The Third Supply Is Coming Soon

Captain Samuel Argall

Captain Samuel Argall, who looms large later in the history of Jamestown, reaches Jamestown on July 13, 1609, in only nine weeks instead of the usual 16 weeks. But the Sea Venture fleet doesn’t know this, as it departs only ten days after Argall. Captain Argall tells the colonists in Jamestown that the Third Supply fleet will be arriving soon.

The Long Ocean Voyage to Virginia

1609 Era English Sailing Ship

On May 5, 1609, the Virginia Company of London sends Captain Samuel Argall to Virginia to explore a more direct route to Virginia instead of going south along the coasts of Europe and Africa and then sailing west to the Caribbean and then north up the Gulf Stream along the Atlantic coast of America. The traditional southern route is the one John Rolfe and the Sea Venture will take ten days later.

The rationale for trying a more northern route is twofold. First, despite the peace treaty of 1604 between England and Spain, the Spanish are attacking English ships in the Caribbean. For example, in 1606, the Richard, a ship of the Virginia Company of Plymouth which holds the royal charter for more northern lands, sails the traditional route to the Americas and is then to head up to Pemaquid on the Maine coast north of the Kennebec River, but it is captured by a Spanish ship and all hands are sent to Spain and imprisoned. The second reason is to see if they can find a faster route to Virginia.

Tobacco Seeds

Rolfe is almost certainly carrying some of the difficult to obtain seeds of Spanish tobacco with him on the Sea Venture. Tobacco seeds are very tiny, so it would be easy to carry a large quantity of them, and many historians believe he did carry them. The seeds are difficult to obtain because the Spanish have a monopoly on the mild sweet tobacco (a much harsher variety is native to Virginia) and forbid anyone to sell tobacco seeds to a non-Spaniard under penalty of death.

Since these tobacco seeds of Caribbean tobacco were central to John Rolfe’s entrepreneurial vision and plan, I can’t imagine he would have left everything he knew and traveled to Virginia with his wife unless he had a supply of tobacco seeds with him.

The Three G’s – Gold, Glory, and God


The Virginia Company of London proclaims that Protestant English colonization of America is God’s will. They get ministers to preach that God wants a Protestant English colony in Virginia rather than a Catholic Spanish colony like Mexico, most of South America and Central America, and St. Augustine in what is now Florida. The Virginia Company of London also preaches that it is God’s will to evangelize and convert the native savages of Virginia to the Protestant religion. So Rolfe’s goals are in line with what today are called the three G’s of colonization, Gold (literally or figuratively), Glory (of self and/or King and country), and God.

John Rolfe Invests In His Venture

Investing In His Venture

Rolfe takes care of the money or investment needed for every entrepreneurial venture by buying shares in the Virginia Company of London. He thereby secures passage to Virginia for himself and his wife, and land for planting in Virginia.

Finding a Market Need

John Rolfe sees an opportunity, he identifies a market need that people will pay for, to break the Spanish monopoly of the mild tobacco the English prefer. Rolfe’s goal in traveling to Virginia is to grow the mild Spanish tobacco in Virginia, cure it, and export it to England at great profit, thereby bettering himself.


In the early 1600’s, tobacco wasn’t the demon that many of us see it as today. In the late 1500’s and early 1600’s, tobacco was used both by the Virginia Indians and by the English for medicinal purposes. The Indians also used it for ceremonial purposes.

Tobacco is introduced into England in 1556 by a sailor, and it is a mild tobacco from the Spanish controlled Caribbean. Tobacco becomes popular in England for recreational purposes sometime between 1565 and 1590. On June 18, 1586, Francis Drake takes the remaining settlers from Roanoke Island back to England, arriving on July 28, 1586. They bring with them tobacco pipes, tobacco seeds, and tobacco plants.

In the early 1600’s, all farming is organic. Chemical pesticides, herbicides, and fertilizers would not be developed for centuries. And mineral fertilizers were not used, unlike today when mineral fertilizers are mined from areas high in radon. Thus, there were no toxic chemicals emanating from the tobacco smoke. Also, tobacco hadn’t yet been bred to maximize the concentration of nicotine. So tobacco didn’t have all the disadvantages it has today.

Tobacco smoking did produce smoke, which could be annoying to others, as King James I noted in his diatribe against tobacco. And it could be bad for one’s lungs, although in the London air thick with coal smoke, one might hardly notice.

