Historical clue formulations

• Like playing Russian roulette — 2023-11-08
• Fit for a daredevil — 2022-11-18
• Having low odds of success — 2020-09-29
• Like investing in a start-up — 2020-07-12
• Like going all in, maybe — 2019-08-18
• ___ business — 2018-08-25
• Dangerous — 2018-06-20
• Parlous — 2015-08-01
• Kind of business — 2014-08-01
• Like some investments — 2012-09-09
• Not secure — 2011-06-05
• Perilous — 2011-01-27
• Hazardous — 2009-10-14
• Perilous — 2008-01-23
• Hazardous — 2006-12-27
• Unsafe — 2005-10-20
• Not sure — 2003-04-13
• Like C-rated bonds — 2000-06-02
• Like venture capital investments — 1999-07-09