Does it matter if I paid an inflated amount for the business myself years ago?

Generally, no — what you originally paid for the business has little bearing on what it's worth today, and buyers value the business based on its current earnings, assets, and risk profile, not on your own purchase history. If you overpaid years ago, that's a loss you may have already absorbed personally or through the business's own accounting, but it doesn't create any claim to a higher price now.

The nuance is that this can matter indirectly if your original purchase price affected how certain assets are recorded on your books, since accounting treatment tied to an inflated original cost can occasionally create confusion during a buyer's due diligence if it isn't clearly explained. That's a bookkeeping and disclosure issue, though, not a reason a buyer should pay more.

If you're hoping the sale will simply make back what you originally invested, it's worth having an honest conversation with your accountant about what the business is actually likely to be worth today, rather than anchoring your expectations to your own purchase price from years earlier. A business lawyer can help you understand how any older transaction terms might still be relevant to the current sale, if at all.