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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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
860-767-3273
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