New top story on Hacker News: Ask HN: Users don't want to pay taxes?

Ask HN: Users don't want to pay taxes?
7 by throwaway5678i | 3 comments on Hacker News.
Our platform caters to small business owners and individual sellers in a very particular niche. On the surface we're doing well; we have no trouble getting more users without spending a dime on marketing, our buyers and sellers are frequently using the platform and are happy, users are engaged and willing to talk with us, and we're even making a bit of money too. However, we have one massive problem: our merchants are not used to paying taxes and are deeply afraid of using our more monetized features because we are legally required to fill out a 1099-K on their behalf. It's one part "I don't want the government taking my money" to two parts "I don't know how taxes work" in most cases that we've looked into. Now, some of our sellers don't mind, but the vast (and growing) majority are not comfortable with taxes. This presents a problem as we're still growing, but not sustainably. We obviously want to keep pursuing this startup idea but unless something changes, it doesn't seem likely to work out. To solve this, we've tried hiring tax experts to explain how taxes work or why it's not as scary as they might think, but it hasn't been very convincing. On the more drastic side we've been thinking about switching business models a bit, but it seems so crazy to me when there is a huge opportunity right in front of us that we can't seem to capitalize on. Anyone have any experience with this sort of thing? What works? What doesn't?