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
The Handyman Startup Podcast
BusinessEducationEntrepreneurshipHow ToMarketing

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

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