Note: This is part 3 of a 5 part essay series.
If you missed part 1 (The Call), you can find it here.
If you missed part 2 (Crossing the Threshold), you can find it here.
Part 3 - Dissolution
“Until you make the unconscious conscious, it will direct your life and you will call it fate.” - Carl Jung
Shortly after we closed our series A in September 2015, I stood in front of grinning Sighten employees as I breathlessly delivered a sermon on all the things Sighten would accomplish with our newly found fuel. Not only would we become the go-to software platform and marketplace for residential solar in the United States, but we would also expand into commercial & industrial solar, energy efficiency, battery storage, and of course, spread our wings and go international. It was all possible, we just had to be all in. As I spoke I could sense a palpable energy rising in the room, excitement that presented as ambient static electricity, and it felt amazing. Afterward, our recently hired Chief Operating Officer (COO), Mariya, pulled me aside to talk.
“All that was awesome and everyone is super excited, but right now we can only focus on one market, maybe two if we’re lucky. That is just the reality given the size of our team and the early stage of our product, so what I want you to do is force rank the items in this spreadsheet, and then I will have what I need to put together our product roadmap,” she said matter-of-factly.
All startups die the same way: starvation, also known as running out of money. But it is said that the proximate cause of this starvation is often actually indigestion—taking on more than a young company can handle and losing sight of its raison d'etre, in the process becoming mediocre at many things instead of indispensable at a core competency. Beware of shiny objects, the oft-repeated advice goes. I had most definitely internalized this wisdom—it was impossible to avoid in Silicon Valley—but like budgeting a decade for building a startup, it seemed like something that applied to other entrepreneurs but not me. CEO exceptionalism ran deep.
Heavily over indexed on the “visionary” aspect of the CEO identity (as opposed to “competent executer”), which seemed prominent in public portrayals of startup CEOs, my imagination would run wild with possibility whenever someone expressed even tepid interest in Sighten. In a vacuum, this wasn’t a bad thing; in fact, seeking out potential under every rock is a very necessary part of running a startup, especially in the early days when you are still looking for product-market fit, that mystical state of union between product, problem, and customer that unlocks everything for a company. The experiments and pivots and discarded minimum viable products that litter the early stage startup path all have this same target: a product that customers are willing to pay for because it solves a real problem.
But when vision and creativity aren’t grounded in reality and focus, it can result in a frenetic type of energy and leadership, like a flag trying to blow in multiple directions at the same time or digging 100 shallow wells instead of a few deep ones. Dying of thirst is even easier than dying of hunger, whether shipwrecked or in the rough and tumble world of Silicon Valley, so Robinson Crusoe and startup CEOs turn out to have the same marching orders: find water fast. Until the product-market fit well is flowing, everything else is a distraction.
In response to Mariya’s simple request for product and market clarity, for direction on which exploratory pits we should try to turn into wells, I threw a tantrum, as reality-denying CEOs and children tend to do. It all felt so constraining, this process of actually building something beyond the pure vision, the Platonic form of Sighten, which could simultaneously exist in all forms by virtue of its non-existence in the world of form. I had a visceral resistance to recognizing almost any constraint on our business, thinking this somehow represented a capitulation to a lesser version of ourselves. If we just believed it was all possible, it would be.
Fortunately for Sighten, Mariya was a force of nature and I respected her immensely, so I eventually did the force rank exercise, more out of deference to her than any real belief in its validity or necessity, and we moved forward with at least some focus. Sighten would continue building software for the residential solar market in the US, with an emphasis on tools for sales and financing. Several legit companies had already signed long-term licensing agreements for the first version of this toolset, so it seemed like we had hit water on our first try. Once again, entrepreneurship seemed easier than everyone said.
In certain quiet moments, walking to work or letting my mind wander before falling asleep, I could feel something bigger than just a refusal to recognize the tradeoffs inherent in running a business where time, personnel, and capital are not infinite. That felt like just the outward manifestation of a non-acceptance that ran deep within my psyche, an active confrontation with the most basic aspects of our universe. I was avoiding, fighting something fundamental, though at the time I couldn’t have told anyone, myself included, exactly what it was. Unbeknownst to me, the universe was preparing to reveal the truth in no uncertain terms, and the intensifying waves of startup life would be her teaching materials.
