From Stock Boy to CFO: The Entrepreneurial Spirit That Built Southwind
Long before Southwind became a thriving enterprise, Tyler was a young stock boy at Hobby Lobby with an entrepreneurial spark that couldn't be contained. While his peers spent their paychecks on typical teenage pursuits, Tyler meticulously saved his first $1,000 to open an E-Trade account—his initial foray into the world of investment. This early financial curiosity foreshadowed his future as a CFO, though the path would be anything but direct.
In the early 2000s, while many were still grappling with the concept of e-commerce, Tyler launched his first venture selling perfume online—a little-unknown chapter in his business journey. After establishing himself as a software engineer in San Francisco's competitive tech landscape, Tyler made the bold decision to leave it all behind. With marriage on the horizon and dreams of starting a family, he returned to Kansas City seeking affordable housing and the comfort of nearby family.
The transition from Silicon Valley programmer to junk hauling entrepreneur came through an unexpected source: a simple magazine advertisement. When Tyler spotted an ad for a 1-800-GOT-JUNK? Franchise for sale in Kansas City, something clicked. Despite having no experience in the industry, he made the call that would change everything. With his parents believing in his vision enough to offer their house as collateral for his first business loan—creating a pressure of $742 in daily revenue needed to meet obligations—Tyler dove headfirst into the unknown.
Those early days tested every limit. Working on trucks daily for three years, handling the most undesirable junk removal jobs during a recession, and pricing services at rock-bottom rates to survive—all while his wife provided crucial financial support at home. It wasn't glamorous, but it was the foundation of something extraordinary. "Just jump. Take risks if you have the opportunity—life begins at the edge of your comfort zone," Tyler now advises aspiring entrepreneurs, embodying the resilience that turned a small operation with just a few jobs a day into the thriving enterprise Southwind would become.
From Small Beginnings to Shared Vision
Tyler & Josh Herron stand in front of their fleet in 2012.
The early days centered on junk hauling services, with everyone learning and adapting together. The team navigated the challenges of building a business through collaborative problem-solving and shared responsibility. Through this collective effort, a modest operation handling only a few jobs daily grew into a business generating over a million dollars in revenue just five and a half years later. In 2010, Tyler and his business partner Josh expanded into carpet cleaning, followed by moving services in 2011 and painting in 2012. "We were throwing darts at the wall and trying to find something to stick," Tyler recalls. This period of experimentation and growth laid the foundation for what would eventually become Southwind's diverse service offerings.
Cultivating a Workplace Community
The workplace culture began to deliberately take shape in 2012 with the introduction of career path programs for front-line teams—a defining moment that reflected their commitment to everyone's growth. "We started at the bottom and moved forward together," Tyler shares. "We wanted to create a space where everyone could envision their future." This foundation of collaborative effort, genuine opportunity, and accessible career advancement naturally fostered loyalty, dedication, and mutual trust throughout the organization.” The company experienced significant growth as a result of this community-focused approach. By 2015, they had expanded into Omaha, with more cities and service offerings following. The emphasis has always been on creating a workplace built on mutual respect and shared purpose.
Support, Commitment, and Growth: Our Foundation
The business began with significant personal investment—including a loan secured against family property as collateral. "There was a network of support that made this possible," Tyler reflects. "And that created a responsibility to build something worthwhile." One milestone stands out in Tyler's memory: "Four or five years in, we did $100,000 in revenue in one month. It was late at night on April 30th, and we had just finished a hot tub job that pushed us over that threshold. That was a moment when we realized what we were building could really work."
These collective early efforts laid the groundwork for what would follow. The company's development has always been a team achievement, with contributions from everyone who joined along the way. What began as straightforward employment opportunities evolved into a workplace offering genuine growth and advancement.
"What I'm most proud of are the awesome success stories of people who have become partners and were just young kids looking for a temporary place when they started," Tyler says. "They got opportunities that weren't possible before."
Our Inclusive and Supportive Workplace
Southwind's workplace philosophy centers on people, creating an environment where team members can thrive professionally and personally. "Our shared purpose is helping everyone get further ahead in life than they might have thought possible," Tyler notes. This mission goes beyond business metrics to focus on creating meaningful opportunities for growth throughout the organization.
Clarity and transparency have been workplace priorities from the beginning. "The only time people are upset at work is when reality doesn't meet expectations," Tyler observes. "We're very aligned on the front end about what winning and losing looks like. When everyone is on the same page, people won't feel bad."
As the company expanded, maintaining these connections became increasingly important. Regular team meetings and open dialogue with department leaders help preserve trust and cultural foundations. "We can't win first. We win together," Tyler emphasizes.
The Road Ahead: Growing Together
As Southwind continues to expand, the focus remains on developing well-defined career paths across all levels and strengthening support departments. The company's future is built on its people and collaborative culture, and maintaining this foundation while scaling remains a priority.
"As we've grown rapidly, we haven't been able to work as hands-on with people across the business," Tyler acknowledges. "Making sure we're hiring the right people to continue replicating the magic as the business grows is crucial to staying on track."
Reflections on Building Something Meaningful
When asked about lessons learned through building Southwind, Tyler's message is clear: "Take the leap. Even if things don't work out, what you learn will be worth it. Who you surround yourself with has an impact. There's nothing more rewarding than taking risks and working with other people toward something you believe in."
The Southwind story highlights how a supportive workplace culture, clear shared vision, and genuine commitment to people's development can create an organization where both the business and its team members flourish together. It's this balance that makes Southwind not just a place to work, but a community where careers and personal growth align with collective achievement.