~c. 594 CE, shortly before the marriage to Khadija RA · 28 BH
Khadija RA was the richest woman in Makkah, a twice-widowed businesswoman who could not travel herself and so hired men on a mudarabah (profit-sharing) basis to run her trading caravans. Having heard Muhammad ﷺ praised by her sister, she sent him an offer through her servant to take charge of her caravan, despite his inexperience in business. Muhammad ﷺ went to his uncle Abu Talib for advice before accepting, and Khadija RA offered him 50% of the profits as an incentive. She sent her servant Maysara along with him, and the caravan traveled to the market town of Bosra, outside Damascus.
Outcome: The caravan returned having made double or triple the profit anyone had made before, which Khadija RA attributed to the Prophet ﷺ's honesty and the barakah in his affairs.
Muhammad ﷺ's honesty and diligence on this trip doubled or tripled the usual profit, deepening Khadija RA's regard for him and setting the stage for their marriage.
Other events recorded in 28 BH. Their order within the year is not established; use the storyline above for the sequence.
He showed such care and concern in the herd and the trade, and was entirely honest in every dealing. And it is said a cloud gave him shade the whole way.
Maysara's report to Khadija RA on their return from Bosra.
O my uncle, Khadija has sent me such-and-such an offer: what do you think?
Asked his uncle Abu Talib for advice after Khadija RA sent an offer, through her servant, asking him to lead her trade caravan to Syria in exchange for a share of the profit.
O my nephew, she is well known to be the richest woman. Allah has blessed you with this opportunity. Do not say no to her.