Around this time, a mystery arrived at Sighten’s door, literally and figuratively, in the form of abandoned athletic shorts containing more human poop than any of us had ever seen. Living in San Francisco, one becomes somewhat accustomed to human feces. I also had firsthand experience of underwear very suddenly becoming disposable, usually in the second it takes for a fart to overachieve. But this was different than all that, a veritable meditation cushion of shit that almost seemed sentient. We all had our theories, ranging from the absurd (one of our competitors was sending us a message) to the more prosaic (there was a hole in a since removed porta potty), but like an elusive software bug, we couldn’t put our finger on what exactly had happened.
The following week a software engineer came in for an interview and as we were exchanging pleasantries he referenced the “heroin shorts'' outside. Our ears perked up—why had he very specifically used that term? He explained that heroin and other opiates can cause severe constipation, so when someone comes off of a particularly long bender there is often a large backlog (or more accurately, a series of logs?), hence the Mount Feces outside our office. I felt resolution tinged with sadness, which lingered until I remembered that we had a large potential customer coming by the office the following day. I had hoped the city of San Francisco would deal with the situation, that one morning I would turn up and the shit would just magically be gone, but it seemed the heroin shorts were too much for even the most intrepid street sweeper.
Minutes later I found myself shoveling shit, something I had described in metaphor and hyperbole but hadn’t expected to encounter in its literal form. None of the CEO books had discussed it. In hindsight, the universe was giving me exactly what I needed, an earthy invitation to recognize the full range of the startup experience, from ecstatic vision to prosaic execution to waste management. At the time I just grumbled about how stupid it was and resolved to move offices ASAP. Thus, the potential wisdom of the poop pile went largely unmetabolized, passing through my system like corn. I would need several more heroin short-sized doses of reality before I would start to get it, so the universe simply smiled and prepared its next larger, shittier serving. We also ended up hiring that software engineer, and when he brought two bongs (a primary and a backup, he told me) to Tahoe one weekend, I could only smile and say a small prayer that his bowel movements would be regular.
My name, Conlan, is an Irish word. It means “Hero”. When I was little I truly hated my name; no one could pronounce it correctly, and with each Colin, Conor, even Coleen, I resolved to make a drastic change. Why had my parents, Michael and Kathleen, cursed my brother (Garren) and me with these strange appellations? One Saturday morning after much discussion while watching cartoons, Garren and I decided we would take the bull by the horns and both adopt the most badass name a three and five year old could think of: Benadryl Butthead Denali. We rushed to inform our parents. They smiled and politely told us that if we still wanted to become the Denali brothers when we turned 18, we could do so, but until then we’d have to make due with Conlan and Garren. A dream deferred.
Sadly, we forgot about Benadryl Butthead Denali, and thus never filed the requisite paperwork to make ourselves unemployable. As I entered adulthood, I had actually started to like my name (except at Starbucks, where I did change my name to Colin), to prize the uniqueness, the specialness that it conferred, though I still liked to joke about resenting how much pressure my parents had heaped on my shoulders by naming me “Hero.” I have still never met another Conlan, at least in person. I did receive an invitation to a “Calling all Conlans” Facebook group during college, and while the promised custom t-shirts and novelty license plates were enticing, I declined.
In those first years of Sighten, if you had asked me to define what it meant to be a good CEO, I probably would have said heroic. That solitary, John Wayne or Steve Jobs-type figure, single-handedly bending reality to his will. The hero archetype is ubiquitous across cultures, from ancient religious epics to modern Hollywood movies, from the Buddha to The Matrix. Mythologist Joseph Campbell coined the term hero's journey, also known as the monomyth, a universal narrative structure seen in many of the world’s major heroic myths and stories, contending that the hero archetype, to show up in such a consistent manner across time and space, must represent some fundamental aspect of the human psyche. Telling tales of heroes and heroic journeys seems part and parcel of being human.
