From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Doug Bonnell, Owner and COO of True North Landscaping, to talk about his journey from automotive engineer to leading and scaling a successful family-owned landscaping company.

This conversation covers the real-life lessons behind building a sustainable service business, creating recurring revenue, making strategic hires, and implementing systems that support long-term growth.

🎧 What You’ll Learn in This Episode:

Why recurring revenue is the foundation of a stable service-based business

How to decide whether to hire, outsource, or acquire to fill business gaps

The systems and software that transformed operations and job costing

How Doug and his wife successfully work together in the business

What every entrepreneur can learn from the landscaping industry's referral culture

⏱️ Episode Timestamps:

00:00 – Introduction

00:35 – Guest introduction: Doug Bonnell & True North Landscaping

01:17 – From automotive engineer to family business COO

03:03 – Taking the leap from corporate life

05:42 – Learning the business from the ground up

06:57 – Building recurring revenue through maintenance services

09:21 – Why recurring revenue matters

11:12 – Acquiring a competitor and expanding services

12:13 – Build, hire, or buy?

14:31 – Managing seasonality and workforce challenges

20:23 – Work-life balance as a business owner

23:43 – Running a business with your spouse

24:51 – Common mistakes customers make when hiring contractors

29:26 – Systems and technology that drive growth

32:12 – Advice for aspiring entrepreneurs

33:05 – What “Do Small Business Like a Big Boss” means to Doug

33:52 – Where to connect with Doug and True North Landscaping

👤 About the Guest:

Doug Bonnell is the Owner and COO of True North Landscaping, a high-end residential design, build, and maintenance company serving Northern Michigan. After earning an engineering degree from Western Michigan University and spending six years in the automotive industry, Doug joined the family business and has helped grow it into a 50-person operation with multiple service lines, including maintenance, irrigation, fertilization, and snow removal.

Connect with Doug:

LinkedIn: Doug Bonnell

Website: True North Landscaping

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Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

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