There Will Be Waves (Part 4) - The Sighten Story (2024)

Note: This is part 4 of a 5 part essay series.

If you missed any of the previous installments, you can find them here: Part 1 (The Call), Part 2 (Crossing the Threshold), Part 3 (Dissolution)

Part 4 - Transformation

“When the storm rages and the shipwreck threatens, we can do nothing more worthy than to sink our anchor into the ground of eternity.” – Johannes Kepler

Mariya and I sent it deep into the night, which in San Francisco means about midnight, until we were asked to leave the W Hotel bar for spilling takeout Thai food everywhere. While I’m sure I was upset, even indignant at the time, I can now appreciate the W’s perspective. The next morning, a Saturday, I awoke to a hangover and a text from Mike. I had extensive experience with hangovers, but a board-foisted, out-of-left field boss was new and strange territory.

I had met Mike a few times since he had joined Obvious as an EIR (entrepreneur-in-residence), but as I perused his LinkedIn profile that morning it dawned on me that he was one of the most experienced and successful climate tech CEOs in the Bay—maybe anywhere. He had founded startups, initiated turnarounds of fledgling companies, and had several lucrative exits under his belt. He was a pro, with the gray hair to prove it. If Obvious had decided that I was not up to the task, Mike would be an easy choice to replace me, maybe even the number one draft pick. A tremor of fear, the existential variety that all animals can feel, made its way up my spine as I tried to remain calm. I thought of buying some Just for Men - Touch of Gray, but I sensed that my problems ran deeper than hair.

Mike wanted to talk as soon as possible, but I wasn’t so sure, my mind still a chaotic storm of anger and confusion and fear. It felt strange and wrong, like admitting defeat, to even acknowledge that this guy I had only met a few times was now my boss—at my own company. What the f*ck had even happened yesterday, and what would Monday bring? It all had the otherworldly texture of a dream—a nightmare, to be sure—and I periodically willed myself to wake up, desperately ready to resume my “normal” (though still pretty f*cked up) CEO life.

Mike, seemingly sensing my mental cacophony, insisted that we chat, if only briefly, so I begrudgingly got on the phone with him that afternoon.

“Conlan, I imagine you’re feeling a lot after what happened yesterday; that must have been hard. So, I just want to be super clear and start by saying this: I don’t want your job. I want to help,” he said.

There was a part of me that desperately wanted to trust Mike, to finally admit that I needed a sh*t ton, or to use a technical term, a heroin-shorts amount of help, and accept it from someone who had been there and done that. Mike’s statement of noble intent helped, and I even felt my nervous system relax slightly for the first time in months, the hero considering putting down his sword, or at least accepting sword lessons.

“I’m an entrepreneur and a founder, not an investor, and I never would have accepted this Executive Chairman role if I was just a Trojan horse for some other purpose. I’m in your corner, and I’m ready to help,” he continued.

But that weekend I was a veritable Jekyll and Hyde of diametrically opposed, surging emotions—a house divided against itself. At times, it felt like the current version of me was coming apart at the seams, the walls closing in tighter and tighter, a caterpillar whose cocoon has become so cramped that it finally turns to goo. Joseph Campbell called the nadir of the Hero’s Journey the dissolution phase, the point where things become so overwhelming and uncomfortable that we break down. This break, which often feels like a type of death, creates the space for the ultimate goal of any heroic journey—transformation—to unfold. But there is a deeply ingrained human instinct to want to skip the incredible discomfort of dissolution, the darkness of the cocoon, instead, going straight to the newness of rebirth, the rising sun of a fresh day, a butterfly flapping its wings for the first time. I was no different, desperately wanting things to change but still refusing to pay the price of admission.

Around midday, I finally spoke to Graham, who told me simply that Andrew had approached him, and that he agreed that something needed to be done. I seethed with anger at what I saw as his betrayal and his naïveté—to make an employee of Obvious our ranking corporate officer when we were in a tense standoff with them over funding, board control, and selling the company seemed beyond stupid. Didn’t he understand that the wolves were at our door, and he had just unwittingly let them in? I chalked it up to a highly technical co-founder being out-of-his-depth in the infinitely more complex analog world of human beings.

