Why Systems Eat Information for Lunch: A 15-Year Expedition
Updated: Aug 9
The presence of fear (false evidence appearing real) is inherent confirmation that this is the right thing at the right time.
My grandmother taught me that the right thing at the wrong time and the wrong thing at the right time are both the wrong thing. The goal is the right thing at the right time.
Allow me start with a confession. I almost didn't write this. Not because I lack meaningful information to share. I have fifteen years of hard-earned experience to share. As a rather private person who takes extraordinary measures to be obscure, sharing my writings give readers insight into my deepest thoughts. Historically the mere suggestion of sharing my thoughts paralyzed me. For weeks after deciding to take the leap, the overthinking part of my brain worked overtime to convince me that someone else, anyone else, was the right person to say them.
I wrote three drafts and deleted two. I sat on the final version for longer than I'm comfortable admitting before finally deciding that confronting the fear of imperfection is the whole point of this exercise. Then like sunlight in a dark room, I had an epiphany. There is absolutely NOTHING to fear. My overthinking brain pivoted and reminded me that the presence of fear (false evidence appearing real) is inherent confirmation that this is the right thing at the right time.
So here we are.
How it Started
When I made Silicon Valley my home, I came filled with ambition but had no idea what I was doing. One hundred percent, genuinely, and embarrassingly no clue. Fear was not a part of the equation. Much like a mad scientist tethered to a lab, I was driven by an insatiable obsession to democratize the innovation process at any cost. My efforts predated AI, so Googling was my only recourse. I spent hours searching for answers to questions that I was too afraid to ask others.
Eventually, I sought guidance and expertise beyond my own reach. I found a community of people who I knew were in the same canoe. Contending with the insecurities of admitting what we collectively did not know left us rifting on our vision and not execution.
After a few months of rifting, or as we call it today vibing, I made three key connections that forever shaped the base of my knowledge and understanding of the systems that steer the tech industry. The irony is they are all men, pillars of Silicon Valley, with diverse social views, cross spectrum political ideologies. In contrast to some prevailing ills of our society, my morphology or given form matters not an iota to either of them. They often ask how they can be supportive of my endeavors. My answer is and has always remained the same. Teach me what you know. I have learned a lot. I have also learned that no matter how much I learn I can never know the depth or the breadth of wisdom that their millions/billions of dollars and years of success have taught them.
I recognize how privileged I am to garner their wisdom. Consequently, I also recognize how much more of a responsibility I bear to pass it on.
The Work Was Never the Problem
I am an INTJ, naturally an introvert, who can be somewhat socially awkward. I am highly effective in small groups (four or less) and one-on-one, and through years of exposure have learned to successfully navigate large gatherings.
Before I knew what it was called, I knew that leaning heavily into hard work and getting the task done was one way to inoculate the challenges created by my social awkwardness. My commitment to hard work is something I'm genuinely proud of. Not in a humble-brag way. In a "this is my reliable thing" way. When there is a problem to excavate, a system to untangle, a mess to make sense of, I am in my element.
I truly love the hard stuff. I like being in the trenches. I like figuring out the hard things.
What do I struggle with? Well, everything else that is on the periphery of the work.
The visibility game.
The social media following.
The personal brand.
The conference circuit of nodding along to talks that are sixty percent slide templates and forty percent explaining repackaged decades old thought leadership. The relentless performance of expertise that tech culture demands, where you're not just good at your job, but also loudly, publicly, constantly, on every platform, forever good at your job. I failed at this part massively. In the past it felt overwhelming to even think about the visibility game.
Visibility often matters more than successful results. Who knows you matters more than what you can do. I missed that memo for a long time. And if I'm being honest, part of me still shutters in discomfort at the thought of it. But reasserting what is intrinsically true, to thrive in tech it is imperative to operate outside of what feels most comfortable.
