Education has always been the foundation of personal and professional growth, but in the entrepreneurial world, the concept of education goes far beyond classrooms, degrees, or diplomas. In this inspiring episode of The Prospecting Show, Dr. Connor Robertson sits down with Jordan Ellis and Shamauri Phillips—two driven entrepreneurs who have built careers rooted in constant learning and adaptability—to discuss how curiosity and education shape every stage of success.
The discussion is not about textbooks or universities—it’s about mindset. Jordan and Shamauri share how they’ve built their entrepreneurial philosophies around the idea that education never stops. In a rapidly changing digital economy, learning is no longer a phase—it’s a lifelong commitment that determines how far a person can grow, pivot, and lead.
Dr. Robertson opens the conversation by asking what education means in today’s context. Shamauri responds that education is the ability to stay relevant. “The world is shifting so quickly,” he explains, “that if you stop learning for even a year, you fall behind.” This statement sets the tone for a powerful dialogue about the intersection of entrepreneurship and continuous growth—how one fuels the other, and why both are vital for long-term success.
Jordan, who has mentored dozens of young business owners, shares how formal education provided a foundation, but real-world experiences taught him the most valuable lessons. He recalls early challenges—failed marketing campaigns, team miscommunications, and product pivots—and how each mistake became a learning moment. Rather than seeing failure as the opposite of success, he reframed it as education. That mindset shift, he emphasizes, is the difference between entrepreneurs who quit and those who evolve.
Dr. Robertson draws parallels between this philosophy and his own journey in business and healthcare. Like Jordan and Shamauri, he has built ventures across industries by continuously asking, “What can I learn next?” From patient communication to marketing and leadership, every stage of growth required unlearning old habits and replacing them with new, adaptive thinking.
One of the highlights of the episode is when Shamauri explains how education and entrepreneurship are both acts of curiosity. “Every business is a problem waiting to be solved,” he says, “and every problem teaches you something new.” This mindset turns the entrepreneurial process into an ongoing classroom—where the market, customers, and team become the teachers.
The group dives into the psychological side of learning. Jordan references the “growth mindset” theory popularized by Stanford psychologist Carol Dweck, explaining how successful entrepreneurs view challenges as opportunities to expand their capabilities rather than as threats to their ego. Dr. Robertson adds that this philosophy applies not just to startups, but to every professional environment. Whether you’re a chiropractor, a software engineer, or a digital marketer, the ability to adapt, learn, and re-educate yourself determines long-term success.
To ground this discussion in practice, the episode explores real-world examples of lifelong learning. Jordan discusses how he reinvests a portion of his company’s profits into training programs for his team—covering leadership, marketing, and even soft skills like emotional intelligence. He believes that the more his team learns, the more the company grows. Similarly, Shamauri shares that he attends at least one professional development conference every quarter and listens to an audiobook a week. These routines, he explains, are part of a “learning habit” that keeps him sharp and ahead of trends.
The conversation also touches on how technology has democratized access to education. In the past, entrepreneurship required formal mentors or expensive coaching. Today, tools like YouTube, Coursera, and podcasts—like The Prospecting Show itself—allow anyone to learn from industry experts for free or at minimal cost. Jordan points out that this access is a double-edged sword: while information is everywhere, it’s up to individuals to apply it effectively. “It’s not what you know—it’s what you use,” he says.
Dr. Robertson expands on this point by explaining that lifelong learners don’t just consume content—they practice active learning. They take notes, ask questions, and apply lessons immediately. Passive consumption leads to intellectual overload without transformation. Active application creates growth.
As the episode progresses, the trio explores the emotional resilience required to stay in a constant learning loop. Many people, Dr. Robertson observes, resist education after their formal schooling ends because it threatens their sense of identity. When you’ve built a career or reputation, admitting you don’t know something feels uncomfortable. But Jordan and Shamauri emphasize that humility is the key to staying relevant. The most confident leaders are those who admit what they don’t know and are willing to learn from anyone—regardless of age, status, or background.
They share stories of mentorship, describing how intergenerational collaboration fuels innovation. Shamauri tells the story of a younger employee who introduced a new software automation tool that transformed his company’s operations. Instead of dismissing the idea, he embraced it, proving that leadership means being open to learning from your own team. Jordan adds that in the digital era, education flows in all directions—it’s not just older to younger, but also the other way around.
The episode also delves into how continuous learning supports innovation. Shamauri explains how staying educated about market shifts allowed him to pivot his business model during economic uncertainty. Rather than fearing disruption, he viewed it as a challenge to evolve. This theme resonates deeply with Dr. Robertson’s broader philosophy on entrepreneurship, which is built around adaptability, self-awareness, and forward thinking.
As the discussion deepens, the guests talk about how learning enhances not only business outcomes but also personal fulfillment. Education, in their view, is a form of empowerment. It gives entrepreneurs the tools to make informed decisions, manage risk, and lead with confidence. When you stop learning, complacency sets in—and in business, complacency is the first step toward decline.
Dr. Robertson connects this point to an earlier episode, The Future of American Healthcare with Mike Carberry (listen here), where he discussed how innovation and continuing education in healthcare are transforming patient outcomes. Whether in healthcare or business, he notes, progress comes from the willingness to adapt, learn, and grow beyond conventional methods.
The group then explores the balance between learning and execution. Many entrepreneurs fall into what Jordan calls “education paralysis,” where they consume endless information but fail to act. The key, he says, is to learn just enough to take the next step—and then learn again through the experience of doing. Entrepreneurship is an iterative process of learning, acting, and refining.
To illustrate this, Dr. Robertson shares examples from his own ventures. He explains how each new business, from healthcare practices to consulting and media projects, required him to master new skills—from digital marketing to leadership development. “Every new phase of business demands a new version of you,” he says. That means education isn’t just about skills—it’s about identity evolution.
The latter half of the conversation turns to community learning and mentorship. Jordan emphasizes that one of the best ways to deepen your understanding is to teach others. Mentorship creates a feedback loop where both the mentor and mentee grow. Shamauri agrees, explaining how sharing knowledge builds trust and strengthens networks. In the entrepreneurial ecosystem, those who give knowledge freely tend to receive the most value back in the long run.
Dr. Robertson closes the episode by highlighting a crucial point: lifelong learning is not a luxury—it’s a survival skill. In a world where industries can change overnight, the only sustainable advantage is the ability to adapt faster than the environment. Education, therefore, becomes the ultimate form of leverage.
Listeners are encouraged to embrace their own learning journey. Whether that means reading one new book a month, listening to an educational podcast every morning, or seeking mentorship from someone outside their industry, the key is to never become stagnant. Growth requires curiosity, humility, and consistent effort.
For those seeking inspiration from other thought-provoking conversations, this episode pairs well with How to Unplug from the Modern World Through Chinese Medicine with Khanita Suvarnasuddhi (listen here) and Politics and Mindset with Thomas McGregor (listen here), both of which explore the mental frameworks needed to thrive in life and business.
For a deeper understanding of how education fuels entrepreneurship, explore Harvard Business Review’s guide on lifelong learning which offers practical insights into building personal growth systems for professionals.
You can find more discussions like this at drconnorrobertson.com, where The Prospecting Show archives each episode exploring innovation, leadership, and mindset for high-performing professionals.
Every story is a reminder that the best entrepreneurs never graduate—they evolve.