Leonardo da Vinci’s financial life was as unconventional and fascinating as his polymath pursuits. Born the illegitimate son of a wealthy notary, he was denied an inheritance and grew up outside the rigid structures that defined his society’s social classes. Despite these challenges – and perhaps because of them – Leonardo navigated a world of art, innovation, and patronage that ultimately enabled him to thrive and achieve unprecedented success.

From his humble beginnings as a young apprentice in Florence to his involvement in groundbreaking stage design and the creation of revolutionary inventions, Leonardo’s financial journey reveals how his creative disposition intersected with the right time and place in history.

The Countryside Classroom

Because Leonardo’s mother, Caterina, was a young peasant woman who had him at the age of 14, he was denied the same privileges as his legitimate half-siblings (9 brothers and 3 sisters). Unable to attend formal school with his brothers, Leonardo was instead educated by tutors. He reportedly struggled with reading and was easily distracted, a challenge his uncle noticed. Rather than reprimanding him for his lack of focus, his uncle took a more progressive approach to learning, immersing Leonardo in nature and offering a form of project-based education. This hands-on, experiential method nurtured Leonardo’s ability to learn through observation and creativity, laying the foundation for his future groundbreaking innovations.

“Study without desire spoils the memory, and it retains nothing that it takes in.” – Leonardo da Vinci

Leonardo da Vinci’s First Creative Dollar

  • The Amount: $100 ducats in the mid 1460s (worth around $15,000-20,000 USD today)
  • The Project: A Painted Dragon Shield

The Backstory

As a young boy, Leonardo da Vinci was asked by his father to paint a shield for a local peasant. To make the shield frightening, Leonardo created a monster akin to a dragon. His painting was inspired by a collection of real animals (lizards, bats, and snakes). Leonardo’s creation was a brilliant use of analogical thinking and creative synthesis, the process of combining elements from different sources to generate a new, imaginative concept. 

Instead of replicating real creatures from nature, he magnified distinctive features – like the venomous mouth of a snake and the wings of a bat – to craft something entirely new (and no doubt frightening)! Throughout the rest of his life, Leonardo continued to use the natural world as a springboard for invention.

His father, impressed by the work, had Leonardo paint a different shield for the peasant and sold the first shield sold for 100 ducats to a Florentine merchant, who then sold it for 300 ducats to the Duke of Milan.

It’s not entirely clear whether Leonardo da Vinci personally received any of the money from the sale of the shield. Based on the context and historical norms of the time, it’s likely Leonardo’s father would have been the one to handle the transaction and keep the money, at least initially.

In the 15th century, 100 ducats was enough to support a modest lifestyle for a middle-class person, and could be seen as the equivalent of a craftsman’s or skilled worker’s yearly income.

As Leonardo grew older and gained more recognition, he became more involved in his finances. By the time he worked for the Duke of Milan and beyond, he was negotiating lucrative contracts directly with patrons. Unfortunately, he was sued a couple of times for not completing projects.  

Social Class

Leonardo was born at a time when social class rigidly determined one’s occupation. As the son of a peasant woman, Leonardo would have likely belonged to the lower class and, without the help of his father, in all probability, would have entered a guild that included trades such as bakers and millers. These guilds were essential to Florentine society, and their members typically followed well-defined career paths based on social standing.

Finding a Mentor

Had Leonardo been born legitimate, he would have been expected to follow in his father’s footsteps and become a notary. Instead, he was left to navigate the uncertain path of self-discovery. Recognizing his son’s natural artistic talent, his father, impressed by Leonardo’s early drawings, took him to a renowned art workshop in Florence, where he found his first serious mentor, Andrea del Verrocchio. His father eventually offered to set Leonardo up with his own studio, but Leonardo remained attached to his mentor. 

In his later notebooks, Leonardo expressed gratitude for his humble beginnings and the freedom they gave him in life. (What a terrible notary or baker he would have been!) His lack of formal education still bugged him, however, and he set out to learn Latin at around age 40. 

