My confidence is lost.

In late 2013, I moved from San Francisco back to my home state to help take care of my ill mother. She’s still ill, but not as bad as she was. I was 22 at the time. I left with six figures in my bank account. Life was good, my mother’s health notwithstanding.

I’m not anything special on paper. College dropout — the number of credits I’ve earned I can count on one hand. I haven’t worked for any big startup. I don’t author any awesome OSS projects, I barely contribute to OSS. I have two exits under my belt (one at 18, another at 20), but they didn’t even deserve a press release. I market myself as an entrepreneur that happens to be technical.

I’m now down to about $1.5k, and I spend my money very wisely. The majority (calculated to 88.41%) has gone towards my mother’s hospital bills. I don’t drive a nice car; it’s a 2006 Mazda3. I love her. My total monthly expenses are less than $1,900 — that includes groceries, insurance, utilities, internet, phone bill, etc.

In 2014, I started an agency. We quickly blew up and did $2.1MM in revenue with only 9 people. Q1 2015, we were on track to do $4.6MM. My co-founder — design/sales to my biz/back-end — was involved in a tragic car accident. After about a week of drinking — I mean thinking — I had to wind things down. I closed up shop on the 1st of this year after. I placed my colleagues in great positions with clients.

The last week of December, I was stiffed for a $50k+ invoice. I’m now playing debt collector. Paperwork’s nice, and counsel is great to have, but some people just suck. That $50k was supposed to get me by while I look for a gig.

The logical thing to do would be to integrate myself into my former client’s companies. A felony conviction doesn’t help you there, even if the charges are 7 years old. Even if you’ve turned around since then. Even if you’ve consulted on CNN talking about the exact subject you were convicted of: fraud.

I’m frustrated with my job hunt. I can’t relocate from Minnesota. I’m not senior; I’m a very competent mid-level. I’m really comfortable with Ruby/Rails and the full-stack, but I’m timid to make a move to another language/framework because of how comfortable I’ve become. I’m incredibly business-minded, and it’s easy to recognize. I’m extremely easy to get along with.

My cat, whom I call “momma” or “izzy”, is amazing. She’ll be 19 in may, had offspring when she was 2 years old. She was indoor/outdoor for 12 years because as we couldn’t keep her inside. She’s still kickin’. I love her.

I’ll talk about my cat next time.

When it comes down to it, I humbly bow my head and mention that I can’t pass a background check because I did stupid shit when I was 18. I’m now 25 years and 1 week old. 

I digress.


  • You don’t need references, or background checks, to stay an entrepreneur. Get some Rails gigs remotely. Do it for 6 months – make good money and rest. Consultancies can be great, and go bad quickly – most don’t study the actual methodologies to running a great consultancy (e.g.: the big consultancies like IBM, PwC, Deloitte) stay in business because they’ve refined the model.

  • Ciao!

    I wish you the best in the future.

    When you will be able to relocate your perspective will change.

    Connecting People,Moving Forward.

  • You are definitely talented and need to get your confidence back. You are in a prime age, not too young and some good experience to propel you. I am sure you will find a nice place to land soon, just keep doing what you are doing and the winds will go your way. Read James Altucher for some crazy biz stories and to avoid going down his same path.

  • Well done for achieving so much by the age of 25, back then I was still working 15+ hours a day for someone else. It’s very easy to under-estimate what you’ve achieved. Don’t.

    The majority of people are consumers, you however are a creator, you did it once, twice and you can keep doing it. I had similar pressures of looking after family and paying off debt, you just need to realise these issues are temporary but your success is permanent… as long as you keep going.

  • You already know how to make money, that pushes you way further in the curve than you’d think. Try to use the freelancing marketplaces around, a google search here and there and you’ll find them. Learn the MEAN stack, with a Sails.js variation instead of Express.js if you are used to RoR. On the felony issue, you are blessed, since you’ll never be able to work for anyone, you are your own boss, accept it (you are the only one who can save you, no one else).

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