Campbell was heavily influenced by Carl Jung and his idea that the unconscious contains not just personal material unique to each individual (repressed memories, dreams, imaginings), but also has a universal element, a collective unconscious, which contains shared unconscious content (symbols, images, identities) common to all humans, maybe even extending beyond humanity to other life. As evidence, Jung pointed to the existence of certain structures, identities, and modes of behavior that seemed universal, the hero being a prime example. He used the word archetype to describe these prepackaged, fundamental structures of the deep collective psyche, kind of like instincts scaled up to big brain animals, and he went on to detail the most common ones: king, mother, lover, warrior, magician, and, of course, hero. Like instincts, archetypes have survival value or else they wouldn’t exist.
Jung famously observed that any unconscious material (including archetypes) not made conscious, “will direct your life and you will call it fate.” Between my initials and my name, like bumpers on a bowling lane, sometimes my own path felt fated, continually funneled in the same direction towards some destiny, or at least into some pins. There were elements of a very modern version of the monomyth, the hero’s journey playing out in the hybrid analog-digital milieu of Silicon Valley CEOdom. The simple act of founding Sighten was certainly a threshold crossing, a stepping into the unknown that entailed great uncertainty but also seemed to align with some deeper knowing. Was I choosing my path or was my path choosing me? Or was I just a narcissist? All possibilities remained on the table.
There is another view of the hero archetype within Jungian psychology as representing the final stage of childhood psychological development, the adolescent bridge to adulthood that mobilizes the psychic resources necessary to break with our parents/caregivers and create our own identity and life. Thus, the courage and energy of the hero are indispensable in reaching psychological maturity, but when we confuse the bridge for the end destination, we can get stuck in a perpetual adolescence defined by almost God-like pretensions and a denial of any and all limitations, especially our own mortality, the greatest limitation of all. Anyone who has spent time with teenagers can attest to the simultaneous presence of ample transformational energy and a seemingly inexhaustible capacity for stupid decisions, often grounded in “that doesn’t apply to me” logic. Valour and emo music put in a blender. The rebellion of the hero is initially positive, a courageous step towards adulthood, but what happens when the rebellion never ends, when we keep searching for battles, quests, and adversaries ad nauseam?
At some point for me, my name had transformed from moniker to marching orders, and I found myself possessed by the hero archetype, both the light of courage, self-belief, charging into the unknown, but also the darkness of rejecting the limits of reality, possessing a grandiose view of myself, and relating to the universe through confrontation. I was an adolescent CEO, a boy not a man. Unfortunately, I was certain of the opposite, of my arrival in the world of adulthood vis-a-vis founding a company.
Outwardly, I continued to present as the super chill, intellectual hippie bro; but periodically, and with increasing frequency as I journeyed further on the CEO path, the low-simmer of confrontation would erupt into volcanic anger, scorching anything in its path. In college, doling out big hits on the rugby pitch had provided a productive outlet for this anger, but I also often crossed the line, getting thrown out of my final collegiate rugby game for menacing the referee and telling him “you fucking ruined this game.” The hilarious / sad part was we were winning by 50 points, so it should have been a moment of celebration, but it was marred by a rage that seemed beyond my control.
When I founded Sighten and the hero archetype met the CEO persona, it was like the golden spike being driven into the ground to complete the transcontinental railroad—something large and solid and durable had been created, and it would prove difficult to dislodge. This psychic marriage of the most outward-facing part of my psyche, conscious persona, and the deepest, most fundamental part of my psyche, unconscious archetype, quickly became the largest planet in the solar system of me, and it wasn’t close. Just as animals possess multiple and varied instincts, so humans possess a pantheon of archetypes, a portfolio of universal deep psychic structures to be drawn on for different ends and in different circumstances. But when we become tightly identified with a single way of being, unwittingly possessed by a single structure, we’re unable to draw on these other resources. We become a one trick pony, a hammer seeing everything in the world as a nail.
By necessity, many early stage startup CEOs must contain multitudes, possessing other titles and identities due to not having the resources or the need to bring on dedicated executives in certain areas. I certainly wore many hats at Sighten, functioning as Chief Financial Officer (CFO) and Head of Sales, in addition to being CEO. Day-to-day, containing startup multitudes is often less a Whitmaneque dream and more like multiple personality disorder, with different identities not always collaborating well, and sometimes descending into outright conflict. My CFO self, for example, generally was not interested in pushing back against Conlan the heroic CEO. The CEO has the big, transformational vision while the CFO is often thinking about what would happen if things were to go completely sideways. To successfully embody both of these energies, a shaman who can also do your taxes, requires a psychic flexibility and ability to context-switch that I did not possess.
