Taking Care of Business Taking Care of Business is a quest available in . This is the second quest pertaining to the Thieves Guild , acquired from Brynjolf . Walkthrough . The Ratway . The Ratway ' s entrance is located on the lower levels of Riften . Once inside , there will be two bandits , Drahff and Hewnon Black - Skeever . After they are dealt with , the Dragonborn will enter into a room . They must either pick the lock on the door to the left or take the path to the right . The Ragged Flagon can be entered after continuing down the path ; Brynjolf can be found conversing at the bar here . He will instruct the Dragonborn to collect debts from three business owners in Riften . If one chooses to ask Brynjolf for advice , he will suggest some alternative ways to collect the debt . Exit the Ragged Flagon by the front door , then go through the second archway on the right wall . Pull the lever to drop the draw bridge across the gap and follow the path to exit The Ratway . Collecting the Debt . The Dragonborn may collect the debts in any order , but will quickly discover that none of the business owners are willing to pay up ; the Dragonborn may opt to brawl the owner for the money , or negotiate a more peaceful solution using Brynjolf ' s advice . Additionally , the final business owner may hear about the Dragonborn ' s activities in advance and decide to pay off their debt immediately , without conflict . Keerava ' s debt in The Bee and Barb . Keerava is the female Argonian behind the counter at The Bee and Barb . Bringing up her debt to her will result in her becoming upset , telling the Dragonborn to go away , and that Brynjolf will not getting anything ; the Dragonborn may leave the conversation or choose to brawl her . Talking to Talen - Jei , a male Argonian and Keerava ' s lover , will reveal information about Keerava ' s family ' s farm in Morrowind . Going back to Keerava and threatening to visit the farm will convince her to pay the owed gold . Bersi Honey - Hand ' s debt in The Pawned Prawn . Upon entering the Pawned Prawn , one will be greeted by Bersi Honey - Hand . Talking to him and bringing up his debt will result in him becoming defensive . One can choose to either walk away from the conversation or brawl him for the gold . If one chooses to walk away , they can then destroy Bersi ' s Dwarven Urn under the window . After it has been destroyed , he will agree to pay . Haelga ' s debt in Haelga ' s Bunkhouse . Upon entering Haelga ' s Bunkhouse , the Dragonborn will be rudely greeted . Speaking to Haelga and bringing up her debt will make her angry . The Dragonborn can either walk away or brawl her . If one chooses to walk away , Haelga respond by saying that she will not pay . To solve this , in the right corner is a statue of Dibella , the goddess which Haelga devoutly worships . Stealing and presenting the statue to her will result in Haelga begging the Dragonborn to not damage the statue and agreeing to pay . The Dragonborn can also commit a crime that forces them to go to jail , and talk to her afterwords . She will ask the Dragonborn to stop committing crimes and will agree to pay . Getting back to Brynjolf . Once the debts have been collected , return to Brynjolf in The Ragged Flagon . He will invite the Dragonborn to follow him to the cistern , where the Guildmaster , Mercer Frey , will give the next quest , " Loud and Clear , " and welcome the Dragonborn to the guild . Rewards . After completing the quest and accepting the follow up , " Loud and Clear , " a few perks are gained :