Building Your Own Path: Lessons in Leadership from Shegun Otulana

What does it mean to be a leader? For our eighth graders, that question took on new meaning during a recent Leadership Speaker Series conversation with Shegun Otulana, a serial entrepreneur, investor, founder of Harmony Venture Labs, and, perhaps most importantly, a proud four-time Highlands parent.

Shegun shared his journey from a young student who loved building things to an entrepreneur who has spent his career building companies, developing people, and solving meaningful problems. His path was not without setbacks. His first company, launched while he was in college, failed within six months. Rather than allowing that experience to define him, he learned to navigate failure, adapt, and keep building. His third venture, TheraNest, went on to grow into a national platform serving mental and behavioral health providers.

His message to students was clear: Failure is not the end of the story. Learning how to manage it is part of the journey.

Throughout the conversation, Shegun emphasized 4 key principles that have shaped his approach to leadership:

Make others look good. Great leaders recognize the value in the people around them and create opportunities for others to succeed.
Responsibility comes before authority. Leadership begins with a willingness to take ownership, serve, and do the work.
Be willing to be wrong. Growth requires humility, curiosity, and the courage to acknowledge mistakes and apologize.
Build people, not just companies. The most meaningful work often comes from investing in others and creating something together.

Perhaps his most memorable advice was directed at the stage of life our eighth graders are entering. As they begin to hear more opinions about who they should be and what paths they should take, he encouraged them to be intentional about where they direct their focus and energy.

"Your life is going to be your own thing you can build."

Rather than allowing the expectations or doubts of others to dictate their futures, students were encouraged to stay focused on their dreams, remain curious, and take ownership of the lives they want to create.

Learning Through Failure: Questions from Our Students

The conversation sparked thoughtful questions from students, including how many businesses Shegun had started and how many had failed before he found success.

Shegun shared that his first two ventures did not succeed before he went on to build TheraNest. His willingness to discuss those experiences offered students a valuable perspective: success is rarely a straight line, and setbacks can become some of our greatest teachers.

As he reminded them, "Failure never stops. You just have to know how to manage it."

He was also asked about the books that have influenced his leadership and personal growth. Shegun explained that reading has helped him build his own personal counsel of mentors, learning from the experiences and wisdom of people he might never otherwise have the opportunity to meet. Through biographies and autobiographies, he has explored what makes great leaders successful. He also shared that he wishes he had read more fiction, recognizing its ability to expand creativity, imagination, and new ways of thinking.

Shegun's Recommended Reading List

For anyone looking to continue learning beyond the classroom, Shegun shared several recommendations:

How to Win Friends and Influence People by Dale Carnegie
Mindset: The New Psychology of Success by Carol S. Dweck
Books by Myles Munroe, particularly those exploring purpose and personal potential
Biographies and autobiographies of influential leaders and entrepreneurs

His advice was to read broadly, remain curious, and seek wisdom from those who have walked the path before us. Books can serve as mentors, helping us expand our perspectives and shape the people we aspire to become.