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Entrepreneurship After Prison: Fresh Start Business Ideas

Updated: Nov 26, 2023

Reintegrating into society after a period of incarceration can be a daunting challenge, especially when it comes to securing employment. Many employers remain hesitant about hiring individuals with a criminal record, regardless of the nature or duration of their sentence. While fair chance hiring is on the rise, it remains difficult for justice-involved people to qualify for meaningful employment with long-term career growth.


Systemic barriers to employment lead many returning citizens to pursue business ownership as an alternative path to financial security and wealth creation.

Entrepreneurship represents exciting possibilities for individuals with a creative mindset and the passion and drive to see their business ideas through. Aspiring entrepreneurs should have a viable business plan, initial capital, and some form of financial support during the startup period. Training programs and qualified mentors can help first-time business owners acquire the knowledge and money management skills they need to start and run a new business.



Factors to Consider When Choosing a Business


The most practical and affordable business opportunities are ventures that require minimal startup capital, have a low barrier to entry, and utilize the skills or knowledge an individual may have acquired during their incarceration. Whether it's a trade learned in a prison program, a hobby someone became good at, or a unique idea, these can be the building blocks for a successful business and a fresh start.


Formerly incarcerated individuals have launched enterprises across a wide range of industries. Some ventures are incredibly successful, like Dave's Killer Bread, Conbody, and Flikshop. But whether your idea becomes the next "unicorn" or your business allows you to do more than just make ends meet, entrepreneurship is worth considering.


Check out the following examples of low-cost, easy-to-start businesses:



Health and Wellness Businesses


Fitness Trainer


Personal trainer helping a client do an excercise

A fitness trainer provides personalized workout routines, guidance, and motivation to individuals or groups striving to achieve health and fitness goals. These services can be provided in a gym, at the client's home, or even virtually.


With an increasing focus on health and wellness, the demand for personal trainers is high. While certification and a deep understanding of human anatomy and nutrition are beneficial, the startup costs can be relatively low, especially if leveraging public spaces or online platforms. This profession is ideal for those passionate about fitness, have strong motivational skills, and enjoy helping others achieve their goals.


Other health and wellness ideas:

  • Yoga/Pilates Instructor - Guides individuals or groups through sequences that focus on flexibility, strength, balance, and mindfulness. Instructors can offer sessions in clients' homes, rented spaces, public areas, or virtually. With the increasing awareness of mental and physical well-being, there's a growing demand for yoga and pilates.

  • Self-Defense Instructor - Teach individuals techniques and strategies to protect themselves from potential threats or physical confrontations.

  • Outdoor Fitness Bootcamp - Offer group exercise sessions in public spaces, focusing on high-intensity, full-body workouts in an open-air environment.

  • Online Nutrition Coaching - Provide personalized workout and nutrition guidance to clients through virtual sessions or digital content.


Food Service Businesses


Personal Chef


Personal Chef preparing a meal.

A personal chef prepares and cooks meals for individuals or families, either in the client's home or delivered from another location. They often tailor meals based on dietary needs, preferences, or health goals.


With the rise of health-conscious consumers and busy lifestyles, there's a growing demand for personalized meal solutions. While culinary training or experience is beneficial, the initial costs can be relatively low, especially if cooking from a home kitchen. This business is ideal for those who are passionate about food, have a creative flair, and enjoy building close relationships with clients.


Additional Food Businesses:

  • Specialty Catering Services - Offer catering focused on specific cuisines, dietary needs, or event themes.

  • Personal Meal Prep Services - Prepare and deliver tailored weekly meals based on individual dietary needs.

  • Cooking Classes and Workshops - Teach various cooking techniques or cuisines in dedicated spaces or online.

  • Artisanal Food Production - Craft and sell unique, homemade food products like jams, sauces, bread, or cheeses.



Personal Care Businesses


Mobile Barber/Hair Stylist


Mobile Barber | Business Ideas for Returning Citizens

A mobile barber or hair stylist travels to clients' locations, whether homes, offices, or other convenient spots, to offer hair cutting, styling, and other related services. This on-the-go approach eliminates the need for clients to visit a traditional salon or barbershop.


