Episode 63: Annual Planning, Bottlenecks, and Taxes: How Real Land CEOs Think at Year-End

Dec 23, 2025

As year-end approaches, the hosts explore the paradox of slowed contracts matching heightened stress for land investors. They reflect on effective sales strategies during busy periods and the importance of team management over the holidays. Key insights include diagnosing true business constraints rather than surface issues, strategic tax planning, and optimizing capital with C-corps for tax efficiency. They emphasize the need for clear goals in annual planning and organizational alignment to successfully navigate these complexities.

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INSIGHT

Year-End Feels Busier For CEOs

Year-end feels busier for CEOs despite slower deal flow because planning and tax work spike.
Clay and Justin describe end-of-year as high-stress administrative season rather than peak transaction activity.

ANECDOTE

Best Sales Month Came From Earlier Work

Clay reports having his best sales month with closed dispositions in December.
He emphasizes those closings were the result of work done in prior months like October and November.

ADVICE

Run Focused Multi-Day Planning

Do run focused annual planning sessions with one or two key people to dig into real constraints.
Set multi-day deep-work blocks to surface root causes rather than skimming issues briefly.

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🎙️ Welcome to The Ground Game Podcast! 🎙️

In this episode of The Ground Game Podcast, co-hosts Clayton Hepler and Justin Piche tackle the unique challenges and opportunities that arise during the busy year-end period for land investors. Join them as they share their experiences and strategies for navigating the complexities of annual planning while managing the ebb and flow of business activity.

Key Highlights:

Year-End Dynamics: Clayton and Justin discuss the paradox of year-end business, where contracts may slow down, but the pressure of annual planning intensifies.
Sales Success: Clayton shares insights from his best sales month, emphasizing the importance of preparation and effort put in during the previous months.
Team Management: The hosts reflect on their holiday schedules and the need for a skeleton crew to handle inquiries while allowing their teams to recharge.
Identifying Constraints: Learn how to diagnose the real constraints in your business, moving beyond surface-level issues to uncover deeper bottlenecks that hinder growth.
Strategic Planning Framework: Discover the structured approach Clayton used during his annual planning sessions, focusing on setting clear goals and actionable steps to overcome identified constraints.
Tax Planning Tips: Justin shares his experiences with tax planning, including the importance of organization and the potential benefits of establishing a management company for expense management.

Whether you're a seasoned land investor or just starting out, this episode is packed with valuable insights and strategies to enhance your business planning and execution. Tune in to gain the knowledge you need to navigate the complexities of land investing and set your business up for success in the coming year.

Don't forget to subscribe, rate, and review the podcast! Your feedback helps us improve and reach more listeners.

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