I’m a Startup Felon: The System Sucks

I’ve written here before as I find it’s a great place to vent. I don’t really surround myself with very startup-ish people as I’ve kind of always just done my own thing — you know, “entrepreneur”.

I’m so frustrated at the system though. Not VCs or anything like that. Just this (United States) country.

See, I’m a felon. I’m 25 now, and I was originally charged with this horrendous violent crime when I was 18.5. I bought pizza with a corporate credit card.


I plead guilty when I was 21 because that’s how god damn long the system takes. I’ve “rehabilitated” myself. I’ve become a “productive member of society”. I’ve had two “startups” (I’d refer to them as companies, but whatever) — one was when I was 19 turning 20, the other was when I was 20 turning 21.

Both were in the hosting industry, both resulted in successful exits.

define successful: I paid my employees a bonus, helped my mom out, and disconnected for a few days. I ended up with a net gain.

I then wandered out east and out west — with the felony. I had a co-founder who (literally) gambled away our entire check before we even finished signing papers. It was a mess, so that concept got thrown out the door while he got laughed out of the room.

I rolled my eyes as I stayed behind to try to reason with the other side of the table.

In 2013 I started a little dev shop/agency. I like to think of myself as an entrepreneur/MBA that happens to code at a fairly competent level. I brought along someone who was great at design and equally great at sales. In 2014 things started to really take off — we hit seven-figures in revenue with 14 remote employees.

I didn’t pay myself enough because I had to buy the respect of the very senior people I was working with, who (I imagined) would otherwise find it hard to take direction from a kid. I also didn’t close the sales. I tagged along, but I definitely was not the person managing the relationship. Understandable.

My co-founder who steered that wheel passed away in a car accident Q2 2015. I folded up shop since I couldn’t really do it without him. It just felt wrong. I placed my employees with clients, and they were very happy.

I wanted to place myself with my clients, but unfortunately they were all BigCo or Big-gerCo, and I didn’t want to put the people who I had worked with in any kind of had they taken a chance on me. One time I sort of did — a guy put his neck on the line for me. When someone found out about my history — who didn’t know, a developer actually — they lost their cool and treated me like the devil from hell. That exec was outed. As was I. Even though HR passed it, the CTO passed it, the CIO passed it, and I’m certain the CEO was involved as well.

“We can’t have this resonate throughout our company and the excellent culture we have worked so hard to create.”

My mom got sick, and the $200k I had saved over 4 years went down to four-figures. Nearly three. I love my mom. She hasn’t always been the best mother, but she’s always been my mother, and despite her shortcomings and diseases, she’s my best friend. She doesn’t know it, but she is.

In reading this[0] I think to myself “how can I get myself one of these jobs” — but then I remember that I’ve tried, and the cards never seem to fall my way. I absolutely kill interviews, given you don’t need me to whiteboard or quiz me on the lingo that you only learn at MIT while getting a PhD in CS.

But then the background check comes up. “Nope, can’t pass”; then it’s a Google, “oh, a bunch of mugshots. Look here, went in on probation violations[1]”

Let’s not mention how hard it is to find a living situation in Minneapolis when you’re a felon, and when you really don’t fit in where other felons live.

My felony is not me. I was on CNN, for fraud: I talked with the news-desk-lady-thing on live TV about how ISIS producing fake passports is only the headline to a much larger story about ISIS’s ability to fund their group. I helped Target and Staples discover who and how and what happened with all their customers’ data. I helped Uber go from the top money laundering app on the marketplace to where they are today.

I’ve worked my ass off to get to this point and all people want to see is a piece of paper. Or the piece of paper that I’m missing: a degree. Dropped out of Caltech and Georgetown because, quite frankly, I’m a terrible fit for the current education system.

I’ve reverse engineered multiple billion-dollar companies tech stacks (and made appropriate, responsible, and timely disclosures to their proper departments). I even offered one of them an implementation to use as they pay their developers 50% market rate and can’t figure out why they can’t attract talent.