The primary advantage of this model is the convenience it offers to clients, especially those with tight schedules or mobility challenges. Initial costs involve hair tools, products, and potentially a modified vehicle. It's perfect for stylists who value flexibility, have strong interpersonal skills, and are looking to differentiate themselves in a crowded market. Opening a storefront location is also an option; however, this will require significant startup capital and have higher ongoing expenses.



Seamstress/Tailor


Seamstress working on a sewing machine

A seamstress or tailor specializes in altering, repairing, or creating garments to fit individual clients. They can work on a range of items from everyday clothing to special occasion wear, ensuring a perfect fit and customized look.


With the increasing demand for personalized and well-fitting clothing, tailoring services remain in high demand. While tailoring requires skill and potentially some formal training, the startup costs can be moderate, especially if working from a home studio. This profession is ideal for detail-oriented individuals with a passion for fashion and a knack for working with their hands.



Service and Maintenance Businesses


Handyman Services


Handyman | Business Ideas for Returning Citizens

Handyman services encompass a broad range of home repair and maintenance tasks, from fixing leaky faucets to assembling furniture or patching walls. A handyman is a jack-of-all-trades, assisting homeowners with various small projects.


Every home requires maintenance, and many people either lack the skills or the time to tackle these tasks. While some tools and a diverse skill set are necessary, the demand is consistent. This business is perfect for versatile individuals who enjoy problem-solving and working with their hands.



Landscaping Services


Man mowing lawn on a sunny day

Landscaping services involve designing, installing, and maintaining outdoor spaces, including gardens, lawns, and hardscapes. They enhance the aesthetic and functional aspects of a property.


A well-maintained landscape not only beautifies a property but also increases its value. Initial costs can vary based on the services offered, but the demand, especially in suburban areas, is high. This business is ideal for those with a green thumb, a creative vision, and a love for working outdoors.



Mobile Mechanic


Man repairing a motorcycle indoors.

A mobile mechanic offers vehicle repair and maintenance services on-the-go, traveling to the client's location to perform the necessary work. This eliminates the need for the client to bring their vehicle to a shop.


The primary advantage is convenience for the client, which can command a premium. Startup costs include tools and a vehicle, but renting a physical shop space isn't necessary. Some certifications or training in auto repair will be beneficial. This business is perfect for those who are mechanically inclined, enjoy problem-solving, and appreciate the flexibility of working in various locations.



Mobile Car Wash/Detailing


Mobile Car Detailing Service | Business Ideas for Returning Citizens

This business offers car cleaning and detailing services at a location convenient for the client, often at their home or workplace. It provides thorough cleaning, both inside and out, to restore a vehicle's appearance.


The convenience factor is a significant selling point, as many people have limited time to visit traditional car washes. Initial costs involve cleaning supplies and a suitable vehicle, but there's no need for a fixed location. It's perfect for those who take pride in meticulous work and enjoy seeing immediate results from their efforts.



Additional Service Businesses

  • Commercial Cleaning: Commercial cleaning businesses specialize in cleaning offices, retail spaces, and other business establishments.

  • Power Washing: Power washing involves using high-pressure water spray to remove dirt, mold, grime, and other contaminants from surfaces like driveways, decks, and home exteriors.

  • Pool Maintenance Technician - Clean, maintain, and repair swimming pools, ensuring they're safe and functional for homeowners.

  • Appliance Repair Technician - Diagnose and fix household appliances, ensuring they operate efficiently and safely for homeowners.


Technology and the Arts Businesses


Computer Repair/Consulting


Woman repairing a computer.

This business involves diagnosing and fixing hardware and software issues in computers, as well as offering advice on system upgrades, cybersecurity, and general computer use.


In our digital age, almost everyone relies on computers, but not everyone is tech-savvy. While some technical training or experience is necessary, the demand for these services is consistently high. This business is perfect for individuals who are tech enthusiasts, problem solvers, and have the patience to explain complex issues in layman's terms.



eBay Seller – Pre-Owned Merchandise

This business involves sourcing, listing, and selling pre-owned items on the eBay platform. Sellers curate a range of products, from vintage collectibles to gently used clothing, capitalizing on the demand for second-hand goods.


