After winding down my startup, I’ve regularly found myself in states of reflection and contemplation. Some of it is self-imposed, but the majority of the self-reflection has been instigated by others: how do you feel? what are you going to do now? what went wrong? are you going to try again? Although the pains of failure are fresh, I don’t take offense. People are naturally curious and I find their questions necessary to answer for myself just as much as for them.
But one question has begged for more thought than the others because of its nuance and importance: was it worth it? Was the last two years of non-stop, mind-bending, night-ending, grit and blood and sweat and tears worth it? More than any other question, this one has stuck with me because I want to be honest about it. Also, when I’m asked this question, I figure it more as a recommendation than a quizzical inquisition. Would I recommend this path for you? Would I choose to do it all over again? Or would I save myself the strain, pain, and bank account drain, by choosing the Good Life of a ‘cozy’ corporate career?
After careful contemplation, I can wholeheartedly say that the entire endeavor was unquestionably worth it. Articulating why has been difficult. I received no significant monetary outcome and, if anything, I’ve stalled rather than progressed my engineering career. But at the same time, I feel like a completely different person in the best way possible; different in how I approach professional situations, different in how I handle conflicts in my personal life, different in how I go about trying to achieve something. In many ways, going through YC and starting a business has been a first-class education in How To Get Shit Done and Not Feel Bad About It. It’s better than any MBA, any business class, any consulting gig, or any side-project-hustle1. I’m more confident about every social situation in and outside of the workplace than I’ve ever been in my life. That’s a big deal for someone whose identity is partly based on being INTJ.
I know what you’re thinking: this sounds an awfully lot like you’re falling for the effect described by British psychologist Peter Wason known as “Confirmation Bias”. Or maybe it’s sunk cost, I don’t know - but you get the point.
I’ve thought about that as well, especially since I had such a hard time articulating why I felt my journey had been justified. So, I thought I’d concretize what I learned into this essay as a means of historical preservation, to formalize my belief in the justness of my decision to be an entrepreneur, and to enlighten others about the less measurable benefits of choosing to ‘do a tech startup’.
Here are the top 5 lessons I learned.
1. Bending of the Spoon:
The first, and by far the most important, thing I learned was that the rules, processes, ways of thinking, systems, and beliefs that govern and inform our day-to-day lives are significantly more flexible and open to change than you would think2. This line of thinking is so prevalent in the startup ecosystem that many argue startups wouldn’t exist without it.
I often describe coming to this realization as “learning to bend the spoon”. The spoon, of course, is the rigid rules and processes, perceived or actual, that we use to govern our behavior: social norms, laws, ‘best practices’, standards, career paths, etc etc. You are Neo, realizing that the rules were made by imperfect, and sometimes nefarious, individuals and are therefore themselves imperfect and deserve to be questioned and challenged.
You’re likely very familiar with the implications of this statement on a macro scale. This is present as social upheaval and activism - the many marches and movements that called for unjust laws to be overturned and overruled. But this principle applies on the micro scale as well. Why do you have to spend three years as a junior engineer before being a team manager? Why do you need to go to four years of higher education to pursue a degree in an advanced field?
I’ve learned that the best founders apply this principle to move and achieve their goals at unimaginable speeds. They find ways to get things done quickly that others felt were impossible because the methods seemed too taboo or they were afraid to break convention. For example, Brex founders argued with their own lawyers about the legality of their first credit card product before they launched. Anecdotally, I knew a founder who, whenever he was pushed by his lawyers on some decision, would respond with “Is this jail time or is it a fine? If it’s the latter, that’s the cost of doing business”3.
2. Unhinged, unbridled, unstoppable Ambition
I’ve learned that successful people have unbounded ambition which I would define as having lofty goals plus the self-confidence that they can achieve them. Your n+1 goal, the goal past the goal you initially set, is probably more achievable than you think and is the one you should be shooting for.
This realization goes hand in hand with the first. What happens to your ambition if you assume the goal you thought would take you 6 years will only take you 1? What more can you achieve now? In the same way, if you set an incredibly ambitious goal you’re naturally forced to find ways around the restrictions preventing you from achieving it.
Setting ambitious goals is not exclusive to founders or those in positions of ‘success’4. What I found to be different, and what I was lacking in my life before, is just how confident founders are that they will actually achieve that goal. Every venerable founder I’ve met has a treasure trove of stories and anecdotes about how close they were to failure or how impossible some setback initially seemed. Yet, each of them persevered through means of sheer willpower and the naked belief that they could do it. Of course, it’s expected that these goals might not come to fruition for decades or even a lifetime, but that’s the nature of ground-shaking ambition.
3. Emotions are information
More precisely, the events and inputs that trigger emotions should be observed rationally and often provide great sources of information. This is one of the core theses of Matt Mochery’s entrepreneurship curriculum. I read that book early into my journey and was able to apply and evaluate its teachings over the course of a few years.
