Legitimate Businessman Image

Growing up, you have always run around in your parents workshop, playfully learning the craft as you grew up. You were expected to take over the business one day, but a heinous crime took your family away from you before you could become a master of your craft. You have survived up to this point by flouting the rules and regulations of society.

Now you run a different kind of business...

 
Skill Proficiencies: Perception
Choose one from: Deception, Intimidation, Persuasion
Tool Proficiencies: One type of artisan’s toolset, gaining expertise if already proficient.
Languages: Up to one Language from one of your parents.
Equipment: A crowbar, a set of [Tooltip Not Found], abacus, and a pouch containing 15 gp
 
Criminal Specialty

There are many kinds of criminals, and many types of businessman. Each have particular specialties. Even the cleanest individuals who operate outside of the law have strong preferences for certain kinds of crimes over others. Choose the role you played in your criminal life, or roll on the table below.

If you take the variant feature, this is the criminal specialty of your character’s guardian instead.

d8 Criminal Specialty
1 Blackmailer
2 Con Artist
3 Enforcer for Hire
4 Fence
5 Highway robber
6 Hired killer
7 Pickpocket
8 Smuggler
 
Feature: Paranoid Peddler

The traumatic event in your past left a large mark on you. Gain partial benefits of the Alert feat.

  • You can’t be surprised while you are conscious.
  • Other creatures have a 50/50 chance to gain advantage on attack rolls against you as a result of being hidden from you. This could be a coin flip or dice roll as determined by the GM.

Your character may or may not have an official shop or market stall to sell goods out of yet, but gain a +1 to deception rolls when trying to pass off an illegal or stolen good as something you came by honestly. 

 
Suggested Characteristics

Criminals might seem like villains on the surface, and many of them are villainous to the core. Showing weakness can be deadly and a tough front is a tool in the hands of a master. Others are able to show their criminal tendencies in much subtler ways. Many have an abundance of endearing, if not redeeming, characteristics. There might be honor among thieves, but criminals rarely show any respect for law or authority.

d8 Personality Trait
1 I always have a plan for what to do when things go wrong.
2 I am always calm, no matter what the situation. I never raise my voice or let my emotions control me.
3 The first thing I do in a new place is note the locations of everything valuable—or where such things could be hidden.
4 I would rather make a new friend than a new enemy.
5 I am incredibly slow to trust. Those who seem the fairest often have the most to hide.
6 I don’t pay attention to the risks in a situation. Never tell me the odds.
7 The best way to get me to do something is to tell me I can’t do it.
8 I have regularly make snarky remarks and get told I need an attitude adjustment.
d6 Ideal
1 Honor. I don’t steal from others in the trade. (Lawful)
2 Freedom. Chains are meant to be broken, as are those who would forge them. (Chaotic)
3 Charity. I steal from the wealthy so that I can help people in need. (Good)
4 Greed. I will do whatever it takes to become wealthy. (Evil)
5 People. I’m loyal to my friends, not to any ideals, and everyone else can take a trip down the Styx for all I care. (Neutral)
6 Redemption. There’s a spark of good in everyone. (Good)
d6 Bond
1 I’m trying to pay off an old debt I owe to a generous benefactor.
2 My ill-gotten gains go to support my quest for revenge.
3 Something important was taken from me, and I aim to steal it back.
4 I will become the greatest thief that ever lived.
5 I’m guilty of a terrible crime. I hope I can redeem myself for it.
6 Someone I loved died because of a mistake I made. That will never happen again.
d6 Flaw
1 When I see something valuable, I can’t think about anything but how to steal it.
2 When faced with a choice between money and my friends, I usually choose the money.
3 If there’s a plan, I’ll forget it. If I don’t forget it, I’ll ignore it.
4 I have a “tell” that reveals when I’m lying.
5 I turn tail and run when things look bad.
6 An innocent person is in prison for a crime that I committed. I’m okay with that.
 
Variant Legitimate Businessman: Raised by a Criminal

You had an unhappy childhood being raised by the worst kind of criminal: one who hid their bad intentions behind a bright smile. Your caretaker conned many customers out of their good coin with his ‘business’. 

Eventually a robber enters the store and your caretaker dies. Your feelings are complex when you discover that the will of the criminal that raised you indicates that his shop and a little gold will be inherited by you. The rest of his belongings were donated to local orphanages.

 
Variant Feature: Actually Legitimate Business

You are the owner of an empty shop that you have recently inherited. It used to be a secret criminal enterprise and you are determined to start this shop from the beginning on the right foot. The merchandise has been sold off, but you still have some raw materials and the business contacts you have made over the years. 

  • You own a shop that has a resell value of less than 120 gold as real estate due to the fact that someone died recently inside. The actual quality of the building will be determined after discussing with your DM.
  • Loyal customers of the previous owner will be more likely to return for follow up visits to your store.
  • Customers with a positive view of your deceased guardian will be sympathetic to you and defend you verbally, although not to the point of fighting to defend you physically.
  • Your store contains 10g of some type of raw material that can be processed into goods to sell.
 

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