How I Build Teams That Win: Culture, Loyalty & Accountability
By Chuck Cuda
When I reflect on the success of my ventures—whether it’s in commercial real estate, cannabis, or charitable work, the through line has always been the teams behind the outcomes. Winning in business is never a solo act. It’s a result of building cultures rooted in loyalty, high expectations, and accountability—something I’ve worked hard to establish in every company I lead.
Purpose, Loyalty & the "It" Factor
When hiring or building teams, I don’t just look for resumes filled with accolades. I look for alignment. If someone’s personal purpose is in sync with our company’s mission and they’re excited about where we’re headed, they’re far more likely to thrive and grow with us. Skills can be taught; alignment can’t.
The “it factor” is rarely about raw talent alone. It’s about coachability and loyalty. If a person has stuck with one company through different roles or has taken the time to lead others, that speaks volumes. They’ve shown adaptability, they’ve built trust, and they’ve worn multiple hats. This is exactly the kind of team member who can grow into a leader. When someone has experience managing others or stepping into new responsibilities, you know they’re capable of more, and they’re likely hungry to keep evolving.
Roles That Fit & Clear Expectations
Leadership isn’t one-size-fits-all. One of the biggest missteps I’ve seen is promoting great employee into management roles they’re not meant for. If someone is a rockstar revenue driver, let them keep doing that. Don’t force leadership if it takes them away from their strengths. That said, I always want to see communication and collaboration across all levels of a company. Team members no matter the role, should interact across departments. That connection shows they’re invested in something bigger than themselves.
I’ve built a reputation for having high expectations, but those come with context, support, and trust. When someone on the team isn’t meeting the bar, we address it by setting clear expectations from leadership on down. It’s not about fear, or do as I say not as I do, it’s about building people up. Asking questions like “Where do you want to go?” and then holding them accountable for getting there. Great leadership means leading by example and showing what’s possible, not just demanding results.
Transparency & Emotional Intelligence
One of the hardest decisions I have to make is consolidating assets in the cannabis industry. It means eliminating positions and breaking tough news. Early on, I made the mistake of sugarcoating the reality, telling people nothing would change. I’ve since learned that transparency—however uncomfortable—is the most respectful route. People can handle the truth, and often they’ll rise to the challenge when you’re honest. When transitions are done with clarity, respect, and vision, they can still inspire buy-in.
I have learned that no two people respond to feedback the same way. Some are motivated by direct challenges, while others need a softer approach. The key is understanding what makes your people tick and adjusting accordingly. Awareness isn’t just a nice-to-have. It’s a leadership must. Emotional intelligence is how you maintain trust in hard conversations.
Mentorship & Multiplying Growth
As a founder and entrepreneur, I embrace failure as a learning tool. I expect my team to do the same. We lead by example, and that includes giving our teams the autonomy to make decisions—even if they’re not always the right ones. What matters is that we learn, we adjust, and we keep moving forward.
Leadership is multiplying yourself. Mentorship is a huge part of how I operate. One standout example is Ian Peak, who is now our Chief Operating Officer at Elevate Cannabis. In his previous role, Ian had the skills and knowledge to lead but was restricted by a lack of opportunity and trust from the previous regime. I saw his potential and gave him the freedom to make decisions and take ownership. Today, Ian runs operations and leads his own teams—something he was fully capable of all along. Watching him grow into his role is what this is all about. My expectation of those I’ve mentored is for them to do the same for the people they lead. That kind of culture—where mentorship is paid forward—is how we multiply growth across the organization.
You can read more about my mentorship approach in Ego Strength, available now on Amazon.
Culture as a Competitive Edge
When culture is off, everything suffers. Without buy-in, you invite gossip (I like to call it the devils radio!), confusion, and burnout. That’s why I’m intentional about creating spaces where employees feel ownership. Take the rebrand of our stores to Key Cannabis—this was about starting fresh, giving our employees buy-in, and building a company we can feel proud of together.
Culture thrives when everyone is encouraged to participate, even when they’re unsure. And as an entrepreneur, I understand failure is part of the process. That mindset gives our teams permission to act, make decisions, and grow without fear. I want them to be experts in their roles—and I trust them to go out and prove it.
Legacy Isn’t a Solo Pursuit
My goal has never been to build empires with my name on them. I want to build platforms that outlive me—where every team member, whether they stay for a season or a decade, walks away better than they arrived. When people leave our companies for leadership roles elsewhere and say the decision wasn’t easy—that’s the kind of legacy I’m proud of.
Stay tuned for our next post: "Legacy on Purpose: How I Defined the Impact I Want to Leave Behind." If you haven’t purchased your copy of Ego Strength yet, you can do so on Amazon HERE.