Business leaders have long sought inspiration in Shakespeare’s work – as much for the tragic mistakes to avoid, as the qualities to emulate. 

Yet history’s finest writer was also a sharp commercial operator in his own right, with sidelines in everything from commodities to real estate, plus a gift for protecting his artistic interests.

Published posthumously in 1623, a line from Cymbeline hints at William Shakespeare’s business credentials: “a right judgement draws us a profit from all things we see.” In truth The Bard had a knack for “right judgements” in all sorts of areas, making him one of Jacobean England’s most intrepid entrepreneurs.

Here are just a few of the many ways the great man displayed an impressive entrepreneurial spirit.


1. All the King’s Men: Invest wisely for dual revenue streams

Shakespeare protected his stake in his own masterpieces by becoming a shareholder in the company that performed them. From Hamlet to Othello the poet wrote many of his greatest plays for one particular theatre company as part of an exclusive deal. Not content with the potentially short-term gains of a playwright, he became a major business partner in ‘The Lord Chamberlain’s Men’ troupe, later to become ‘The King’s Men’.

Paying £70 for his share, this investment secured a friendly route to market for his future plays, plus earnings for each and every one of the group’s successful performances. This wise investment created an effective loop of literary prosperity.


2. Turn foe to friend: Seek allies amongst the competition

In Henry V, Constable ponders whether “there is flattery in friendship” and the same question could be asked of Shakespeare himself. Despite strong rivalry with contemporary dramatists like Ben Jonson and Christopher Marlowe, Shakespeare formed friendships with both playwrights. These positive relationships were key to creating what is remembered as a golden age of drama as each learned from their peers and endeavoured to best the other’s last success.

This perfect balance between healthy competition and friendship can be read as evidence of Shakespeare’s tact in business. Developing allies within his profession gave him opportunities for feedback and further insight. This led to some of his greatest work and prompted Jonson to preface his 1623 folio of Shakespeare’s work, “To the memory of my beloved, the author, Mr William Shakespeare.”


3. A Global success: Create your own opportunities

The Bard’s appetite for enterprise didn’t end at the King’s Men. A 12.5% stake in The Globe Theatre on the Southbank saw him part-owning the very stage on which his plays were performed.

In 1600, his interests moved north of the river when he became a shareholder in The Blackfriars Theatre, an indoor playhouse. In doing so Shakespeare secured direct control over both outdoor and indoor performance spaces, creating a year-round opportunity to attract crowds to his new plays and ultimately generating a steady stream of revenue.


4. Breaking bard: Opportunities can be found anywhere

While agriculture may not immediately spring to mind when thinking of the Elizabethan playwright, Shakespeare was known to hoard grain, malt and barley then re-sell at inflated prices. It was a smart and simple business, as poor harvests saw good trade during shortages.

If this sounds a little callous from the genius who taught humanity so much about itself, perhaps it speaks to his preoccupation with duality. Shakespeare was living proof a person can feel intense understanding and sympathy with others, while occasionally profiting from their misfortune.


5. All’s well that ends well: Plan for the finish line

Shakespeare re-invested many of his earnings into real estate in what turned out to be an excellent way to fund his retirement. In 1597 the poet purchased the second largest property in Stratford-upon-Avon. This timely investment allowing him to leave London in favour of a quiet life around 1610, just in time to escape the Bubonic Plague.

While the full appreciation of his works only took effect hundreds of years after his death, Shakespeare’s business acumen allowed him to generate a good nest egg to retire on and eventually leave a generous inheritance for his children. He left an estimated £470 (roughly £50,000 in today’s currency) to his family and also donated £10 (around £1,000) to “the poor of Stratford”. The only person who failed to financially profit from Shakespeare’s entrepreneurial talent was his wife, whom on the playwright’s death, received nothing more than his “second-best bed”.
Of course Shakespeare was first and foremost an artist. But the question remains as to whether The Bard would occupy the same unrivalled position in the literary canon had he not employed his entrepreneurial skills to promote his plays and earned himself time to write.

An Elizabethan playwright was a career lacking in wealth or stability. Yet Shakespeare’s timely investments and strategic business decisions, alongside his ability to secure powerful patrons, freed him up to spend all his time creating, making him the world’s most famous writer some 400 years after his death.

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