Developing a Winning Team: Lessons I Gained Building a Painting, Repair & Remodeling Business

Building a team: A painting project that showcases cooperation and teamwork in remodeling ventures

April 07, 2024

Hey there, it's Matt Levenhagen! Today, I’m taking a walk down memory lane, sharing lessons from my entrepreneurial journey over 20 years ago, diving into the remodeling and painting business for a couple years. This chapter of my life was a masterclass in team building, navigating the challenges and triumphs of creating a successful business from the ground up. So, buckle up as we explore these pivotal experiences and the timeless lessons they impart.

The Humble Beginnings

In the early 2000s, my life embarked on an unexpected journey. At that time, I found myself deeply entrenched in the world of insurance, working as an agent and co-managing a book of business. Despite the stability and promise this career offered, there was an insistent inner voice seeking something more. I yearned for a venture that would not only complement and add to my income but also echo my passions and utilize my inherent skills.

This longing for deeper fulfillment and the drive to leverage my abilities set the stage for a transformative venture. It was a journey poised to align closely with my interests, opening new avenues for both personal and professional growth.

Reflecting on what truly resonated with me, I reconnected with my love for painting — a passion rooted in my artistic endeavors from a decade earlier — along with an emerging interest in woodworking, carpentry, and the art of ‘building stuff'. This burgeoning curiosity later inspired “The Builders Podcast“, a testament to my enduring passion for creativity, craftsmanship and entrepreneurship.

Building a team: A diverse workforce working together on a renovation project, highlighting the value of cooperation.

Driven by these passions, I launched “Matt's Painting & Repair” as a side hustle, aimed not just at supplementing my income but at immersing myself in work that brought genuine joy and satisfaction. Initially, our main focus was on painting (tackling both interior and exterior projects) and drywall repairs, aided by my first few hires.

The demand for our services soon urged us to diversify, propelling us into both residential and commercial projects and expanding our offerings to include remodeling work. This pivotal transition highlighted a key entrepreneurial lesson: the essence of versatility. It emphasized the importance of responding to market needs and being open to expanding one’s skill set as opportunities arise — a philosophy I carried into my web design agency.

Our ability to adapt and evolve our services in response to emerging needs and opportunities became the bedrock of our business philosophy. This adaptability not only secured our success in a competitive landscape but also allowed us to explore and fulfill a wide array of interests and capabilities, paving the way for a truly rewarding entrepreneurial journey.

The Ebb and Flow of Workforce Dynamics

In navigating the complexities of a growing business, I stumbled upon a pivotal realization — the intrinsic value of a flexible workforce and adding team members as they were needed (or vice versa). This insight was not merely theoretical; it was a practical solution to the fluctuating demands of our projects.

As the nature and volume of work ebbed and flowed, I adopted a hiring strategy that changed with the seasons, requirements and types of work we were doing. This approach granted us the agility to respond to project demands without sacrificing the quality of our output. It was a balancing act that allowed us to maintain efficiency in the face of variability.

This lesson in flexibility finds its echo in the operations of my current agency. Despite having a core team of about 10 people, we've cultivated a remarkable capacity for elasticity. Our model allows us to accommodate short-term contracts or projects requiring specific resources for a finite period. Seamlessly integrating new team members for the duration of these projects has become a hallmark of our adaptability.

Moreover, within our established team, there exists a dynamic fluidity. We have the agility to reassign team members across various projects and accounts, assembling diverse groups to tackle both short and long-term initiatives. This internal versatility enhances our capability to meet client needs with precision and efficiency.

However, achieving this balance is not without its challenges. Ensuring a steady stream of work to support our core team, while navigating the peaks and troughs of demand, requires keen insight and strategic planning. It's a complex dance of resource management that demands constant attention. Yet, the rewards of this system are undeniable. When this delicate balance works, it exemplifies operational brilliance, underscoring the strength and resilience of our team.

The evolution from my early days in the contracting business to the sophisticated operations of my agency today reflects a continuous learning curve. It underscores the universal importance of workforce flexibility across different business models and industries. This adaptability not only sustains our business but also propels us forward, allowing us to thrive in an ever-changing landscape.

Partnerships: A Double-Edged Sword

Building a team: A team meeting discussing project strategies and goals

Partnerships in business are akin to navigating a complex labyrinth; they offer paths that can lead to unprecedented growth or unforeseen pitfalls. My venture into the realm of partnerships began six months after launching my business, when I allied with someone who seemed equally impressed by my team-building prowess.

Yet, my initial optimism was met with a harsh reality check. This partnership not only strained our working relationship but also exposed me to the darker side of collaborative ventures — a breach of trust that saw my partner redirecting our collective resources for his personal gain and withholding payments for projects we undertook together.

This ordeal taught me invaluable lessons in vigilance and underscored the necessity of maintaining direct oversight over every aspect of my business, especially the team that stands as its backbone. While I acknowledge the potential benefits of business partnerships, particularly those where mutual operations and goals align, my experiences have instilled a cautious approach.

