Jeff Glass: Entrepreneurs of the Underground Railroad

“The price of anything is the amount of life you exchange for it.”

-Henry David Thoreau

As I sat across from her, I asked the question. . .

“What’s it like to be Black?”

She gave a half-smile and a gaze as she waited silently for an explanation to my question.

“As a White male, I believe there are things I just will never fully understand. I see such strength in every Black person I know, or do I say African American?”

She laughed, “Either is fine with me,” she said. “It’s true. As someone who is half White and half Black, we are conditioned to be strong by daily struggles and challenges.”

“What do you mean?” I asked.

“Well, have you ever felt judged by the color of your skin?”

“No. I cannot say that I have.”

We are surrounded by people who are positioned to teach us about life. I grew up in the east side of San Jose, California, one of the most multicultural cities in The United States.

As kids, there was not much judgement because of our skin color. I was one of the only Whites in my group of friends. It was not until I got older and moved out of my hometown that I noticed high levels of racial discrimination toward Blacks, Asians, and Latinos.

History is one of greatest places to search for answers to understand our world today. The Underground Railroad, one of the most interesting stories of American history is an amazing story of courage and leadership, and it tells one of the most compelling stories of entrepreneurship. The Underground Railroad marks the first time in American history, as a major movement, that Blacks and Whites came together and took risks to complete a mission.

According to, an entrepreneur is “a person who organizes and manages any enterprise, usually with considerable initiative and risk.” Brett Nelson in his article, “The Real Definition of Entrepreneur—And Why It Matters”, defines it thusly: “Entrepreneurs in the purest sense, are those who identify a need—any need—and fill it. It’s a primordial urge, independent of product, service, industry, or market.”

Entrepreneurs are those who set out to transform society. They are serial problem solvers. Some of the most incredible entrepreneurs of our history are those who set out to solve one of America’s biggest problems: slavery. Exporting cotton, along with other commodities, was business. Slaves were free labor. Abolition was a societal shift to disrupt a corrupt market. The organization was the Underground Railroad, a network of slaves, abolitionists, business owners, and politicians.

The Visionary, A Woman Called Moses

“Every great dream begins with a dreamer. Always remember, you have within you the strength, the patience, and the passion to reach for the stars to change the world.”

-Harriet Tubman

Entrepreneurial endeavors begin with the heart. It takes a leader with grit to stand out from the crowd, and before becoming a leader with a following, they are visionaries with an idea to bring to the world. They are not blinded by the limits around them; they can see the outcome before it happens. Harriet Tubman was a visionary. Her mission to free slaves was clear, and her leadership was impeccable, making her one of the greatest entrepreneurs to ever live, a pioneer, a force toward the abolition of slavery in America.

Facing fears: Tubman took a stand against slavery in the worst of conditions.

Overcoming failure: She initially failed twice while trying to escape slavery.

Courage: She showed incredible persistence. She even went back to free her family, and freed several other slaves by escaping with them to freedom.

Sacrifice: She traded in her most prized possession, a quilt, for information on the Underground Railroad.

Passion: She burned with desire to achieve her mission, and still she was disappointed, believing she could have freed more, when she died many years later.

Leadership: Harriet Tubman inspired others not only to follow, but brought out the leader in many as well. She did not lead for power; she was a relentless force against slavery from the position of a servant.

Determination: She had an incredible drive coupled with efficiency toward success.

“I’ve never ran my train off the track and I’ve never lost a passenger.”

-Harriet Tubman

The Investors, Men Who Believed in the Dream

“Friend, I haven’t a dollar in the world, but if thee knows a fugitive who needs a breakfast, send him to me.”

-Thomas Garrett

Entrepreneurship takes a team; success is not achieved alone. Often the people behind the scenes give a substantial rise to the growth of an organization. Dr. Martin Luther King, Jr. had Ralph Abernathy. Walt Disney had Roy Disney. Without Roy Disney, the financial expert and partner of his brother Walt, we would never have experienced the motion picture of Snow White, and thus never heard of Walt Disney. Harriet Tubman had Thomas Garrett.

Finances, gifts, and skills keep a movement progressing forward. Tubman had a vision, the work ethic, and the drive to lead in the Underground Railroad movement. But, she needed fuel; she needed a team.

Thomas Garrett was a Quaker born into prosperity. He was motivated to participate as an abolitionist. A stationmaster in the last stop for slaves trying to gain their freedom on a route to Pennsylvania, he helped thousands by supplying housing, money, shoes, and even physical and legal defense of Blacks escaping from the South. Garrett provided the means for Tubman to free her own parents from slavery. Upon his death, he was acknowledged with the highest regard by those he served. They honored their leader by carrying his body to a final resting place.

William Still was another investor in the Underground Railroad. He gave of his time and money, and housed many Blacks escaping to freedom. He was the “Father” and the “Bookkeeper” of the movement, keeping careful records of facts, authentic narratives, and letters


While names like Garrett and Still are lightly whispered in history, without them and the sacrifices of thousands of others, the Underground Railroad would have failed as an unrealized dream.

The Evangelists: Carrying the Mission, Creating Permanent Change

“Little boldness is needed to assail the opinions and practices of notoriously wicked men; but to rebuke great and good men for their conduct, and to impeach their discernment, is the highest effort of moral courage.”

-William Lloyd Garrison, Journalist

“I was broken in body, soul, and spirit. My natural elasticity was crushed, my intellect languished, the disposition to read departed, the cheerful spark that lingered about my eye died; the dark night of slavery closed in upon me; and behold a man transformed into a brute!”

-Frederick Douglass, A Narrative of the Life of Frederick Douglass, An American Slave

“I do order and declare that all persons held as slaves within said designated States, and parts of States, are and henceforward shall be free.”

-Abraham Lincoln, The 16th President of the United States

In life, and on our entrepreneurial journey, there are people that come along side our mission to give us “the big break.” More well-known than Garrett, William Lloyd Garrison was one of the most famous White abolitionists. Garrison was a pivotal participant in the success of the Underground Railroad paving the way, in the public sector and through media for our evangelist of the mission, Frederick Douglass.

Douglass, born a slave, was a bridge between the voice of Blacks seeking freedom and politicians willing to support the radical change of emancipation. Douglass was a firm believer in the equality of all people, whether Black or White, male or female. His voice and actions complimented the vision of Tubman. His mark in history transformed the movement of freeing slaves into making slavery illegal.

Douglass knew that truly breaking free was only possible when slavery was no longer an option. When he first met Abraham Lincoln it was apparent both men shared more than just an idea, they shared an obsession for freedom. Their first meeting was the start of a relationship in which a former slave influenced the President to lead a national change for the freedom and equality of all people.

Unfortunately, slavery of Blacks cannot be erased from our history, but by the efforts of thousands across hundreds of years, it was abolished from our future.

As I read history, I find the majority of people in each era are blinded and guilty of justifying the slavery of their time. The greatest murderer of a person’s soul is the indifference in his or her own heart.

Entrepreneurship is a movement toward freedom from the shackles that limit us. It is more than a song to be sung. It is more than a proclamation to be shared. It is liberating ourselves while freeing others.

Our nation is still in need. We still have many problems left to solve. Slavery of Blacks in the United States is abolished, but racial tension continues in our society. It is time for all of us to come together. We the people, are the evangelists for social change in our world. We are the entrepreneurs.

This story is dedicated to my strong, beautiful Elsie, (descendent of Frederick Douglass). Papa loves you.

Jeff Glass is a children’s book author, youth advocate and social entrepreneur. Jeff writes entrepreneurial curriculums for the state of Nevada and the juvenile justice system. He lives in Carson City.


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