I don’t think I could survive in any other context than what I live in now, and it scares me because sometimes I don’t even know how I’m doing or what I’m doing.
Disclosure: This is more of a rant than a story; my mind is all over the place, as is my thought process and writing style. Please bear with me.
I’m an entrepreneur that has somehow rocked the boat with a pair of lucky exits. They’re nothing to write home about, but I did make a nice chunk of change. Both were in the hosting industry when I was 20-turning-21.
When I was 19, 4 years ago, I got into a bit of legal trouble and was (gifted) three felonies. Nothing life-threatening — security-related stuff mostly. I didn’t do any time, had less than $1k in restiution to pay. Had to do some community service but that was it.
It hasn’t hindered me on a serious-enough level to really write about it. The only thing it has really hurt is my housing situation, however I’m usually able to find a way around it. But regarding my paper: It’s scary because I think that, if someone decides to lose it at me (for whatever reason), they’ll bring that up and promptly terminate my hot streak. I’m very candid with what happened, and it’s always one of the first things I bring up when an offer is about to come my way. “Just an FYI, there’s no way in hell I can pass a background check.” “Why not?” “Well, when I was 19, I …”
I didn’t mean to hurt anyone, financially or emotionally. I had hit rock-bottom and I was just trying to survive. Trying to live. Trying to feel normal in a middle-class family where everything else went right, except for me. I didn’t have a place to go mentally, or emotionally. I was a black sheep.
I did one semester at Caltech and then dropped out. I couldn’t afford it — out-of-state or in-state tuition (from Minneapolis). I wanted a fresh start, but I didn’t realize what I was up against. I had plans to major in Neurology, and looking back on it, I should have done something with CompSci. Why didn’t I? Everyone who ever told me I was a whiz with computers, I just disregarded as “they just don’t spend enough time with me; they’re smarter than me, just not as devoted.”
It was a confidence play.
I have never participated in a user group of any kind. I don’t submit to OSS because I just don’t think that my code is good enough. I’m not an expert programmer at all, but I can figure shit out. I’m not an expert marketer, but I can break down campaigns and products. I can write ad copy, but it’s as free-wheeling as that of early-Groupon’s copy; before Groupon turned into a complete shithole.
I market myself as an entrepreneur who just happens to code, or the tech version of Baseball’s Utility Player. However, I try to use entrepreneur lightly because I haven’t created Facebook. I don’t have self-made success like Atlassian. I didn’t sell something to SalesForce. And while I have done okay, I just don’t know. I have the gusto, mindset, curiosity, creativity, and endless drive of an entrepreneur though, which is a good take-away.
Again, confidence…
I’ve turned down jobs. Amazon, Google, and Tumblr all came to me and tried to get me on board. When it came time for the offer, I couldn’t comprehend what they were trying to say, so I said, no thanks. I don’t know why I did it. The self-starter in me just couldn’t justify the fact it was happening. I didn’t want to be compared to guys who had been committing to huge OSS projects like Rails or Memecached either… because I’m not one of those, and even though I may have passed the tech interview, I was convinced it was because I had a likable, loose personality that’s always upbeat.
I’ve sat next to Mark Andreessen in meetings, and he has phoned me more than a dozen times to me to get high-level feedback about x, y, or z. I find him flattering, and he finds me insightful. It’s a good takeaway, but no matter what, I still feel like that puppy that everyone wants to pet because it only has three limbs to walk on.
I have all four (+1, as a male), don’t get me wrong.
My mentor, who has raked in over $400,000 since he was 26 (now 39), says that one day I’ll be hiring him and he’ll be working for me. People almost always say that I’m the smartest guy in the room, but it depends on how I use my intelligence: how I filter and channel it.
Everyone thinks I’m smart, and I just think I’m curious. I’m curious enough to figure things out. I’m curious enough to make an exceptional living with a beaten, rough past. I’m curious enough to want to yearn towards greater goals and aspirations.
I just think I’m me. While other’s opinions are taken gracefully in stride, and gratefully recipricated. That’s great, but when it comes down to it, I’m just confused.
But what if this bubble bursts?
I’m scared. I’m scared for my future. Optimistic, but scared. I know I’ll always have a job one way or another, don’t get me wrong.
The future freaks me out.