Libsyn Directory

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

Release Date: 09/01/2026

E749. Contractor Horror Stories | Naylor Taliaferro (LCR Media)

Kid Contractor Podcast with Caleb Auman

Naylor Taliaferro details the trials and lessons of running a contracting business. During the October contractor horror stories series, shares a chaotic memory of his first major leaf removal job, which nearly caused him to quit due to a lack of preparation and equipment. He emphasizes that hope is not a plan, highlighting the importance of property walks, proper equipment setup, and clear customer communication. The conversation also touches on unexpected field encounters, such as dodging domestic drama and navigating holiday obstacles on job sites. Key Takeaways: Establish a...

E748. Contractor Horror Stories | Paul Jamison (Green Industry Podcast)

Kid Contractor Podcast with Caleb Auman

Entrepreneurship and contracting present numerous operational hurdles, as highlighted by green industry experts Caleb Auman and . The discussion covers major professional challenges, including financial stress, unreliable customers, and the difficulties of managing organic materials like sod during extreme weather conditions. The guys also share personal disaster stories, ranging from surviving hurricanes to technical recording failures during high-profile interviews. The conversation also emphasizes the importance of proper business software, overcommunication, and cash-flow...

E747. Contractor Horror Stories | Paul Capote (The Miami Landscaper)

Kid Contractor Podcast with Caleb Auman

Wild field errors, equipment mishaps, and essential business lessons in the green industry are the focus of today's episode. shares harrowing early-career experiences, including a nearly fatal chainsaw injury that severed a worker's main artery, a terrifying trailer detachment on I-95, and utility strikes caused by blind auger drilling. Throughout the conversation, Paul emphasizes the hard knocks of starting a business young without guidance, the necessity of proper safety gear (PPE) like tourniquets, and the importance of upgrading to reliable dump trucks to eliminate costly downtime. ...

E746. Contractor Horror Stories | Harlan Jones (Jones Property Management)

Kid Contractor Podcast with Caleb Auman

Get ready for some chaotic real-world incidents with as he recounts as a new hire drinking a beer during a safety meeting, mistakenly landscaping the wrong property, and accidentally cutting down a neighbor's trees. Harlan also shares expensive operational blunders, including a disastrous truck purchase, an HVAC gas line mishap, and a severe saw accident that ruined a client's pool. Key Takeaways: Always verify property boundaries and project specifications before starting physical work to prevent costly liabilities and performing unauthorized labor. Do not sacrifice reliability to...

E745. Contractor Horror Stories | Brian Fullerton (Brian's Lawn Maintenance)

Kid Contractor Podcast with Caleb Auman

Fullerton recounts a mortifying past mistake where he accidentally sent an inappropriate text message of himself to a group chat that included both his wife and a female client. Despite the initial panic and dread of potential severe consequences, the situation ultimately resolved when the client's husband jokingly confronted about the incident. The conversation highlights the unpredictability of entrepreneurship while promoting community events such as the upcoming conference. Key Takeaways: Shift your primary focus from the technical mechanics of work to prioritizing the people and...

E744. Contractor Horror Stories | Tommy Cole EVP of Industry Relations at LeanScaper

Kid Contractor Podcast with Caleb Auman

Veteran contractor Tommy Cole shares a wealth of experience from decades in the landscape construction and civil engineering industries. recounts numerous job site mishaps, ranging from an accidental skid steer intrusion onto a protected prairie meadow to the astonishing coincidence of plastering the wrong pool on the exact same street. Through these humorous and challenging anecdotes, he emphasizes the critical importance of owning one's mistakes and never complaining about clients. The conversation highlights how vital clear communication and accessible data are for growing a successful...

E743. The Contractor's Purpose: Why You Don't Need a Wall Slogan to Build a Business That Matters

Kid Contractor Podcast with Caleb Auman

Finding deep fulfillment in sharing hands-on trade skills with others, and focusing on raising good humans is what motivates Caleb and Brittany. The couple emphasizes the importance of tracking financial numbers and understanding revenue per hour to make informed decisions and pivot when seasons are slow. They highlight the value of hands-on education through their Hardscape Academy and share personal anecdotes about learning HVAC systems while building their new home. The conversation also explores the concept of finding one’s purpose through service, mentorship, and professional...

E742. Don't Be Afraid to Make the Jump: Navigating Year Two of an Excavation Business

Kid Contractor Podcast with Caleb Auman

Zach Taylor shares the realities of launching , taking the leap into solo entrepreneurship, managing cash flow, and leveraging past connections. He highlights the importance of leveraging professional networks to secure work while navigating the complexities of cash flow, equipment acquisition, and the multi-faceted role of a solo business owner. Taylor also shares his expertise in trench safety, detailing his efforts to educate the industry through presentations and his leadership role with the nonprofit Crew Collab. The conversation covers the practical difficulties of winter construction...

E741. The Cost of Thinking Small: Why Playing It Safe Kills Growth

Kid Contractor Podcast with Caleb Auman

Why making a decision and being slightly wrong beats standing still. Caleb explores how the power of imagination directly shapes the trajectory of a business and personal life. Following a trip to Canada, Auman reflects on a conversation about limiting beliefs and how entrepreneurs often subconsciously cap their own potential. He shares personal anecdotes about manifesting his company’s design-build facility while admitting that fear sometimes hindered him from dreaming even bigger. The short episode emphasizes that a current business is often the physical manifestation of past thoughts,...

E740. $3 Million + Series | Carla Policastro Co-Founder Cycle CPA

Kid Contractor Podcast with Caleb Auman

Bookkeeper, CPA, or Fractional CFO: Who You Actually Need at $3M+ Caleb and Carla discuss the complexities of scaling a service business beyond the $3 million revenue mark. They emphasize that transitioning from a hands-on owner to a leader requires robust financial infrastructure, delegation, and the implementation of accountability systems. Carla highlights critical financial practices, such as capacity planning, divisional reporting, and monitoring gross profit margins to identify hidden waste. A significant portion of the conversation focuses on the...

More Episodes

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.