Late in the afternoon, overcome by another wave of what I can only describe as “f*ck this sh*t,” I started to pack my dilapidated Subaru, intent on driving to Jackson, Wyoming the following day, where I would leave the sh*t-show that was Sighten behind and begin a new life in the mountains, far from conference rooms, board resolutions, and backstabbing investors / co-founders. But by Sunday morning that plan seemed quixotic and stupid, mostly because it neglected the not-so-small-matter of having zero dollars to my name. I could couch-surf and find a random job and ski a bunch, but as I imagined living that life it all had the undeniable scent of running away, of retreating into Peter Pan-esque boyhood instead of looking my problems square in the eye. I felt paralyzed, in no man’s land—unable to run but seemingly incapable of staying.

Something compelled me to move my body, if only to confirm that I still possessed some degree of agency amidst a storm that felt completely outside of my control, and as I wandered the streets of San Francisco and then through Golden Gate Park, my thoughts turned to all the people that had signed up for the Sighten journey so far: employees, early customers, investors, vendors, advisors. It was still a smallish ecosystem, to be sure, but there were beings and entities that depended on us, lifeforms that had come to rely on the light and warmth of the Sighten sun. However unjust my current situation appeared, I remained the face of the company, the person who had made commitments and promises, shaken hands and signed contracts.

I awoke Monday morning with something approaching clarity, though a clarity born of conflicting motivations. I had to stay—to prove Andrew and Graham wrong, to try to honor the promises I had made, and because I didn’t really have a choice financially. Anger and aggrievement still predominated in my mind, but the simple decision to remain, like the first crack in a chrysalis, had allowed a tiny sliver of light to creep inside the dark and cramped space of my psyche. The outcome was still highly uncertain, both for Sighten and for me, and betting markets would have pegged us both as steep underdogs, but I would at least show up, if only to try and best my numerous and multiplying adversaries.

Mike and I met early that morning in the first of what would be many 1:1s over the coming months. We covered all aspects of Sighten, an overview of what was working (a few things, mostly our core product and our team) and what wasn’t working (a lot of things, mostly business and finance related, aka what I was responsible for). As the meeting ended, it was clear to me that Mike could be a valuable, potentially life-saving asset for Sighten. I could learn a lot from him, if I could admit that I had a lot to learn.

Ultimately, there was just so much to do, and Mike proved so helpful, that we developed a working momentum despite my lingering uncertainty regarding my need for mentorship and my seething anger at the circ*mstances that had occasioned it. It helped that we seemed to be cut from a similar cloth, rugby players who liked to wax poetic, aka nerds trying to present as warriors, or maybe bros in recovery from broness. But Mike had a groundedness, a stability that I conspicuously lacked. If I was the adolescent CEO waving my sword wildly in all directions, Mike was the seasoned general pouring over maps and intelligence, diligently pursuing a comprehensive war plan. While I lamented my situation and often lashed out, Mike operated from a place of radical acceptance, working with whatever the universe was giving him instead of wasting precious time, money, and energy rejecting what was arising.

Even though I don’t think he thought of it in this way, I came to view it as a form of spiritual attainment, this constant orientation towards the present moment, without judgment or resistance, even when the waves of startup life got big and messy (and scary). No matter what super f*cked up aspect of Sighten’s situation I brought up, Mike never winced; a true business samurai, not someone cosplaying one.

With Mike’s guidance and help from our team, I set about examining the areas of Sighten that we had identified as needing significant change, which is to say nearly all aspects of the business. It was a lot, and it was often painful to see how far I had let our boat drift; but slowly, oftentimes reluctantly, I was realizing that this was the only way. I’d have to look into the CEO mirror and not turn away, no matter how grim things looked, no matter how haggard the reflection staring back at me.

While fixing Sighten as a business was the most important task in the medium and long term, figuring out how to survive financially was the immediate existential imperative, a quandary that threatened to sink the Sighten ship before we could complete any of the necessary repair work. It was a problem that felt intractable because of how dead-f*cking-simple it was: we just had to make payroll until we had a deal for additional funding, from Obvious or someone else. Could we scrounge up enough cash or not? The math was unforgiving, like a giant buzzsaw inexorably inching closer.

If building a large, successful startup over the long run feels like launching a rocket into space—expansive, growth-oriented, methodical—surviving in the short term feels more like being a co*ckroach. It’s less grand plans or big-picture blueprints and more just avoiding getting squished. Every founder must confront this eternal dance between short-term survival and long-term building, and the first necessary move is always to correctly ascertain the current season. Is it a spring of abundance where you can afford to dream big or a harsh winter where you need to batten down the hatches? In the fall of 2016, Sighten was a co*ckroach trying to survive a Russian winter.