So, I perfected my socialization skills. I navigated all the conference circuits, coffee meetings, parties, hangouts etc. At the end of each day, I retreated to solitude to regather my strength. Just as I mastered the art of socialization, the Covid lockdown happened. Santa Clara County was the first in the U.S. to mandate quarantine and Silicon Valley became the epicenter. Amid the contentious debate over lockdown, it inadvertently became a temporary reprieve for us introverts. I could do business from our fortresses of solitude, absent the social commitments. I would turn our cameras on, work, turn our cameras off and retreat. The lack of social contact bothered me less than most. The downside is the progress I made to maximize socialization was all unraveled by quarantine mandates.
There were some small wins during Covid lockdown. I penned the first part of a three-part fantasy series, learned to make authentic sushi rice, and begin organizing all the knowledge I gained about tech culture and systems into a library of resources. This exercise opened my eyes to how my peers and I were often being misguided by people with great intentions, but who barely knew more, in some cases less than we did. The "I have no idea what I'm doing" experience I later realized was not a personal failing or a gap in my wiring. It is, by most accounts, the default state of anyone who has ever tried to build something in tech for the first time.
The Mistakes (Just the Greatest Hits)
I've made a lot of mistakes and when it comes to mistakes, I am no one-hit wonder. Of course, there have been moments where I lifted the trophy, but the playlist of mistakes vastly out number. The losses, ironically, have been far more instructive than basking in the fleeting glory of the wins. It would require a multi-volume work to share an exhaustive list of missteps, so I will focus only on the greatest hits.
Hit 1: The Ride or Die (Lingerer)
I stayed too long in situations that weren't working, convinced that if I just put my head down and worked harder, the results would speak for themselves and open doors for me.
It didn't.
Hit 2: The Yes Person
I assumed good intentions too quickly, gave away my time too freely, and extended trust too broadly. A few people took real advantage of that. I became more cynical than I should have, and it took years to recalibrate back to something like healthy skepticism.
Hit 3: The Imposter Syndrome Queen
And then there's the imposter syndrome.
This one requires much more than one sentence because for me it isn't a passing inconvenience. It is the constant grinding background noise that shaped nearly every career decision I made for over a decade. It was the thorn in my side, the bane of my very existence.
I passed on opportunities because I didn't feel ready. I stayed quiet in rooms where I had something valuable to contribute. I watched people with less experience and less skill take up space with complete confidence. Instead of using it as inspiration, I was mostly left feeling like I was missing some internal attributes others had been born with. The cruelest part of imposter syndrome is that it tends to hit hardest the people who are most qualified to feel otherwise. Competent people often second-guess themselves. Confident people rarely do, regardless of whether the confidence is merited. Tech culture rewards a brand of unexamined certainty that has less to do with actual ability.
My IQ embraced this truth for years before my EQ finally boarded the train.
What I know definitively is this; no one is immune to imposter syndrome. We all doubt ourselves and our capabilities at times. The people who look the most confident usually have a greater capability of masking their doubt, not eliminating it. Having doubt or questioning your ability is often evidence that you are more prepared than those who emanate unmovable confidence.
In short, I learned to limit my missteps with three simple principles:
Exit situations faster than you enter them.
Get comfortable with simply saying no.
Enjoy the journey. We are all finding our way in this life and no one has it all together.
Curiosity Killed The…Startup?
I find "personal brand strategy" absolutely necessary, but also somewhere at the crossroads of mildly nauseating and completely disorienting...
I'm not the popular thought leader with the crisp takes and the speaking circuit. I don’t have the newsletter or SubStack channel with seven figures of subscribers; yet. I've never been the person who networks effortlessly at industry events. In all honesty I find "personal brand strategy" absolutely necessary, but also somewhere at the crossroads of mildly nauseating and disorienting. I once saw this as a problem that required a solution. Now I embrace who I am. This in no way excuses the responsibility for successfully executing a personal brand strategy. As I previously stated it is absolutely necessary. The necessity, however, in no way means that conformity to the status quo is required.
