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How My Life as an Entrepreneur Shaped My Time in Prison What other business owners can learn from how I used my startup skills during the two years I spent behind bars.

By Andrew Medal Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


Ten years ago, I made one of the biggest mistakes in my life, and got into a fight in a Las Vegas nightclub. It eventually landed me in state prison for two to five years. So you see kids, decisions we make when we're young can in fact affect our future.

As a big mental note: prison totally sucks (just ask Piper Kerman) -- I'd recommend not going. I would like to show you though how my experience as an entrepreneur helped me survive and thrive while in prison. The goal of writing this is to help shine light on how you how you can use your different entrepreneurial skills to overcome extravagant obstacles, and ultimately accomplish your dreams.

There are few people who have the experience to show you the parallels in building startups and going to prison, but I'm here to bridge the gap for you. You're welcome.

I'm an entrepreneur. I've always been an entrepreneur. It's not simply because I enjoy starting and building businesses, but because of my character traits, as I believe that being an entrepreneur is a part of my genetic makeup. Prior to being sentenced to prison, my life was consumed with launching and building startups. So you can guess what I still do today.

Funny enough, prison culture is a hotbed for entrepreneurial endeavors. The startup spirit is very much alive in the system -- from the creative types who tattoo and draw, the tinkerers who fix all of your electronics, the barbers, the laundrymen and the rest of the all-out hustlers who will figure out how to get you whatever you want or need for the right price. When viewed under the right lens, it can be said that the foundation that holds prison culture together is firmly rooted in entrepreneurship.

Related: Mexican Mobster Becomes Business Mentor at LA Event

Let's take a closer look at how I used my startup skills to thrive in prison, and how it can help you today.

1. Effective time management

I'm not talking about normal people time management, but startup people time management. There's a difference. As anyone who has done it can attest, when building a startup you have two options: Make the most out of every second of your day to advance your mission, build your startup and take over whatever world you're leading the charge against; or don't.

How this helped in prison, and how it can help you today.

When the initial shock wore off, and I accepted the fact that prison would be my home for the next two years, I got serious about how I wanted to spend my time. While building a startup, even if you have employees, co-founders, investors, or you're just a one-man (or woman) shop, there is nobody standing over you telling you what to do on a daily basis. It's up to you to figure out long-term, mid-term and short-term goals, and chunk them into manageable tasks that can be accomplished and prioritized.

Utilizing this startup experience, I was able to figure out grand plans to put in action during my time, with daily systems to keep me accountable. The Seven Habits of Highly Effective People by Steven Covey had changed my life when I was young, so I used the Important/Urgent Not Important/Not Urgent grid to help me prioritize. I made a promise to myself that no matter what, I'd use the two years proactively to better my mind, body and soul, and be relentless in my execution. It's a life skill I still use to this day.

2. Embracing uncertainty, and persevering in the face of the unknown

My startup experience has been a voyage of volatility, mystery and excitement. I have gone from trying to figure out how to pay rent one day to having a six-figure investment the next. No matter the obstacle, however, like all of my startup founder counterparts, I have learned how to embrace uncertainty and persevere in the face of the unknown.

How this helped in prison, and how it can help you today.

As a somewhat geeky white boy from the southern California suburbs, I'm sure you can understand my apprehension about going to prison. You watch movies, hear stories and listen to rap music -- prison never sounded like a great place to visit in any of those different scenarios. Pair that with the fact that my prison sentence was two to five years, as in a range, not a set date. This was dependent on a number of items including "good time" and "work credits." However, not even knowing when I was going to get out of prison was a mental obstacle to overcome unto itself.

In moments when I would feel stressed out, or burdened by my surroundings, I would reflect back to my startup experiences of accomplishment and perseverance. Simply having different memories of times when I pushed through the unknown gave me courage and bravery in the moments when I felt down. More important, however, was my experience in knowing how to embrace this uncertainty to successfully overcome my prison experience. Understanding how to remain calm and stay mentally strong, in the face of any adversity, was a vital skill in doing my time. These skills should be something we as entrepreneurs use to overcome our wildest challenges and the basis of how we solve unforeseen obstacles.

Related: Learning to Embrace Struggles

3. Connecting the dots and people

As an entrepreneur, I make it my business to know what's going on with my friends and my network, so that I can connect the dots and connect people. I believe it translates to real value, which is the primary reason I do it. Plus, it provides me startup karma points, which are never a bad thing to have.

How this helped in prison, and how it can help you today.

In prison, I learned that being liked is a good thing. Eventually, when I got comfortable in my surroundings, I used this same skill to connect dots and people.

For instance, if I knew Jo-Jo was looking to trade some books, and knew Jonny K. was looking for some new books, I'd connect the two. If Harry was selling a pair of shoes, and Bryan just busted his playing handball, then I'd tell Harry to go talk to Bryan.

Ironically enough, the same way this helped in my startup career helped during my two years "studying abroad" (as my family and I eventually came to calling it). It helped me meet people, helped me get things I needed (new shoes, books, CDs, etc.) and helped provide tangible value to others. And, in case you're wondering, prison karma points are even better than startup points.

Helping others in any situation feels good, and as entrepreneurs we should always be trying to figure out how to help others, even if it's as minor as new handball shoes. I challenge you to try this today. Call, email or text a startup friend, and ask them what introductions you can make. You'd be surprised at how much value you can provide just by understanding someone else's needs. I make it a goal to do this once per day throughout my network.