To give us some type of survival map, Graham and I created a daily cash flow model complete with every single bill and invoice to our name, which enabled us to forecast our cash position down to the day, sometimes even the hour. I had partially reconciled with Graham, if only because we sat a few feet from each other every day and giving him the silent treatment in perpetuity felt impossibly awkward (at least for me). I also desperately wanted him to really see the enormity of my CEO challenges, if only for him to finally get how hard my job was. He couldn’t selectively sit at the big boy table, participating in Board coups but then retreating to the relative anonymity of writing code, leaving me to clean up the wreckage. So, I made him ride shotgun with me, at least on the financial front, and we started looking under every rock and couch cushion for the equivalent of startup loose change, initiating a set of runway-extending, cash flow machinations, like getting prepayments from the two startups subleasing office space from us and pausing payments to any vendor that wasn’t actively banging down our door (more on this shortly).

There were also temporary, voluntary salary reductions from employees in exchange for additional Sighten equity, which I had requested at an all-hands (company-wide meeting), much in the manner the US government had asked Americans to buy bonds during WWII. We were on a wartime footing, and their general needed their unequivocal support. I was heartened by the number of employees who said yes, and I took it as a sign that morale was good. But in hindsight, I wonder if they felt manipulated, put in a position where saying no felt awkward, if not impossible. The employee attrition over the subsequent months seemed to confirm that I had misread the room, in some instances, badly.

At the time I justified the ask by telling myself that I was leading from the front, as I had cut my own salary from the post-series A norm of $150K to $50K, before eventually taking it all the way to zero. There was undoubtedly a noble, “I’m in the trenches, too” intent, and it certainly did help to extend our runway. But I can now see it was also a form of self-harm, the hero turning into a martyr, a way to self-flagellate while appearing righteous and sidestepping the really hard decisions, like laying off staff. Avoidant heroic masochism.

One thing stood out in our financial forecast, a large cash outflow that seemed to taunt me each month. Right after our series A, I had signed a long-term lease for an entire floor of office space in downtown San Francisco, assuming that our explosive (projected, and ultimately, imaginary) growth would necessitate filling every nook and cranny with Sightenites in the very near future. Now, staring at our cavernous office each day, more than half empty while our bank account rapidly marched toward zero, it was a daily reminder of my failures as a CEO, the most damning evidence of getting lost in the flash, of confusing the costume of success for the real thing. A gorgeous, light-filled space with high ceilings and big windows, it now felt heavy, like my own personal corporate scarlet letter. Striving to be Steve Jobs, I had become Hester Prynne.

This scarlet letter, far from an inanimate brand, reached out to grab me one day in October. I had just wrapped up a call with our landlord’s attorneys about temporarily using a portion of our large security deposit to pay the current month’s rent (another cash-hoarding, runway-extending move) and now found myself in a sales pitch with the CEO of the largest solar installer in Hawaii, who happened to be in California that week. Signing up large, strategic customers to big revenue contracts was the closest thing to a panacea for what ailed Sighten, simultaneously bringing in cash and making it easier to raise additional investment dollars. I was firmly in Head of Sales mode, giving him the full-court press; but just as I was getting ready to go for the close, I heard a loud commotion outside the conference room, and then someone yelling–loudly.

Moments later, Sighten’s Head of People, Sam, nervously opened the conference room door. “Umm, Conlan, there is someone looking for you,” she said.

I told the Hawaii CEO I would be back in a minute, and when I stepped out into our open floorplan office, I saw a bike messenger–tall and tatted, still with his bike shoes on–wildly walking around the office, repeatedly yelling a single phrase: “WHO IS THE BUSINESS OWNER?”

Sighten had ground to a halt, as employees stared, jaws agape at the strange spectacle, a level of interest I hadn’t seen since the heroin shorts. Jogging over to the biker, I told him that I was the business owner (assuming he didn’t want to hop on a Zoom with our entire cap table) and quickly escorted him out to the elevator bay, all the while quietly (and desperately) imploring him to take it down one or 17 levels.

Once outside, he “served me” with a summons that gave us three days to pay rent for the current month or be declared in default of our lease agreement. He hadn’t lowered the volume on his voice, despite us being in a very small space now, so his words reverberated like an ambulance driving through my skull. Our landlord, apparently defying his attorney and taking matters into his own hands, had set f*ck it and gone old school, sending a dude on a bike to give me a piece of paper that essentially said, “pay us right f*cking now–or else.”

