Small Business DNA: Shannon Ross of D’s Trucks and The Community

Author: Fundbox Team | May 2, 2022

Small businesses have the power to transform their communities for the better. In Shannon Ross’s experience, being an entrepreneur has empowered him to advocate for the marginalized community he belongs to: the population of previously incarcerated people, also known as system-impacted individuals. 

Shannon is the co-founder of D’s Trucks, a trucking business he started with a childhood friend in the spring of 2021. However, the company is just one facet of Shannon’s overarching mission to support his fellow system-impacted individuals. 

He is also the executive director of The Community, an organization he started while still incarcerated. The Community is dedicated to helping system-impacted individuals fulfill their potential and decreasing the stigma associated with having a criminal record. In addition, Shannon is a consultant with Paradigm Shyft, a firm that provides education about equity and inclusion practices for hiring, teaching, and working with system-impacted people. 

Shannon believes that when employers embrace the humanity of people with criminal records, they can change lives and shape their communities for the better. Here, Shannon shares his experiences re-entering the workforce after being incarcerated, how he helps others do the same, and what small business owners can do to make a difference in their own communities by investing in system-impacted individuals. 

Re-entering the workforce with a criminal record

During his 17 years in the Wisconsin prison system, Shannon was committed to working and furthering his education despite incarceration. Throughout his sentence, Shannon spent time writing about his experiences and building a Buddhist meditation practice which led to the opportunity to design and run a coping skills program at the Stanley Correctional Institution. 

One of the major challenges Shannon faced as an inmate was completing his university education, which he had begun before his arrest. He faced many systemic obstacles in his pursuit of a Bachelor of Arts in business administration, which he detailed in an article for the Boston Review.

In light of these challenges, Shannon’s family stepped in to help him search for funding and courses that he could take while in prison. This ongoing support and his commitment to his studies enabled him to graduate in 2017. Toward the end of his sentence, he won a fellowship to a Master’s program in sustainable peacebuilding from the School of Nursing at the University of Wisconsin-Milwaukee. He began his first semester a week before he was released. 

Shannon’s graduate program fellowship supported his transition back into the workforce and enabled him to earn an income for going to school. During the transition, he also continued to expand his work through The Community. Shannon’s experience with overcoming adversity as he prepared for re-entry into the workforce has made him particularly passionate about ensuring that people who are still incarcerated get the support they need through The Community’s pre-entry resources. 

A few months after being released, Shannon connected with his childhood friend, Brian Adams, who had recently left his job and was looking to start his own business. In March 2021, the two began operating D’s Trucks with Brian behind the wheel and Shannon overseeing business development.

Transforming community through business

  • Move past stereotypes and get curious about how the business can make a positive impact on an individual’s life. 
  • Tap into a wider talent pool by providing opportunities for upskilling and apprenticeship to system-impacted individuals. 
  • Cultivate an empathetic workplace with a culture of connection and understanding that encourages employee loyalty. 

Uplifting system-impacted individuals

One of the imperatives of D’s Trucks is providing employment opportunities for other system-impacted individuals. This includes prioritizing hiring previously incarcerated people as well as providing business development support for those with criminal records who are interested in starting their own trucking companies. 

This work goes hand-in-hand with Shannon’s advocacy work through The Community’s Correcting the Narrative Campaign and extends to his consulting practice at Paradigm Shyft. Through Paradigm Shyft, Shannon helps educate businesses on what previously incarcerated people need from their employers to attract, retain, and thoughtfully manage workers who are system impacted. 

Shannon believes that there is a wealth of untapped talent among those who have a criminal record. Based on his extensive experience as a community leader who deals with many people with criminal records, Shannon has seen firsthand the character development that individuals experience while in the prison system. “There’s a significant level of potential, a great level of humility, and oftentimes, a high level of willingness to be on a team and move forward in life,” he says. 

Shannon knows that when employers see system-impacted individuals as people with unique skill sets and valuable perspectives to bring to the table, they stand to gain loyal, driven employees

“The general bias toward [the label of ex-convict] overlooks the fact that people who are incarcerated are usually very hungry to come out and get their life going,” says Shannon. “In this group, in particular, they’re very open to being given that chance and recognize that this is something they should hold on to. They respect the opportunities they’re given; they’re not entitled all the time. They’re willing to communicate and deal with [challenging] situations that other people may not be willing to tolerate.” 

Other small businesses can have a significant effect on their communities when they choose to hire system-impacted individuals. Shannon emphasizes that “when you have people who are getting a good wage and have autonomy in their job and have a sense of self-respect, they’re going to be better in their neighborhoods and with their families, which is what we all want.” 

Small businesses looking to support workers in the system-impacted community can start by providing training programs or apprenticeship opportunities that allow those whose job-related skill building has been interrupted by their time in prison. From a human resources standpoint, another key area to focus on is engaging in company-wide communication about destigmatizing employees with criminal records and ensuring that these team members feel welcomed, understood, and respected. 

Cultivating empathy in the workplace

Shannon’s experiences in prison made him a humble leader with deep empathy for employees, an attitude he hopes to instill in other small business leaders in his community. Shannon’s frustrations about being an employee at the mercy of the emotions of his managers were mirrored by interactions he often had with security staff while in prison. 

“Being incarcerated and dealing with security staff every day who have so many traumas and difficulties — they’d take it out on us,” Shannon recalls, “And so, I love being in a position where I can say, ‘Hey, I do have [things] going on in my life, but I’m never going to bring that to you. And I’m going to listen and I’m going to be open.’” 

Because of his experiences, Shannon is committed to showing up for his community, employees, and consulting clients with a willingness to treat people with exceptional respect. “Every single person you deal with every day is going through something. We should just try to deal with each other as individuals in the moment.” 

This approach underpins Shannon’s foundational desire to help people improve and heal, regardless of their background. In his own life, he’s seen how transformative having compassionate support from family and community can be for making lasting change for the better.

“I call myself an inevitability,” Shannon says. “I was given things that made it very, very unlikely for me to not succeed. When you offer that support to an individual, you’re giving them the nourishment to grow into their potential, and they’re not likely to fail.” His mission is to give people the care they deserve to reach their full potential and the resources they need to make their success a certainty, too. 

Small businesses have the opportunity to push systemic change forward with simple steps that make it possible for individuals from marginalized communities to thrive. Focusing on finding talent that can bring innovative ideas, team spirit, and a new approach to the business — rather than giving into stereotypes — enables small businesses to differentiate themselves and get ahead. Above all, cultivating an empathetic, inclusive workplace improves the communities your business serves, contributing to a better world for all. 

If you’re curious about how your business can support system-impacted individuals, learn more through The Community’s resources page. You can also follow Shannon on LinkedIn to stay up to date on the community advocacy initiatives he’s working on.

Disclaimer: Fundbox and its affiliates do not provide tax, legal or accounting advice. This material has been prepared for informational purposes only, and is not intended to provide, and should not be relied on for, tax, legal or accounting advice. You should consult your own tax, legal, and accounting advisors before engaging in any transaction.

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