, was gradually disappearing, slipping deeper under the surface, retreating into the undifferentiated darkness of the unconscious sea. Unaware, I single-mindedly turned my gaze to the instruments on my boat, as they diligently measured the undulations of the waves on the surface.
Had the UI and API gotten out of sync with its core code, an increasingly buggy program careening towards a superficial infinite loop? Was I the actor so committed to his role that he had forgotten he wore a mask? Or, as I wholeheartedly believed at the time, was I simply learning my role so completely that I was in contention for best actor? At the outset, losing yourself in a good way can be almost indistinguishable from getting lost.
The data at the time seemed to indicate an invitation to the Academy Awards was imminent, as my intellectual bro CEO energy, seasoned with a side of hippie environmentalist, found a lot of willing recipients in Silicon Valley. I was good at talking the talk, at recognizing what people needed to hear, at donning just the right mask at just the right moment, which I realized made me good at fundraising, recruiting, selling—basically convincing people to do things. The Irish charm part of my heritage, rather than any ancestral, Germanic proclivity for technical order, was to form the basis of my contribution to Sighten. As I started to have success pitching Sighten’s wares, we desperately needed to grow our team to support our customers and turn these initial sparks into a truly valuable fire. We needed fuel, and in Silicon Valley the most potent fuel is venture capital.
In my experience, great meetings between entrepreneurs and venture investors feel like a meeting of the minds. Theses and beliefs about reality, independently arrived at, converge in an orgy of excitement containing many “TOTALLY!”s and “100%!”s. There can be a bit of “no, you’re so smart!” energy that is not dissimilar to a circle jerk, but when it’s real and authentic, it is the fertile ground upon which capital and idea can birth a valuable business. That’s how it felt the first time I met Andrew at Obvious Ventures, though there was no actual masturbation.
In our meeting that day in the summer of 2015, we violently agreed that the solar market needed industry-specific software to fully realize its potential. We were also in profound further agreement that as you owned more of the market with a technology platform, there would be opportunities to build a software-enabled marketplace for things like financing, which would further increase revenue and create barriers to entry through network effects. Sentences like the preceding one can simultaneously be true, at least theoretically, while also devolving into such farcical startup mad-lib speak that both entrepreneur and investor want to punch themselves in the face.
A week after our first meeting we had a term sheet from Obvious for our series A, and a month after that we closed the round.
I remember walking out of Obvious’ offices that day. The early afternoon sun waded gently through the leafy trees lining the Presidio, the light turning everything it touched into a honey dew gold, one of those Eden-like San Francisco days when the sun has beaten back the fog. I paused and smiled as I waited for my Uber. We had done it. It seemed that Sighten stood on a precipice—from a crazy idea in the minds of the founders to a real company, an IRL thing with investors, employees, millions of dollars. Assets but also obligations. The magma of raw potential was slowly cooling into new earth.
As I sat in the back of a black Prius heading back to our office in the “SOMA-loin,” I could feel a twinge of fear running up my spine, impinging, uninvited, on the pure excitement of the milestone. Would I be a good steward of this money? Was I a capable captain of the Sighten ship? As my co-founders greeted me with wide grins and joyous hugs, I felt a surge of confidence—of course I would be a good CEO; I was already a good CEO. I had just secured a series A from a leading climate tech investor at an eye-popping valuation. Being an entrepreneur just didn’t seem that hard.
The investment was a celebration of Sighten’s potential and initial success at translating that promise into reality, but even as the money made its way into our bank account, cracks were becoming visible in the foundation of the Sighten ship. It was an idyllic late summer day, but the ocean had developed wind chop as far as the eye could see.
Thanks for reading! Continue the story with Part 3 (Dissolution)!
Enjoyable to read and well-written (plus a calculated butter knife reference)