Enjoying a Pipe


Colonial Clay Pipe

As a young adult, John Rolfe likes to smoke a pipe of tobacco. A gentleman typically smokes only one bowl of a pipe in an evening. So the quantity of tobacco smoked is nothing like the quantity of cigarettes, which were developed 200 years later, smoked by a typical smoker today.

In Rolfe’s time in the early 1600’s, clay pipes for smoking tobacco are very small. The tiny bowl of the pipe holds only about one twenty-fifth of an ounce of tobacco. You can see an historic pipe in the museum at Jamestown. The entire bowl of the clay pipe is about the size of the tip of my little finger from the bottom of the fingernail to the end, and I have small hands.

John Rolfe’s Family History

John Rolfe and a twin brother Eustacius were born and baptized in the parish church in the village of Heacham, county of Norfolk, England, about 110 miles north of London, on May 6, 1585, during the reign of Queen Elizabeth I. This was three years before the English navy under Sir Francis Drake defeated the Spanish Armada on August 8, 1588, and thus became the most powerful European nation. John’s twin brother Eustacius died 27 days after his birth, on June 2, 1585.

John Rolfe is named for his father John Rolfe. His father was born October 17, 1562. John Rolfe’s mother was Dorothea or Dorothy Mason, born in 1559. John Rolfe the father died when John Rolfe was eight years old, on November 29, 1593. John Rolfe’s grandfather died the same year. His mother Dorothy remarried on March 9, 1594, to Robert Redman. So we can assume John Rolfe’s childhood was difficult.

Seeking His Fortune Across the Sea in Virginia

The Sea Venture is the flagship of the nine vessel fleet assembled to rescue the so-far disastrous two year old attempt to establish an English colony in Jamestown, Virginia. John Rolfe had his 24th birthday just nine days before, on May 6, 1609. He is a gentleman farmer, not an adventurer, soldier, or craftsman like most of the passengers. And to underscore the fact he is a settler not an adventurer, he is accompanied by his wife, Sarah Hacker, whom he married the previous year. Although she probably doesn’t realize it yet, Sarah is likely pregnant with their first child when she boards the Sea Venture.

Seeing Possibilities

As John Rolfe boards the Sea Venture in London, England on May 15, 1609, for his epic adventure, who would have thought that he, John Rolfe, a 24 year old gentleman farmer, would in a period of only seven years assure the success of English colonial efforts in America, marry the most important woman in Colonial America, succeed as America’s first entrepreneur becoming the father of American capitalism, create America’s largest export for the next 150 years, and create a billion dollar industry that still thrives after 400 years. In addition, who would have thought he would become a member of the first representative legislative body in the Americas, a fundamental institution that would lead to our uniquely American form of government. Certainly not John Rolfe, and most certainly not anyone else.

William Shakespeare’s “The Tempest”

William Shakespeare - Author of The Tempest

Before he could accomplish all this, as you will soon see, John Rolfe’s entrepreneurial challenges included an Atlantic crossing on the Sea Venture that was so extraordinary that it became the inspiration for William Shakespeare’s play The Tempest.

Financial Success and Political Peace in Which to Thrive

Financial Success and Expansion

John Rolfe’s two important contributions, the financial success and the period of peace for the first permanent English colony in the Americas, led to the establishment of the English common law and the English cultural heritage of representative government and religious freedom on which the United States of America was founded. If John Rolfe hadn’t created a financially successful industry and fallen in love with Pocahontas, we could have a French, Spanish, or even Dutch heritage.

First Interracial Church Wedding in the Americas

Wedding of John Rolfe and Pocahontas

Notably, the wedding of John Rolfe and Pocahontas was the first interracial church marriage in the New World. John Rolfe’s initiative in his personal life as well as his business life set an enduring precedent for American life.

Pocahontas’ marriage to Rolfe led to a period of peace, known as The Peace of Pocahontas, which allowed the English foothold in Jamestown to expand until there were too many English for the natives to kill or expel. This period of peace was directly responsible for the success of the Virginia colony, and John Rolfe was responsible for it.

