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Educated Guesser
Obtain 10 stacks of Vested Interest in the Brawler's Guild.
Educated Guesser requires you to obtain 10 stacks of Vested Interest by placing winning bets on Brawler's Guild fights.
Purchase the Contract
Buy a 
High Roller's Contract from Ulaani for 100 Brawler's Gold, then bring it to Harold G. Goldsprocket to complete the setup (Alliance). Horde players follow the same process with their equivalent NPCs.
Place Your Bet
Alliance players speak to Lord Winifred Browne — he gains the Financial Participation Incentive buff once the contract has been turned in. Horde players speak to Pit Boss Buxdoggle while a fight is actively happening.
Gauge Fighters Before Betting
Watch the current brawler during the Oso fight to assess their DPS and movement — landing a bet on that fight is a reliable way to earn a stack and also tells you whether they are worth betting on in subsequent rounds.
Reach 10 Stacks
Continue placing informed bets on fighters you have observed — such as rank 8 regulars or raiders visibly familiar with the fights — until you accumulate 10 stacks of Vested Interest without leaving the zone, as leaving will reset the buff.
Tips
See the video guide for a walkthrough of the betting process and NPC locations.