4 Ways Going to Prison Made Me a Better Entrepreneur


From the solitude of prison, I had months to dwell on my misdeeds and to learn from my surroundings. Despite the violence, drugs and dread, I learned about living righteously and how to become a better entrepreneur.

Between the ages of 17 and 20, I stole historical documents and sold them to fund my college education. I spent three and a half years free pending an acquittal or conviction before I was sentenced to prison. With the sentence came fear, denial and anger, but also acceptance and wisdom.

After being released from prison, I’ve had the opportunity to add to my wisdom by starting my second business. Through lessons from prison, I have a much healthier outlook on the process of building and scaling a successful business.

1. Patience

I spent my life savings and four months preparing my new business, and it launched with a whopping $800 in sales in the first two weeks. I could feel discouraged, but I choose not to because I understand the importance of patience far more.

In prison, when I had no power or control over my schedule, I was taught patience against my will time and time again. The duration of my prison stay was a practice in extended patience as I waited for my release back into the free world.

The important thing about patience is that it allows you to make less fear and anxiety-driven decisions. I can stick to one project much more easily when I recognize that success does not happen overnight and patience is required.

For example, in previous businesses I have lacked patience when a marketing channel did not yield quick results (sales). I would quit or un-invest in that marketing channel before it really had a chance to prove whether it was useful or not. The lack of patience cost me a lot of time and money.

2. Self-acceptance

When I feel scared about the possible outcomes of my business, I remind myself that the fear is driven by self-doubt about worthiness. Deep down, the messages are clear: I’m not good enough, I’m not smart enough, I’m not savvy enough.

All these messages come from a lack of self-acceptance. I had to accept and love myself for the misdeeds that led me to prison. I have to accept and love myself when it comes to my relationships with women. By doing those things, I have learned to love and accept myself more in general, which obviously helps me accept my actions in business.

There will always be a measure of self-doubt, but I can accept the tools I have (or don’t have) at my disposal and do the best that I can.

3. Relationships matter

I’ve been guilty of flinging business cards around like ninja stars, but these aren’t real relationships. Connecting with other people by being vulnerable and having a genuine curiosity about their lives is far more fulfilling. It leads to better business results as a side benefit, but it also creates a healthier and happier ecosystem of individuals in my life.

When I meet people and instantly want or need something from them, it is easy to tell from my subconscious body language. When I want a female for gratification purposes, when I want an introduction to an investor, it is always obvious and it always drives people away.

Being myself in prison got me a lot more respect than I expected. As an upper-middle class geek with wire-frame glasses, speaking proper English rather than putting on an act made other inmates recognize I was not trying to get acceptance from them. I was just being me, and that made the relationships stronger.

4. Letting go

This is one of those “do as I say, not as I do” philosophies. While letting go can be difficult, it’s a requirement for entrepreneurship. There are many elements out of my control in a new business that makes me nervous, but I cannot allow that to dictate my actions. Market forces, competitors and timing are all things that I must look at objectively.

As soon as I am attached to an outcome in one way or another, that is when I find the most heartache and make the worst decisions. Even as I write this, I’m thinking about a girl I recently dated and how I still need to let her go.

Validation, affection and approval are hard to let go, but that is the definition of mental toughness — the relinquishment and giving way to all of the things the ego would like to attach to. In prison, I had to let go of the outside world, of seeing my family, having control over my life.

Because I was forced to let go during those months, I can utilize that skill and practice in my business.

Entrepreneurship is stressful and often gut-wrenching, but it is rewarding and worthwhile. My experience in prison has shaped my view of life and how I do business. Sometimes my methods are counterintuitive, but I have the unique experiences of prison to help guide me to success.

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