The second-hand market has seen consistent growth, driven by both economic and environmental considerations. The initial investment can be minimal, especially if starting with items from one's home. This venture is suitable for those with a keen eye for valuable or in-demand items, possess strong organizational skills, and are familiar with online selling platforms.



Photographer / Videographer


Videographer | Business Ideas for Returning Citizens

Photographers capture moments, emotions, and stories through their cameras. They can specialize in various niches, including weddings, portraits, commercial photography, or events.


In our visual-centric world, quality photography is always in demand, whether for personal memories or business branding. While a good camera and editing software are essential, the most significant investment is in skill development. This profession is perfect for creative individuals with an eye for detail and a passion for storytelling.



Mobile Disc Jockey


Mobile Disc Jockey DJ | Business Ideas for Returning Citizens

A mobile disc jockey (DJ) provides music and entertainment for events like weddings, parties, and corporate functions. They come equipped with their sound equipment, music collection, and often lighting to set the mood.


Music is a crucial element for many events, and a skilled DJ can elevate the experience. The initial investment involves sound equipment and music libraries, but with a growing number of events seeking entertainment, the potential for earnings is high. This business is ideal for those who love music, have a good sense of crowd dynamics, and enjoy creating memorable experiences.



Additional Technology and the Arts Business Ideas:

  • Virtual Assistant - Provide remote administrative support to businesses or professionals, handling tasks like email management, scheduling, and data entry.

  • Website Design - Craft aesthetically pleasing and functional websites tailored to a client's brand and objectives.

  • Tutoring - Offer educational guidance and expertise in specific subjects to enhance students' understanding and performance.

  • Graphic Design - Create visual content and designs for various mediums, such as advertisements, logos, and publications, to communicate messages effectively and aesthetically.



Other Popular Businesses


Box Truck Driver/Owner


Box truck outside a warehouse.

A box truck driver operates a medium-sized truck, typically used for transporting goods, furniture, or other cargo within a city or over short to medium distances. These drivers often work with businesses, moving companies, or as independent contractors to deliver goods safely and efficiently.


The demand for localized delivery and transportation services has surged, especially with the rise of online shopping and businesses needing "last-mile" delivery solutions. While the initial investment includes the purchase or lease of a box truck and potential licensing, the consistent need for transportation services can provide steady income. This business is ideal for individuals who enjoy driving, have a strong sense of responsibility, and can manage time effectively to ensure timely deliveries.



Food Truck Owner



A food truck restaurant or caterer operates out of a large vehicle equipped with a kitchen, serving a variety of dishes directly from the truck at different locations. These mobile eateries can cater to events, set up at popular spots, or move around to reach diverse crowds.


Food trucks offer a unique dining experience and allow for flexibility in changing locations based on demand, events, or seasons. The initial investment involves the truck, kitchen equipment, and permits, but operating costs can be lower than a traditional brick-and-mortar restaurant. This venture is perfect for culinary entrepreneurs who want to test their menu in various markets, enjoy interacting directly with customers, and value the flexibility of a mobile business.


Note that startup costs for these businesses are generally higher than for others presented in this article. If you do not have access to this level of capital, consider first becoming an employee of an existing company and starting your own business later.



Don't be Afraid to Start

In embarking on your entrepreneurial journey, it's essential to remember that not all businesses need to start as full-time ventures. Many can begin as side hustles, allowing you to grow at your own pace and comfort level, while continuing to earn income elsewhere.


Before you launch your business, there are many things to consider, like registering the business, whether you require any licenses, and how to create a business plan. If you need assistance figuring out how or where to begin, entrepreneurship programs for returning citizens help you cultivate the business and financial knowledge you need to start and run a business.


Entrepreneurship offers justice-involved people hope and autonomy and can help them create a path to a more secure financial future. Business ownership provides an alternative to the limited employment opportunities in today's labor market and a chance for returning citizens to rebuild, find purpose, and contribute positively to their communities and society.





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