From Brand to Impact: How E18hteen Wheeln Enterprises Expanded into Workforce Reentry
- Devin Smith
- 10 minutes ago
- 2 min read
Recently, a valued Ship and Anchor client, Eighteen Wheelin Enterprises, was featured on the Prison to Promise podcast discussing the personal reentry journey of its CEO, Kevin Palmer. Kevin's story is a powerful example of what strategic growth can look like when mission and market align — and one that hits close to home for me: Kevin and I were incarcerated together, literally bunkmates, while I was developing the What's Your Anchor Framework, the personal and professional development model designed to align passion, purpose, and ability. That experience informs how we approach reentry-focused work today, both in strategy and in empowering leadership.
Over the past few years, Ship and Anchor partnered with Eighteen Wheelin Enterprises on two major initiatives: expanding their brand influence within the trucking community and launching a new workforce training pathway for individuals returning from incarceration.
Expanding from Lifestyle Brand to Workforce Pipeline
Originally known for its strong presence in trucking culture through apparel and community engagement, Eighteen Wheelin Enterprises sought to deepen its impact. Ship and Anchor supported the company in refining its brand strategy, strengthening industry visibility, and building momentum toward a larger vision — launching a Commercial Driver’s License (CDL) training school.
Through targeted marketing strategy, strategic collaborations, and media positioning, the company increased recognition across the trucking community and successfully launched its CDL training program.
Entering the Reentry Services Market
Building on that momentum, Ship and Anchor guided the company through the development of a new business line focused on workforce reentry.
This work included:
Designing a CDL training model tailored to individuals returning from incarceration
Identifying and securing nonprofit and institutional funding partners
Supporting partnership development with correctional facilities
Structuring a sustainable program delivering no-cost training through third-party contracts
The result: a fully operational training pathway that expands opportunity while creating a new revenue stream aligned with social impact.
Measurable Results
Launch of a dedicated CDL training program serving returning citizens
Partnerships secured with nonprofit workforce organizations and a correctional facility
Expanded brand credibility as a socially responsible workforce development provider
Increased industry visibility leading to media and podcast features
Learn more about Ship and Anchor's work with E18hteen Wheeln by reading the following case studies: Case Study 1 | Case Study 2
Why This Work Matters
This collaboration demonstrates the power of intentionally centering people with lived experience of incarceration in reentry workforce solutions. By creating opportunities where skills, passion, and purpose align — the very principle behind the What's Your Anchor Framework — Eighteen Wheelin Enterprises not only builds pathways into living-wage careers but also empowers individuals to take leadership roles in reentry support. This approach strengthens programs, deepens community impact, and shows how social impact and entrepreneurship can advance together.
You can hear more about their journey in the podcast feature below.