Venturing Out is a response to two critical problems – and an opportunity. First, people coming out of prison struggle to find jobs because employers are dissuaded by criminal records. Second, unemployment is one of the leading reasons for reoffending. However, people in prison have higher than average entrepreneurial aptitude.

I came to the realization that if we could teach people in prison how to start their own businesses, we could enable them to become economically self-sufficient – and help reduce their chances of reoffending.

In 2008, with the generous help of friends, colleagues and mentors, I founded “Entrepreneurship 101” (the predecessor to Venturing Out), beginning at the Suffolk County House of Correction. Thanks to the work of our volunteer team and under the guidance of our Executive Director, Laura Winig, Venturing Out is currently running comprehensive entrepreneurship courses at multiple prisons and community-based sites for adults and youth.

I have some observations about starting a successful organization, based on my experience with Venturing Out as well as my current role founding a second business.

First, successful entrepreneurs are flexible about the means by which they achieve their goals. As entrepreneurs, we perceive an unfulfilled market need – and we devise a way to address the mismatch. But what if our solution doesn’t fit the problem? We need to rigorously evaluate our performance to ensure that we are producing our expected outcomes, and be prepared to come up with an alternative strategy as required. This process of trials and pilots, targeted performance review, and innovative and reflexive adaptation should be ongoing.

Second, while entrepreneurs can easily lose sight of the big picture and get caught up in mission statements and catchy slogans, what really matters is our purpose, values, and vision. Why do we exist – what is the fundamental role that we are fulfilling? And what, in an ideal world, would we be able to achieve in thirty or fifty years time? The answers to these questions are complex but shape the way in which we run our businesses. Our purpose and vision motivate employees to join and commit to our organizations, influence customers to purchase our products and services, and encourage funders to offer financial support.

Third, recognition of the realities of entrepreneurship in the 21st century is critical for organizational success. For social entrepreneurs, this means considering alternative financial sources, besides donations. The traditional non-profit approach is not always sustainable, and there are ways to strategically earn revenue without deviating from our core purpose. For all entrepreneurs, while we may be driven (at least in part) by the bottom line, we must not lose sight of the less quantifiable impact that our business can have on the economy, environment, and society. We should consider the mechanisms by which we can increase employment opportunities, decrease our carbon footprint, and create positive social change through our business model.

Finally, just as coaches are recognized for winning championships, entrepreneurs often get the credit for their companies – but there is a team behind each success story. It is said that we are only as good as the people around us; to be successful entrepreneurs, we need to identify our deficiencies, and surround ourselves with the best and brightest people that complement our skillsets. Moreover, we should develop these individuals as leaders by building on their strengths, encouraging them to innovate, and showing our appreciation for their support.

Entrepreneurs are an integral part of this country’s history and culture; “rags to riches” stories continue to inspire individuals to pursue self-employment and the American dream. Entrepreneurs can transcend class structures and break through glass ceilings; innovate where growth has stagnated; and effect change where it is desperately needed. In today’s economy, we need enterprising individuals more than ever to develop businesses and create new jobs – as well as mentors, who can invest time and resources into encouraging budding entrepreneurs’ visions for social and economic change.

Founding Venturing Out in order to enable aspiring entrepreneurs from all walks of life to realize their business visions, has taught me that those of us who seek self-employment share certain traits. We tend to have a greater inclination for risk-taking; a more visionary, idealistic, and optimistic approach to problem-solving; and, of course, a greater passion for creating and founding new organizations.

We also share a willingness to work hard and act on our ideas. The entrepreneurial dream is not an easy one to achieve – starting any project takes an immense amount of effort, and to paraphrase Roy Ash, entrepreneurs tend to bite off more than they can chew (hoping they’ll quickly learn how to chew it). I hope my observations will help you as you move forward with your ideas and ventures. Best of luck with your entrepreneurial journeys!

created at: 2010-10-29Baillie Aaron
2010 PresenTense Boston Fellow

Venturing Out, Founder and Board Chair
RISE, Co-Founder


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