Leadership & Scalability
I kicked off this series with The Art of Coffee Catering — Part I, where I distilled eight years of wins, failures, and hard lessons into four foundational principles centered on Identity & Performance.
Part II shifts the lens. This blog post is about Leadership & Scaling. Leadership is my passion—but real leadership doesn’t start with a team. It starts with yourself.
When I think about leadership, I think about surrendering the direction of this business to God's will (a topic worthy of its own blog post). I think about waking up at 4:40am to train my body before I ever lead a meeting. I think about discipline—dietary, physical, mental. I think about making time to be in God's Word—the original SOP. I think about my marriage, our family's vacations, and the time I make to be with my two boys. I think about the legacy I want to leave my children and the standard I want every Nightowl employee to be proud of.
But let's be clear—my goal isn’t to make everyone happy. It isn’t to always be nice. My goal is to do what’s right for Nightowl—guided by conviction, confidence, and data.
That means firing people when it’s necessary and strengthening my muscle of firing fast.
Having hard, intense conversations—always better earlier rather than later.
Promoting boldly.
Praising aggressively.
Leadership starts long before you interact with your team and long before you build corporate framework. It starts in the quiet disciplines no one sees.
In the four principles of Part II, we’ll eliminate fear and promote ambitious creativity. We’ll double down on cash flow and talk about profitability without flinching. We’ll define exactly who belongs in our culture—and be just as excited to remove who doesn’t. Because scaling isn’t about adding more. It’s about becoming stronger. In the words of many writers, thought leaders, and my friends at Northern Vessel in Des Moines, Iowa—getting 1% better each day.
5. The Best Invoice Is the One You Can’t Perform Yet
The best invoice you’ll ever send is the one you can’t perform today. This has been an internal motto since day one. There is no greater honor in business than earning enough trust that a client pays you for something you haven’t quite built yet. That’s entrepreneurship at its purest—courage before capability.
In 2019 Nightowl had one coffee cart. Concord Church requested two carts for their annual women’s conference on a night when our only cart was booked for a wedding. I didn’t hesitate. I quoted it. Then I had seven weeks to build two more carts and buy two additional sets of equipment. That moment shaped our company and our scaling framework. I call it risk-free scaling. The market validates your growth before you fund it. Instead of gambling on hypothetical demand, you build in response to real demand. Cash flow funds expansion. Confidence replaces fear.
Say yes. Then rise to the occasion. That’s how momentum compounds.
6. Profit Is the Oxygen of Leadership
If you can’t run a profitable business, you can’t be trusted to lead others. That might sound harsh—but it’s true.
In The Everything Store, Jeff Bezos notes a healthy businesses operate above 27% profitability. Below that threshold, cracks begin to show. Leaders get emotional. Teams feel instability. Decisions become reactive instead of strategic.
Profit isn’t greed. It’s stewardship. Profit funds innovation. Profit protects payroll. Profit creates opportunity.
When a founder is financially confident, the entire organization can operate with focus. Vision becomes bold. Culture becomes stable. Growth becomes intentional. You can’t build a high-performance team on thin margins and hope. Profitability isn’t optional. It’s leadership.
7. Build a Culture of Competition
Mediocrity thrives in silence. Excellence thrives on scoreboards.
Internally, we broadcast key metrics—gratuities earned, monthly revenue, Google reviews received, events completed—to create transparency and healthy competition across the team. We gamify performance through our 100 Club. Complete 100 events in a year? You earn a paid vacation. No excuses. No participation trophies. Results and rewards.
After every event, our baristas submit reviews—over 750 per year. Wins are celebrated. Mistakes are dissected. Insights are shared. The result?
Friendly banter.
Relentless improvement.
Performance-driven pride.
Competition isn’t a side effect of our culture. It’s the engine.
8. Define Your People With Absolute Clarity
At Nightowl, we have complete clarity on who fits our culture. We don’t hire for convenience (although this is always a temptation). We hire for alignment.
Our people are physically active, disciplined, driven (some even entrepreneurial) and intentional about how they present themselves. Image matters—because perception matters. How you show up communicates everything before you speak. In the business of staffing and agency, our responsibility is to represent our clients to the best of our ability. But image alone doesn't cut it.
We look for:
• Selfless hospitality
• Coachability
• Intellectual curiosity
• Problem-solving ability
• Grit (work-ethic)
• Team mentality
• Desire for greatness
We want hustlers.
We want competitors.
We want people who value who God created them to be and steward it well.
When you build a team that is sharp, motivated, and aligned—everything else becomes easier. Systems work better. Energy improves. Clients feel it. The right people don’t just execute the vision. They amplify it.
Don't know where to start in building a great team?
