“Timothy Dexter: The Eccentric Millionaire Who Made Fortune Out of Folly!”

• Alias: The Unconventional Merchant
• Gender: Male
• Race: Human
• Occupation: Entrepreneur, Businessman
• Religion: Unknown
• Allies: Varies depending on business associations
• Enemies: Rivals in business and those skeptical of his methods
• Abode/Base of Operations: Primarily based in Newburyport, Massachusetts
• Nationality: American
• Languages: English
• Alignment: Chaotic Neutral
• Affiliation(s): Independent entrepreneur
• Significant Others: Wife, Elizabeth Dexter

Timothy Dexter is a man of extraordinary ambition and eccentricity. With a stout build and a shock of unruly hair, he possesses a distinct appearance that mirrors his unorthodox nature. He dresses in extravagant attire, showcasing his flamboyant personality and self-perceived status as a successful entrepreneur. But behind his eccentric facade lies a relentless drive for wealth and recognition.

Born into modest means, Timothy yearns for a life of opulence and grandeur. He is convinced that fortune and success are within his grasp, despite his lack of formal education and social standing. Fuelled by an unquenchable thirst for validation, he embarks on a journey that defies conventional wisdom.

Timothy’s path to prosperity is as unpredictable as the man himself. With audacious decisions and an uncanny ability to seize opportunities, he navigates the business world with calculated risk-taking and unwavering confidence. His unconventional methods often baffle those around him, but he remains undeterred by their skepticism.

Driven by his desire for wealth and status, Timothy plunges into various ventures and investments. His choices appear nonsensical to many, yet they yield unexpected results. Through a combination of sheer luck and unorthodox strategies, he amasses a significant fortune, leaving onlookers bewildered and intrigued.

Despite his unconventional approach, Timothy embraces the role of an outsider. He revels in challenging societal norms and defying the expectations of others. His unyielding determination propels him forward, as he seeks not only material success but also a place in history. He yearns to leave an indelible mark, showcasing his unconventional path to success and solidifying his name as a legend in the world of business and finance.

Timothy Dexter’s story is one of audacity, eccentricity, and an unwavering belief in his own abilities. He strives to achieve the unimaginable, defying the odds and rewriting the rules of success. Whether he is seen as a visionary or a fool, Timothy’s legacy is one that will be remembered for generations to come.

Timothy Dexter, The Unconventional Merchant

Medium humanoid (human), chaotic neutral

Armor Class: 14 (leather armor)

Hit Points: 71 (13d8 + 13)

Speed: 30 ft.

STR	DEX	CON	INT	WIS	CHA
8 (-1)	14 (+2)	12 (+1)	18 (+4)	10 (+0)	16 (+3)

Skills: Deception +7, Insight +4, Persuasion +7

Senses: passive Perception 10

Languages: Common

Challenge Rating: 6

Actions

• Cane: Melee Weapon Attack: +4 to hit, reach 5 ft., one target. Hit: 4 (1d4+2) bludgeoning damage.
• Pocket Sand: Ranged Weapon Attack: +5 to hit, range 10/30 ft., one target. Hit: 3 (1d4+2) bludgeoning damage and target is blinded for 1 round.

Special Abilities

• Lucky: Timothy can reroll any attack roll, ability check, or saving throw that he doesn’t like. He must use the new roll.
• Inventive Entrepreneur: Timothy can always find a way to profit from any situation. Once per day, he can gain double the usual amount of gold or treasure from any transaction, even if it doesn’t make sense.
• Unorthodox Tactics: Timothy is known for his unconventional tactics in battle. Once per encounter, he can take a bonus action to distract an opponent. The opponent must make a Wisdom saving throw (DC 14) or be unable to take a reaction until the end of its next turn.

Equipment

Timothy Dexter carries a cane, leather armor, a satchel of pocket sand, and a small bag of gold.