What I found is that ignoring your emotions like some Vulcanian archetype is just as destructive as letting your emotions control all your decisions. Instead, as the book suggests, you should let the emotions come, recognize them, and let them pass. I found this often required stepping away from my computer and going for a walk before I was fully reset and ready to rumble. Once the emotion had come and gone, I began examining them objectively: “why did that statement upset me, do I think we should do something else, if so, why?”, “why is my ‘gut’ telling me this is wrong, what would an alternative be?”.
I’ve found this practice most compelling with respect to emotions of anger or fear5, where escalation to a point past civility is not uncommon even in the workplace. However, if you’re like me and are ‘easily excited’ by ideas and suggestions, it can be applied just as effectively for emotions of joy and excitement.
The benefits speak for themselves: fewer workplace arguments, better empathy for your coworkers, and more rational decisions. Of course, you don’t always have the luxury of ‘letting emotions pass over you’ such as in situations demanding prompt input. But I’ve found you often have more time to respond to a fiery comment or inquiry than you would think; just because we live in the age of instant communication, doesn’t mean that every response should be instant.
The longer I practiced, the more easily I could recognize when I was feeling an emotion and begin processing it. Over time, I was surprised to see this did far more than just help me prevent unnecessary escalations, it made me less afraid of confrontation entirely. When I approached uncomfortable conversations with the promise of feeling-then-releasing associated negative emotions, I noticed that they never seemed to be as bad as I initially thought.
The value of that realization cannot be understated. Life is full of uncomfortable confrontations or social situations and the best founders learn to get comfortable with them reaaaaaalll fast. In fact, I’d argue a large part of the job is intentionally placing yourself in these uncomfortable situations: firing, resolving workplace disputes, confronting underachievers, asking for the Big Bucks from prospects, dealing with unhappy customers, etc. The longer you avoid those situations, the more drastically uncomfortable they become. Learning to identify them and how to appropriately handle them by leveraging my emotions rather than letting my emotions control my behavior was instrumental in surviving the last two years.
Although founders and those in leadership positions most likely find themselves in these situations more often, I doubt there is a single functioning member of our great society who doesn’t regularly find themselves in an uncomfortable social situation. Common ones for the demographic reading this article might include: asking for a raise, negotiating, confronting a coworker about undesired or uncomfortable behavior, mediating a discussion.
Next time you find yourself in a situation of high emotion (either positive or negative). Try hard to acknowledge the emotions you’re feeling, step aside and let them pass, and then approach the situation again.
4. Ask
I’ve learned that the vast majority of people who are accessible via email, phone, or the internet are far more receptive to talking with you than you would think.
A well-crafted email, Twitter DM, LinkedIn connection request, or other outreach method can unlock opportunities and doors that you would have otherwise assumed to be closed.
Many of the most influential people in their respective fields are eager to converse with and meet equally enthusiastic people, especially newcomers. I’ve learned that if you can effectively communicate your enthusiasm about something to someone who is equally enthusiastic, they’re almost always willing to at least listen to what you have to say.
Where I’ve personally failed the most, and seen others fail the most, is “effectively communicate”. At times, I felt a boiling ocean of enthusiasm, seeping through every pour, consuming every late-night binge session, dominating my dinner-time conversations, only for that enthusiasm to be transpiled as a gentle whisper when communicated via text. Over time, I’ve gotten better at articulating how I feel about something. In part, this is just a matter of becoming a better writer. But it’s also about learning to show enthusiasm through other means than text. This could be a video, a small GitHub repo, a demo, or another that shows considerable time and thought went into that particular email.
The best founders I know apply this in all sorts of situations. Most commonly, I’ve seen it used to acquire customers that the company has no right to obtain. A carefully crafted and creatively constructed email can get most people’s attention. Assuming the intent and contents of the email are relevant to the reader, a conversation is bound to be sparked6.
As I’ve begun applying this to my personal life post-startup, I’ve noticed a huge variety of doors that I assumed to be closed last time I was job hunting are actually slightly ajar.
5. The Founder Uncertainty Principle
The last important lesson I’ve learned is how to get comfortable making decisions with imperfect and sometimes nonexistent information. I wouldn’t say being a great entrepreneur is like gambling but I wouldn’t scrutinize the comparison either. In fact, many VCs I’ve met encourage -and even praise - founders who are willing to make ‘big bets’. Of course, much like Vegas, the praise often only comes when the ‘big bet’ actually works, but that’s irrelevant.
