HS 015 – How To Go From Mowing Lawns to $32 Million In Revenue With Christy Webber

HS 015 – How To Go From Mowing Lawns to $32 Million In Revenue With Christy Webber

Author: Dan Perry: Handyman | Small Business Owner April 1, 2014 Duration: 44:22

In this episode of the Handyman Startup Podcast, I’ve got something special for all you landscaping contractors out there.

I bring on Christy Webber of Christy Webber Landscapes in Chicago, IL and uncover her story and how she went from a small town lady mowing lawns, to running one of the largest Landscaping companies in Chicago.

I know this isn’t the typical type of guest I bring on the show and Christy isn’t a handyman, but the lessons she shares are applicable to all trades.

Christy’s story is incredible, especially considering that she didn’t graduate with a business degree.  In fact, her education was in physical education.  She knew nothing about operating a business and just got started mowing lawns.  And that’s the key to her success, she just got started.

Her determined attitude and love for her job helped her build a business that currently employs roughly 400 people!  Listen in to find out how.

Here’s what we cover in this episode:

  • Why some companies fail in bad economic times and others succeed.
  • How to scale a service business even if business isn’t your strong suit.
  • How integrating your story into your business can get your customers working to help you.
  • Struggles with employees and how to deal with them.
  • How to overcome fear and finally get started with your business.
  • How brutal honesty with your customers can take your business to the next level.
  • The importance of letting go and allowing others to help you.

Links and Resources

As always, thanks for listening!  And a special thanks to Christy Webber for joining me on the podcast and sharing her story to help others succeed.

CLICK HERE to subscribe to the podcast on iTunes.

Comments or Questions

Did you find Christy’s story inspiring?  If so, let me know in the comments below.  Then, sign up for my e-mail newsletter to get updates when future episodes are released.

The post HS 015 – How To Go From Mowing Lawns to $32 Million In Revenue With Christy Webber appeared first on Handyman Startup.


Dan Perry has spent years building his own successful handyman business from the ground up, and in The Handyman Startup Podcast, he shares that hard-won knowledge without the fluff. Each episode feels like a practical conversation with a seasoned pro who’s been in your shoes, tackling the real-world challenges of turning skilled labor into a sustainable enterprise. You’ll hear specific advice on navigating client pricing, managing a fluctuating schedule, and implementing marketing strategies that actually work for local service businesses. This isn't just theoretical business talk; it's a focused discussion on the operational details that make or break a trades-based venture, from your first truck and tools to hiring your first employee. Dan’s perspective as a working handyman and small business owner provides a unique blend of street-smart tactics and long-term planning. Whether you're just considering hanging your own shingle or you're several years in and hitting growth plateaus, this podcast delivers actionable insights to help you build something solid and profitable. Tune in for a straightforward guide through the nuts and bolts of entrepreneurship in the skilled trades.
Author: Language: en-us Episodes: 50

The Handyman Startup Podcast
Podcast Episodes
Pricing Pitfalls – Nine Ways Handymen Leave Money on the Table [not-audio_url] [/not-audio_url]

Duration: 37:31
Pricing is one of the top two most important topics when running a profitable service business - only second to marketing. Whether you're a pro handyman, contractor, or any service provider, pricing directly impacts your…
Specialist vs. Generalist: Six Reasons it Pays to Specialize [not-audio_url] [/not-audio_url]

Duration: 25:59
The variety of jobs you see as a pro handyman is stimulating and enjoyable but can also limit your profits. In this episode, I discuss how choosing one or more services to specialize in can boost your income and even you…
7 Profitable Handyman Business Models That Can Replace Your Income [not-audio_url] [/not-audio_url]

Duration: 42:57
The handyman business is versatile, with many paths to generating a profit. In this episode, I break down seven different business models that are proven and profitable within the realm of handyman services. I talk about…
Handyman Business Names: The Ultimate Guide [not-audio_url] [/not-audio_url]

Duration: 27:56
Many handyman business names have already been taken, but that doesn't mean you can't find a great name that helps you attract customers. In this episode, I talk about key business name criteria, ways to generate unique…
How to Start a Business While Working Full-Time [not-audio_url] [/not-audio_url]

Duration: 0:00
Starting a business while working a full-time job can be challenging because you have limited time and energy to apply to your business. However, it is totally doable with the right mindset and a methodical approach. I'v…
Should You Get a Contractors License? [not-audio_url] [/not-audio_url]

Duration: 27:09
Despite what many people assume, you don't need a contractor's license to operate a profitable home repair business. In fact, in some cases, it can actually be a hindrance. In this episode, I share my story of how I grew…
How to Start a Handyman Business in 10 Steps (2026 Guide) [not-audio_url] [/not-audio_url]

Duration: 40:06
Starting a handyman business can be profitable and fun with the right approach. I know this because I’ve been doing it for over ten years. However, it’s important to understand that a truck full of tools and some home re…
How Much Does it Cost to Start a Handyman Business? [not-audio_url] [/not-audio_url]

Duration: 37:55
In this episode, I dive deep into the start-up costs for a typical handyman business. I share a list of common expenses as well as provide insights into where to invest your money for the highest ROI. Not only will you l…