Understanding the Entrepreneur
Challenges and Lessons that Create Success
By: Ethan Sutton and Corey Wichansky
Entrepreneurship is not a game that everyone can play. While people can sit and envision the perks of being their own boss, managing others, and achieving lucrative rewards, they often fail to see the uphill battle that a successful entrepreneur must overcome. From conceptualizing and developing a business plan to executing the plan and scaling the business, an entrepreneur must navigate several challenges and uncertainties. As students in our university’s venture capital fund, Hillside Ventures, we have grown accustomed to speaking to founders with a critical lens. One of the most important elements that makes a company an attractive investment is a founder with acclaimed entrepreneurial experience. To help better understand the characteristics of a successful entrepreneur, we have interviewed two successful entrepreneurs, Robert Mazzucchelli and Connie Zhang. In this article, we will examine the experiences, challenges, and lessons of these two entrepreneurs to discover what the entrepreneurial experience is really about.
Robert Mazzucchelli Founder of SportsEdTV
Our first interview was with the accomplished entrepreneur Robert Mazzucchelli. Robert is the Co-founder, Chairman, and CMO of SportsEdTV, an online video platform that provides access to high-quality coaching and educational content across a wide range of sports. His entrepreneurial spirit shone through from a young age as he started several businesses as a child. Whether it was selling tennis rackets or washing cars, he found various ventures to earn additional income. His drive and initiative, coupled with his willingness to take risks and learn from his experiences, laid the foundation for his success as an entrepreneur in the future. Robert’s first successful exit came from a company he founded called Pinnacle Promotions, an integrated marketing agency. Robert described his initial venture as a tumultuous journey, likening the business to “a cat with nine lives” due to the many times they almost ran out of money. Despite these setbacks, Robert refused to give up, and his commitment paid off when he successfully sold the business six years later.
Robert’s entry into the sports and EdTech space with SportsEdTV was a natural transition. Tennis was a key piece of his childhood, and he went on to play for the University of Richmond and a few years professionally. Robert was not planning on creating another large business after a thirty-year entrepreneurial career, but when approached about a tennis media project in 2014, it sparked a new idea that he couldn’t resist. Realizing that books alone were insufficient in promoting optimal learning for aspiring athletes in a world of digital transformation and dissatisfied with the quality of instructional videos currently available, SportsEdTV came to life. Robert recognized the sports market as an ideal platform to capitalize on business opportunities as over 2.5 billion people worldwide are engaged in some form of sports or physical activity. Moreover, Robert calls sports, “a training ground for life,” as the lessons learned from improving in a sport can be translated into other aspects of life. For example, Robert pointed out Microsoft CEO, Satya Nadella, who attributes much of his success in business to the skills learned playing cricket as a child in India. Robert explained that if customers feel that a product or service provides real value and benefits, they are more likely to continue using it and recommending it to others. Even though 99% of Robert’s customers are not planning on becoming professional athletes, they can use the platform to improve at the sport they enjoy and learn valuable life skills along the way.
When asked about the key factor leading to his success, Robert explained “every day is a battle, you are never out of the woods and you must be ready to put in the time and effort to deal with unexpected challenges,” he paused as three airplanes suddenly flew over his head, “or obstacles that could come flying at you at any moment” he concluded with a smile.
Entrepreneurs face an endless list of unexpected challenges and can never truly know what the the next day will bring. As Robert looked back on his journey as an entrepreneur, he shared some incredible lessons and insights with us. At a young age playing tennis, Robert had the privilege of working with world-renowned sports psychologist Jim Loehr. Jim Loehr simplified the game for Robert when he said “in tennis, you are facing someone who is trying to create problems for you. Whoever is better at solving those problems will win.” For a while, this quote resonated deeply for Robert within the lines of a tennis court. However, he soon learned this quote extended much further. Robert told us “Business is just like that, it is all about solving problems to win. I have learned to enjoy solving the problems.” Successful entrepreneurship requires problem-solving and decision-making. Obviously, not every decision will be perfect. Robert recognizes this and shares that although there are a million things he would love to go back and change, that is where the biggest lessons have been learned. When asked if he would change anything if given the opportunity to start his career from scratch, he responded “I would leave everything just the way it was.”
Connie Zhang Founder of Mocaa
Our next interview was with Connie Zhang, the founder of mocaa.com. Mocaa is an innovative platform that bridges the gap between college admissions advisors and students. Mocaa, short for Marketplace Online for College Admissions Application, emerged from Connie’s own experience as a student. She observed the inequality in access to higher education resources and decided to create a solution for this global problem. During her time at Cambridge, Connie worked with industry professionals and Cambridge professors to study the inequity in higher education, which was how Mocaa was born.
Mocaa revolutionizes the way students can access college advisors by bringing in affordability and transparency. Connie aptly described Mocaa as the "Etsy" for college admissions advising, as it provides a massive network of college and career advisors eager to help with test prep, essay guidance, mock interviews, and other application services. The platform is available to all students and parents, making it easier for them to access reliable private college counselors without struggling to pay for an expensive agency consultant. For Connie, the key to her success was understanding her customers and what they wanted. She realized that talking to customers was essential to identifying the underlying problem and designing a product that addressed their needs. However, building a marketplace was not easy, and the first question was how to build it. To build a community, one needs to be mission-driven and see beyond revenue. Mocaa's mission to democratize access to admissions consulting services for all students and close the education inequality gap was a driving force for the team.
As an entrepreneur, Connie learned many valuable lessons, and she advises aspiring entrepreneurs to do their homework before starting a business. She explained “it's not as glamorous as the movies make it out to be. One needs to put in hard work, work smart, and maintain a healthy work-life balance, especially at the start.” Connie also learned that a team that shares your passion is crucial to success. "You don't just raise money and suddenly you're rich." Says Connie, emphasizing the importance of understanding that raising funds is just the beginning. Bootstrapping and investing in the business are also important signs of commitment and sincerity an entrepreneur should show to investors and customers.
In the future, Connie plans to expand Mocaa to the international market and connect students worldwide. She hopes to level out the playing field in higher education and encourage more students to pursue their dreams. In conclusion, Connie Zhang’s story is a testament to the power of education and the impact one can make in creating opportunities for others. Mocaa is a game-changer in the world of college applications and serves as an example of how technology can be used to democratize access to education.
Final Thoughts
Robert and Connie's exceptional storytelling and impressive perseverance are a testament to the qualities required to thrive as an entrepreneur. Our interaction with them was an absolute pleasure, and we wish nothing but the best for the future of SportsEdTV and Mocaa. It's easy to become consumed by the analytical and financial aspects of the VC industry, but every remarkable company has a remarkable founder with a story full of achievements, obstacles, teachings, blunders, triumphs, and failures. Robert and Connie's experience has rekindled our understanding of this reality, and we will certainly keep this in mind as we communicate with future founders.