Onex Corp. CEO Le Blanc has taken a page from Warren Buffett's playbook, making a substantial investment in an insurance startup that's already showing signs of trouble. The move mirrors Buffett's strategy of betting big on insurance businesses, but Onex's gamble appears to be heading south faster than anticipated.

The timing couldn't be worse for Onex, which has been navigating a challenging investment landscape. Insurance startups often require significant capital to build out underwriting capabilities and establish market presence, and early losses are common as companies work to refine their risk models and pricing strategies.

For Le Blanc, this high-profile misstep could raise questions about the firm's investment strategy and risk assessment capabilities. Insurance investments typically require patience and deep industry expertise to succeed, qualities that have defined Buffett's approach for decades. Whether Onex can weather the initial losses and find its footing in the competitive insurance market remains to be seen.