Fail Forward and Show Up Consistently: The Culture Playbook from a Second-Generation Owner episode artwork

EPISODE · Jun 11, 2026 · 37 MIN

Fail Forward and Show Up Consistently: The Culture Playbook from a Second-Generation Owner

from Roots of Success · host Chris Psencik

What separates the companies people want to work for from the ones they can't wait to leave? In this episode of Roots of Success, host Chris Psencik sits down with Ryan Malone of Malone's Landscape in Seattle, Washington — a second-generation owner, ACE Chairman member and endurance athlete — to talk about one of the most important assets in a growing company: culture. From monthly culture rallies and the Beast Mode award to a bilingual onboarding program and a weekly team newsletter, Ryan shares the real, repeatable traditions that have helped Malone's become a destination workplace. If your team feels stagnant or your retention is slipping, this episode is your playbook. THE BIG IDEA:   Intentional Culture Is Your Biggest Competitive Advantage  KEY MOMENTS:   [01:30] Ryan's Background: From Collegiate Baseball to Second-Generation Owner [04:00] Why Culture Gets Left Behind — and Why It Shouldn't [07:00] Culture Rallies: Getting Construction and Maintenance on the Same Team [10:00] What Ryan Has Stolen (and Improved) From ACE Peer Group Members [12:00] Building Trust Through Consistency: The Culture Committee [14:00] How the Culture Committee Is Structured, Who's On It, and How It Runs [16:00] Becoming a Destination Workplace — and What That Actually Means [21:00] Bilingual Onboarding: How Myra Bridged the Gap for Field Teams [23:00] The Weekly Team Newsletter — What's In It and Why It Works [27:00] Selling Value at a Premium: How Culture Justifies Top-of-Market Pricing [29:00] Leadership Action Steps: Three Things to Start Right Now [33:00] From Operator to Owner: Ryan's Biggest Lesson [34:00] Final Advice: Join a Peer Group and Fail Forward   QUESTIONS WE ANSWER  How do you build a strong company culture in a landscaping business?  What are some real traditions that create team engagement and retention?  How do you fix the construction vs. maintenance divide at company events?  What should a culture committee look like, and who should be on it?  What are the most common onboarding mistakes — and how do you fix them?  How do 30-60-90 day check-ins improve new hire retention?  How do you communicate core values consistently across a growing team?  What should a weekly team newsletter include?  How does a strong culture help you justify premium pricing with clients?  What's the best advice for a second-generation owner stepping into a family business?  How do you avoid letting culture initiatives go stagnant over time?  What does "fail forward" actually mean in practice for a business owner? 

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Fail Forward and Show Up Consistently: The Culture Playbook from a Second-Generation Owner

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This episode was published on June 11, 2026.

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What separates the companies people want to work for from the ones they can't wait to leave? In this episode of Roots of Success, host Chris Psencik sits down with Ryan Malone of Malone's Landscape in Seattle, Washington — a second-generation owner,...

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