In October 2025, we partnered with Acquiring Minds to dive into the key considerations behind asset versus stock sales, F-reorganization, QSBS, and the differences between S-corporations and partnerships, clarifying how each structure can shape outcomes for buyers and sellers from both legal and tax perspectives. We were also joined by guest speaker Josh Siegel, a tax attorney, who added practical insight on how these structures play out in real transactions.
Question Timestamps
- 03:27: One of the questions we get frequently asked is, under what circumstances do I buy the assets? What? And wonder, what circumstances do I buy the equity?
- 32:35: Josh, the state conforming bit, that means that the state taxes in conforming states would also be exempted. There would be the same exact, so there’d be no state tax either in the states that conform. That’s what that means.
- 40:54: So Wheeling says, my CPA told me that I could create a C Corp and set it aside, let the clock start ticking, and years later, if I move my LLC into the C Corp and then sell as a C Corp, I could still get the tax benefit. Is that technique of setting up a shell to start the clock accurate?
- 43:33: What’s beneficial for a seller? The forgivable seller note structure or the earn-out structure?
- 46:24: I’m under LOI and in diligence to acquire the assets of an LLC where the seller currently files as an S Corp. It’s an SBA deal. Any advice on how I should structure my side of the transaction? I feel like this is cut and dry with an operating LLC buying the assets, but wanted to ask. That would be the normal thing from your perspective as a buyer, likely, unless you find a reason to change it, whether that be government contracts or something like that. My assumption would be that you would structure it exactly the way you are.
- 42:27: I’m looking at acquiring a family business, since it’s a pass-down to me. So I guess their family business—my acquisition cost is essentially paying the seller 40% of their salary for the next 15 years, which will effectively be the seller’s retirement. How do I best structure this purchase for both me and the seller? Interesting one, too in the weeds. We can, we can put a pin in.
- 48:53: When I buy an S Corp, can I change it to a C Corp or LLC? What will be the impact?
- 49:52: Any SBA-specific constraints that affect deal structure or equity requirements that you routinely see in transactions like this?
- 51:31: Can you speak to acquiring with ROBS and how to then convert that to a QSBS strategy? Like many in middle age, most of my capital is tied up in my 401(k).
- 54:13: I’ve heard that for independent sponsor deals, it’s something of a gray area as to whether the sponsor’s carry is eligible for QSBS, assuming the deal is otherwise structured such that shareholders are eligible for QSBS. Do you know of any ways to ensure that sponsor carry also gets the benefit of the QSBS?
If you need further assistance or are in the process of negotiating a letter of intent, contact us at info@barlowwilliams.law and we will be happy to discuss your situation.