The phrase "risky endeavor" means a task or activity that has the potential to be dangerous or uncertain, with a high chance of negative outcomes. Full definition
Financing such a politically risky endeavour was problematic, but London - headquartered behemoth Rio Tinto ponied up with a private placement for Ivanhoe in 2006. (canadianbusiness.com)
Trying to take such a decision in Germany without the necessary public support would be a very risky endeavour. (blog.politics.ox.ac.uk)
It's a risky endeavour that could be a runaway success or a colossal failure, but it comes at a time when Canada's media businesses are struggling to keep pace with both dramatic shifts in technology and evolving reader habits. (canadianbusiness.com)