Political Success of English in America

Pocahontas and John Rolfe

Second, John Rolfe fell in love with Princess Pocahontas. He asked for and received permission from the Governor of Virginia to marry Pocahontas, recognizing that interracial marriage was at least discouraged if not prohibited. No white man had ever married a Native American. He also asked for and received permission from Pocahontas’ father, Chief Powhatan, the paramount chief of 31 Algonquin tribes. John Rolfe and Princess Pocahontas were married on April 5, 1614.

Economic Success of English in America

Jamestown, Virginia

John Rolfe’s first accomplishment was his sole responsibility for the economic success of the Virginia colony. For years the colony could find no gold, silver, pearls, or cash crop. John Rolfe developed the first and only cash crop, which assured the success of the colony and made it not only viable but wildly successful financially. The History Channel’s 2010 production America: The Story of Us called Jamestown after the success of John Rolfe’s tobacco America’s first boomtown. Without the entrepreneurship of John Rolfe, Jamestown would have been a ghost town.


Jamestown, Virginia

Jamestown was the first permanent English settlement in the Americas, thirteen years before the Virginia Company of London granted a land patent to colonists on the Mayflower allowing them to settle at the mouth of the Hudson River in 1620. However, they sailed to the north and settled in what is now New England.


The Virginia colony was in serious trouble financially and the colonists were constantly dwindling in number and strength because of disease, starvation, and Indian attacks, and likely wouldn’t survive. Two accomplishments by John Rolfe turned things around for Jamestown, for Virginia, and ultimately for the future United States.

Unique American Spirit of Entrepreneurship

Tower of Bable

Because of my name, I’ve heard about John Rolfe and Pocahontas my entire life. I didn’t appreciate his critical role in the success of England colonizing America until a visit to Jamestown, Virginia, set me on a path of serious research into the life of John Rolfe. I spent four years researching this book. By a happy coincidence, I was already researching entrepreneurship. I discovered that John Rolfe was America’s first entrepreneur and he set the tone for the unique American spirit of entrepreneurship.


As you will see, without John Rolfe’s two major contributions, the Virginia colony would have failed and the French, Spanish, and Dutch, rather than the English, would have colonized not only New Mexico, California, Florida, Canada, Delaware, and New York, but most of what is now the United States. In a very real sense, John Rolfe is responsible for the United States being an English speaking nation.

Starting Your New Business

Starting Your Business

Getting Started

I’m sure you’ve already read all the dire statistics about how the odds are stacked against you in starting a business and how few new businesses succeed. Yet you are right to have confidence that your business will beat the odds and succeed. Without that belief you and your business will fail.


This book will help you avoid the mistakes that may not be obvious to many of the entrepreneurs who start businesses. I certainly hope your challenges won’t be nearly as tough as those actually faced and overcome by America’s first entrepreneur. But the dramatic events of his life graphically illustrate the kinds of challenges every entrepreneur faces. And it’s a great story even if you’re not an entrepreneur.


In each chapter you will find the inspiring true and epic story of the challenges faced by America’s first entrepreneur. As you enjoy the historical narrative, think about your own entrepreneurial venture and consider whether you have met your similar business challenges. It was an amazing time in history, and the end of each chapter highlights some key events going on elsewhere in the world at the same time.


Once you have absorbed the wisdom presented by the story of America’s first entrepreneur, you can be sure your belief that your business is going to succeed is rooted in sound entrepreneurial principles, not in la-la land like your relatives probably think and say.


One entrepreneurial goal.


What is being an entrepreneur all about? The dictionary defines an entrepreneur as “a person who organizes and manages any enterprise, especially a business, usually with considerable initiative and risk.”

Who becomes an entrepreneur, and why would you want to be an entrepreneur? Here it is in four words.

Creation. Freedom. Money. Legacy.

Being an entrepreneur is all about creating a venture that you have some control over, achieving the freedom to live life as you wish – doing what you want, when you want, where you want, and how you want – acquiring the money or wealth to do so, and leaving a business or financial legacy. And, oh, enjoying the game along the way.

Why do you need this book? This book will give you time-tested principles of entrepreneurship which will help you succeed in reaching your goals. America’s first entrepreneur illustrates all the important principles of entrepreneurship. America’s first entrepreneur was wildly successful within seven years using these principles after a series of seemingly insurmountable obstacles. His epic story is very inspiring. The industry America’s first entrepreneur created is not only still successful in America after 400 years, but has multi-billion dollar sales year in and year out.