Entrepreneurship: A Viable Off-Ramp After Prison

Catherine Hoke
4 min readDec 19, 2014

There’s a stereotype that people in prison are natural-born hustlers. Many often run illegal businesses inside prison, providing tattoo services or reselling cigarettes. Coming from difficult life circumstances, many were forced to adopt creative survival strategies at a very young age.

Unfortunately, many people fall back on these old habits after their release because employment is difficult to find. According to The National Institute of Justice, up to 60 percent of people with criminal histories are unemployed one year out of prison, and 89 percent of parole and probation violators are unemployed at the time of re-arrest.

However, there are legal avenues these resourceful men and women can pursue after incarceration. Their criminal pasts helped them develop some of the same skills that make excellent entrepreneurs, which is why starting a legal business can be great for getting their lives back on track.

Here are eight reasons why formerly incarcerated men and women make great entrepreneurs:

1. They have sales skills. There isn’t much difference between a professional salesperson and a drug dealer on the streets — besides the legality of what they’re selling. Many former drug dealers have the ability to understand what a customer wants or needs and how to pitch a product. Being able to turn a “no” into a “yes” is key to successfully launching a business and generating customers. Great salesmanship can get a business off the ground.

2. They have customer service skills. Many former street hustlers have run illegal businesses. To retain their clientele, they had to position themselves as likable, reputable, and trustworthy. These people had to follow up on their sales and ensure that their customers were satisfied with the product.

3. They understand quality assurance. Just as successful businesspeople know that having a good product is critical to success, former drug dealers had to ensure that their products met quality standards to remain competitive. Many parolees understand that excellent products generate repeat customers.

4. They can manage people. Many successful illegal businesses are run by groups, gangs, sets, or cliques — organized crime. Many people with felonies know how to manage teams to generate results.

5. They understand profit margins. The goal of any business, legal or not, is to make money. A good businessperson is always looking for ways to maximize profit margins and increase revenue.

6. They have marketing skills. Marketing is about finding ways to make your product stand out within a specific market. Since those who run illegal businesses can’t rely on paid advertising, they have to be creative in promoting their product. They may differentiate their drugs with colored bags or a distinctive logo, or give out free samples to hook customers. These same creative tactics can help formerly incarcerated people market legal businesses.

7. They are willing to take risks. Although getting caught for illegal business activity indicates poor risk management, a willingness to take risks is important for running a successful legal business. As an entrepreneur, a formerly incarcerated person will face uncertainty, and the ability to identify and jump on a worthwhile opportunity is essential.

8. They are driven and persistent. In the illegal business world, drug dealers have to go “all in” to achieve success. They’ve experienced failure and setbacks without allowing these obstacles to derail their determination and drive. This is a very helpful mindset when starting a new business venture.

Entrepreneurship gives formerly incarcerated people something to be passionate about, which cannot usually be said for the minimum-wage jobs they may find after release. Plus, the entrepreneurial path holds the potential for a higher monetary return, an important consideration in staving off criminal activity among those who are accustomed to making a lot of money.

For all of these reasons, you may want to encourage the natural-born hustlers you know to become successful entrepreneurs as a means of leaving their illegal activity behind, moving forward, and building a better life for themselves.

Catherine Hoke is the founder and CEO of Defy Ventures, a nonprofit serving people with criminal histories nationally. Defy Ventures “transforms street hustle” by providing entrepreneurship training, executive mentoring, startup funding, career development, and job placement. The company hosts “Shark Tank”-style business plan competitions in which people compete for $100,000 in startup funding. Defy Ventures is currently enrolling its next class of entrepreneurs. To find out more about how Defy can help you or someone you care about, click here.

--

--