Punch Club

In order to meet street thugs, you need the following:

• You need at least $151 on hand when walking around the city, from then you'll have a chance to meet thugs.
• Your total stats must not be less than 17

Once you beat a thug, they take 4 days to re-spawn. After beating three of them, you'll get this achievement and the option to meet 'Bobo' at the biker camp. Beat his ass and you'll get the Triple B achievement. After all this, you will not be harassed by thugs anymore on the street walking around with money.

I used the start of bear strategy to beat them pretty handily. Stats are 8/2/3 with this build (at the time of just beating Bobo):

Started with Punch/Block and chose "great hook" when meeting Mickey. Skills unlocked (in no particular order, just what I had at the time)

• Tactics Learner
• High Punch
• Uppercut
• Active Skill 1
• Skip Attacks
• Muscle Memory 1
• Crosspunch
• Some motivation
• Way of the Bear
• Active Skill 2
• Boxing Punch (in WOTB)
• Clothesline
• Triple Punch
• Muscle Memory 2

Setup was Slugger stance with Block, Skip Attacks, Boxing Punch, Triple Punch.

He went down like a sack of bricks. Barely lost any health.