Inner Circle
← Back to Listen
Content

Ep 105. From Bushmaster to Baker: Scaling a 300‑Employee Landscape Company

⏱️ 1:11:33 🎤 Jordan Upcavage, Ryan Hudson
AUDIO EPISODE
Ep 105. From Bushmaster to Baker: Scaling a 300‑Employee Landscape Company
0:00
0:00

Chapters

Click to jump to section

  • 0:00
    Landscape Rodeo Promotion
    An advertisement for the first-ever Landscape Rodeo event, including details on challenges, VIP dinner, and scholarship support.
  • 0:59
    Green Side Up Intro
    Introduction to the Green Side Up podcast, its hosts Jason Lee and Jordan Upcavage, and the target audience of small business entrepreneurs in the landscaping industry.
  • 3:12
    Guest Introduction: Ryan Hudson
    Jason and Jordan welcome Ryan Hudson from Baker Landscape as an in-person guest, and playfully discuss their mutual friend, Tray Rolquin.
  • 4:05
    Ryan's Introduction to Tray
    Ryan recounts his first meeting with Tray Rolquin and their initial interaction concerning a challenging irrigation project.
  • 7:45
    Ryan's Background & Career
    Ryan details his early start in landscaping with his father, his educational path, and his career progression within the green industry, including his current role at Baker Landscape.
  • 17:38
    Managing a Large Landscape Company
    Ryan explains his responsibilities as General Manager for the Tampa branch of Baker Landscape, including P&L oversight, quality control, and client relations.
  • 34:02
    Client Relationship Strategies
    Ryan discusses Baker Landscape's proactive approach to client communication and relationship building to ensure satisfaction and address issues before they escalate.
  • 39:16
    Commercial Landscaping Nuances
    The hosts and Ryan delve into the specific challenges of commercial landscaping, particularly the role of palm tree maintenance and its impact on contract bidding.
  • 41:05
    Closing & Caliente Story
    The episode concludes with a final plug for the Landscape Rodeo, playful banter about Tray, and Jason sharing a memorable anecdote about tree work at a nudist resort.

Speakers

J
Jordan Upcavage
Host
R
Ryan Hudson
General Manager at Baker Landscape

Key Takeaways

Proactively communicate with clients through regular updates and site visits to prevent issues and build trust, even if it feels like 'spam' to some.

Recognize the constant tension between sales and production in landscaping; effectively manage this dynamic to ensure smooth operations and client satisfaction.

Prioritize relationship-building with property managers and clients by engaging in casual networking events, offering a 'partner' approach rather than just a vendor.

Develop clear systems for tracking site visits and client interactions to maintain quality control and ensure operational managers are meeting their responsibilities.

Understand that while competitive pricing is important, building a reputation on strong relationships and consistent quality can secure long-term contracts and client loyalty, even if you're not the lowest bidder.

Invest in a robust internal training or hiring process for specialized tasks like irrigation and tree care, as these can significantly impact contract profitability and client satisfaction.

Want the full experience?

Join the Inner Circle for full access to every episode, AI-powered insights, personalized coaching, and a network of industry leaders.

Join Inner Circle →

Inner Circle Membership Portal © 2026 Power100. All rights reserved.

power100.io