The Founder Dilemma
I'm naturally an inquisitive person committed to finding solutions. When something is unclear, I ask questions until I have the clarity I need to act. The tradeoff of being curious is it exposes the gaps in your knowledge and understanding to others. The performative confidence that tech culture demands tend to bear a limited tolerance for genuine curiosity. So, I learned quite early in my tech career to be measured. I find this contradiction difficult to reconcile at times; given the curious mind is often esteemed as the true alchemy of Silicon Valley.
Like most who invest or advise tech companies, I began my career as a founder in pursuit of the alchemy of Silicon Valley. As a first-time founder, I knew very little about how to navigate the ecosystem. The meaningful connections I made helped, but there were limits. I often found myself operating on the knife’s edge of what I knew, versus what the ecosystem expected me to know, versus what information I could garner while being measured in my curiosity. What the ecosystem expected me to know was never delivered in a clear system that made execution on the expectations ever seem approachable. I never desired someone to do it for me. I never wanted someone to decide how I should do it. I simply wanted access to systems that would empower me to direct and decide what to do to meet the expectations.
Most founders at some point in their journey are operating well beyond the edge of what they know. They are making decisions with incomplete information, in domains they are still learning, under pressure that would buckle most people. A pressure that is universally understood amongst those who take the entrepreneurial dive. As such, it mints those who persevere despite the obstacles as near superhuman.
So, what exactly do founders do with the uncertainty that comes with living on the edge. The answer, far too often, is they hide it.
Founders hide uncertainty from their teams, because leadership is expected to project confidence.
Founders hide it from their peers, because no one wants to be the one who has yet to figured out.
And they hide it from investors, because the entirety of fundraising performance is built upon the appearance of certainty.
Founders are expected to enter an investor meeting and tell a story of inevitability. They present a world where a revelation of the future has been unveiled to them, where the risks are understood and manageable. Where the perfect plan to achieve success has been identified and the only hinderance to execution is the securing of capital. What founders do not typically say is "I genuinely don't know if this is going to work, and there are x number of foundational assumptions in this model that we have yet to fully validate." This level of transparency rarely, if ever happens although it may be a more accurate statement or depiction. Why, because the ecosystem values virtue signals of perceived strength; perceived certainty over vulnerability. The battle of balancing transparency is far more dangerous that it presents on the surface.
Donald Rumsfeld shared a framework that has since been enshrined in my psyche. In 2002, in a context that had nothing to do with tech, he described three categories of knowledge:
Known Knowns (KKs) | Known Unknowns (KUs) | Unknown Unknowns (UUs) |
"There are known knowns (KKs); there are things we know we know. We also know there are known unknowns (KUs); that is to say, there are things we know we do not know. But there are also unknown unknowns (UUs), the ones we don't know we don't know."
Regardless of your opinion of the source, the framework is exactly right. Unless a founder is a serial entrepreneur, the known knowns (KKs) are infrequent at best and at worst obscure. The reality is most founders are navigating the minefields of the known unknowns (KUs) and the unknown unknowns (UUs)
When founders hide what they know, they don't know, meaning the known unknowns (KUs), left unmitigated it opens a sinkhole primed to be the pit where companies get buried. It is recoverable, but the cost of recovery can be insurmountable. Absent the hesitancy to reveal what they do not know, an investor or advisor with the right experience can fill the knowledge gap. A mentor can identify the obstacle. A co-founder or employee can leverage their skills to compensate for it, but only if there is open communication and transparency. KUs pose a threat to a company's health, but most are common enough that engaging with others in the ecosystem can illuminate fissures or pull back the veil to avoid missteps. As problematic as KUs can be, the cryptic nature of the unknown unknowns (UUs) are malignant.
