Von Staden was born the son of a burgher (bourgeoisie) in Ahlen, outside of Munster, Germany. His mother, Kattarina Ossenbach, died in the plague, and he had a brother, Herr Bernhardus von Staden, a vicar in Ahlen, and a sister. When at school studying to be a priest in Ahlen, he was accused of stabbing another student in the arm with an awl. His cousin, Steffan Hovener, invited him to live in Livonia with him, where "he would not be disturbed." In Livonia, he worked on building the city walls, but didn't like the labor and ran away to the Wolgarten estate in Wolmar, Valmiera. There, the wife of Wolgarten entrusted him with her estates when she learned he could read and write in Latin and German, and was learning Latvian.After Wolgarten remarried and moved away, Von Staden also moved, to Karkus, and became a merchant. After trouble erupted in the Livonian government, von Staden sent a letter to his friend, Joachim Schroter at the border town of Dorpat, which was held by the Russians. He wrote that he would serve the Grand Prince if he would be paid. He was invited to Moscow, where he met the Grand Prince Ivan IV. Ivan was impressed with von Staden, and invited him to dinner; soon after, he became a member of the Oprichnina.

His account of Russia, The Land and Government of Muscovy: A Sixteenth Century Account, was addressed to the German emperor, Rudolf II. It consisted of four parts: a petition, a description of Russia, a plan for the invasion of Russia from the north, and the author's autobiography. Von Staden hoped to influence the emperor to invade Muscovite Russia, restore the region to the German Order of Knights, and be rewarded. The Count of the Palatinate, Georg Hans von Veldenz-Lutzelstein, had a similar plan and drafted von Staden into his employ. Between 1578 and 1582 von Staden worked as a sort of spy for the German Order. He sent his proposal to the Master of the German Order, later to the Polish and Swedish courts as well, on behalf of the count.Historians discovered this document in 1839 in the Prussian state archives, knowing of the count's plans, but no link to von Staden was discovered until a few years later. His accounts are the most insightful and descriptive of the day, and displayed the disorder of the Russian government in the 1560s-70s. He calls Ivan IV a "horrid tryant", but wrote more neutrally than his contemporaries. His narratives of the Oprichnina are the only accounts written by a member, and the history of the Oprichnina was rewritten after von Staden's accounts were found. He describes the targets of Ivan's terror as individuals who Ivan believed to be dangerous to his authority, not against the entire aristocratic class as previously thought.

Tsar_ a 2009 Russian drama film directed by Pavel Lungin.