“I understand, thank you for delivering this; have a great day!” was all I could think of saying, my only objective getting him out of our office before he found something else to yell about. Content that he had completed his mission, he got on the elevator and left. The relief lasted mere seconds, as my thoughts immediately turned to how this would drive a bus through our fragile runway calculations. I felt an overwhelming urge to cry or scream or both. My hands were shaking. And then I remembered the Hawaii CEO, seemingly in a different universe, sitting in our glass-enclosed, brick-walled conference room, potentially ready to become a Sighten customer if only this kerfuffle hadn’t sufficiently rattled him. f*ck!

I made a beeline for the bathroom, past our still-shocked employees, and splashed water on my face as I started to take slow, deep breaths, trying to will the cortisol out of my system and somehow re-assume the breezy, confident CEO persona who closed big software licensing deals. Suddenly, and seemingly against all odds, the heaviness evaporated, and I found myself laughing uncontrollably. Had I achieved some kind of ecstatic, temporary enlightenment based on the sheer absurdity of my situation? Or, more likely, per Ockham’s Razor, had I simply finally lost my mind? Whether nirvana or insanity, the sudden lightness of being seemed like a useful tool, and a minute later, calm and smiling, I stepped back into the conference room, summons notice hidden in my pocket.

“What was that?” the CEO asked.

“Oh, just a legal messenger on the wrong floor. Where were we? Ah yes, so given that you guys will want API access and some workflow customization, I think discussing an enterprise-level agreement makes the most sense.”

We didn’t close that installer, which kind of makes the story less cool, but that had more to do with public policy challenges in Hawaii than their CEO intuiting that Sighten was teetering on the edge of non-existence. I counted it as a non-win win.

There are efficient paths to learning and then there is the path of just being bludgeoned so many times that it’s impossible to not internalize something. I was mostly walking the latter path, but if you squinted hard enough, you could see the beginnings of actual growth, the nascent shoots of real CEO transformation. I still felt like I could drown at any moment, but like a surfer going limp (rag dolling) to allow the ocean’s energy to pass through him, I had started to internalize that acceptance, even equanimity, was the best (and maybe the only) way through raging seas. The bike messenger wave pounded my nervous system with such ferocity that it did kind of break me, my mind reaching a point where it categorically declared: this is too much. But paradoxically, on the other side of that complete overwhelm was what felt like a new version of me.

More prosaically, the summons meant that we had no choice but to pay our hefty rent bill, which put us further behind the financial eight ball. It seemed like everyone who wanted to be our best friend when our coffers were overflowing with fresh venture capital suddenly saw us as carrying bubonic plague—to be avoided at all costs.

In the weeks since the Board meeting, as Mike and I had become fast friends, I had given Andrew the silent treatment, as my anger transformed into a deep desire to prove him wrong, whatever that meant. It was Mike who convinced me to re-open regular communication, if only to try to further negotiate the term sheet that Obvious had provided. He encouraged me to de-personalize it all, to just view it as one potential funding option (at the moment, the only option) and at least do the work to ascertain what their best offer might be (especially if we could demonstrate real business progress). A good CEO, Mike explained, like a good general, doesn’t let his own emotions so overwhelm him that he can’t explore all options, including negotiating a truce to end hostilities.

Of course, concurrently, I was talking to any investor with a pulse who might want to do a several million dollar bridge round for a climatetech SaaS company. There was some interest, but the whole endeavor reeked of desperation; the fact that Obvious wasn’t willing to lead the round, even as we were basically out-of-cash, told other investors all they needed to know. They could sense all was not right in Sightenland, and I began to feel like I entered each pitch meeting smelling like I had sh*t my pants, a heavy stench overwhelming whatever slides I had put together. But I kept trying, sometimes ending my day near tears, exhausted from pitching all day and from feeling like a dying fish with sharks circling. I blamed Andrew and Obvious for forcing me into this CEO walk of shame.

Mike and I prepared a counteroffer to Obvious’ term sheet, proposing a higher valuation and a split Board of Directors (2 founder seats, 2 investor seats, 1 independent seat) instead of an investor-controlled Board (2 investor seats, 1 founder seat). Later that same week, I got on the phone with Andrew to discuss the details, ready for the confrontation my mind had come to expect, maybe even crave.

“Conlan, thanks for sending this over; I’ll take it to the other Obvious partners right away and do my best to get their buy-in,” he said. “I’ve heard from Mike that he’s really enjoying working with you and that you guys are making a lot of progress. That’s awesome—thank you for making things work with him, I really appreciate it. At the end of the day, I truly want nothing more than for Sighten to succeed, and succeed with you as its leader.”

