In this episode of Hard Lessons, host Charlie sits down with Matt Morehouse, who transformed his childhood passion for tractors into a thriving snow removal business in Eastern Canada. Matt shares his remarkable journey from being a top student headed to medical school to building (and nearly losing) a massive snow removal operation. He opens up about the painful lessons learned from scaling too quickly, dealing with equipment debt, managing difficult clients, and how divine intervention through a local business mentor helped save his company. This raw and honest conversation covers everything from the nitty-gritty of snow removal operations to navigating business finances and customer expectations.

Lucas Iraola, founder of Home Keys Landscaping and Real Estate, shares how he's building a business empire in Washington DC. After selling his first landscaping company to pursue real estate, he came full circle by purchasing his father's landscaping business and implementing modern systems to drive explosive growth.

Key insights:

• How he transformed a pen-and-paper business into a scalable operation
• Creating unique incentive programs to build company culture
• Structuring SBA loans for business acquisitions with minimal money down
• Managing the growth of multiple businesses simultaneously
• Balancing rapid expansion while maintaining service quality
• Building systems that support both real estate and landscaping operations

A must-listen for service business owners looking to modernize operations and scale through strategic acquisitions.

Julian Brass, bestselling author and wellness expert, reveals how he transformed from a stressed-out tech CEO to helping successful men achieve total life transformation. He shares insights from his bestselling book "Own Your Anxiety" and explains why anxiety is actually a compass pointing us toward necessary life changes.

Key insights:

• Why anxiety is often a signal of misalignment in your life
• The three C's of transformation: Content, Coaching, Community
• How to use the "Lion's Mind" to overcome self-sabotage
• The importance of purpose in sustainable transformation
• Why you can't lose unless you give up

Perfect for entrepreneurs, executives, and anyone looking to transform anxiety into their competitive edge while building a healthier, more aligned life.

Dan Givon, founder of Shine Windows and The Deck People, breaks down how he built a $5M service business in Toronto by mastering the fundamentals. He shares his systematic approach to hiring, why he tells potential customers all the reasons NOT to work with his company, and how he tracks customer satisfaction through tips and complaints.

Key insights:

• Why he calls 25+ job applicants daily and what he looks for
• His unique "reverse sell" approach that maintains a 96% close rate
• How he manages multiple service lines without losing focus
• The metrics he uses to track customer satisfaction
• Why most contractors fail by trying to grow too quickly
• Raw advice for trade business owners on building sustainable growth

A must-listen for any service business owner looking to scale while maintaining quality and culture.

Julian Brass, former CEO of Notable Life and bestselling author, reveals how his own struggles with anxiety and fitness led him to create a revolutionary health program for successful men over 40. Learn how he helps high-performing executives and business owners transform their bodies without giving up their lifestyle, and why physical health is the key to unlocking next-level business performance.

In this raw conversation, Julian shares how he went from being a stressed-out tech founder to helping household names get into the best shape of their lives. He breaks down why most successful men struggle with fitness after 40, and how his program helps them build sustainable habits while still enjoying business dinners, drinks, and life's pleasures.

If you're a busy professional wondering how to balance health with a demanding career, this episode is packed with actionable insights from someone who's been there.

From a broken-down internet cafe in Columbia to building a $5M home services empire in Toronto, Dan Givon shares his journey of building Shine Windows and The Deck People. Unlike most modern entrepreneurs, Dan rejected the typical path of marketing automation and scaling quickly. Instead, he focused on the fundamentals: knocking on doors in snowstorms, working 7-day weeks, and building systems that could maintain quality at scale. He discusses why most companies delegate wrong, how to build a winter strategy that crushes the competition, and why avoiding the hard work is the biggest mistake new entrepreneurs make. The conversation goes deep into operational systems, leadership development, and how to build a sustainable service business without sacrificing quality or team culture.

In Part 2 of our conversation with Caleb Auman, founder of Almon Landscape, we dive deep into the nitty-gritty of building and maintaining company culture. Caleb shares hard-earned wisdom about employee management, including their bonus structure, handling insubordination, and why being "too nice" can be just as damaging as being too harsh. He discusses their journey with four-day work weeks, the importance of setting clear expectations, and why he'll "never hire another bottom-of-the-barrel person again." The conversation explores the delicate balance between being respected versus liked as a leader, and why running any business - from landscaping to plumbing - ultimately comes down to managing people and numbers. Caleb also opens up about his own mistakes and how they've shaped his leadership style, including a particularly humbling incident with a concrete basin that taught him valuable lessons about compassion and accountability.

Contractor and business owner Caleb Bowman joins Charlie to discuss the complex challenges of scaling a construction business. Drawing from 25 years of experience, Caleb shares insights on managing company culture, the pros and cons of long-term employees, and the importance of continuous evolution.

Key discussion points include the difficulty of changing established culture, setting productivity standards, managing growth with a small team, and the delicate balance between maintaining loyal staff and driving company evolution.

Caleb provides candid examples from his own journey, including how letting certain behaviors slide created deep-rooted challenges, and how he's working to transform his company culture while retaining valuable long-term employees.

Guest: Caleb Bowman Position: Owner, Construction Company Notable Quote: "You don't just get what you tolerate - you get more of it."

Join Charlie, founder of an Oakville-based construction company, as he hosts the Hard Lessons Podcast. In this episode, Amanda Dacosta discusses transforming hard lessons into steps for success, emphasizing resilience as a strategic move rather than self-care. Explore deep dives into personal development, business strategies, and resilience with lessons from successful entrepreneurs. Learn the importance of self-talk, scheduling, visualization, and mental rehearsal for achieving your goals. Discover how to balance humility and confidence, handle family dynamics, and navigate through life's challenges to become your best self. Tune in for actionable advice and inspiration for your entrepreneurial journey.

Performance coach Amanda DaCosta joins Charlie to discuss the delicate balance between achievement and wellbeing. Drawing from her experience helping high-performing individuals, Amanda shares insights on recognizing emotional patterns, avoiding burnout, and making decisions without getting trapped by ego or fear.

Key discussion points include understanding the role of emotions in decision-making, creating sustainable success habits, and why many successful people find themselves unfulfilled after achieving their goals. Amanda offers practical frameworks for maintaining peak performance while prioritizing genuine wellbeing.

Whether you're building a business or leading a team, this episode provides valuable insights on achieving success without sacrificing your mental and physical health.

Guest: Amanda DaCosta Expertise: Wellbeing & Mindset Coach Notable Quote: "Emotions are information. They get a voice, but not the final vote."