Imagine advising an aspiring entrepreneur who is starting a business ... after being in prison. What advice would you give on key things to do/avoid?

BEST PEOPLE TO ANSWER 1. Those who have bootstrapped their own business without any support from family, friends, investors (especially those who come from a challenging background) 2. Those who have worked with low-income entrepreneurs who are pursuing "Main Street" businesses ... restaurants, car repair, home repair, courier services, shoe shining, etc. BACKGROUND ON WHO WE ARE For the past ten years, the Prison Entrepreneurship Program has offered "entrepreneurship boot camps" in prison, coached incarcerated participants through writing a full business plan and then helped them to refine their plans through "Shark Tank"-style pitch events to executive volunteers who visit them inside a Texas prison. Our graduates now earn a Certificate in Entrepreneurship from Baylor University's Hankamer School of Business. We then continue to support these graduates after release from prison, providing them with housing, job placement and start-up support. We have had 150 of our graduates start their own businesses, including two that are now generating over $1MM in annual sales. While we are proud of these results, we want to do even more in the future. Your advice could be very beneficial to us as we expand our post-release support for small business development. (Learn more about us at


Fantastic question! First, a little about me and why I am qualified to answer. My father served 19 years of a 20 year sentence in prison where he passed and I had challenging background. I never met my birth mother and met my birth father at the age of 18. I've been on my own since I was 16 and have lived in the YWCA, homeless shelter's etc. I don't have any family support financial or otherwise. I haven't even had a call on a birthday, holiday, wedding day or even the birth of a child. I have a GED and now a Master's, built my first home before 30 and all while a single mom at the time. I worked very hard throughout my life and now I am retiring from a position at a Fortune 500 company after 10 years of service in my 30's. My husband has had challenges with his background and we opened a gym here in Atlanta for 8 months before closing and I also own several businesses online that focus on teaching part-time entrepreneurs how to convert their passion into profits. I have dozens of courses published on the world's largest destination for online courses including 3 best selling books on Amazon. Okay, now that ALL of that is out the way, here is my response.

Yes, I have begun working with local entrepreneurs and small business owners in Atlanta, GA to build their Internet properties and protect their reputations online and off. I help them create and develop "trust based marketing" through email, books and online and I am partnered with the #1 trusted marketer online to accomplish this and a group of over 10,000 offline business entrepreneurs.

Key things to avoid:
- excessively talking about your past
- blaming others for your current situation
- the old environment

Key things to do:
- Read (or listen to) Dale Carnegie's "How to Win Friends and Influence People"
- Find a mentor/coach that you can share your goals with and get feedback
- Invest in small business and personal development classes online or at a center (most are free)
- Think outside the box
- Build a community online
- Transfer life skills into your business
- Understand the pricing structure for your business
- Set goals and create plans to achieve them
- Invest financially and reinvest back into your business
- Create a business and financial plan (on paper)

I could go on and on and would love to connect with your organization. A 15 minute chat to provide more clarity would be great! ~Montina

Answered 10 years ago

Every business and product has strengths and weaknesses. Great positioning can overcome this. There are many business specific tactics that can also control the customer experience so prison is not the focus or an issue that comes up.

Answered 10 years ago

I have to say Ms Portis overview seems to reflect really what you need to know right away. It really reflects the "getting started" stage. The only thing I would add is the keys for continuing success are innovation and marketing ...and it's usually marketing where startups get it wrong wrong wrong. You can see what a mean through I love what your group is doing!

Answered 10 years ago

THIS IS AWESOME! I love what you guys do! I actually co-founded an organization ( that empowers inner city disconnected youth in Harlem NYC through entrepreneurship and education. I have about 10 years of research on youth development and engagement, especially on ho to curb disconnection and strongly feel that entrepreneurship with sound education is that vehicle that could help turn things around. In fact, all our programs are themed around entrepreneurship, so I am very excited and interested in what PEP represents.
Based on our new pilot program The URBN Youth StartUP, which just ended last month, there are several tips I could give. We spent 12 hours a week with the students (4 days per week, covering concepts and fundamentals of entrepreneurship, basic life and soft skills, financial literacy and micro-finance and innovation/tech day) in addition to having 2 mentors per student (one entrepreneur and one professional). These alongside implementing our HEROES Model for effective youth development ( helped us have a successful pilot.
Let me know if you are interested, Id love to talk more.

Answered 10 years ago

The only thing I might add to this set of answers is that you should consider reaching out to your 150 success stories and asking them the same question. They likely meet your "best people to answer" criteria and have a good understanding of the particular challenges of your constituents.

Some of the best mentors and advisors come from within the community. Your existing graduates, especially the two with over $1MM in annual sales, can probably give the most robust answer to your question.

Answered 10 years ago

Have you considered speaking with people involved in helping veterans through their military-to-civilian transitions? Re-entering the civilian work force after 6, 10, or 20 years in the disciplined, insulated environment of the armed forces is a bit like getting out of jail. Not that I regard my own Navy background as a prison sentence, by any means! Quite the contrary! Only it's a disorienting readjustment that poses career and personal challenges very similar to what former prisoners must be facing.

It may be worthwhile to compare notes with programs that assist veterans with job placement, career retraining, franchises, and startups. Perhaps some veterans would themselves be able to share tips. Most people, when they get out of the military, plug themselves into a salaried position in another established organization. But quite a few do try their hand at startups. Since their network outside the military is often minimal, many veterans have a tough road too and will probably sympathize with what your program is doing.

Incidentally, if your program (or a sister program) needs a name, I've been holding onto this one for just such an endeavor:

Answered 10 years ago

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