His words so differed from my expectations that my mind briefly went blank. Expecting a punch, I had received a hug. Feeling blindsided by his support, it was again like a zen koan that instantly pried my awareness away from its default mode of being: the heroic CEO waging a righteous war. His statement about advocating for Sighten with the Obvious partners also led credence to something Mike had emphasized: Andrew had his own constraints within Obvious, as any VC partner does, and a decision to put millions of additional dollars into a company that hadn’t come to close to hitting any of its projections is necessarily a collective decision, potentially even a contentious one.

My mind flashed with my interactions with Obvious over the past year. I remembered Andrew, a few months after we had closed our series A, imploring me to “not treat Board meetings like fundraising meetings. We said yes, we’re all in on Sighten, let us into the boat with you and let’s all row in the same direction together.” But I hadn’t let them into the boat, and our Board meetings continued to be barely functional, with slide decks sent out an hour before and agendas so garbled that we barely had time to discuss financials.

Why had I kept Andrew at such a distance, oftentimes flatly ignoring his feedback? He was a serial founder and CEO himself, with the successes and scar tissue to prove it, but for some reason I couldn’t let my guard down, I couldn’t truly let him see the real Sighten or the real me. He was right—I had treated everything as a continuation of the fundraising process, all sunshine and roses, refusing to drop the performance, be real, and ask for help in the prosaic, messy, and insanely difficult task of building a business. I saw, for the first time, how I had pushed him to do what he had done by pushing him away.

Around this time, as all this churned in my mind, I received a cryptic text from a friend: “Do you want to go on a spiritual journey with me?”

This was a high var friend, someone you wouldn’t be surprised to hear had IPOed his company, moved to an ashram, or been arrested—or all of the above. The fact that I was the recipient of this mysterious text probably confirms that in his eyes, I was the high var friend. Two wild peas in a volatile pod. I thought about it for a few hours before replying with a simple “yes.” After all, with my company and my life seemingly crumbling before my eyes, what did I have to lose?

And so, a few weeks later, we found ourselves driving into the Sierra Nevada foothills to “sit” in an ayahuasca ceremony, a sacred entheogenic (psychedelic) plant native to the Amazon rainforest. I had been a fan of psychedelics ever since my first mushroom trip my freshman year of college, when I wandered on the Appalachian Trail until I suddenly felt the presence of God, or at least some infinite power / awareness, as the light tumbled through the treetops at just the right angle. I had also experienced full ego dissolution, which was confirmed when I tried to play my friend in FIFA and I could not, for the life of me, understand that I was controlling a single player—a single, contained self. My friend kept pointing to the highlighted player on the screen, saying “that is you, you are him,” to which I would reply “I am not anyone.” He left in a huff, ostensibly to find an opponent with a firmer connection to everyday reality. FIFA debacle aside, it was my first true mystical experience, the direct, felt sense of unity or oneness, and it had a formative influence on my life, in no small part supporting my decision to give monastery life in Southeast Asia a go.

Psychedelics, like good writers, employ a “show, don’t tell” style, which is what makes them so powerful; but it can also make the act of writing about psychedelics tricky. How does one maintain the vividness, the felt truth of the original experience when entering the comparatively staid world of language? That’s why trip reports can be a risky business, as it’s easy to dead-end in what sound like Hallmark bromides (everything is beautiful!) to the uninitiated. I initially decided against including any psychedelic journeys in telling the Sighten story given these well-documented limitations, but the reality is these experiences were so powerful and so transformative that not including them would be a sin of omission, like randomly breaking the 100 meter world record and saying you had just hit the elliptical a little harder. Clearly, something else (performance enhancing) was going on.

The first night of the retreat, despite drinking several cups of “the medicine,” nothing happened; but the second night, as soon as I sat back down on my mat after downing my first cup, the room started to sway in a type of comprehensive vertigo. Within minutes I found myself traveling through various fractal portals before some type of kaleidoscope-being appeared, asking me, simply, “what do you want to know?” I thought for a second before the answer became obvious: “everything.” The kaleidoscope-being gave a laugh, possibly at my earnestness or, more likely, in a “be careful what you wish for / you have no f*cking idea” kind of way.

