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Meet the Entrepreneurs Shaping New Apprenticeship Pathways

May 6, 2025

At A Glance

Meet 18 impressive leaders expanding apprenticeship opportunities for today’s learners—designing tech-driven, community-rooted, and industry-aligned models that open doors to meaningful, learner-centered career pathways.

Contributors
Heather Terenzio Director
Practices & Centers Topics

Apprenticeship is a proven workforce training model that has offered people pathways to quality jobs for generations. But today’s learners—especially those navigating early-career experiences without built-in networks or financial safety nets—often face a system that wasn’t designed with their needs or potential in mind. 

At Jobs for the Future (JFF), we set out to recruit a cohort of innovators and entrepreneurs with bold ideas about the future of work-based learning—some already running Registered Apprenticeship programs, others just beginning to build their vision—who are reimagining what apprenticeship can look like.  

The result is a dynamic group of 18 leaders who are expanding apprenticeship into new industries and designing a new generation of experiences that are accessible to all.

A New Generation of Apprenticeship Innovators 

JFF’s 2025 College Talent Pathways to Apprenticeship entrepreneurs-in-residence cohort is a dynamic mix of early-stage companies, emerging ventures, and experienced leaders scaling high-impact solutions. Some are building tech-enabled tools to simplify apprenticeship design, management, and outreach. Others are developing sector-based models tailored to industries like tech, media, clean energy, or health care. Many are creating apprenticeships rooted in community impact, blending career training with mentorship, wraparound support, and social enterprise. 

What unites the members of the cohort is a commitment to building learner-centered models that move learners toward meaningful careers. These entrepreneurs bring bold visions and innovative thinking to the table—and together, they are reshaping the future of workforce development. 

Read on to meet these inspiring innovators.

For-Profit Entrepreneurs

Changemakers developing market-driven apprenticeship models that scale across industries and geographies.
Ola sits in an office chair wearing a brown plaid suit and blue bow tie, smiling at the camera against a plain background.
Claim Academy

Ola Ayeni

Ola Ayeni is the founder of Claim Academy, a coding and cybersecurity boot camp based in St. Louis. With a mission to expand the developer talent pipeline, Claim Academy trains students for high-demand tech careers—equipping them with the skills to earn competitive salaries, often without a college degree.
Joi has short curly hair and is smiling at the camera, wearing a light-colored top with a dark floral pattern. The photo is in black and white.
Remnant Strategy

Joi Freeman

Joi Freeman is the founder of Remnant Strategy, a brand consultancy developing Aspire, a tech-enabled storytelling tool for nonprofits. With plans to launch an apprenticeship program, she’s focused on creating accessible marketing pathways for early-career talent and aligning workforce development with purpose-driven innovation.
Bianca sits on a staircase next to a white brick wall, smiling at the camera. She is wearing a yellow wrap sweater and jewelry, and has medium-length dreadlocks.
BrickRose Exchange

Bianca J. Jackson

Bianca J. Jackson is an entrepreneur, futurist, and technologist who uses artificial intelligence and virtual reality for workforce development and social impact. As the founder and chief innovation officer of BrickRose Exchange, she creates equitable solutions connecting technology with education, job training, and entrepreneurship.
Penny stands with arms crossed in front of colorful abstract artwork. She has short hair and is wearing a teal sleeveless dress.
Mickey’s Popcorn

Penny Mickey

Penny Mickey is the cofounder of Mickey’s Popcorn, a social enterprise that blends gourmet food manufacturing with workforce development. She’s also a cofounder of the Gradus Project, which is building pathways to economic mobility in the food and beverage sector by creating paid transitional employment and training opportunities for people navigating barriers to employment.
Jackie looks directly at the camera against a dark gray background. She has long dark hair, wearing a black blazer and a pink blouse.
Boost Strategy Group

Jackie P. Taylor

Jackie P. Taylor is a business strategist, workforce leader, and founder of Boost Strategy Group, a workforce and economic development consulting firm dedicated to activating the entrepreneurial ecosystem. The company brings together businesses, government agencies, and community organizations to break down barriers to economic growth and build stronger, more inclusive local economies.
Carlos sits with his hand resting on his chin, looking at the camera. He has short brown hair, a beard and mustache. The background is softly blurred.
GoSprout

Carlos Vazquez

Carlos Vazquez, the founder and CEO of GoSprout, is driven by a mission to transform talent pipelines and create equitable career pathways in fast-growing industries. GoSprout is an apprenticeship management platform that streamlines apprenticeship programs for employers, educators, and workforce organizations, ensuring efficiency, compliance, and long-term success.

Nonprofit Entrepreneurs

Entrepreneurs embedding apprenticeship into mission-aligned workforce and education solutions.
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Flipp Inc

Raye Elliott

Raye Elliott is the cofounder and executive director of FLIPP Inc., a nonprofit building pathways into clean energy careers through work-based learning and entrepreneurship training. With experience in hydropower, workforce strategy, and government contracting, she leads efforts to support communities often excluded from the energy sector and strengthen the clean energy talent pipeline across Virginia.
James sits at a wooden table in a dimly lit room with arched stained glass windows, smiling at the camera.
Emerging Technology Institute

James Freeman

James Freeman, founder of the Emerging Technology Institute (ETI), has been motivated to help others grow through entrepreneurship since an early age. ETI is a research and development firm for the U.S. Department of Defense, specializing in emerging technologies and engaging students ages 10 to 24 in STEM activities, internships, and career pathway programs.
Dan is wearing a blue blazer and white shirt, smiling at the camera against a white background. He has short brown hair and a beard.
Polymath University

