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Brian Will, Serial Entrepreneur & Industry Leading Business & Sales Management Consultant

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In this blog based on the newest episode of The Dropout Multi-Millionaire Podcast, let’s dive into the world of entrepreneurship and ponder a crucial question: Should you be an entrepreneur? It’s a topic that sparks debate, and I firmly believe that not everyone is cut out to start their own business—at least, not right away. Moreover, some individuals who have already launched their companies may not be best suited to run them. This discussion revolves around the roles of being the top dog or potentially serving as second-in-command.

Personal Reflections on Entrepreneurship

Reflecting on my own journey, I launched my first business at the age of 21 and spent the next 15 years as CEO. While I managed to make some money, it never quite reached the level I had hoped for. Despite selling a company for a million dollars, the funds disappeared quickly. Now, some might think I’m crazy for saying this, but unless you’ve experienced a million-dollar net worth, you might not fully grasp the financial realities. It wasn’t until I met my mentor and business partner, Steve, that I realized the importance of stepping back and learning. By observing and absorbing his expertise, I found myself in a more profitable position.

Learning from Experience

Sometimes, it’s crucial to acknowledge what you don’t know and let someone else take the lead. Serving as the second-in-command allowed me to accumulate wealth without the stressors of being at the top. However, I’ve also thrived as the CEO of my own ventures. That said, if the right opportunity arose today, I wouldn’t hesitate to step back into a supporting role. There’s an old saying about being the captain of your own rowboat versus the first mate on a battleship, but in my experience, the battleship is where the real learning happens.

Roles in Business Leadership

Whether you’re the first mate, second mate, or even third mate, each position offers valuable learning experiences. This is particularly relevant for individuals who have already started their own businesses. Often, those who excel in technical or sales roles may not be the best fit for managing the backend operations. In such cases, bringing in a skilled COO can drive faster growth and smoother scaling.


In conclusion, entrepreneurship is not a one-size-fits-all endeavor. Whether you’re considering starting your own business or already deep in the trenches, it’s essential to evaluate your skills and determine where you can make the most impact. Remember, success in business isn’t just about titles—it’s about playing to your strengths and surrounding yourself with the right team. So, before you take the plunge, consider where you truly belong in the entrepreneurial landscape.

If you’re ready to break free from the status quo and join the ranks of the mavericks, the rebels, and the renegades who refuse to conform and instead build multi-million dollar businesses, subscribe to The Dropout Multi-Millionaire Podcast wherever you choose to listen!

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