“One can have no smaller or greater mastery than mastery of oneself.” – Leonardo da Vinci

Additional Interesting Facts:

  • As a teenager, many of Leonardo’s early works were completed in collaboration with established artists.
  • The Annunciation is believed to be Leonardo’s first solo painting at age 20, and it took him about three years to complete. This early work showcases his meticulous attention to detail and innovative approach, setting the stage for his future masterpieces.
  • At 28 to 30, it is believed that Leonardo experienced a period of deep depression. Researchers draw this conclusion from rare glimpses into his personal thoughts, found in his notebooks (though he seldom wrote about himself), as well as from a poem written by a friend, which lamented, “Leonardo, why so troubled?” These sources suggest that Leonardo grappled with inner turmoil.
  • At around age 30, da Vinci used nuts to experiment with dying the gray out of his hair.
  • He was a vegetarian and mainly strove to create war machines specializing in defense (rather than weaponry).
  • He played an instrument similar to the violin and also gave music lessons – how I wish we could hear some of his music recorded!
  • Leonardo kept his cadaver sketches a secret, leading a double life as he secretly dissected bodies to create detailed anatomical drawings. These studies not only deepened his understanding of human anatomy but also greatly enhanced the realism and precision of his art.
  • Leonardo had several books he intended to publish, but his perfectionism prevented him from ever completing them.
  • The lifestyle of a traditional artist never quite suited Leonardo. In fact, he once sent a “letter of interest” to Ludovico Sforza, the Duke of Milan, highlighting his expertise in engineering, design, and war machines, only briefly mentioning his skills in painting and sculpture at the end.
  • When Leonardo returned to Florence in the early 1500s, he developed a fierce rivalry and deep disdain for Michelangelo. While da Vinci was known for his polished appearance, clean-shaven face, and fine clothing, he saw Michelangelo as “dirty” and representing a younger generation whose values, in his view, were in decline. This contrast in personalities and artistic approaches fueled their animosity, with Leonardo viewing Michelangelo’s style as crude and a step backward.
  • Leonardo was known for his tendency to start multiple projects without finishing them, often jumping between subjects and ideas – from painting to engineering to anatomy – driven by curiosity, but struggling to focus on completing one task at a time.
  • Leonardo da Vinci is believed to have completed fewer than 20 paintings that survive today, with many of his works left unfinished.
  • Leonardo da Vinci created approximately 13,000 pages of notes over the course of his lifetime. Of these, around 7,000 pages have survived to the present day. He wrote in mirror image, using his left hand, likely to prevent smudging the ink. This method that also added an element of privacy to his work. In 1994, Bill Gates purchased some of Leonardo’s most remarkable scientific drawings, known as the Codex Leicester, for a staggering $30,802,500.

His Most Lucrative Endeavor

While Leonardo da Vinci is best known for his art and scientific inventions, much of his daily income actually came from theater production and stage design. In the courts of Milan and other Italian cities, he was commissioned to design elaborate sets and stage machinery for theatrical productions, a lucrative and highly sought-after service at the time.

His work in theater not only provided financial support but also sparked some of his most inventive ideas. For example, it was his involvement in designing complex stage effects that led him to conceptualize a machine resembling a modern-day helicopter. His fascination with mechanics and flight, stimulated by his work in stage design, would later contribute to his pioneering ideas on flight and mechanical devices.

Most of all, Leonardo da Vinci’s life is a striking example of how the right person can intersect with the right moment in history. Many scholars believe the Renaissance was sparked by the aftermath of the Black Death, which decimated a large portion of Europe’s population in the 14th century.

The plague not only caused immense social and economic upheaval but also broke down the rigid structures of medieval society. Florence, at the heart of this cultural rebirth, became a thriving center of scientific and artistic innovation, with a political climate that supported and nurtured the talents of dedicated artists, enabling them to reach their fullest potential.

“Art is never finished, only abandoned.” – Leonardo da Vinci

Go Deeper/Resources

Leonardo Da Vinci by Walter Isaacson 

How to Think Like Leonardo da Vinci by Michael J. Gelb 

*This post was written in celebration of the new Ken Burn’s documentary

*It should be noted that the above First Creative Dollar story comes from Giorgio Vasari’s “Lives of the Most Excellent Painters, Sculptors, and Architects” (1550), which provides a mix of biographical details, some factual, some anecdotal, about artists like Leonardo da Vinci. While it was the first account I could find of Leonardo’s early earnings, unfortunately the story itself is often taken with a grain of salt. We must remember that Vasari’s accounts, while historically valuable, are sometimes exaggerated or stylized for dramatic effect. As a result, let’s imagine the shield was sold for a substantially lower amount. Even at the price of $1000- $5000, I think we would still be impressed. Imagine if that shield were discovered today!



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