In one of the recent episodes of The Shades of Entrepreneurship, I had the pleasure of sitting down with Jacob Gray, co-founder of Chosen Family Wine.
Jacob embodies the essence of a true leader—he operates like a point guard, bringing the team together, executing plays, and ensuring everyone gets credit for the wins.
When things go wrong, however, he takes full responsibility.
This is the kind of leadership every entrepreneur should strive for.
But what is leadership? Why is it so important, and why should entrepreneurs care?
Read: The Leadership Playbook: Lessons from Jacob Gray, Co-Founder of Chosen Family Wine
What Makes a Leader?
First, let’s clear up a common misconception—leadership is not defined by seniority or position within a company. I majored in Business Management and Leadership at Portland State University, but that didn’t automatically make me a leader. Leadership isn’t something you earn by title; it’s something you practice.
According to Harvard Business Review, leadership isn’t about popularity, power, or wisdom in long-term planning. These traits, while valuable, don’t necessarily make someone a leader.
One of my favorite definitions comes from TechTarget: "Leadership is the ability of an individual or group to influence and guide others within an organization".
Why Entrepreneurs Should Care About Leadership
As entrepreneurs, leadership isn’t about barking orders. It’s about guiding others through actions that reflect the kind of behavior you’d want to see.
Remember Dale Carnegie’s Golden Rule from How to Win Friends and Influence People: "Treat others as you would like to be treated".
True leadership demands a hands-on approach. It means showing up, whether that’s cleaning the floors, putting in weekend hours, or staying late to get the job done.
Leaders also recognize that mistakes are inevitable. Instead of assigning blame, they view errors as opportunities for learning and growth. Leadership is about building trust and resilience in your team.
The Difference Between Leadership and Management
Leadership is often confused with management, but they are not the same. Managers may focus on rationality and control, while leaders inspire innovation and creativity.
A manager doesn’t have to be a leader, and a leader doesn’t have to be a manager. However, an entrepreneur should strive to be both—a visionary who can lead by example and also manage the day-to-day effectively.
Key Traits of Effective Leadership
So, how can you become a better leader? Here are a few essential skills:
Listening: Leaders listen more than they speak. They give their full attention, ask questions, and observe body language. Listening also means being open to feedback, which is critical for personal and team growth.
Time Management: Effective leaders know how to balance short-term, long-term, and daily goals. They plan meticulously and implement decisively, ensuring that decisions are actionable and clear.
Delegation & Motivation: No leader can do everything. Delegating tasks not only frees up time but also empowers others to step up and take responsibility. When people feel valued and motivated, they’re more likely to give their best.
Engaging Your Team
In every company, you’ll find three types of employees: CAVE, RIP, and Engaged.
CAVE employees: These are the "Constantly Against Virtually Everything" employees. They have a complaint for everything—whether it’s the traffic, the coffee, or the coworker next to them.
RIP employees: These team members are "Retired In Place". They do the bare minimum, just coasting until retirement. Believe it or not, I was once one of these employees—check out my self-interview episode for more on that.
Engaged employees: These are the team members who show up every day ready to make a difference. They are your future leaders.
As a leader, your job is to transform those CAVE and RIP employees into engaged team members. It’s not about forcing them to change, but about creating an environment where they feel valued, supported, and inspired.
Leadership is About Growth
At the end of the day, a great leader ensures that everyone on the team grows. The better the leader, the more opportunities for career advancement and personal growth the team will have. Maya Angelou once said, "A leader sees greatness in other people. He nor she can be much of a leader if all she sees is herself."
As entrepreneurs, people in our communities often look up to us. Leadership is about more than running a successful business—it’s about lifting everyone around you, ensuring that we all grow and thrive together.
Because leadership, like entrepreneurship, is a collective effort. We all have a role to play.
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