The Elder Scrolls V: Skyrim/Taking Care of Business

Taking care of Business is the second quest provided by the Thieves Guild. It is obtained by reaching Brynjolf at the Ragged Flagon after you complete his initial test.

Locate Brynjolf at the Ragged Flagon
To reach the Ragged Flagon, you need to find the entrance to The Ratways. This entrance is found somewhere on the lower level.

The entrance tunnel to the Ratways have two named bandits who will attack when you approach. The tunnel will lead to a large room with a skeever. From here, you can pick the Expert-level lock on the gate to the left, or take the longer path to the right where you fight more bandits.

When you reach Brynjolf, he will assign you your first task - to speak with three people in Riten to collect their debts. You can talk with Brynjolf to get information on how to get leverage on the three people or simply brawl the targets. The third mark will give you the money without the need to take extra steps.

Collect Keerava's debt
Keerava is the owner of the Bee and the Barb, where you first met the contact or the Thieves Guild. To convince her to pay the debt, you can speak with Talen-Jei for some information, and use it against Keerava.

Note that Talen-Jei will dislike you after collecting Keerava's debt. However, you can regain his favor by completing his quest to obtain three flawless sapphires for the marriage quest.

Collect Bersi Honey-Hand's debt
Bersi Honey-Hand is found in The Pawned Prawn. He can be convinced through a brawl, or by destroying the urn located in the shop.

Collect Haelga's debt
Haelga is found in Haelga's Bunkhouse. She values the statue located around one corner. Steal the statue while undetected, and talk with her to get the debt.

Return to Brynjolf
With all three debts collected, you may return to Brynjolf. He will bring you into the back room, and recruit you into the guild.

Aside from providing a shortcut into and out of the Ragged Flagon, you can also speak with Tonilia to receive the Thieves Guild Armor, as well as using her as a fence. You can also receive randomly chosen quests from Vex and Delvin.

Due to minor bugs, you will need to keep the guild armor as you progress during the quest. However, you can store the armor in a secure location (such as your home), or rebuild the armor from the randomly generated pieces that will appear in the guild.