George Henry's brother Frederick had immigrated years earlier to work with their uncle, George Repold. George Repold immigrated to America soon after the Revolution, and had become a successful merchant and influential figure in Baltimore. Margaret B. wrote of him, "His Clipper Ships plied the seas, and he directed with great foresight his wholesale business with England, Germany, and the Indies." Three of his ships were destroyed in the Napoleonic wars after their illegal seizures by the French. It is interesting to note, that the compensation claims for the ships have never been entirely settled. Frederick received the inheritence of their uncle's real estate. Although he was mentioned Repold's will, George wasn't qualified to inherit as he was not yet an american citizen and considered "an alien."
After George Henry joined his brother in Baltimore in 1821, he made a trip to Europe and around Cape Horn on one of the Waesche clipper ships. His itch for seafaring life, as we will see, transcended the generations and has manifest in the lives of many Waesche decedents.
When his adventures turned back to the mainland, George was sent to Carroll County Maryland to become a farmer. While his brother was busy in Baltimore, George paid two hundred and fifty dollars each year for boarding and to be taught farming in the home of David Cassell.
Margaret B. recounts, "How well farming was learned, the writer knows not, but from family gossip, he learned better how to love David's niece, Catherine Cassell."