Mar 2024

Ep 33: Joe Hennessey - From push mowers to landscaping business owner

Hennessey Landscaping is a top lawn care and landscaping company in Southwest Connecticut, led by Joe Hennessey, an entrepreneur who started his landscaping journey at 12 years old, initially helping neighbors with snow plowing and lawn mowing. Officially founded in 2019 after Joe graduated from college, Hennessey Landscaping has grown to include two trucks, several employees, and a diverse array of services, pivoting from Joe’s initial casual work to a professional and ambitious business with aspirations for further growth. The company has navigated challenges such as scaling, hiring, and effective marketing, embracing digital marketing and website development to enhance visibility and customer engagement.

About the Business


“I made the decision to get a website built and invest in advertising… that’s kind of the way that it’s going is, you know, digital marketing and all of that.”

1. Joe Hennessey’s early foray into landscaping began with snow plowing and lawn mowing in his neighborhood as a young teen. 2. Hennessey Landscaping officially started as an LLC in 2019, soon after Joe graduated college. 3. Joe’s shift from primarily residential accounts to seeking commercial accounts and adopting digital marketing strategies to grow Hennessey Landscaping. 4. Joe’s innovative marketing strategy involved distributing flyers in Ziploc bags with stones to prevent them from blowing away, a tactic used to generate local business leads.


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