4. Startup founder adaptablility

Whether it's dealing with investors, customers, the marketplace, employees, partners, press or whoever, a startup founder is constantly figuring out how to adapt to his or her surroundings. Sometimes the difference between success and failure, in certain situations, can come down to the founder's ability to adapt to whatever situation he or she is faced with.

How this helped in prison, and how it can help you today.

I had never been to prison. I didn't know anyone in prison. I didn't know prison culture, prison behavior or prison language, and had no clue what to expect.

However, through my experience as an entrepreneur, I learned how to adapt to an ever-changing environment in a number of different roles. For instance, I learned how to adopt terminology when doing business in different industries by listening to key words and phrases industry veterans used. Through raising capital, I learned how to match the behavior patterns of investors when dealing with investors in different settings. As a startup founder, I learned how to passively shape a culture to my liking, through shepherd leadership. I've learned how to effectively meet people and network, while building my different companies.

All of these skills helped acclimate me to prison culture effortlessly, and adapt very quickly to a new and unknown environment. For instance, I was able to pick up on prison slang pretty quickly, I matched my behavior to the other inmates and by setting an example in my different housing units, was able ultimately to bend the culture to my liking. I read constantly, and would share different things I was learning, at different times, with the people around me.

By sharing and showing what I was learning, more people became interested in some of the stuff I was interested in (namely the tech sector). This spurred them to get books and magazines of their own, and helped shape our housing unit culture. My ability to adapt to the prison culture helped me fit in, and allowed me to get assimilated very quickly without any issue.

Be aware of your surroundings, know how to match the energy levels of clients and employees and use your adaptability to strengthen your leadership. The first step is being aware, and having that awareness will help you understand how to use your ability to adapt to situations.

Related: 5 Key Lessons Every Entrepreneur Can Learn From 'Unbroken' Louis Zamperini

5. The never-ending learning game

Startup founders have to constantly feed their brains new information, whether it's a new skill to help grow their company, upcoming trends in their industry, or new software or new tools for their employees to use.

How this helped in prison, and how it can help you today.

Building startups actually taught me how I learn. I realized after building companies that the way I had learned in school all of those years wasn't actually an effective way for me to learn. I am much more receptive to practical knowledge vs. theory-based learning.

In two years I read 197 books (I could have read more, but I was writing my two books every day as well, plus working out and mentoring other inmates). I subscribed to every major magazine and newspaper related to the tech space and startup world, including Entrepreneur, Inc., Fast Company, Wired, Bloomberg BusinessWeek, the San Jose Mercury, Wall Street Journal. I knew everything going on over those two years in the tech space and wrote and published a book based on all of that research called Hacking the Valley.

My startup program was infectious with some of the people around me. The group of guys I spent my time with were more motivated than everyone else, we worked out harder, we read more books and we ended up enjoying ourselves even in the worst of environments because we were bettering ourselves.

I do this on a daily basis, whether it's strengthening my coding game on Codecademy, watching past episodes of Foundation by Kevin Rose to hear stories for motivation, or improving my olympic lifting skills by following Max Mormont's training program (quick shout out to my coach). We should always be learning, in all we do, proactively and reactively. It's what makes us better as startup founders.


I've been back home for about 20 months now, and my focus and drive is more clear than ever. I found two charities that support men and women in the prison system. I used to hand write and mail articles to Entrepreneur Magazine from my prison cell, in hopes they would publish my writings, and now I am a contributor. I have a growing, thriving digital agency that has been a longtime dream company for me. I have a handful of other startup projects that are showing progress and promise. I have an interesting story that I can create buzz around to help build my personal brand, where I plan to offer valuable products, programs, ebooks and webinars.

Here's the bottom line: Prison sucks, so don't go. If you leave with one lesson, that's it. Seriously.

Prison sucked a lot less due to my startup experience. Thanks to my decision to be proactive about my time, I walked away smarter, emotionally enlightened and physically and spiritually stronger, with two books (one published) in hand (the second is called How I Survived State F&cking Prison, The Factual Story of a 20-Something-Year-Old White Boy From the Southern California 'Burbs), in depth-relevant knowledge of the tech space, a better communicator, a better visionary and even better looking (that's what my mom tells me at least).

Entrepreneurs make this world go 'round. Everything we see around us was once just an idea in someone's mind. No matter the circumstance, the scenario, the obstacle, we should always be progressing forward. You may have had bad luck come your way, or have made mistakes in your past, but don't let those obstacles deter you from accomplishing your dreams. We all make mistakes, but we can use those experiences to help us be better entrepreneurs, and ultimately better people. As entrepreneurs our lives should be in a perpetual state of growth and development as we're designed to figure out how to accomplish our dreams.

Being an entrepreneur is all about our state of mind, and nothing should stop us from accomplishing our dreams -- even prison.

I'd love to hear about obstacles you've overcome through your startup skills, if you'd like to share in the comments section below. Check out my blog for more about my life and experiences.

Related: Meet the Company Creating Jobs for Former Gang Members

Andrew Medal

Entrepreneur & Angel Investor

Andrew Medal is the founder of The Paper Chase, which is a bi-weekly newsletter. He is an entrepreneur and angel investor.

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