Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Helen Russell, Founder and Executive Director of Apprentice Learning, located in Boston, MA, USA.

What's your business, and who are your customers?

Apprentice Learning is a 10-year-old nonprofit providing real-world work experiences for middle-grade youth. We leverage career exploration to teach skills, ignite purpose, and nurture dreams.

Apprentice Learning partners with Boston Public Schools (BPS) and, as part of the academic school day, leverages real-world work experiences to expand students' skills, social networks, and opportunities to thrive. We envision an equitable world in which young people use real-world work experiences) as catalysts to create their own futures. Since 2012, we have provided over 1,000 young people in Boston with career education programs.

Tell us about yourself

Ten years ago, before I launched Apprentice Learning, I met a middle school student, Amaya, who was passionate about becoming a lawyer. Her family had been homeless, and a lawyer helped them secure housing. Amaya was so deeply impacted by that experience that she, too, wanted to help others in this way. Except—she hated reading and thought it was a waste of time. What if this young person could visit a lawyer and learn what skills and knowledge it takes to reach her career dreams? As an educator, I knew the value of learning firsthand through direct experience. Wouldn't seeing a lawyer at work in a law firm motivate her to use reading to reach her career dream? This experience inspired me to start a program--as part of the school day--that would give young people like Amaya an opportunity to see, feel, and hear what a career as a lawyer could be. In 2012, we launched our program in one school with 15 eighth graders. Today, we are in five schools and provide over 200 eighth graders with a workplace learning career program called an Apprenticeship.

I continue to be inspired by the resiliency and drive of young people. Even during the darkest days of COVID and school closures, these young people held on to their dreams and imagined a time when the world would be better. As an Executive Director, my time working directly with young people is divided by organizational responsibilities like fundraising, finances, and being responsive to our incredible board of trustees. I still make time to meet and learn from our apprentices. They have so much to offer the world and are my inspiration.

What's your biggest accomplishment as a business owner?

Nonprofit businesses are not owned by individuals; they are stewarded by a Board of Trustees, volunteers who give make a commitment to our organization and ensure our continued health and well-being. I am especially proud of the talented board and staff who have helped create our success: staff who consistently deliver high-quality programming and inspire young people to reach into the future and our board members whose meeting attendance averaged 90% throughout the last two years of the pandemic. Our trustees, many of whom are parents of young children, provided steady leadership throughout the uncertainty of the pandemic. I am proud that, together, we have a diverse community of such dedicated and committed people.

What's one of the hardest things that come with being a business owner?

As the Executive Director of a nonprofit, one of the hardest parts of my job is managing the many unglamorous—yet vital--parts of the job. I do not have an MBA, and we don't have the resources to hire a CFO. And yet, the health and well-being of an organization depend on the integrity of these often unseen financial and administrative operations. I also recognize that these tasks can make a real difference in the lives of our staff. For example, when we add benefits such as a contribution to a retirement account, a wellness program, and subsidized health care, we send an important message that staff are valued and appreciated. We have grown over the past 10 years, and so have the administrative hours required to manage the organization. Many nonprofits cannot afford these benefits. Our board has made benefits such as these a priority and part of the vision for a sustainable organization that values its staff.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

After 10 years of Apprentice Learning, I still believe deeply that our programs are immensely effective, imaginative, and authentic. Eighth graders (and our alumni) tell us how relevant our programs are for them and how helpful AL has been in introducing them to the world of work in a positive way. The program continues to be driven by the needs of our young people. And my three tips?

  1. Believe in what you do. Really believe.
  2. Hire great people and pay them as much as you possibly can. They will be your soulmates in creating an organization.
  3. Build a Board of Directors and create meetings that your trustees find engaging, informative, and inspiring. It will help them feel authentic purpose and accountability.

Is there anything else you'd like to share?

All kids have career dreams. Not all have plans to get there. At Apprentice Learning, we aim to nurture dreams and help kids make plans. Please join us if you are interested in becoming a partner and hosting young people at your business.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.