The Hard Lessons Podcast

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."

In this explosive episode of Hard Lessons, host Charlie sits down with Mark Bradley, who transformed his experience from the nuclear industry into a $20 million landscaping empire. Mark shares his remarkable journey and the systems that made it possible.

Key Discussion Points:

• How Mark leveraged his nuclear industry experience to create scalable business systems
• The critical metrics that increased business efficiency from 72% to 94.1%
• Why being an excellent tradesperson can actually hinder business growth
• The apprenticeship model that built and retained high-performing teams
• How to create effective meetings using four simple questions
• The exact budget ratios that guided strategic decisions
• Converting highly skilled work into teachable systems

Mark reveals his uncommon approach to hiring, explaining why he completely eliminated "laborer" from job postings and how this single change attracted better talent. He also shares his framework for training that helped scale quality across multiple crews.

Whether you're a skilled tradesperson looking to scale your business or an entrepreneur seeking proven systems for growth, this episode provides actionable insights from someone who's built and exited a multi-million dollar company.

Special attention is paid to Mark's unique perspective on metrics-driven management and how removing emotion from business decisions through data transformed his company's performance.

In this episode of Hard Lessons, host Charlie interviews Joe Apps, founder of Jobs Technology Support. Joe shares his journey from tech enthusiast to successful entrepreneur, offering valuable insights for aspiring business owners and established entrepreneurs alike.

Key topics discussed:

1. The importance of finding your niche and focusing on core services
2. Implementing standardized processes for consistent service delivery
3. Building and managing a high-performing team
4. Effective marketing strategies for IT businesses
5. The value of peer accountability groups for entrepreneurs
6. Balancing growth with maintaining quality service
7. The challenges of scaling a business and how to overcome them

Joe also discusses the implementation of the Entrepreneurial Operating System (EOS) and how it has transformed his business operations. Listeners will gain practical advice on time management, decision-making, and creating a strong company culture.

Whether you're in the IT industry or running a business in any sector, this episode offers valuable lessons on growth, leadership, and maintaining work-life balance as an entrepreneur.

In this insightful episode of the Hard Lessons podcast, host Charlie Kerrigan interviews Kevin Scott, the successful founder of Muskoka Landscaping. Kevin shares his journey in the landscaping industry and offers valuable advice for navigating current market challenges.

Key points discussed:

1. Kevin's business portfolio, including Muskoka Landscaping, Granite Warehouse, and Vast design business
2. The current state of the landscaping market and predictions for the next 1-2 years
3. Strategies for businesses to weather economic downturns, including financial restructuring and vendor negotiations
4. The importance of maintaining strong relationships with clients, vendors, and contractors during tough times
5. Kevin's emphasis on team focus and how it contributed to reaching $10M+ in annual revenue
6. The value of nurturing existing relationships and seeking new connections in the industry

Kevin provides practical advice for landscaping businesses of all sizes, emphasizing the need for financial prudence, relationship-building, and adaptability in the face of market fluctuations. This episode offers valuable insights for anyone in the landscaping industry looking to navigate challenges and position their business for future success.

In this insightful episode of the Hard Lessons podcast, host Charlie Kerrigan interviews Kevin Scott, the successful founder of Muskoka Landscaping. Kevin shares his journey in the landscaping industry and offers valuable advice for navigating current market challenges.

Key points discussed:

1. Kevin's business portfolio, including Muskoka Landscaping, Granite Warehouse, and Vast design business
2. The current state of the landscaping market and predictions for the next 1-2 years
3. Strategies for businesses to weather economic downturns, including financial restructuring and vendor negotiations
4. The importance of maintaining strong relationships with clients, vendors, and contractors during tough times
5. Kevin's emphasis on team focus and how it contributed to reaching $10M+ in annual revenue
6. The value of nurturing existing relationships and seeking new connections in the industry

Kevin provides practical advice for landscaping businesses of all sizes, emphasizing the need for financial prudence, relationship-building, and adaptability in the face of market fluctuations. This episode offers valuable insights for anyone in the landscaping industry looking to navigate challenges and position their business for future success.

In this eye-opening episode of the Hard Lessons podcast, host Charlie Kerrigan interviews Syd Budhu, a former TV engineer turned wealth management expert. Syd shares invaluable insights on financial strategies for business owners that are often overlooked by traditional financial institutions.

Key topics discussed:

1. The importance of holding companies for incorporated business owners
2. Why RRSPs might not be the best option for business owners
3. Protecting your most valuable asset: yourself
4. The balance between reinvesting in your business and personal wealth building
5. Strategies for preparing your business for a future sale
6. The significance of proper corporate structuring for tax optimization
7. How to find the right financial advisor who can provide comprehensive wealth management

Syd emphasizes the importance of holistic financial planning that considers taxation, insurance, legal aspects, and investment strategies. He also highlights common mistakes business owners make and provides actionable advice for optimizing wealth creation and protection.

Whether you're a seasoned entrepreneur or just starting your business journey, this episode offers crucial insights that could potentially save you millions in taxes and set you up for long-term financial success.

In this eye-opening episode of the Hard Lessons Podcast, host Charlie Kerrigan interviews Justin Georgopoulos, a young entrepreneur who transformed his life from a university dropout to building a million-dollar painting business in just 16 months.

Key topics discussed:

1. Justin's journey from working in a butcher shop to starting his own business

2. The power of door-to-door sales in scaling a service business

3. Strategies for building and managing an effective sales team

4. The importance of in-person quotes vs. emailing estimates

5. How to structure your business for potential future sale

6. The concept of "unicorn employees" and why they can be problematic

7. Balancing personal development with business growth

8. Justin's coaching program, Trade Launch, and its impact on other entrepreneurs

Takeaways:

- The effectiveness of door-to-door marketing in the digital age

- The importance of systems and SOPs in scaling a business

- How to transition from working in your business to working on your business

- The value of personal development in entrepreneurial success

Whether you're a tradesperson looking to scale your business or an entrepreneur seeking unconventional growth strategies, this episode offers valuable insights and actionable advice.

Don't miss this inspiring conversation about entrepreneurship, sales strategies, and personal growth!