Today, any prospective partnership proposition would need to navigate through a series of rigorous vetting processes before consideration.

These experiences, as tough as they were, proved instrumental in shaping my business acumen. In the early stages of my entrepreneurial journey, the thought of someone acting in bad faith was beyond my comprehension. My naivety, albeit a vulnerability at the time, became one of my most profound learning curves.

These lessons, learned in the hard knocks of real-world business, now inform my decisions and strategies at every level. They've sculpted a resilience in me, ensuring that the foundation of trust within my current business operations is both solid and discerning.

Reflecting on these episodes, I realize their integral role in my growth. They didn't just teach me about the pitfalls of partnerships but also about the importance of prudence, trust, and integrity in business. These principles have become the pillars upon which I build and sustain my ventures, ensuring that while I remain open to collaboration, I do so with both eyes wide open, informed by the past but looking towards a brighter, more informed future.

The Power of Diversity and Loyalty

In the heart of inner-city Milwaukee, my team and I navigated through diverse and unified efforts. With half of my crew being African American, their hard work and cultural insights were invaluable, bridging gaps and fostering understanding within the communities we served.

Picture this scenario: myself, a white guy from the suburbs, alongside my shiny new truck loaded with ladders and equipment, stationed at a job site for prolonged periods. This setup, while seemingly benign to me, stood out starkly against the backdrop of our urban work environment. It was a spectacle that certainly didn't escape the notice of local onlookers.

Significantly, my main guy on the crew, far more attuned to the nuances of our surroundings, served as my guide and educator through these landscapes. His awareness of the potential risks and deep understanding of the environments we worked in was a beacon, illuminating aspects of our operations that I may have overlooked. And with a black belt in Tae Kwon Do, I was probably.. over confident in general. haha

This partnership and shared vigilance not only heightened our safety measures but also deepened my appreciation for the complex dynamics at play in the neighborhoods we served.

Building a team: Tools and equipment that are necessary for painting, repairing, and remodeling projects and that are vital for creating a cohesive team atmosphere.

As an example, in an attempt to safeguard our tools, I had secured our ladders with a heavy chain overnight within the confines of our locked worksite. Despite our precautions, we were met with a rude awakening when we discovered the ladders missing one morning. This theft, albeit disheartening, was made even more memorable by the sight of thieves reportedly dashing across a cemetery, our ladders still chained together, in a bizarre twist of events.

The community's response to this incident was remarkable. The property owner, along with friends and neighbors, rallied in an effort to recover the stolen goods. Their solidarity and willingness to stand with us underscored a profound sense of loyalty and communal spirit, even though the ladders were never retrieved.

This experience wasn't just a lesson in physical security; it was a powerful endorsement of the richness brought about by diversity within our team and the broader community. It highlighted the importance of embracing varied perspectives and experiences, significantly enriching our operations and enhancing our connectivity with the communities we aimed to serve.

The incident reinforced the critical role that diversity and loyalty play in overcoming challenges. It was a testament to the collective spirit of our team and the strength derived from our commitment to one another and to our shared mission. This unity and shared understanding became the bedrock of our approach, driving us forward with integrity and empathy in every project we undertook.

The Essence of Our Team: Beyond Skills and Leadership

In building a team, we ventured beyond mere skills to embrace personality and culture fit, understanding these elements to be just as crucial. Our hiring philosophy matured, prioritizing a cohesive, positive workplace culture where fun, humor, and music became integral. This environment didn’t just make daily work more enjoyable; it cultivated a resilient and motivated team dynamic.

Among us emerged natural leaders, individuals who, when confronted with challenges, stepped forward to guide the way. Their acts of initiative and courage served as great lessons on the importance of recognizing and nurturing leadership qualities, reinforcing the belief in the untapped potential within our ranks.

Solidifying My Entrepreneurial Philosophy

This journey, marked by its triumphs and trials, has been foundational, cementing my conviction in the transformative power of teamwork. Leading my first team taught me that the right blend of skills, personality, and commitment can propel a group to exceed all expectations. It's a testament to the idea that collective effort and diversity of thought are invaluable assets to any endeavor.

Conclusion: A Reflection on Our Journey

The path to building a successful team and business is complex, interwoven with lessons on flexibility, partnership dynamics, cultural diversity, and the cultivation of a positive working environment. Each story from the trenches has contributed to a broader understanding, offering both inspiration and practical guidance for navigating the multifaceted world of team dynamics.

As we move forward, the essence of these experiences continues to inform and shape our approach, reminding us of the profound impact that thoughtful, dedicated team-building can have. So, here's to the ongoing adventure of entrepreneurship — to dreaming big, nurturing our teams, and recognizing that the true strength of our businesses lies in the collective spirit and effort of the people behind them.

Until we meet again, may we all continue to build, learn, and grow together.

Matt Levenhagen


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