The UUs are often critical gaps that founders don’t know they have. The market dynamic they have never encountered, the legal exposure nobody flagged. The customer behavioral insights that seem obvious in hindsight, that were invisible until they weren't. These failure pits only become obvious at scale, long after the patterns that caused them are baked in. UUs are the killing field where startups go to die. Not loudly, but quietly. UUs catalyze an accumulation of uninformed decisions that seem reasonable at the time, but in hindsight are obvious. UUs, that if known could have been mitigated. And here is the brutal irony: the culture of performed certainty metastasizes the impacts UUs.
When founders perform confidence they do not possess, they close off the engagements that may surface UUs. The investor who could have asked the poignant question never gets an opening beyond the veil to ask. The advisor who has seen this exact failure mode before has no leading indication that it should be addressed. The team member who noticed something strange stays quiet, because the official story is that there is a plan. The environment enabled by performed confidence accelerates the impact that UUs have on a company's demise. The impetus to portray perfection undermines companies who otherwise might have survived.
There is a real and endemic cost to the company and the industry. UUs are a leading contributor of why failure rates are so high. Ninety percent (90%) of startups and seventy-five (75%) of venture backed startups fail not because of poor ideas, but rather because of poor execution tied to UUs. The culture of performed certainty makes it impossible to address the actual execution errors that lurk behind UUs before the errors become fatal. Let's be sober, advocating for founders to walk into pitch meetings and lead with their doubts would be malpractice. That is not how the game is played, and pretending otherwise is naive. But there is a meaningful difference between strategic confidence and performed confidence.
Answers Are on the Menu
Answers have a shelf life. Systems are nonperishable.
The end goal of an advisor is to help founders develop strategic confidence about the problem they are solving and the viability of their solution. The pathway to achieve this objective requires not only the transparency to identity both the KUs and UUs but also grunt work to implement solutions that ensure long-term mitigation. Typically, when KUs and UUs surface it is in a moment of cure, not prevention. In these moments founders are seeking fast answers, not long-term solutions.
My natural instinct as a problem solver is to simply give founders answers to the questions they are seeking. There are obvious occasions when answers are useful, but there are times when providing answers alone create a long-term dependency. The best version of advising that renders capable, successful founders looks nothing like question answering. It looks like system-building.
“Give a man a fish and he'll eat for a day, teach him to fish and he'll eat for a lifetime.”
This adage is a wonderful launching point, but in practice it still misses something. The challenge is not a lack of specific skills like baiting the hook, casting the reel, etc. Rather, it’s the overwhelming nature of standing in front of an enormous body of water with no map, no sense of what, if any fish live there, no framework for deciding which tools are required to catch a fish, and no understanding of how to locate the best spot to fish. Long before purchasing fishing gear, stocking the cooler, baiting the hook, or casting the line; success is predicated on frameworks and systems that help locate fish based on their feeding and breeding habits.
Similarly, systems help founders identify which objectives matter right now for their company (the right thing at the right time) and which ones are distractions dressed up as urgencies. Systems empower founders to build operational and decision-making frameworks that give companies the agency to navigate through current challenges, the next set of challenges, and the ones after that without dependence on advisors.
The goal of a good advisor working with founders is not dependency; it’s empowerment to operate independently and execute with confidence. Answers have a shelf life. Systems are nonperishable.
Often founders are time-constrained, and they need solutions they can act on imminently. As I first time founder, I found myself there quite a few times. At a time of constraint answers should always be given. It is also important in those moments to remind founders that answers alone create handicaps. The superseding objective of fostering founder independence must be paramount. These moments of constraints are ideal to demonstrate to founders how leveraging systems help companies avoid urgent actions like the one they are facing and the waterfall of undesirable consequences that inevitably follow.
How I've Tried to Help
Flash Fades, Fundamentals Stick
The lessons of the past fifteen years have come from some who have big titles and impressive credentials. A surprising number of the lessons learned did not. The best teachers I've encountered were the ones who while encouraging me through transparency to strive for strategic confidence, were also being honest with me about what they didn't know. The ones who said "I'm not sure, let's figure it out together" instead of promoting performed certainty. The ones who experienced enough hard cycles to know that flash fades and fundamentals stick. More than anything, the biggest lessons I have learned arose from witnessing myself miss the mark. My quest evolved to understand why, not just accept missing the mark as an inevitable outcome.
