Dati was politically active in Florence, repeatedly serving as consul of the Silk Guild and, later in life, holding a series of public offices.

Dati's diary and Libro Segreto represent a major source of information on the economics and social aspects of Florence during this time.

According to his diary entry, her dowry of 800 gold florins that came from Betta's first cousins was soon invested in the shop of Buanccorso Berardi, another silk merchant.

At this time, merchants used the putting-out system, which meant that the silk firm owner, like Dati, would buy raw materials and have them processed by workers (e.g. weavers) for a price set by the guild.

[30][31] He chose his wives based their dowries;[32] borrowed from banks, friends and his brother Leonardo;[33] and used his own money in order to raise the capital necessary to have a substantial stake in the company and its profits.

According to the 1427 catasto (Florence's tax survey), Dati's total wealth—including private investments, e.g. cash and silk; real estate; and public debt investment—at 64 years old was 3,368 florins.

[38] This is demonstrated by Dati, who seems to have sold a lot of his product in Valencia, a bustling emporium in southern Spain that was well-populated with Florentine merchants and served as an important trading hub for the Mediterranean rim.

He laments that this trip would not be expensed by the business and that he did not manage to collect 4000 Barcelona pounds—a considerable sum—from one client, instead returning to Florence in 1392 with a notarized deed.

On September 10, 1393, while returning to Valencia (perhaps in another effort to collect the outstanding debt—he mentions he wants to "finish up business") he was robbed by a Neapolitan galley and taken prisoner to Naples.

However, a war between the Florentines and the combined forces of the Genoese and Neapolitans under the aggressive expansionist King Ladislaus caused him to delay in Valencia.

[52] He finally returned to Florence in March 1411, but the delay, robberies and kidnappings speak to the volatile environment 15th century merchants operated in due to tensions between the northern Italian city-states.

It is evident that the use of account books was standard practice in the thousands of surviving Mercanzia documents today,[53] and Lana's failure to do so left Dati bitter.

[57] The Arte di Por Santa Maria was a conglomerate guild that originally governed Florence's retail cloth merchants, silk manufacturers, and small artisans like tailors.

[64][65] Dati also reports serving on the two advisory councils which worked closely with the Signoria, advocating for their parts of the city and voting on important issues.

[69][70] He also served as among the Ten on Liberty in 1405, primarily settling small quarrels between citizens but also handling foreign affairs,[71][72] and among the Five Defenders of the Contado and District through which he advocated for peasants in his neighborhood.

[73] He also held the position of Overseer of the Ospedale degli Innocenti,[74] a lavish orphanage patronized by the Arte di Por San Maria, Dati's guild.

As Gene Brucker argues in his book, Renaissance Florence, the church was so venerable and so deeply enmeshed in the city's history and traditions that it was one of the most conservative forces in Florentine life.

[78] Florentines continued to grow in their faith, like Dati, despite death, plague, famine, and war striving to atone for previous sin.

"[79] When his first wife, Bandecca died on July 15, 1390, as a result of illness from miscarriage, Dati states in his book that "she peacefully returned her soul to her Creator".

[80] Also, for his first child's death, Dati states that, "Our Lord God was pleased to take Himself the fruits which He has lent us, and He took first our most beloved, Stagio, our darling and blessed first-born.

[92][93][94] Dati's diary is an example of a Florentine trader who struggled in making a successful business and had a marginally more prominent civic career.

[99] Failure to do so would lead to paying 5-20 solidus to "God’s poor," distributing alms, and doing 20 Hail Mary's, depending on the severity of the pledge broken.

[107] The reality of daily life recorded by Dati reflects an unstable political environment; people were caught between agreeing with the papacy or the Commune of Florence itself regarding supremacy and obedience.

[111] The focus on the Milanese-Florentine war unified his work, allowing him to write Istoria for future guidance, not relying overmuch on morality or historical examples like previous chroniclers.

[122] Fortune was actively manifested and personified in human action and reaction: the rise and fall of the Duke was because he could not see that his greed was a temptress, luring him.

[125] Dati engendered civic pride when discussing past events and the mood of the people when confronted with an oligarchical power, believing that the government of the Commune was superior to that of Milan and fell into agreement with the papacy.

Finally, Dati's Istoria succeeded his contemporaries because he removed divine intervention as the central agent, replacing it with human nature.

[131] Filiberto Segatto determined that La Sfera was written between the early fifteenth century and Dati's death in 1435 because there is a 1403 codex in the library of the University of Pavia.

The exclusion of the rest of the Mediterranean ports despite other sources documenting Florentine trading suggests that the manuscript was incomplete, possibly due to Gregorio's death in 1435.

[145] As such, La Sfera is considered an important early Italian source for vernacular writing pertaining to geography, called "geografi metriche".