Most entrepreneurs dream of escaping the grind, but Craig Atkinson walked away from the golf course industry at 22 with nothing but childhood lawn-mowing savings and a handful of contracts. By 24, he'd hired his first employee. Today, he runs Greenside Up Landscaping with multiple crews while living in a 350-square-foot tiny house on family land. Craig shares how systemizing his business transformed efficiency, why he questions every societal norm (including homeownership), and how treating entrepreneurship as his "biggest life hack" accelerated his path to financial independence.
Key Topics Discussed
Craig's Transition from Golf Course to Entrepreneurship
Craig shares his educational background and initial dissatisfaction with the golf course industry leading him to start his own landscaping business.
Challenges Faced as a New Entrepreneur
The difficulties of being a one-man operation and the pressure of wearing multiple hats as he tried to grow his business.
Scaling the Business through Systematization
Craig discusses the importance of implementing systems and clear expectations for his teams, which led to improved efficiency and profitability.
How Close Are You to Financial Independence?
Free calculators, a personalized FI roadmap, and a community of 25K+ on the same journey.
Living in a Tiny House and Emphasizing Minimalism
He talks about his choice to live in a well-designed tiny house, highlighting the benefits of minimalism in achieving financial independence.
Ready to take the next step?
Put what you heard into action with these tools and community.
Advice on Professional Growth and Systems
Strategies for personal and business growth through operational systems and partnerships, and the evolution of his role within the company.
Timestamps & Key Quotes
"Never regret not taking a leap; at least try."
"Clear expectations lead to better performance."
"You must systematize your knowledge for business success."
"Embrace ownership for control and savings."
"Challenge conformity; not every norm is right for you."
Related Resources
Top Travel Card
Ready to unlock a world of free travel? Start with the Chase Sapphire Preferred® Card
$95 annual fee | Earn 75,000 bonus points
Best Card for Side Hustlers and Business Owners
Side hustlers! With the Ink Business Preferred® Credit Card you can earn free travel from your business expenses.
$95 annual fee | Earn 100,000 bonus points
Most Flexible Travel Card
The Capital One Venture Rewards Credit Card can be used to offset almost any travel expense.
$95 annual fee | Earn more than $1,000 in Travel Bonuses with a limited-time $300 Capital One Travel stays credit, plus earn 75,000 bonus miles once you spend $4,000 on purchases within the first 3 months of account opening—that's more than $1,000 in travel value
ChooseFI has partnered with CardRatings for our coverage of credit card products. ChooseFI and CardRatings may receive a commission from card issuers.