I’m an honest person. Sometimes too honest. My mind runs a million miles a minute. I’m a kind person. I’m a thoughtful and genuine person.

Unfortunately, all this system sees is the f-word and it hurts, discourages, and belittles people like me who have worked their ass off to show the word that they aren’t what it says on paper. Because, in this country, and in this system, do we only want people to be glued to their convictions.

Share your story with me personally or in the comments. I’m sure I’m not alone. I can be found at (anonymously) sathesystem[at]gmail

[0] https://news.ycombinator.com/item?id=12336661
[1] stupid system that wants to keep you around as long as possible for as petty of reasons as they get, like “sorry, but we couldn’t print off your file for court so we’ll reschedule your hearing.  …. oh, we know you’re here, but we’ll just put out a body warrant for you when we want to see you next” (twice)

  • Some of what you say could be affected by a medical condition called bipolar disease. I’m not saying you have it, but you have some elements of grandiose thoughts, and talk about “My mind runs a million miles a minute”.

    Please consider making an appointment with a psychiatrist, and discussing these aspects of your personality with them.

  • I think that you overestimate yourself a lot. You do everything right, but sadly, the world is a shit and everything goes wrong? Wake up, dude. You are a felony? Well, I guess that compared with the rest of the world, you walk with very comfortable shoes.

  • This is something that affects me also put myself in a bad situation 11 years ago and now creating businesses is an employment strategy for me because I can’t get past a background check.

    I understand the large corporations viewpoint on this so am not suggesting forcing them to change, just hoping that at some point for understanding that sometimes people are not their criminal record.

  • Start talking with a lawyer about getting your records sealed and if possible eventually expunged. I have a felony conviction from years ago and it really hasn’t affected me that much. I work as a state employee and am open and honest about my past transgressions. Additionally after 7 years your criminal record becomes less of an issue with many employers. The big thing is don’t lie, be open and honest. But I’m also lucky in that my conviction was for marijuana and I’m a white educated male.

    Additionally I think you should get mental help, you portray things with a victim mentality/attitude. If your skills and talents are as you proclaim then you should be able to setup your own freelance site and make mad loot being a consultant. Setup an LLC and use that as a way to get your foot in the door. If a manager/client sees you have the skills and like you they will back you up. The advantage of being open and honest is that it gives the other side info to decide right away if they want to take a chance.

    Your crime and probation violations are pretty minor. People that get labeled as sex offenders, assault chargers and other harsher crimes get screwed way more. Also consider working with a recruiter, as much as I dislike most recruiters in your case you might be able to find one that has connections to companies that don’t give a hit about many past convictions.

    Also you are in tech, being a convicted felon in tech isn’t as bad as having that record and not having skills.

    • This guy knows what he’s talking about. Get that record cleaned up and push forward because you are in the tech sector! Your future is really bright, my friend!

      • Given the credit card aspect, it’s very possible his conviction was federal and there is only one way to “erase” those: a Presidential pardon.

    • I’m not sure which state you live in, but have you thought of trying to get your record expunged? Check with your local police department, or, hire an attorney if you can afford it.

      Good luck!

  • I used to be You. I spent most of my late teens doing things that im not proud off today. But that had to do wth my situation at the time. Not the person i am. I will dropp you a line on the email.

    Take care.

  • I earned a federal F – I have my own business & cofounder of a somewhat successful startup. You can’t clean your record. What you can do is take control of your life and stop trying to work for small minded people and corporations. You describe yourself as intelligent yet you want so badly to work for and enrich those who you claim unfairly judge you. Why would you want to work for people more close minded than you are? Why would you want to be a cog in a system that you know sucks?

    Describing yourself as a victim does not make you mentally unstable as some commenters suggest, it just makes you emotionally immature. But then again, you are only 25 so that makes sense. Oh yeah, and get the fuck out of Minneapolis. You need to be somewhere progressive, you are a federal felon. Shame on you for letting the outside world define your worth and mind state. You don’t live in the world you make it. Look in the mirror you are an adult, you build the world … that shit is up to you.

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