Ultimately, on the playground of my mind, the stronger identity, the heroic CEO, started to bully all others, and my CFO self bent the knee, putting together wildly optimistic (read: unrealistic) assumptions and projections about the trajectory of Sighten customer and revenue growth, which justified rapid hiring and increasing other costs to support this projected growth. We had found it relatively easy to sign up our first customers on large enterprise software licensing contracts that would generate millions of dollars in revenue, if only our customers’ projections came to fruition, so it seemed logical (to me) to assume the same going forward.
But what seemed like durable product-market fit would turn out to be a false summit, a milestone to be sure, but a small one on the way to the much higher actual peak of a truly sustainable and scalable business model. Sighten’s first customers were early adopters who uniquely needed our software and had sufficient funding to pay real money to get it. Other potential customers, the fat part of the belle curve, had different needs and less money to spend on software, which became all too apparent, demo by demo, failed sales call by failed sales call. Each month we fell further and further behind our revenue projections as our costs continued to grow, thus increasing our burn rate (net cash spent). Financially, the Sighten dinghy was speeding up towards Niagara Falls. But rather than face reality, in consultation with our Head of Sales and CFO (both me), I just increased future revenue projections, essentially robbing March to pay November.
Within the tidy spreadsheets of Excel, all of our problems could be fixed with a few quick updates to a couple of inputs and voila—we were on a glide path to our series B or profitability. Just as the map isn’t the territory, the financial model isn’t the company; but the world of abstraction seemed so much more manageable, controllable, and safer than the seemingly completely chaotic real world. I was still frantically trying to sell Sighten’s wares, to close the revenue that would fix our upside down financial math, but the more things didn’t go our way, the more I started to retreat from reality. And in many small, unconscious choices each day, I chose to manipulate the symbols that abstractly represented Sighten, playing with the Platonic form rather than picking up a shovel and dealing with the shit that was piling up in the real world.
At the time, I truly believed things would work out, that we would miraculously close enough revenue to reduce our burn rate or raise more money and avert disaster. Sighten had led a charmed existence to date, with many just-in-time saves, including our series A money hitting the bank account just as a payroll went out that would not have otherwise run. But miracles, though great when they occur, are not something to build a corporate strategy around. Unfortunately, these heroic outcomes had, over time, altered my view of our world, and allowed the indefatigable self-belief necessary for startup creation to metastasize into a potentially fatal disconnection from reality.
Things started to come to a head in the summer of 2016. We had closed our series A in September 2015 and by the following August Sighten was almost out of money. The expectation, based on the general norm in Silicon Valley, was that Obvious Ventures would provide more money (an “inside round”), and Andrew called me one day to discuss the details.
“Look, Conlan, I spoke to the other partners and there is a sense that the company just isn’t working. We might not be able to provide additional capital, which I know is not the news you wanted to hear. I’m working hard on my end and I’ll know more soon, but in the meantime you should reach out to the investment banks and start a process to sell Sighten, and quickly.”
The room seemed to rise and fall like a wave, and a sea sickness suddenly rose in my stomach in spite of standing on concrete floor. Sell the company? We were just getting started. Obvious eventually did provide a term sheet, but it was grim: our valuation was a fraction of what it had been just a year ago and the composition of the Board of Directors would flip from majority founder to majority investor. Practically speaking, a board majority meant they would have complete control over the company, and given what had been said just a few weeks prior, I interpreted the deal as a hostile takeover with the goal of selling Sighten for parts. But with almost no money in the bank and employees expecting paychecks, how could I possibly fight it? Like a wolf taking off its sheep’s clothing, our largest investor had become Sighten’s gravest threat, and I saw no alternative but to gird myself for the fight of my life. Hero-mode times 1000. In early September 2016, we had a board meeting, and I had a sense all the energy that had been building would reach its crescendo there.
Despite desperately trying to maintain some semblance of normalcy, mostly via slides with lots of information, the tension hung in the air like concrete-baked NYC humidity, and no one in the board meeting that day felt comfortable. The warm embers of late afternoon sun intermingled with barely repressed anger, frustration, and conflict that felt so real, so corporeal, they might as well have been people or demons sitting in the room nodding at each slide. I felt like I was sitting near a black hole, just barely on the safe side of the event horizon, hoping to avoid being sucked into the blackness by not looking at the blackness.
