5 Tips for Going from Prisoner to Entrepreneur

Finding jobs after federal prison can be difficult, and many former federal prisoners explore opening their own businesses. How do I know? Well, I am one of those federal prisoners! So are my co-founders of Prison Professors, Michael Santos and Shon Hopwood.

If you have interest in going from prisoner to entrepreneur, here are five tips to get started:

1. Set A Productive Routine

One thing about entrepreneurship is that it does not exactly lend itself to a good work-life balance. Depending on the reasons you were (or are) in prison, it could be even more important for you to have a routine to avoid falling back on certain habits. Set aside specific times every day for exercising, checking email and focusing on the business. Go into your venture with a plan that helps you stay stable.

2. Start Small

If you are like many people, you need money as quickly as possible. You don’t have the time to waste. Before you focus on money (especially if you are implementing this plan from federal prison), begin to think about re branding and creating a new record, as Shon and Michael did. Rather than ask, “what can I do NOW to make money?”, they asked, “What small thing can I do today to make a difference in the life of someone else?” From there, opportunities opened for them.

5 Tips for Going from Prisoner to Entrepreneur

You could focus on a service-oriented business such as freelance writing, marketing, or developing apps. If you have a product such as cupcakes, frozen yogurt or handmade jewelry, use the concept of a MVP to ensure that there is demand for your item before you sink too much money into it. For example, you can take your jewelry to farmers markets and local shops to gauge interest before continuing with the idea. When I began public speaking, I did it initially for free. I just wanted to help others and learn from their feedback.

3. Own Your Experience

You can choose to hide that you used to be in prison, but in many circumstances, being open about your experience boosts your business prospects. Consumers love businesses that are driven by compelling stories and people. Plus, there were skills that you likely learned or honed in federal prison such as tenaciousness, observation and collaboration that you can put to good use when developing your business narrative and brand. This can lead to more money if you crowdfund or seek grants.

5 Tips for Going from Prisoner to Entrepreneur

4. Know Your Goals

Setting goals is important before you go into your venture. Do you want to start a business mainly to pay the bills? To occupy your time to stay out of trouble? Identifying your goals helps you decide which ideas may or may not be worth pursuing. Keep your aims realistic; it is unlikely that your business will turn you into an overnight millionaire. But as I wrote in Lessons From Prison if you are authentic, deliberate and embrace the slow and steady wins the race approach you will succeed.

5. Establish a Support Network

Many business owners need friendly faces to succeed. Your support network could be comprised of a pastor, a few family members and friends you meet doing new activities. But you do need a network of some sort to get you through challenges and setbacks.

If you have already cracked the code on how to go from prisoner to entrepreneur please let us know. We would love to profile your story in our soon to be published Prison Professor podcast.

Thank you,
Justin Paperny