Does it hurt my asking price if the business can't run without me?

Generally, yes — buyers price in the risk that the business's performance depends on you personally, since that risk becomes theirs the moment you leave. If key customer relationships, critical decisions, or specialized know-how live only with you, a buyer has to either pay you to stay on for a transition, build in time and cost to replace what you provide, or simply discount what they're willing to offer to reflect the uncertainty.

The nuance is that owner dependency isn't a single yes-or-no fact — it's a matter of degree, and buyers and their advisors will look closely at exactly which parts of the business depend on you and which don't. A business where you handle sales personally but operations run independently is a different risk than one where nothing happens without your direct involvement.

This is also one of the more addressable factors before you sell. Delegating relationships, documenting processes, and letting others make decisions while you're still there to correct course can meaningfully reduce this discount over time. Where dependency can't be fully resolved before a sale, it typically shows up instead as a transition period, an earn-out, or a holdback rather than an outright lower price — a business lawyer can help you understand how buyers usually structure around it.