Is it a bad sign if a business has been listed for a long time?

Not automatically, but it's a reasonable question to probe rather than ignore. A listing can sit unsold for reasons that have nothing to do with the business itself — an unrealistic asking price, weak marketing, a narrow buyer pool for a specialized industry, or a seller who isn't actually motivated to move quickly. None of that tells you the business is a bad buy.

That said, a long time on the market is also consistent with real problems: declining revenue the financials haven't caught up with yet, a lease that's hard to assign, key-employee or customer concentration that scares off serious buyers once they see it, or undisclosed issues that surfaced during a previous buyer's due diligence and killed that deal. The honest answer is that time-on-market alone doesn't tell you which story you're in — it just tells you to ask why, directly, and to treat the answer as a starting point for your own due diligence rather than a final answer. Reviewing financials, contracts, and the reason previous negotiations (if any) fell through with a Treadstone business lawyer before you commit is the practical next step.