From LOI to Close: The Hardest Part of Selling a Business

2025-05-22

In this episode, we welcome back Rachel Fearnley, CEO of Dreamscapes Marketing + Design, for a candid conversation about life on the other side of the deal. After years of marketing for a winery, Rachel stepped into a whole new role—selling it. She walks us through the unexpected twists that followed signing the Letter of Intent (LOI)—when she thought the hard part was over. Spoiler: it was just beginning. From underestimated emotions to the complexities of due diligence, Rachel shares wha...

In this episode, we welcome back Rachel Fearnley, CEO of Dreamscapes Marketing + Design, for a candid conversation about life on the other side of the deal. After years of marketing for a winery, Rachel stepped into a whole new role—selling it.

She walks us through the unexpected twists that followed signing the Letter of Intent (LOI)—when she thought the hard part was over. Spoiler: it was just beginning.

From underestimated emotions to the complexities of due diligence, Rachel shares what surprised her most, what she wishes she knew sooner, and why clear communication (with a steady M&A advisor in the mix) was key to keeping the deal on track.

Whether you're a business owner considering a sale or just curious about what really happens behind the scenes, this episode is packed with honest insights and valuable lessons.

Contact Keith: Osage Advisors, LLC

osageadvisors.com

kdee@osageadvisors.com

860-767-3273

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