When she turned six, she entered school at a Friend's Quaker school. Besides reading, arithmetic, and other subjects, Betsy had two hours every day for her trade of sewing. Betsy loved to sew. Every spare minute she had, she would take up some thread and a needle. During her school years, there was a sewing contest for all ages. It was going to be judged by creativity and originality. The prizes were five, three and one pound of money. She didn't know what to do, but her sisters gave her an idea of creating a sampler. Her sampler was the Liberty Bell in the night with stars (six pointed stars) and she won first place. Later her mom taught her a trick for making five pointed stars. In those days it was normally expected for girls to stop going to school at age twelve because they had a lot to learn about running a house.

Since Betsy's father knew she loved to sew he sent her to be an apprentice in an upholstery shop when she was a teenager. Another apprentice in the shop caught her attention--John Ross. After a few months, John Ross and Betsy Grimscom who was from a Quaker family fell deeply in love. John wanted to have an upholstery shop and Betsy longed to work with him. Unfortunately for Betsy, John was not a Quaker and in the Quaker religion, they believed that Quakers should marry Quakers. Betsy's religious parents objected when John proposed to Betsy because of the fact that John was not a Quaker. Sneakily, John and Betsy, who were about-to-be a couple, asked Sarah, Betsy's older sister, and Sarah's husband to row them across the river to elope. Since Betsy got married to John, the Quakers forced Betsy out of their religion.

John and Betsy had to work extremely hard because now they had their own upholstery shop. Although a war was going on and it was hard to get the supplies they needed, John and Betsy did not give up, like salmon trying to go upstream. Since Betsy had no church to attend now, she accompanied her husband to the Anglican Church where sometimes George Washington who was a general at the time, sat in a front row when he was in town. Although they had very few customers and very meager supplies, they kept working diligently and going to church regularly.

John and Betsy were both Patriots who supported the Revolutionary cause. John wanted to help all he could so he volunteered to be a night guard protecting the harbor. One ghastly night, John glanced toward the dock and noticed a spark by some explosives. He tried to run, but it was too late. Betsy waited patiently for her husband, but when he didn't come, she went to sleep. In the morning, she observed several men carrying a limp body. She ran out and she relized the man was her beloved John. The men tried to explain what had happened, but Betsy wasn't listening. She was trying to take care of her husband. Months later it was hopeless. John died. Betsy had some choices: go home to her parents or keep the shop. She knew that if John were alive, he would have wanted her to keep the shop open because he had started it, so she kept the shop. Although she would miss her husband who had died, she kept working in the upholstery business.

General George Washington was convinced that if the colonies had one flag, it would help them be more united and fight better against the British. John's uncle who was a friend of George Washington recommended Betsy to make the colony's flag because he knew she was a skillful seamstress. Since she wanted to help the revolutionary cause in any way she could, she replied, "Yes." Agreeing with most of Washington's original flag pattern, Betsy suggested a minor change. Instead of using six-pointed stars, she urged Washington to use five-pointed stars. The final plan ended up being thirteen horizontal red and white stripes and in the top left corner a blue box with thirteen five-pointed stars in a circle. General George Washington was satisfied with the revolutionary army flag when it was finished.