'...is to start with a large one' that you've borrowed. The Splendid Pauper certainly did, well-dressed and well-fed to the end of his days, despite borrowing so much and so unfruitfully from his friends and family and own children that he was nicknamed 'Mortal Ruin', after his actual name.
He was high Victorian gentry, the uncle of the eventual Prime Minister, a second son; and his plans to make big fortunes ranged over the US (cattle ranching, silver mining, currency reform), Canada (cattle ranching, developing a new city), South Africa (mining), Kenya (land-grab colonialism), India (financial interest in proving corruption in other people's mines), Australia (mining). He was physically tough, reasonably kindly, not exactly financially honest but not nearly as much a scammer as some of his famous peers, clearly golden-tongued, well-connected, lucky in his marriage, and not even stupid about the schemes he was investing in; but he didn't make up with persistence and thrift for the capital he lacked, so the plans that did come to fruit made fortunes for other people.
His biographer winds up the story by arguing that Frewen was trapped by his emotional connection to a gentry that made its money from agriculture, when English agriculture was becoming a money-sink rather than a source of wealth. Still, some people made the jump from the old connections to the new money, and Frewen had more chances than most. His children had pretty good lives, the ones that survived the wars, and at least one of the houses stayed in the family until the twenty-first century.
The Hills at Home is fiction, the first of three novels, about a New England family down on its upper crusts, retreating to the family home pour mieux sauter. It's charming for its review of many irritatingly self-absorbed people, irritating each other; and fun in a flashy movie way for the family wealth they casually ruin to make themselves feel better (chipping the Ming vases, dragging the fur coat in the mud), and fun because they do rebound, they make clever connections and pull in favors and turn out to be more ruthless than feckless and the family fortunes bend upwards again.
If you actually found yourself near anyone like any of these people, historical or fictional, the safest plan would clearly be to attend one delightful dinner -- with your wallet left at home -- and never see them again.
Find in a Library: The Splendid Pauper
Find in a Library: The Hills at HomeSo wrote clew in Fiction (21st c.). , History (19th c.).