Money? No Problem. Benefits? No Worries. Job Stability? That’s a Check. Low Chance of AI Takeover? 10-4, Roger That.

Healthy Culture?

From an operational standpoint, the passenger transit industry has everything an average person could want in a career. I’ve written countless blogs about how transit helped me escape poverty and became the catalyst for completely redirecting my family’s financial trajectory. More importantly, this can be the story for anyone.

But with all this going for it, why is the culture so bad? Why is it getting worse? And more importantly, how can we fix it?

I’ve discussed the roots of toxic transit culture in other posts, and I encourage you to check those out. Today, I’m going to break down four principals I’ve learned to build a winning culture in bus operations and how I've utilized them at Transit Gigs.

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Lead with Influence and Experience, Not Authority

Some of the most influential leaders in any industry often have front-line experience and excelled at it. This gives them an undeniable credibility that makes leadership much easier. When you’ve done the work, and done it well, you earn a level of respect that no amount of authority, degree or title can buy.

I actually learned this principle from watching professional wrestling. Influence, when harnessed correctly, is incredibly powerful. Being relatable, cool, and respected matters. When people like and respect you, things run smoother—it’s as simple as that.

Take JJ Redick, recently hired as the head coach of the LA Lakers. Or look at Colorado’s football program, which turned itself around under a leader with no traditional Division I coaching background. Or consider the wrestler-turned-executive who’s led the world’s largest wrestling promotion to its most profitable years ever, including a multibillion-dollar Netflix deal. What do these people have in common? They’ve mastered the art of influence—leveraging charisma, relatability, reputation, and frontline knowledge to inspire their teams.

Transit culture, in contrast, is deeply authoritative. This kind of leadership breeds toxicity, especially among newer generations who reject it outright. Leaders need to leverage their front-line experience and relatable successes to build influence, not command authority. I’ve had a great career, doing the same work I ask others to do and doing it at a high level. This allows me to inspire my team by tying my cool experiences—traveling for work, driving great cars, and enjoying good food—back to the opportunities transit provided me. I make it about them, not about the Transit Gigs agenda.

Every new account we win, the first thing I tell my team is: “This will give us an opportunity to create new jobs.” And I’m right there with them—working accounts, rain or shine, and proving I’ll never ask anyone to do something I wouldn’t do myself.

Unfortunately, transit often strips leaders of their influence by micromanaging them. This creates a disconnected workforce and perpetuates the same toxic culture. Let leaders lead. Leverage their influence to manage teams and products effectively—they know their teams, and areas of expertise better than anyone else. Don't tell a cat how to meow.

Get Bigger by Getting Smaller

I learned this lesson while working for mega-churches, where they assign a specific overseer for every aspect: Media Pastor, Parking Lot Pastor, Social Media Pastor—you name it. Coming from a small Baptist church, this seemed quite strange to me. Why do we need an Internet Pastor? The truth is, this approach was first implemented in the Bible. Jesus Christ himself worked closely with 12 disciples, leaving a blueprint in the Bible, and over 2000 years later, his teachings remain influential.

Ultimately, this structure helps prevent individuals from feeling lost in a large organization. Similarly, transit operators often feel overlooked or displaced within vast infrastructures.

At Transit Gigs, we’ve embraced a model that emphasizes smaller, individual pods over large teams. We appoint Community Managers, who function as account managers with a primary focus on community building while overseeing operations. Their role goes beyond client relations—it involves understanding their team’s unique challenges and motivations. While we provide a general framework, our Community Managers tailor it to meet their team’s specific needs. The reality is, every team is different. This isn’t McDonald’s where burgers are burgers and fries are fries. No matter how many computers or MDTs you have, you can never fully automate and predict people.

I regularly consult with my Community Managers to gather their insights. Why? Because they are closer to their workforce and possess insights I’ll never have. My philosophy is simple: How can I create blanket rules for people I’ve never met? Instead, I set goals and let them guide me toward practical solutions.

This approach fosters trust, respect, and a culture where people feel acknowledged and valued.

Play to Win

During my tenure at Ecolane, a scheduling and dispatch software company, I observed a distinctive practice that transformed my perspective on a Slack channel: every achievement was celebrated across the organization, regardless of its size or relevance to one's role. Whether it was a new sale or a new account, recognition was given. I realized that this approach helps employees understand that every contribution is significant, no matter how small. By highlighting every success, Ecolane made employees feel part of something larger. In the transit industry, especially for those behind the wheel, success is often measured by "days since the last accident"—a discouraging and negative metric that doesn't foster progress.

At Transit Gigs, we fostered a winning culture by sharing our objectives and celebrating achievements. We also support each other during challenges and collaborate when things get tough. I recall a time when we had to manage our largest operation to date—across multiple states and time zones. I was transparent with my team about the stakes and my own anxieties. We were severely understaffed and inexperienced, but the exciting part was that teamwork could make it happen, and I ensured everyone understood that. I knew it was possible, but it required everyone's best effort. It was like, how amazing would it be if we could pull this off? That kind of motivation resonates with people.

I even used a Katt Williams clip to inspire my younger workforce: it essentially said, "On paper, other companies may have more resources, but let's get on the line and see if that matters. I guarantee it won't." That day, we aimed to win—and we did.

Winning isn't just about revenue; it's about creating a legacy and setting a standard. If we could achieve this, the sky's the limit.

Invest in Ideas

The quickest way to lose employee engagement is by outright rejecting their ideas. Collaboration is essential, especially since employees often have unique insights that executives might miss.

I've always been someone who values ideas. In 2017, I created a VR route trainer out of frustration with outdated training methods. Although it wasn't a commercial success, it taught me the importance of nurturing innovation. Not everyone is meant to be an entrepreneur, which is why we adopt an intrapreneurial approach.  It's never a "we can't," but rather "here's how."

Our team's ideas have led to some of our most successful initiatives and business ventures. For instance, our branded T-shirts came from a team member's suggestion. Personally, I'm quite traditional. If it were up to me, everyone would wear ties and blazers, but my team preferred T-shirts to show off their stylish sneakers. Did I fully understand this? Not really. But do I need to? The reality is this cost us a few hundred bucks and made me look cool and related in the eyes of my team. Thats important.

But here is what I've discover in life--Ultimately, the human mind performs best when creativity is encouraged. If anything, a huge fear of mine, as it should be for most leaders, is that our team might stop sharing ideas if they feel they won't be taken seriously.

Encouraging employees to innovate not only enhances our operations but also keeps them engaged in our mission. There's a ton of low hanging small win fruit to pass around. 

Transit, driving—transportation as a whole is challenging, which is why gaining buy-in is crucial.

Conclusion

Building a healthy culture in transit isn’t easy, but it’s worth it. By leading with influence, creating smaller, community-focused teams, playing to win, and investing in ideas, we can transform this industry. At Transit Gigs, we’re not just creating jobs; we’re building a movement—one that proves transit can be a force for good in people’s lives.