When Yaakov Avinu arrives in Charan, he finds most of the city’s shepherds lounging near the town’s well. After they tell him that they need to wait for all of the shepherds to arrive before they will have sufficient strength to roll off a big rock from on top of the well, Yaakov singlehandedly rolls the rock off, proving that he is a man of great physical strength. Upon removing the stone, Yaakov begins watering the sheep of Rachel, his first cousin and future wife. When he finishes watering her sheep, he cries that he does not have any gifts to give her and introduces himself to her. Thereafter, she runs home and tells Lavan of the previous events, and Lavan then invites Yaakov into his home where Yaakov stays for a month.
At the end of the month, Lavan tells Yaakov that even though they are relatives, it is unfair for Yaakov to be working in his uncle’s employ (presumably shepherding) for free and asks Yaakov what he thinks a fair salary is. Ramban notes that the Pasuk never states that Yaakov begins working for Lavan, and he gives two explanations for what could have transpired (29:15 s.v. HaChi Achi Atah, etc.). Considering what the Torah describes about the personality of Lavan, Ramban explains that Lavan attempts to exploit Yaakov’s great physical strength. He knows that Yaakov will feel guilty for staying in Lavan’s house without earning his upkeep, and he essentially offers Yaakov a job to ensure that Yaakov does not seek employment elsewhere to pay rent. However, this does not bode well with the first part of the Pasuk in which Lavan points out that they are relatives and therefore Yaakov shouldn’t work for free; what difference does the fact that he is a relative make in Yaakov’s future employment? Whether they are relatives or not, Yaakov should not be working for Lavan for free. If Lavan really is the wicked and conniving person we perceive him to be, why wouldn’t he just tell Yaakov that he cannot afford to keep Yaakov in his home without Yaakov paying rent? Then, he could convince Yaakov to stay and work for his rent and nothing more, instead of enabling Yaakov to request a reasonable salary for a man of his strength, which would be far more than the cost of his rent? Furthermore, Lavan has no need to worry that Yaakov would leave Charan to find work! Lavan is intelligent enough to know that Yaakov does not come merely to visit his relatives because it is clear that Yaakov had never before come for a visit, given that he needs to introduce himself to Rachel; rather, he must have come for a different reason. Perhaps this reason is to get married, (which is logical because Eliezer went to Charan to find a wife for Yitzchak), in which case Yaakov is unlikely to leave without first getting married, or to escape the wrath of Eisav (Kli Yakar (29:14 D”H Ach Atzmi UVsari Atah) explains that Yaakov told Lavan this) in which case Yaakov is even less likely to leave.
According to the other explanation of Ramban, as well as the explanations of Seforno, Rashi (29:14), and Rabbeinu Bachya (29:15), Yaakov had been working for Lavan for free from the start. Given that we know that Lavan is a dishonest trickster, why would he suddenly approach Yaakov about a salary instead of continuing to take advantage of Yaakov’s free labor? A relatively common answer, which the Yalkut Mei’am Lo’eiz and Chatam Sofeir, among others, offer, states that Lavan is responding to Yaakov’s statement to Rachel that he is the relative of Lavan. Rashi explains that with this statement, Yaakov implies that he can be as dishonest as Lavan (29:12 s.v. Ki Achi Aviha Hu). Lavan is worried that Yaakov is planning to rob him and tries to give Yaakov just enough money to avoid a robbery, but enough to keep his fortune. However, if he thinks Yaakov is deceitful, why would Lavan allow Yaakov to work without a salary in the first place?
The Yalkut David explains that it is to Lavan’s benefit for Yaakov to receive a minimal salary because by receiving an actual salary, Yaakov is no longer considered a Shomeir Chinam (someone who guards something for free) of Lavan’s sheep, but a Shomeir Sachar (someone who is paid to guard something). As a Shomeir Sachar, if Yaakov were to lose one of the sheep or if one of the sheep would be stolen from Yaakov’s care, he would have to pay Lavan, whereas he would not be obligated to do so if he were still a Shomeir Chinam. As long as Lavan would keep the salary low, he would make a minimal investment with a very high potential payoff.
A later episode further supports our picture of Lavan as a sneaky and clever businessman. When Yaakov stops working for wives and begins working for an actual salary fourteen years later, he is paid in sheep and goats that have unusual markings, meaning that he is a Shomeir Sachar with a minimal chance of actually being paid. This appears to be a very good bargain for the clever trickster Lavan. It is only through a miracle that Yaakov receives more than a few animals in his six years of shepherding for salary.