The weeks between Thanksgiving and New Year’s Day create a strange split in the entrepreneurial world. Some founders treat it as a full shutdown. Others see opportunity in the quiet.
Jack, who runs an AI competing company and is considering an exit, chooses the first route. He’s out skiing, unplugged, confident that nothing meaningful will happen until mid-January.
Mary, CEO of a competitor to Jack’s company, is also looking for a buyer, and is taking a different approach. Yes, her team is mostly out of office, year-end reporting is messy, and everyone is juggling personal commitments. But over a series of short check-ins with her banker, she realizes that this quieter season offers something rare: space. Space to think, prepare and get ahead while the market’s attention is elsewhere.
She doesn’t cancel her holidays. She simply doesn’t disappear.
While others wind down, Mary works through the less glamorous parts of preparing for a potential M&A process, the data cleanup, clarifying metrics, shaping the narrative, and starting to map the buyer landscape. Nothing moves quickly, but everything moves forward.
Her banker helps keep things structured, focusing on what’s realistically achievable rather than forcing deadlines into a holiday calendar. They go step by step, building the foundations that always take longer than founders expect.
When the new year arrives, buyers come back energized. Their inboxes are clear, their attention is reset, and they’re ready to look at new opportunities. Mary’s materials are not only ready, they’ve been thoughtfully crafted without the noise of regular workweeks. She’s positioned to launch conversations immediately.
Jack returns from the mountains to a backlog of emails, an unorganized data trail, and the realization that Mary is already in motion. In a competitive environment, timing and readiness matter as much as performance. While he waited for the race to begin, Mary was already at full speed.
Entrepreneurs often face strategic balancing acts, navigating constraints, timing and judgment under imperfect conditions. December is no different. It doesn’t require nonstop work, just deliberate engagement.
Jack may have had the better ski trip, Mary may have the better shot at an acquisition.
Itay Sagie is a strategic adviser to tech companies and investors, specializing in strategy, growth and M&A, a guest contributor to Crunchbase News, and a seasoned lecturer. Learn more about his advisory services, lectures and courses at SagieCapital.com. Connect with him on LinkedIn for further insights and discussions.
Illustration: Dom Guzman
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