Title: Our platform caters to small business owners and individual sellers in a very particular niche. On the surface we&#x27;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&#x27;re even making a bit of money too.<p>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&#x27;s one part &quot;I don&#x27;t want the government taking my money&quot; to two parts &quot;I don&#x27;t know how taxes work&quot; in most cases that we&#x27;ve looked into.<p>Now, some of our sellers don&#x27;t mind, but the vast (and growing) majority are not comfortable with taxes. This presents a problem as we&#x27;re still growing, but not sustainably. We obviously want to keep pursuing this startup idea but unless something changes, it doesn&#x27;t seem likely to work out.<p>To solve this, we&#x27;ve tried hiring tax experts to explain how taxes work or why it&#x27;s not as scary as they might think, but it hasn&#x27;t been very convincing. On the more drastic side we&#x27;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&#x27;t seem to capitalize on.<p>Anyone have any experience with this sort of thing? What works? What doesn&#x27;t?
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