Taking Care of Business (quest)

Brynjolf is impressed with the talent the Dragonborn has shown while performing his initial task. He has asked that you come meet him at the Ragged Flagon beneath Riften for further work.

Locate Brynjolf at the Ragged Flagon
To get to the Ragged Flagon, you need to make your way through the Ratway. Head down to the second level of Riften, and follow your quest marker to the entrance of the Ratway. When you enter the Ratway, just go down the passage. In front of you will be two thugs warming themselves around a campfire. Take care of them and go out the exit to the right. Once in the next room, just turn right again and you will see a raised drawbridge in front of you. Drop down and take the right exit again.

Down a short passage will be a trapped door in front of you. You can either disable the trigger device, or open the door and quickly back up. It causes spikes to appear from the left of the door. Go through, turn left and you will encounter a Skeever. Kill it and go through the door to find an unarmed beggar who will attack you anyway. Kill him and go through the door then turn left and go up some steps. You will enter a circular room that is quite overgrown.

Take the exit at 10 o'clock and you will fight another bandit standing at a table. Once he is dead, turn right and head down some steps to the Ragged Flagon. You will find Brynjolf on the other side of the area, in front of the bar. Speak to Brynjolf and he will tell you that he needs you to play debt collector and remind people that the Thieves Guild is still alive and well. He will stress that there is to be no killing. Head back out of the Flagon from the way you came and turn right at the room where you killed the last bandit. Lower the drawbridge with the nearby lever and go back out into Riften.

You can collect the debts in any order, but it is recommended that you do Bersi and Haelga first if your persuasion skill is not that high. All of the targets are hard to convince without first doing the optional objective to soften them up. Whichever two you do first, by the time you reach the third one your reputation would have preceded you and you would not have to do the optional objective for the final target. If all else fails it is possible to brawl the targets into paying up, not very subtle though.

Collect Keerava's debt
Keerava is the proprietor of the Bee and Barb and can be found behind the bar counter. Talen-Jei is a waiter in the same place and can be found wandering around the place.

Use Talen-Jei to get to Keerava (Optional)
Speak to Talen-Jei first. He will tell you he is in love with Keevara. Press him for Keevara's history and convince him that it is for her own protection that he divulges the information. He will tell you about Keevara's family in the Black Marsh in Morrowind.

Go to Keevara with the information and she will cave very quickly once you mention her family and give you the gold.

Collect Bersi Honey-Hand's debt
You can find Bersi in his store, The Pawned Prawn, in Riften. He will be adamant about not paying the money and just outright refuse you and will not continue the conversation.

Smash Bersi's prized Dwarven Urn (Optional)
To remedy this, just turn around and smash the Dwarven Urn just under the window. When you start attacking it, Bersi will start protesting. Ignore him and continue hitting until it breaks in half.

Talk to him after breaking the vase and he will hand over the money without a fuss.

Collect Haelga's debt
Haelga can be found at Haelga's Bunkhouse. If you plan to steal the Statue, come during the middle of the day when all her tenants are out and there are less witnesses around.

Steal Haelga's statue of Dibella (Optional)
When you enter the building, turn left, go past a wall and turn left again. You cannot miss the statue, it is a giant golden thing sitting on a small altar. Just swipe it and speak to Haelga.

At first she will be stubborn, but just threaten to 'accidentally' drop the statue and she will hand over the money.

Return to Brynjolf
Go back to Byrnjolf when you have visited all three and gotten their money. It was 100 in each case. He will thank you, give you three potions and take you to meet the current guild master, Mercer Frey. Who will give you a new job and tell you to collect your uniform from Tonilia.