Off we went, proceeding on an in-depth tour of the universe, which turned out to be quite simple. At first there was a fundamental unity (my brain kept wanting to call it “the unconditioned”), but then this oneness split in two, into consciousness and energy, and the being showed me how this was the first step in the creation of world of 10,000 things, the primordial duality. These two core constituents of reality flowed in a never-ending dance, awareness apprehending and influencing energy, and energy, in turn, being perceived by and influencing awareness. I thought of Purusha and Prakriti, also often translated as consciousness and energy, the core duality of all Hindu cosmology.

I opened my eyes and the entire room was a flowing, vibrating mosaic of energy, all the boundaries that normally defined the world dissolved, shown to be provisional or even illusory. And these flowing rivers of energy were directed not by riverbanks or canyons, but by consciousness, or more specifically, intention, which my kaleidoscope guide described as “the arrowhead of awareness”, consciousness directed. It felt like seeing, really and truly seeing, the quantum mechanical universe of waves and potentialities, as opposed to the solid and demarcated Newtonian world of everyday experience. Everything was fungible, dynamic, connected, responsive. It was clear that awareness was not passive, but fundamentally constitutive of reality, shaping how it unfolded in every moment.

I noticed dark masses within other people’s bodies and minds, and saw the moving swirls of energy slowing down and ossifying, seemingly getting stuck and becoming dense, a deep energetic torpor. My fractal-colleague explained that these densities represented “stuck” consciousness (the mathematical term “local minima” popped into my brain), patterns of unconscious thinking, feeling, and being that, while infinite in variety, all have the same effect: to take us away from Presence, presence being consciousness directed toward the current moment. When the being said “Presence,” it was like a universe-sized bell tolled, and the expansive truth of that word rang throughout my being. “Presence is our true nature,” I whispered to myself.

Suddenly, the person next to me started violently throwing up (“purging” is very common on ayahuasca), and I found myself disgusted and angry as vomit splattered in my direction. Despite my time in a fraternity, where, for better or worse, a certain complacency, maybe even acceptance, and at times, adulation, with respect to vomiting was the norm, I thought it wildly inappropriate for my fellow journeyer to be desecrating my spot. But my geometric-guide grabbed hold of me and whispered, not so much in my ear as directly in my mind: “look again—he is ‘getting well’—it’s beautiful.” And in that moment, everything shifted, the cacophonous screams and cries and puking sounds transforming into Beethoven’s Ninth, albeit a very strange version, as I felt huge waves of compassion and love wash over me.

I looked again, this time seeing with new eyes: the dark masses, appearing like energetic tumors, were slowly starting to unravel as he faced them. The kaleidoscope-being said it was a simple process (though clearly not easy), one just needs to bring enough Presence to bear, and our consciousness becomes like a super powerful laser that melts these masses under its steady gaze. I could see how hard it was for my neighbor to truly look at these tumors, as he seemed to be in profound anguish, alternately crying, contorting, and screaming as he continued to fill his bucket with puke. At least he was getting his money’s worth.

I could feel his terror and his courage, and it brought tears to my eyes; I could tell he was staring down something extremely dark that he had been carrying for a long time. I felt myself naturally getting as present as possible, sending him pure, unadulterated Love, maybe the purest love I had ever experienced. This love, this pure benevolence for another being seemed to form a bridge between our individual consciousnesses, not metaphorically but literally, as for a brief moment, I could feel exactly what he was feeling. It was incredible and terrifying, the feeling of your own awareness merging into something greater. “You” no longer exist, but you’re still there. Slowly but surely, the “stuckness” tumors dissolved, and in their wake, there was what looked like Space, space where consciousness and energy could now flow freely. Back in my own psyche, as I watched this unfold in rapt awe, one word started flashing in my mind: Freedom. My neighbor was claiming his Freedom.

I journaled 20+ pages the next day, but the key takeaway, written over and over was simple: The universe is consciousness and energy, I am Presence, and I am only Free when I am honoring my true nature as Presence. Though it may sound like a mad lib-generated card plucked from the Hallmark new age section, I had seen it with my own two eyes, felt it all with all my heart, and knew it to be true at a level fathoms deeper than my logical mind. The only analogous experience I could think of was deep meditation, especially my time in the monastery, and as I searched for the right words to describe what initially felt ineffable, I found an eastern vernacular the most helpful.

From Buddhism, I recalled the Sanskrit word Samskara, often translated as “mental formations” or “habit patterns of the mind”, and I realized that the “stuckness” that I had seen, the energetic tumors, were all samskaras. I also thought of Carl Jung and what he called Complexes— “knots of unconscious feelings and beliefs.” The Buddha and Jung, despite being separated by thousands of miles and several millennia, had observed this same phenomenon of “stuck” consciousness. As I turned my gaze inward, it led to obvious questions: how was I stuck? What were my samskaras / complexes? Or as Jung would put it, what unconscious aspects of my psyche, disguised as fate, were running my life?

