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From Square One to Success: Richard Rierson Doses up Leadership Insights with Square Founder, Jim McKelvey

Richard Rierson is a renowned leadership coach, speaker, and host of the popular podcast, Dose of Leadership. Based in Wichita, Kansas, Rierson is recognized as an expert in leadership development, and his podcast has become a go-to resource for individuals seeking to improve their leadership skills. With over a decade of experience as a corporate executive, Rierson brings a wealth of knowledge and expertise to his podcast, which features interviews with top leaders from a variety of industries. Through his podcast and coaching, Rierson inspires and empowers individuals to become better leaders and make a positive impact in their organizations and communities.

In a recent episode of Dose of Leadership, host Richard Rierson sat down with Jim McKelvey, the co-founder of Square, for a candid and inspiring conversation about entrepreneurship, problem-solving, and the importance of taking risks.

Jim McKelvey is a serial entrepreneur who has founded multiple companies, including Mira and LaunchCode. Still, he is best known as the co-founder of Square. This revolutionary mobile payment company has transformed how small businesses and entrepreneurs handle transactions. In this interview, McKelvey reflects on his entrepreneurial experiences and offers valuable insights into what it takes to succeed in business.

One of the key themes of the conversation is the importance of identifying and solving problems. McKelvey emphasizes that entrepreneurs must deeply understand the issues they are trying to solve and be willing to take risks to develop innovative solutions. He also notes that the most successful entrepreneurs can identify problems others have overlooked or dismissed as too difficult to solve.

McKelvey’s journey as an entrepreneur is a testament to the power of problem-solving. When he could not sell a piece of glass art because he could not accept credit card payments, he teamed up with Jack Dorsey to create Square. This mobile payment system allows anyone with a smartphone to accept credit card payments. Today, Square is a billion-dollar company with millions of users worldwide.

Another theme that emerges in the interview is the importance of taking risks. McKelvey acknowledges that starting a business is inherently risky. Still, he argues that entrepreneurs must be willing to take calculated risks to succeed. He notes that many people are held back by their fear of failure. Still, he encourages listeners to embrace failure as a necessary learning process.

Throughout the interview, McKelvey’s irreverent and self-deprecating humor adds a touch of levity to the conversation. He admits that he has made plenty of mistakes along the way and encourages listeners to learn from his failures and successes. He also emphasizes the importance of perseverance, noting that the road to success is often long and challenging.

Overall, the conversation between Richard Rierson and Jim McKelvey is a valuable resource for anyone interested in entrepreneurship or problem-solving. McKelvey’s insights and advice are grounded in his entrepreneurial experiences, and his enthusiasm for innovation and risk-taking is contagious. 

Whether you are a seasoned entrepreneur or just starting on your journey, this interview will inspire and motivate you to pursue your crazy ideas and make a difference in the world.

To learn more about Richard Rierson and the ‘Dose of Leadership’ podcast, you can listen on Spotify.

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