Kid Contractor Podcast with Caleb Auman: E736. $3 Million + Series | Cooper Leary Founder CLS Landscape Construction

E736. $3 Million + Series | Cooper Leary Founder CLS Landscape Construction

Sep 1, 2026

Cooper Leary is a Canadian entrepreneur who manages a multimillion-dollar enterprise encompassing landscape supply, construction, and snow removal companny. Based in Calgary, Leary shares his journey from starting the business during university to overseeing nearly 90 employees and generating $16 million in annual revenue. The discussion with Caleb highlights the transition from an owner-operator mindset to an enterprise-level leadership style, emphasizing the importance of systemization, data-driven decision-making, and high-level delegation. Leary attributes his success to being customer-obsessed, maintaining a growth mindset, and fostering a team culture defined by grit and lifelong learning.

Key Takeaways:

Optimize your crew sizes by keeping teams to a lean three-person setup and using equipment to maintain high productivity.
Delegate key responsibilities early to competent people so you can step away from daily tasks and focus on strategic growth.
Have ongoing conversations about performance with your team members so that a final, difficult talk never comes as a surprise.
Establish core guiding principles and rely on solid business data to make your largest, most impactful decisions.
Prioritize weekly one-on-one meetings to genuinely show up for your employees and help them develop professionally.