The Hardest Leadership Lessons of Last Year + What’s Next at Ramblin Jackson in 2026

In this solo episode of The Landscaper’s Guide Podcast, host Jack Jostes reflects on the hardest leadership lessons he learned last year—particularly around letting the wrong people stay too long, dealing with toxic behavior, and the personal toll poor people decisions can take on business owners. Jack shares real stories from his own company and from client conversations, offering an honest look at why leadership often gets harder before it gets clearer.

In the second half of the episode, Jack shifts gears and looks ahead to 2026. He previews what’s coming next at Ramblin Jackson, including new products, services, and systems designed to help landscape and snow companies grow with better sales processes, smarter automation, and less stress. This episode blends leadership insight with practical business direction for owners who want to build stronger teams and more scalable companies.

You’ll Learn

• Why waiting too long to let people go creates long-term stress and culture issues
• How to identify toxic behavior—even when performance looks “good on paper”
• What Jack learned about leadership fear, clarity, and accountability
• What new tools and services are coming to Ramblin Jackson in 2026
• Where Jack sees the biggest opportunities for landscape and snow companies next year

Connect With Jack Jostes

🌳 Ramblin Jackson: https://ramblinjackson.com/
👤 Connect with Jack Jostes on LinkedIn: https://www.linkedin.com/in/jackjostes/
📸 https://www.instagram.com/jackjostes/
🏢 https://www.instagram.com/ramblinjackson/

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