Time Machines and Identity

Sometimes I am struck with a brief and rare mental moment of clarity and introspection. I stop and wonder why I’m doing something and where I’m going with things. I think to myself, who am I and what have I become? What is my definition of self, am I still the guy I was several months ago, or even a few years ago when my life was in the throes of a funded startup? I think I know who I am, and I try to make that consistently clear to others: I’m an entrepreneur who loves to do what he wants to do. Someone who is driven by passion, someone who is not afraid to commit time and money to try something and fail, and someone who is not afraid to get up and try again. People know I’m a techie, they know I’m a metalhead, but they may not know what those mean, at least to me. They may not know of my undying hatred for Apple, my happiness with Microsoft and Blackberry, and my disdain of mobile phone use in general, nor may they realize that the metal I listen to is something that would never fit into what they think is metal (or even realize it’s existence).

I think I am someone who is afraid of time machines, the kinds that will suck my life away and leave me with nothing but a few dots on a time map that are utterly unimpressive. Yet in my quest for passion and promise, I am in essence seeking a time machine, one that carries me forward faster than ever, but with a different set of predilections and results, one that gives many dots on the time graph, those that would take others years to accumulate, if ever, and to be lost in flow and end up with a giant prize at the end.


If you’ve ever worked as a wage-slave in corporate hell, or lived a few years too long in your hometown flipping burgers, you know what a time machine is. You may not recognize it, you may not be aware you are riding in one, but if you ever step off to introspect, you will realize you were in one. I think though, it is all relative, for you need to speak to someone who hasn’t lived in the accelerated time sphere, whose hours were your seconds, whose years were your months. Being on either side and talking to the other can be a shock both joyful and sad, one for the realization that you can change the future going forward, and sad for the past lost to nothing. But this of course ties deeply to identity. If you have no ambition to be more in the way that I do, or an entrepreneur does, then living your life, just being, is the final end game already and you’ve truly lost nothing if this is your cause. But for those with ambition, it can be incredibly sad to see that the yearly highlights of your friends include getting a dog and switching apartments before falling to silence in your annual catch up. You can describe more that has happened in 2 weeks than what has happened in their last year, and you have forgotten more action and learning than you can recall. Different lenses, different priorities, different relativities. In the same lens, when I compare myself to those peers in my entrepreneurial cohort who succeeded when I failed, who now run multimillion dollar operations with 50+ people, I think, what have I been doing? Are he and I truly the same? Did we not start in the same spot? I thought I was moving faster than ever, and yet here he is, knowing and experiencing more than I have much faster and on a much grander scale. It can turn a man bitter, it can cause fuel for hate, envy and disdain, while still having respect, and knowing that it could have been a simple flap of the butterfly’s wings that reversed our positions. Relativity.

We seek what we are, and we believe what we do will define it, but much like poor product definition, we try to fit our actions to our belief, as the entrepreneur shapes a user’s feedback into what they have already built.

This journey has guided me astray at times I think, away from the upwards of where I wanted to go and who I wanted to be, but I’ve realized that you don’t have to be the best or at the top to be successful or happy or to have the lifestyle that you want, you just need to find the plateau along the winding mountain climb that gives you the living that you will be most happy with, and that plateau may be a completely different type of business then the largely funded startup you see at the zenith. It’s too easy in the startup game to seek big investment, to want to raise that Series A and shoot for the IPO or 9 digit exit without consulting yourself first. It’s what everyone talks about, it’s what everyone reads and it’s what every startup/business twitter account tweets. I hate TechCrunch, yet I cannot unfollow for fear I might miss out on something new. I find my disdain grows more and more as I see shittier companies, ideas and people raise massive rounds with less than what I had. It makes the claws in the back of your brains swing harder and faster forward, it makes you feel like you are behind and need to panic quickly to speed up. It doesn’t encourage you to peek under the veil to see the real truth of the deals, and like poor statisticians that we are, we are leaving out the millions that failed, only to see the 1% that succeed. Much like how on Facebook, everyone has big events but you, but what we are seeing is a collection of rare events per user andstacked together in such an amount that you feel left out. Survivorship bias.


I feel as an entrepreneur that success is whatever will make me happy, the most free to pursue what I desire, and not chain me to my email and an airplane, thus it doesn’t make as much sense at this time to jump into something that requires a lot of money to successfully grow and run. Before I found out what a startup was, that it was even a word, I had already tried to start several businesses and failed, many of which were local, small or Internet only. I know deep down that what I truly am before a startup entrepreneur, is an entrepreneur, and sometimes it’s easy to confuse the two. In truth they are much different and there are varying degrees of what comes in between, but I believe now that I have dialed it back from full startup to straddling the line as I learn, take my time, and focus more on what success means to me.

When it comes to identity, people always ask me what kind of startup I want to make, like it matters or drives or defines me, like I’m here because of some single problem. I always disappoint and confuse them when I say it doesn’t matter, I just want a good business opportunity that is fun to exploit, because that is where I derive my pleasure. If there was ever such a satisfying non-answer. “He’s a gamer, so he must want to do a gaming startup”, “Why are you doing hardware now, I thought you made games”, “Real estate? What’s that got to do with you, you don’t seem to fit”. I’ve discovered that it definitely helps to have some passion for the industry, or at least in ruining it, enough so that you want to work in it, otherwise you are trapped in another lame SaaS business market that you hate. I have nothing against those who come to entrepreneurship for the sole purpose of defeating some problem, they are some of the best and most successful entrepreneurs, but for those who don’t make the cut, do they stick around in this world? I thrive in this world and have known many failures, some of which I still recall randomly and think to myself, holy crap I was so obsessed with that idea and spent 8 months on it, but until this trigger it was completely erased from my mind. I do this because I enjoy it, because I don’t see any other plausible path for me, not because of some particular itch. I can also be jealous of those with such direction and conviction, but knowing it’s such a double edge sword keeps me in check. Riding the line being in love with your solution to your problem vs what a customer needs is why most companies fail, and those too gungho on their solution, and whose solution isn’t the right answer, are the ones who fail tragically.

On time machines: they are your friends and your foes, and flow is just the medium that takes you forward, it does not judge. Make sure that you that you spend your flow on something you enjoy, make sure it has some legs or at least a strong learning opportunity, or else you are just killing time. Another year at big co will teach you 5% extra. One month on your own will teach you 1000% extra. It’s hard to understand until you do it, and most people won’t believe you when you tell them, but we all know it’s the truth.


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