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

Leohadaproblem.Don'tbelikeLeo!Itwasn'tthathewaspoor.Itwasn'tthathewasunlucky.Itwasthathehadbeencursed,orblessedbytheAccidentalTycoonSystem.Therulesweredeceptivelysimple.Anymoneyhelostonaninvestmentwouldbereturnedtohim,doubled.Andanymoneyhegained,asidefromsystemreimbursementcouldn'tbeusedbyhimonhimself.Hislife'snewmissionwascrystalclear.Hehadtogobankrupt.Inahigh-techworldofS-RankHeroes,magic,andnewly-contactedaliencivilizations,thisshouldhavebeentheeasiestthingtoachieveinthegalaxy.Hejusthadtobecomethebiggest,mostspectacularlosertheuniversehadeverseen.So,hetried.Oh,howhetried...Hethrewbillionsatpublishingadungeonguidewrittenbya10-year-old.Themapswereincrayon,anditlistedthefinalbossasaBigGrumpyBadger.[Breaking:NewS-Rankdungeoncalled'TheWhisperingLabyrinth'appears!Allhigh-techmappingdronesfail.AlostF-Rankporterusedthecrayonguide...andit's100%accurate.Thefinalbossisa50-footdivinebadger.TheGalacticUnionhasdeclaredtheguidea'holytext'forexploration!]Heboughtthegalaxy'smostuselessmoon,planningtobuilda'MuseumofPaint'.[Alert:Ancientmagicalley-linesdiscoveredunderthemoon'ssurface!It'stheonlyplaceintheuniversethatcansafelygrowthe'Star-Lotus,'thekeyingredientforimmortality!]TotheIntergalacticHero'sGuild,theMagicAcademies,andtheAlienFederations,Leowasthegodofinvestmentwhoseeverymovewaslike5Dchessthatordinarypeoplecouldn'tunderstand.Heroeswouldsoarwithhissponsorship.Alienemperorsofferedhimtheirdaughters'handsinmarriageforasingle'tip'.ButLeojuststaredathisbankaccount,whichnowdisplayedhiswealththathecouldn'tuseonhimself,withtearsstreamingdownhisface.“Please,”hecried,“I'mtryingtofail!Whywon'tyoujustletmebepoor?!”