The meeting was mercifully ending, or so I thought, when Lou, Sighten’s attorney, said ominously, “I believe there is one more order of business?”
Andrew started to speak: “Yes, I’d like to introduce a resolution to appoint Mike Miskovsky, Obvious Ventures Entrepreneur-in-Residence, as Sighten Chairman reporting to the Sighten Board of Directors, with Conlan, in his capacity as CEO, reporting to Mike.”
The auditory processing center of my brain must have malfunctioned, as I couldn’t believe what my brain was telling me I was hearing. Was Andrew, and by extension Obvious, trying to put me out to pasture by hiring my replacement? Was this their way of trying to take control of Sighten to sell it for parts, as they had insinuated a few weeks prior?
As my brain slowly started to process this dream-like unfolding, my first thought was: they can’t do this without Board approval, and Graham and I constitute a majority of the Board.
This coup attempt against me was destined to fail.
I watched with a mix of stunned and bemused silence as the motion was put to a vote before I could say anything.
“Andrew?”
“Yay.”
“Conlan?”
“Nay.”
“Graham?”
“Yay.”
“With a 2 to 1 majority, the board resolution appointing Mike Miskovsky as Chairman and ranking corporate officer of Sighten has passed,” Lou said matter-of-factly.
Andrew said something about this being best for the company and for me, but I didn’t hear any of it. I looked towards Graham as adrenaline, closely followed by lava-hot rage, coursed through my body; but he kept his gaze firmly fixed on the ground. In a small room in such close proximity to other human beings, I was completely alone, suddenly persona-non-grata at my own company, given orders to prepare to walk the plank.
After the board meeting ended, I knew I needed to get away from myself, from CEO Conlan, because he was in the process of completely falling apart, his existence existentially threatened. I conscripted Mariya, and in short order we found ourselves drinking whiskey on the rocks at the Pied Piper Bar at the Palace Hotel. This OG San Francisco bar had a special place in Sighten history, as Graham and I would come here after work to drink and concoct our grand plans for Sighten, the dreams getting more audacious with each round. Seated beneath old, dark wood paneling that felt like the interior of a ship, Mariya and I ordered our second drink, and suddenly a dam broke inside me—tears flowed like storm surge, all the tension and fear and anger and confusion of the proceeding weeks bursting forth in a torrent of energy.
I spoke about the company but really my lamentations were about me: “How could this be happening? I have tried so fucking hard; I’ve given everything to this company, only to be repaid like this!”
Mariya, quickly becoming the glue that held Sighten together, just held my hand as the tears flowed. We were close friends but I was also her boss, so I can’t imagine the kaleidoscope of thoughts that were running through her mind as a dear friend, and the CEO of her company, apparently completely lost his shit. Finally, feeling that the flood inside me had abated, if only for a moment, and sensing an opportunity to pivot the pity party, she spoke.
“Conlan, we need help. We have so much going for us, but we need help. We can’t continue like this.”
Her words hit me like a zen koan, instantly breaking through all the layers of stories, judgements, and assumptions, penetrating deep into my being. For the first time, I entertained the thought that maybe there was a shred of truth in what Andrew and others had been saying. Maybe I was not a good CEO. Maybe I had driven this company to the brink of extinction, and rather than blaming others, I needed to turn my gaze inward.
Like clouds briefly parting only to obscure the sun again a few seconds later, I quickly returned to my preferred narrative of a heroic CEO battling the malevolent forces of the universe, which now included a villainous, machinating cabal of greedy investor and betraying co-founder. But there had been an opening, an invitation to shift, a call to see reality and myself as it really was, with all of its waves and currents, darkness and light. Would I take it before it was too late?
Giant, chaotic waves were now pounding the Sighten ship from all sides, and as the sky turned an inky black, it seemed only a matter of time before the raging sea turned our tiny skiff into a coffin.
I’m rapt. What a tale so far, with so many layers so skillfully woven together! Wisdom, humor, humility, artistry and practical awareness all in one.
Amazing work my friend. Stoked for parts 4 and 5!
I got a kick out of the closing image 😂