I'm Trying To Go Broke, So Why Do I Keep Getting Richer?!

Leo had a problem. Don't be like Leo! It wasn't that he was poor. It wasn't that he was unlucky. It was that he had been cursed, or blessed by the Accidental Tycoon System. The rules were deceptively simple. Any money he lost on an investment would be returned to him, doubled. His life's new mission was crystal clear. He had to go bankrupt. In a high-tech world of S-Rank Heroes, magic, and newly-contacted alien civilizations, this should have been the easiest thing to achieve in the galaxy. He just had to become the biggest, most spectacular loser the universe had ever seen. So, he tried. Oh, how he tried... He threw billions at publishing a dungeon guide written by a 10-year-old. The maps were in crayon, and it listed the final boss as a Big Grumpy Badger. [Breaking: New S-Rank dungeon called 'The Whispering Labyrinth' appears! All high-tech mapping drones fail. A lost F-Rank porter used the crayon guide... and it's 100% accurate. The final boss is a 50-foot divine badger. The Galactic Union has declared the guide a 'holy text' for exploration!] He bought the galaxy's most useless moon, planning to build a 'Museum of Paint'. [Alert: Ancient magical ley-lines discovered under the moon's surface! It's the only place in the universe that can safely grow the 'Star-Lotus,' the key ingredient for immortality!] To the Intergalactic Hero's Guild, the Magic Academies, and the Alien Federations, Leo was the god of investment whose every move was like 5D chess that ordinary people couldn't understand. Heroes would soar with his sponsorship. Alien emperors offered him their daughters' hands in marriage for a single 'tip'. But Leo just stared at his bank account, which now displayed his wealth that he couldn't use on himself, with tears streaming down his face. "Please," he cried, "I'm trying to fail! Why won't you just let me be poor?!"