Psychedelics are like taking a helicopter from the forest floor to the top of the mountain, as vistas and perspectives come into view that completely transform our understanding of reality. This “piercing of the veil”, of becoming aware of a completely different world, is valuable but not sufficient, and a common mistake psychonauts make is assuming they’ve achieved a durable transformation simply based on the profundity of their trip. But you can’t live in a helicopter (at least currently), so the real work always begins after the ceremony, during the integration phase, when we must return to the forest and find the trails that will take us to the mountaintop one step at a time, a path that our everyday selves can understand, remember, and repeat. Psychedelics can give us a glimpse of the destination, but it is up to us to forge a path there.

Returning to San Francisco, one thing became immediately clear: over the last few years, almost half a decade, I had lost the plot in a big way, allowing the world, more specifically the startup arena of techno-capitalism, to consume me, in the process forgetting something core about what it meant to be alive and to be aware. It had happened slowly, spiritual death by a thousand cuts, the main assailant being the widespread materialism of the modern world, the (often implicit) belief that only physical reality, objects with extent in spacetime, have any validity or reality. Far from finding myself, becoming a CEO and entering the heart of techno-capitalism had deposited me directly in a ditch / local minima on the side of the spiritual path. If nothing else, I resolved, I would get out of the ditch and start walking again.

Within materialism, consciousness is simply an emergent phenomenon of sufficiently complex physical stuff, not something that might be critical, even foundational, in its own right. Ayahuasca, in a single night, had emphatically pointed to a different paradigm, a paradigm where physical reality was dynamic and where consciousness played a constitutive role in shaping it. As I landed back at Sighten, things were hard—everything felt so heavy compared to the rarefied air of my high-altitude journey. I was super sensitive, which is common after big journeys (I like the metaphor of psychedelic journeys as “spiritual surgery”), but as the week progressed and I gradually regained my footing, I sensed an opportunity to be a different type of CEO.

There is an oft repeated quote in Silicon Valley: “as a CEO, it’s all your fault.” The buck stops with you, so no matter what series of events or decisions led to the current f*cked up situation, you must own it, completely, every day, even if on some level you feel like you had nothing to do with the specifics. I saw clearly how I had done everything but take responsibility for Sighten, instead blaming everyone and everything: investors, co-founders, employees, market dynamics, customers, policies, on and on, a never-ending game of hot potato, constantly placing agency outside of me. What would it look like to take radical responsibility for Sighten? What would it look like to do the same for my life in general, for myself as a human being?

The rivers of energy directed by consciousness, a sacred image apparently indelibly burned into my psyche, kept appearing, offering a path forward. Maybe taking responsibility simply meant honoring my own consciousness, owning its ability to be an active participant and co-creator in constructing reality. To date, I had mostly shirked this responsibility, but that didn’t mean I wasn’t co-creating. It just meant I was unconsciously co-creating, allowing my samskaras and complexes to to be the architects of my life and my company. Unconsciousness disguised as fate.

I saw now that life wasn’t giving me some arbitrary series of events, it was giving me exactly what I wanted, unconsciously, and each wave, down to the minute and myriad ways the energy flowed, eddied, or got stuck around the fulcrum of my awareness, offered me a mirror, reflecting back my own psyche. Far from malevolent or uncaring, life was a set of benevolent waves constantly nudging us towards the truth of who we are, by providing clues about how we’re currently showing up. This isn’t to say we can fully control what waves come to our shore, and sometimes tragic, inexplicable things do seem to happen, but we always retain the freedom of how to respond. Do we allow these waves, especially the bigger, scarier ones, to push us into unconsciousness (samskaras and complexes) or do we use them to come more fully into presence?

Looking back, I saw how my decision to stay, to not run away after that fateful Board meeting in September, had been the start of a process that was now coming to fruition. With each day that I just showed up and focused on whatever detail of the Sighten ship needed to be rebuilt or whatever (slightly sketchy) cash flow machination needed to be executed, my anger, my sense of aggrievement, my victim narrative dissolved slightly, leaving me with a little more psychic space. The work was hard, sometimes overwhelming, but it was healing, even if I couldn’t always tell. The fall of 2016 felt like my startup MBA as I drank from the firehose of Mike’s tutelage, but it was also a spiritual rebirth. And while I still had lots to figure out and many questions left to answer, something fundamental had shifted in my relationship with the universe and, in turn, in my relationship to Sighten.

