Life is full of surprises. You can think you understand something thoroughly and then find out that you are mistaken.
Like many people, I believed Shakespeare to be born into an impoverished home, and that he never made much money.
How wrong I was.

To explain how Shakespeare made enough money to buy New Place in Stratford, which cost him £120 in 1597, it is helpful, I think, to go back in time and understand how his father John Shakespeare and his grandfather Richard Shakespeare made a living.
Richard Shakespeare (1490-1561) came from Wroxall, a village not far from Kenilworth Warwickshire, which boasted a large abbey. For some reason now obscured by the mists of history, Richard decided ~ at the age of forty ~ to move ten miles south to the village of Snitterfield, to become a tenant farmer on land owned by Robert Arden. In those days, a tenant farmer was a free man who had the opportunity to become rich, depending on what kind of contract he signed with the owner of the land. Richard Shakespeare must have signed an advantageous contract with Robert Arden, because he is described as being a “prosperous farmer with livestock” in the manorial records. By the time of his death in 1561, he was leasing 80 acres of land and possessing an estate worth £38 17 shillings, which is worth more than $22,000 in 2019 USD. Not a large sum to be sure, but enough to keep the wolf from the door at a time when people rarely bought luxuries, and when a barter economy was very much in force between friends, relations and neighbors.

John Shakespeare (1531-1601) was born in Snitterfield, which lies approximately 4 miles to the north of Stratford-upon-Avon. We can surmise that John must have been bright and ambitious for he did not become a tenant farmer like his father, dependent upon the whims of others. Instead he became apprenticed to a glover, so that by the end of his seven years of apprenticeship, John Shakespeare was a skilled artisan. In order to belong to the local Guild of Glovers, he would have had to produce gloves of the finest quality. John Shakespeare must have passed these exams because when his son William was growing up, he was making gloves for the well-heeled and employing several apprentices to help him.
But John did more than that. He “diversified his portfolio,” as we would say today. He got into the wool trade, presumably because it was making so many of his compatriots wealthy. And then he leant money at exorbitant interest rates. If you visit Shakespeare’s birthplace on Henley Street, you will see that far from being born in poverty, William Shakespeare was born into a prosperous upper-middle class family, headed by a very talented businessman in the shape of John Shakespeare.

And so, I hear you asking, who was Shakespeare’s mother? She was one Mary Arden (1536-1608.) Yes, you have heard that name before, as she was the youngest daughter of Robert Arden, the landowner who leased 80 acres of his land for Richard Shakespeare to farm as a tenant farmer.
The Ardens were landowners, rich enough to to be Yeomen farmers who could vote in local elections as they held a 40-shilling freehold to the King of England. They were also were well-connected with ancestors who fought in the Second Barons’ War (1264–67) on the side of Simon de Montfort (Thomas Arden), the Wars of the Roses (Robert Arden senior), and at the court of Henry VII (John Arden.) Thus, they were several notches above the likes of Richard Shakespeare. This means that his son John must have impressed Robert Arden with his brights, hard work, and ability to become wealthy, which convinced Robert Arden that his darling daughter could continue to live a life to which she was accustomed upon her marriage to John Shakespeare.

This leaves us with William Shakespeare (1564-1616) the most famous writer in the English Language. John Shakespeare had risen so high in Stratford – becoming mayor of the town ~ that he was able to arrange for his son and heir William to get a classical education at the local grammar school, something that his own father, the tenant farmer, had been unable to give him. This was a wonderful start in life in the 1570s for a bright boy, and anyone who has experienced the famous plays knows that they are replete with references to the Classics.
But during his lifetime Shakespeare was almost unknown. Apparently his neighbors in Stratford did not realize they had a great bard within their midst. Shakespeare did not become famous until about 150 years after his death, when the great actor David Garrick introduced him to English audiences in the 1760s.
Which leaves us with my original question ~ How did Shakespeare make £60 pounds a year?
Of course, he wasn’t becoming rich from acting ~ Actors then and now are never paid much for their work. He also wasn’t becoming rich from his plays, because the ones that were published only earned him about £8 each (in the 1590s.)

So what did Shakespeare do?
In order to understand that, we have to remember that when Shakespeare was only 18 years old he married Anne Hathaway, a woman who was about eight years older than himself. As a minor, William Shakespeare had to ask his father’s permission for this marriage to take place. One can imagine John’s disappointment that his son and heir had thrown away an opportunity to become an apprentice, as one couldn’t do that if one was married. But a baby was on the way and respectability was everything in those days, meaning that the child had to be born after the parents were married.
So it really wouldn’t have been wise for William Shakespeare to tell his already-disappointed-father that he was going to London to act. A much better way of presenting his plan to go to London, was to offer to sell gloves to all the fine aristocrats who graced Elizabeth’s court. John Shakespeare could understand that line of reasoning, and probably packed William off to London with his blessing, and his finest gloves stowed in Williams’ saddlebags.

In London, William was able to give full reign to his acting and play-writing passions. But it turns out that not only could William pen sonnets, he was also a very talented businessman. Like his father, he didn’t do just one thing. Not only did he act and write plays, but he could also make gloves. And he was really good with money.
Shakespeare himself lived a frugal life in cheap lodgings in London so that he could send the bulk of his earnings back to his family in Stratford. But the stroke of genius was buying shares in the Lord Chamberlain’s Men, an acting company that was founded in 1594, which he also worked for as an actor and playwright. This was a very lucrative venture as there were roughly 3,000 playwrights in London at the time, all dying to see their plays performed. Luckily, the English audiences of the day had a voracious appetite for new plays and so ticket sales boomed. Therefore, if you were a young man who actually owned shares in such a company, you would be doing very well indeed.
And so it was that in 1597, when William Shakespeare was only 33 years old, he was able to buy the largest house in Stratford, New Place, which he’d passed every day on his way to school. The price was £120, equivalent to two years of his earnings. That is just over $37,000.00 in 2019 dollars. It seems that William negotiated a bargain price for this magnificent house!
And so this is a story not about a genius playwright, but three talented businessmen
~ Richard who signed an advantageous deal with his landlord,
~ John, who had fingers in many pies in Stratford, including making gloves,
the wool trade, and usury,
~ William, who owned shares in the Lord Chamberlain’s men.