Dan Futrell

Dan Futrell is driven by his early years in foster care and later being raised by a single dad who worked rotating shifts at an insulation factory for 50 years. Today, he is the founder of Polymath University, a nonprofit interdisciplinary, apprenticeship-based, and debt-free postsecondary institution.
Rio-Karlo sits outdoors on a woven chair, wearing a black V-neck shirt, with greenery in the blurred background.
Handy Foundation

Ri-Karlo Handy

Ri-Karlo Handy is a media executive and founder of the Handy Foundation, a nonprofit that works to close gaps between education and long-term careers in film and television. The foundation runs six Registered Apprenticeship programs in highly sought-after media roles. Handy also leads HandyED, a platform that helps schools launch pre-apprenticeship programs aligned with real-world industry pathways.
Waymond smiles while wearing a gray blazer, light blue shirt, and pocket square, standing indoors with a modern abstract background.
Ed Farm

Waymond Jackson

Waymond Jackson is the president and CEO of Ed Farm, a nonprofit expanding digital fluency through tech-focused learning programs across the Southeast. Based in Birmingham, Alabama, he leads initiatives that prepare learners for the future of work, including Ed Farm Learn and the Innovation Challenge, while expanding workforce and economic opportunities.
Candace is in a tan suit and striped shirt smiling while sitting on a wooden desk, with books and a plant in the background.
The Live Out L!ve Foundation

Candace Newman

Candace Newman is the founder of the Live Out L!ve Foundation, a nonprofit dedicated to expanding pathways into the touring and live music industry. She launched Live Out L!ve to equip teens and young adults with the tools, mentorship, and experiences needed to thrive in entertainment careers.

Blended Model Entrepreneurs

Entrepreneurs who use a blend of for-profit and nonprofit strategies to drive change through dynamic organizational structures and a multifaceted approach to solutions.
Cara, a blended model entrepreneur, wearing a black outfit and gray plaid sleeveless vest. She is standing indoors at the Build Carolina facility, smiling and resting one hand on a railing.
Build Carolina

Cara Davis Anderson

Cara Davis Anderson is the program director of apprenticeships at Build Carolina, a nonprofit that works to expand access to tech careers in South Carolina. She leads Registered Apprenticeship programs in software, data, and cloud roles while partnering with employers and universities to strengthen pathways into the tech workforce through work-based learning.
Joy smiles confidently while seated in an office chair—capturing the inspiring spirit of modern entrepreneurs. She has long curly hair, wearing a black top, gold hoop earrings, and a gold necklace.
One Cedar Valley

Joy Briscoe

Joy Briscoe is the executive director of ONE Cedar Valley, a nonprofit committed to removing barriers to meaningful employment through increased access and educational opportunity. With a background in entrepreneurship and workforce strategy, she leads efforts to expand pre-apprenticeship pathways and close wealth gaps across the Midwest through high-quality job training programs.
Martin is seated in front of a blue background, smiling, while wearing a light gray blazer over a maroon shirt—capturing the spirit of modern entrepreneurs. He has a short beard and close-cropped hair.
ImaginED Georgia

Martin Chaplin

Martin Chaplin is the founder and CEO of ImaginED Georgia, a nonprofit advancing economic mobility through education and workforce innovation. A former educator and impact investor, he focuses on bridging opportunity gaps by strengthening apprenticeship pipelines, modernizing local programs, and building partnerships that support learners facing barriers to advancement.
A woman with long curly hair, wearing glasses and a blue-and-white striped blouse, smiles confidently in front of a plain blue background—capturing the vibrant spirit of modern entrepreneurs.
Genesys Works

Antiqua Cleggett

Antiqua Cleggett is the director of growth initiatives at Genesys Works, where she expands access to career-connected learning for students. With deep experience in workforce development, she has led the creation of Registered Apprenticeship programs and industry-aligned training programs that support economic mobility across the Southeast.
Vanessa is wearing a dark blazer and smiling in front of a gray background. She has long, curled dark hair with lighter highlights.
Boss Kidz Inc.

Vanessa Hardiman

Vanessa Hardiman is the founder and CEO of Boss Kidz Inc., a nonprofit that offers young people training to build entrepreneurship, financial literacy, and career skills. Her hands-on programs, which also include mentorship supports, reach more than 4,000 students annually, helping them gain the confidence to launch ventures and pursue long-term economic opportunity.
Katrina sits in front of a woven rope chair, smiling with her hand resting on her chin. She has shoulder-length dark hair and wears a white blouse.
DJH Express

Katrina Hawkins

Katrina Hawkins is the founder of DJH Express National Training Academy, which helps participants build skills for careers in transportation. Her work focuses on building pathways for people with records of arrest, conviction, and incarceration; veterans; and women of all backgrounds through commercial driver’s license training programs and Registered Apprenticeship experiences that promote opportunity and economic independence.

Entrepreneurship is a driving force for economic growth, innovation, and job creation—and a powerful tool for building vibrant and resilient communities. The JFFLabs Entrepreneurs-in-Residence (EIR) program accelerates early-stage ventures by providing mentorship, strategic support, and access to a powerful network across the education and workforce ecosystem.  

Over the coming months, the entrepreneurs in the College Talent Pathways to Apprenticeship cohort will continue to develop and refine their solutions—designing apprenticeship models that move learners into promising careers without forcing them to compromise on opportunity, support, or belonging.

Follow along to see how these entrepreneurs are using technology, creativity, and lived experience to modernize apprenticeship and expand access to opportunity. 

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