We teach founders to embrace failure through the "fail fast" methodology, but we fail in teaching founders to embrace the uncertainty inherent to transparency. The people who have longevity in the industry aren't always the smartest or the most talented. They're often the most honest about their limitations and are the most willing to be transparent about their KUs and UUs. This transparency unlocks the systems necessary for success.
Why This & Why Now?
Prior to the emergence of AI, cycles of innovation were compounding at a rate of 10x multiple year over year from the late 90s to 2020. With injection of AI, cycles of innovation are no longer compounding in multiples but are now compounding exponentially. Companies are moving faster, breaking things faster, burning through capital faster, with higher valuations. We can debate the sustainability of the current environment. However, the fundamentals and systems companies need to demonstrate the viability of being a great investment continue to increase as the injection of AI continues to drive cycles of innovation.
For years I was quietly frustrated by the opacity of the industry. How much of what determines success is undocumented, unspoken, and unevenly distributed. There are endless citations, courses, talks, podcasts, shorts, not to mention GPTs that share the information on the success and failures of founders. Amazingly, there is still a gap. It’s not the lack of information. In fact, there is more information than ever. It’s the lack of system building and implementation.
As innovators, creators, scientists, engineers, we are taught to take data and turn it into information. Then to take information and turn it into systems. Somehow, we confine these principles to building our product or delivering useful value to our end user or customer.
Over the past fifteen years I have witnessed PhD scientists, MBA graduates, people with super high intelligence fail at building successful companies. I have watched them spin their wheels not because they are anything less than brilliantly intelligent and not because they lack access to information. Rather it’s the lack of understanding of how to apply the right context, the right systems, at the right time to their company.
I abandoned my fortress of solitude because of an unquenchable obsession with the advancement of innovation and technology. I've spent years accumulating genuinely hard-won knowledge about how the industry works; not how it presents itself. I'd rather put all of this out into the world than keep it to myself.
The legacy I desire to leave is not a body of content, a platform, or a personal brand. It is a genuine, ground-level shift in who gets to participate meaningfully in building the future. That sounds enormous even as I pen it. Maybe it is. But it starts small. It starts with one person finally cracking the code on something that has been needlessly mystified or finding the system that unlocks execution of the next great technology.
Grassroots innovation does not come from the top down. It does not come from the people who already have the megaphone. It comes from the people in the trenches, the ones doing the actual hard work, the ones who may appear to be not quite the right fit for the room they are standing in. This is where the world’s reserves of generational altering innovations have yet to mined.
Why this and why now?
Legacy. Not legacy in the sense of monuments, but legacy in the sense of leaving the path a little clearer for the persons coming after us than it was when we arrived.
I Would Love to Hear From You
Since arriving in 2012 I have openly embraced Silicon Valley's core tenant, "pay it forward". It is now instinctual to water the garden of others and to give back in any way I can. I strive each day to be ever more intentional and to share the many wisdoms I have amassed on this journey. Of the things I have learned about helping founders, the most useful is founders don't need more information. They need guidance in making sense of the information they already have.
More importantly, founders benefit greatly from those who have enough experience and boldness to warn when a path the company is considering could lead somewhere the company would prefer to avoid.
I am a believer in dialogue. Conversations only work if it goes both directions. The whole point of grassroots is that it grows from the ground up, and that means it requires more than one voice.
So, here's my question for you: What's the thing nobody told you when you were getting started, or that you're still trying to figure out now?
Drop it in the comments. Or find me wherever you found this and tell me directly.
This is the first post of what I hope becomes something useful. Not a platform. Not a brand. Just an honest attempt to make the road a little easier for the founders walking it. Stick around if any of this resonated. Either way, I'm glad we made it to the end together.
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