On any given day, a founder might be tasked with making some indelible decision - one which can have tremendous unforeseen impacts on the entire operation. At these times, you’re often faced with a tradeoff: wait and observe, collect data, and delay or act quickly before competitors7. As your organization grows, more capital and livelihoods hang in the balance making the decisions ostensibly even more important. For the uninitiated, such as myself early in the journey, it can be daunting and even suffocating to make a single important decision.
What I’ve learned is that the best founders develop their own tailored concoctions and procedures for unblocking themselves in the face of uncertainty and indecision. This might be retreating to deep thought, consulting with trusted advisors, running quick experiments, trusting their gut, or some combination of all of the above.
Like a vice, they learn to squeeze every ounce of information and confidence from a problem such that they can, hopefully, declare their decision with more certainty than they initially had.
Now, at the end of my journey, I’ve learned to embrace and accept that life is full of uncertainty. Decisions need to be made and the results of those decisions should be examined rationally with no feelings of regret. I especially try to keep this principle in mind as I prepare to decide what I’ll do next.
If you’ve never had the opportunity to go down the founder path, or are perhaps in a position where it is impractical or impossible, then I hope this list serves to enlighten you about some of the principles and values you learn while starting a company. If you’re an experienced founder, I hope this was a refreshing distillation of many key points and topics you already knew.
Of course, if you disagree, (preferably vehemently, otherwise - why comment?), with the inclusion or exclusion of anything on this list then please don’t hesitate to comment.
Honorable Mentions
Other valuable lessons and life skills I’ve learned that I didn’t feel compelled to include in the final list above. Maybe because I ran out of energy after writing #5, maybe because I thought the article was getting too long, or maybe because I believe that forcibly excluding items from a list ensures that only the most important ones remain. Probably all three.
Bias towards action because action creates information. Another well-documented and repeated phrase in the YC community. The best founders start from nothing by doing something. It doesn’t have to be the perfect first step, it just needs to be a step.
The power of No. No and Yes are the most powerful words in the English language and should be wielded with extreme caution and precious. Protecting your time and being diligent about what you commit to is crucial to achieving an ambitious goal. Annie Dillard once said, “How we spend our days is of course how we spend our lives”. I believe that wholeheartedly and I’ve learned to be very careful and protective of how I spend my time. I’ve done this by simply saying “no” to things I don’t feel extremely compelled to do.
The greatest cost: Sunk cost. Sunk cost is one of the most powerful fallacies plaguing any great do-er. Learning to throw away months or even years of work in the pursuit of something better is instrumental in ensuring you’re only working on the most important things.
Persistence is worth 30 IQ points. There’s a common saying in YC: “More startups die from suicide than from murder”. The general ethos is that you’re more likely to give up than you are to be edged out by some competitor8. Having an undying passion and confidence in the fast of repeated failure has been mentioned multiple times throughout this article for good reason. Sometimes you just need to keep going9. Why? I believe the answer is twofold. First, any success, business or otherwise, will have an element of timing and luck. The longer you pursue one idea or goal, the higher the probability you have of eventually encountering a lucky break. Second, the longer you stick to one particular goal, the more you learn and the better prepared you become to achieve that goal.
Of course, I’m speaking only about my situation (a former engineer from the Bay Area starting a SaaS business). There are plenty of good reasons to pursue something like an MBA if you’re not in my situation. In fact, any reader should understand the biases and privileges I’m writing this article with since they’re implicit throughout.
This loosely corresponds to Sam Altman’s “Be Willful” advice.
Let me be clear - there is, of course, a line. I’m (mostly) not advocating for breaking the law and the founder in question never did anything that would harm or swindle someone. But understanding that the rules of society aren’t as ridged and unchangeable as they appear is a fundamental first step to changing them for the better.
I’ve used that word ‘success’ a lot now but I have mixed feelings on what it means to be successful and how success should be measured. Perhaps an essay for another time.
It’s worth noting these are the only one’s Matt actually calls out in the book. You should read it, it’s a good book.
I’m intentionally speaking in broad strokes. There are many factors that go into someone viewing and reading your email such as if it went to spam or inbox or if they happen to see it at all. But, on average, and given that you follow-up enough, I stand by this statement.
It’s obviously not as black and white or nearly as drastic as I’m painting it to be. Decisions can be undone (after all, not every decision is a one-way door), but these choices do compound and can have real effects.
I actually don’t think it’s entirely true as your competitors and your desire to keep going are not independent variables. If you’re in a crowded market where you feel constantly beaten by others, you’re less likely to want to continue. Or, as in our case, you’re in a crowded market that you don’t feel is big enough to sustain all your competitors and you spend more time articulating why you’re different to your prospects than you spend showing them the product (but maybe that’s a separate issue entirely).
Knowing when to stop going is a whole other can of worms I’d love to write about soon.
Great read! Distilling your founder experience as a crash course in decision making under uncertainty is compelling. Thanks for sharing!