107 | Entrepreneur Case Study | Craig Attkinson | GreenSide Up Landscaping

107 | Entrepreneur Case Study | Craig Attkinson | GreenSide Up Landscaping


Craig Attkinson, owner and founder of Green Side Up, a landscaping company in Richmond, Va., explains how he started his business in his mid-20s, what it took to grow and optimize the business, and how he’s optimized other aspects of his life as well.

  • Craig started out his career on a golf course, with a degree from Virginia Tech in turf grass and horticulture.
  • Green Side Up started in one weekend when Craig bought a truck, a trailer and a mower all at once.
  • Craig mowed lawns since he was 10 years old and saved it all until he bought his supplies.
  • Jumping straight into landscaping required Craig to do everything himself, and learn on the go.
  • When Craig brought on his first partner, he gave him 50% of the company, and guaranteed a salary, knowing that they would have to build up that amount of business.
  • How did Craig get contracts in the mid 2000s?
  • Craig has a marketing company now that helps now, but early marketing for Green Side Up involved phone books, purchasing ads and a lot of networking.
  • Having a partner to build ideas, and watching to see how other similar businesses function is helpful to build efficiency.
  • Finding a good system for managing the work processes and clarifying expectations for employees hugely increased the business’ efficiency.
  • How can Craig build the company to a point that he can step away?
  • As the business gets bigger, purchasing things in bulk, or at higher volumes, helps Craig get better prices.
  • How did Craig find the FI community?
  • Craig’s goal in life is to not have to ever worry about money.
  • Craig’s saving rate is about 70-80% because he benefits from company vehicles, cell phone plan, etc., which makes his personal expenses much lower.
  • Craig’s family farm houses the equipment for the business.
  • How and why did Craig design his own tiny home, next to his sister’s house?

  • Craig loves life optimization; what aspects of his tiny home are most optimized?
    • Took advantage of a 4’ x 6’ nook for his office.

    • Used leftover granite from someone else’s kitchen remodel for his own small kitchen.

  • Built a bed with drawers underneath for his closet.

  • Craig is technically FI, but is still loving his work, so he’s not retiring anytime soon.
  • His next adventures are climbing in Patagonia and biking in Norway.

Listen to Brad and Jonathan's thoughts about this episode here.


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5 thoughts on “107 | Entrepreneur Case Study | Craig Attkinson | GreenSide Up Landscaping”

  1. I am so excited to hear Craig’s story! FINALLY a business owner that has build a successful business and pursuing FI. As a business owner myself, his story gave me some ideas how to utilize my systems better. I’m glad you’ve started interviewing people from different walks of life

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