It was no coincidence that Sighten went through its own rebirth, “creative destruction” in the capitalist vernacular, old structures not conducive to enterprise value maximization dissolving such that new, more valuable corporate ways of being could be created. As a CEO, everything that happened at my company was indeed my fault. But it wasn’t a burden; quite the opposite, it was the opportunity of a lifetime. Sighten was many things to many people, but for the first time I saw what it was to me: my guru.

Before my weekend jaunt to alternate dimensions, Andrew had come back with a new funding proposal: Obvious would accept a split Board of Directors, but they could only move a small amount on the valuation front, their logic being that the company had been overvalued previously. While I certainly would have preferred a higher valuation or to simply do a convertible note, I recognized that their reasoning made sense. We also didn’t have any other good options, as our broader fundraising process continued to yield encouraging words but few term sheets. I saw clearly it was time to just take the deal and turn our attention back to building Sighten.

I reached out to Andrew and told him I had signed the revised term sheet—could he have the lawyers draw up the official paperwork? He said yes, and he seemed genuinely excited, like we had re-discovered some our initial spark from that first ebullient, circle jerk, non-circle jerk meeting back in 2015. We signed the official investment docs in mid-December, and I gathered the Sighten team in an all-hands later that same day. The relief was palpable, from everyone. I realized how I had let this battle, and its related stress and uncertainty, continue for too long, largely due to my own anger, only dimly aware of the huge toll it was taking on Sighten, especially its employees. I probably could have gotten this basic deal done a month earlier, but I had wanted to keep fighting, for reasons related to me that had diverged from what was best for the company.

At that all-hands, as late afternoon transitioned to evening on a cool yet bright day, I stood in front of everyone employed by Sighten and said something that I had never said before. It simultaneously felt extremely vulnerable, downright scary, and like I was showing up as a man and not a boy for the first time in my tenure as CEO.

“All of this was my fault, and for that I apologize. We have too awesome a product and too incredible a team to let sloppy financial management sink our ship. I will learn from this experience, and we will move forward stronger for it. Thank you for everything you have done this fall to keep us from capsizing—I am grateful beyond words, and I feel so lucky that each and every one of you chose to stick it out with Sighten.”

Of course, not everyone would stick it out going forward, and several team members had already planned their exits, although I didn’t know it at the time. I couldn’t blame them, and it was a good lesson that mistakes, even those that are corrected, have permanent costs, the most important being the erosion of trust. While our immediate wound had healed, I saw there would always be scar tissue.

A few days later, I met Andrew at Presidio Social Club for dinner. It had been his suggestion, an opportunity for us to “bury the hatchet”, reset our relationship, and get ready for what we were both hoping would be a less eventful 2017. As we ordered our third round of drinks and both let our guard down, Andrew suddenly got serious, his tone of voice changing.

“Conlan, I wanted to say I’m sorry. While I do think there needed to be some type of big change at Sighten, I think my communication and the specifics how things went down were often not the best, sometimes far from it. And I recognize how that probably made your life hell for a while. The reality is I’m also new to my job—I’ve spent almost my whole career as an entrepreneur, not an investor—and with Sighten being my first investment, and it seeming to be going off the rails so quickly, I was honestly scared, especially when my partners started asking hard questions about how I had let it get to this point. I eventually caught myself and realized what had happened, but in the moment I felt like I was in survival mode, and that made me say and do some things I regret.”

Once again, Andrew’s words shocked me, their candor and vulnerability instantly softening me. I felt seen for the suffering I had endured, even if I had co-created it. I thanked him for saying all those things and issued my own lengthy apology for all of my missteps and miscommunications, which were ample. We toasted as we decided to call 2016 our year of “learning on the job,” and we vowed to be in constant communication and walk lockstep in the same direction going forward. We would emerge stronger for going through this storm together. His vulnerability had opened me up, and I finally did what I should have done all along: I invited him into the boat.

After dinner, I walked down to where the ocean meets the bay. It was close to the shortest day of the year, and thus the longest night, but as I looked out at the Pacific, quietly churning away under an overcast night sky, I didn’t feel despair. Instead, there was a cozy intimacy with the dark waves, and I could see a savage beauty in their ceaseless rising and falling, all her movements a mirror trying to show me the way home. For the first time in a long time, I felt hope.

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