Can an expert in family-owned business transfer & / or creative financing weigh in?

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May 27, 2026

by a searcher from Cornell University - SC Johnson College of Business in Salt Lake City, UT, USA

I'm looking for advice on the cleanest way to transfer ownership from 2nd generation owner of family business to a new buyer that is a very close family friend. The goal is to do the transfer without the need for putting capital down, or go through SBA or Private Credit, etc. and create a "win-win" for both buyer and seller. Since the seller currently generates $1 million+ in EBITDA, and has a building that houses the business that was appraised for $15 million, with $2 million remaining on the real estate loan, the current thinking on structuring the deal is as follows: 1) Buyer and Seller agree that Buyer will eventually buy out seller at $14 million EV (both real estate and business included) in a staged partnership transition. The seller initially transfers 49% ownership to the buyer in exchange for a $3 million interest-only seller note (rather than requiring a large cash down payment), allowing the parties to establish a real operating partnership and avoid triggering an immediate full change-of-control event with the bank. 2) After a 6–12 month seasoning period demonstrating stable operations and EBITDA (ideally is now growing with the additional new partner), the company refinances the real estate—leveraging the large equity cushion created by the ~$15 million property value and only ~$2 million of existing debt—to generate meaningful cash-out proceeds for the seller while maintaining acceptable DSCR. 3) The seller then gradually transfers additional ownership over time through a combination of pre-negotiated call options, seller-note-to-equity conversion mechanics, and/or company-funded equity redemptions, allowing the buyer’s ownership to increase from 49% to 81% using future cash flow and refinancing capacity rather than large upfront capital contributions. This staged structure helps preserve lender comfort, spreads the seller’s taxable gains over time through installment-sale treatment, reduces disguised-sale risk, and creates a more stable long-term succession plan for both parties. Thoughts on why this will or will not work? Thoughts on a better structure?
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