Heraclio was born in a (still) small town called Palomar, somewhere south of the United States. His town had resisted modernization over time, but the ubiquity of technology under the UFP ended that. Careful not to turn Palomar into a ghetto, leaders emphasized education and opportunity for travel.
Heraclio was a born talker, with a vocabulary always twice what it should have been. He was known in town as a nice boy (at first) and was popular with both local girls and visitors. Over time, he came to realize he could use his charm and charisma to his own benefit. He began scamming tourists, and eventually branching out to larger cities. While in Los Angeles, Heraclio got caught up in some rather shady business involving illegal drugs and extortion. He got scared. But he was also scared to either quit or report what was going on. He began leaving coded clues in various languages and in various places (grafitti, classified ads, etc), that eventually a cryptologist working for the Starfleet stumbled upon. The cryptologist tracked Heraclio down and offered him a way out: Starfleet. Heraclio had always loved travel, and he saw nothing good happening if he stayed on Earth, so he quickly joined up.
At Starfleet Academy it became quickly apparent that Heraclio was gifted with languages and codes. Untrained as a child, he had a natural knack for the work that put him on the fast track in those fields. Unfortunately, Heraclio often clashed with bull-headed authority figures, privileged wealthy cadets, and especially cadets (or professors) he'd scammed or cuckolded. Two steps forward and three steps back.
Heraclio graduated with extremely high marks in his field and a discipline record that nearly got him expelled or even jailed. His skills were deemed useful, if only he could get his bad habits under control.