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For many entrepreneurs, launching a single successful startup is enough. But for Jim McKelvey, his success involves six different startups that he still owns. Though best known as the Square founder, along with Jack Dorsey, Jim McKelvey has created an array of innovative businesses. In addition to founding Square, he is also involved in companies related to glass-blowing, venture capital, employee training, and digital publishing. Indeed, Jim McKelvey appears to have the Midas touch when it comes to entrepreneurship and Bold Leadership.

Tremendous success does not come without a great deal of hard work and powerful leadership. Though Bold Leader Jim McKelvey admittedly appreciates the importance of luck, he thought it unlikely that Lady Luck would shower him with favor so many times. Instead, Jim McKelvey applies his unique and bold style of leadership in an array of different areas. By taking an in-depth look inside the Square founder’s leadership philosophy, entrepreneurs and leaders everywhere can benefit.

Jim McKelvey’s Bold Leadership Foundation—Perseverance and Diligence

In each of Jim McKelvey’s businesses, he identifies a specific problem that needs a solution. As the Square founder, his inability to sell his own glass-blown art pinpointed a need for an accessible payment platform for small business owners. Another of his businesses, LaunchCode, fills the lack of technologically skilled workers through employee training and apprenticeships. And, Invisibly is now striving to fix the broken digital ad ecosystem that plagues the digital publishing world—thus, allowing content creators to sustainably monetize their content. In each instance, Jim McKelvey succeeded, because he started with the problem.

While recognizing a need is great, creating a solution is not easy. As Jim McKelvey describes, great leaders need to expect failure and rejection. Perseverance is an important secret to leadership success and often is the difference between bold leadership and startup failure.

Mentor, Educator, and a True Believer in the Team

Bold leadership has been defined in part as fostering success in others while having the ability to delegate effectively. These characteristics certainly apply to Jim McKelvey. The Square founder recognized talent in Jack Dorsey during his previous interactions with him. This insight along with his keen problem-solving skillset and bold leadership allowed Square, a $30 billion-plus market cap public company, to become a reality. In nearly all of Jim McKelvey’s pursuits, he has collaborated with others to co-create a vision. His capacity to encourage others to utilize their talents and work together are among his boldest leadership traits.

A key part of fostering talent also involves serving as a mentor and educator to others. Jim McKelvey is a published author of three internationally recognized textbooks that seek to enhance others’ understanding. His first book, a computer science textbook—which he wrote when he was in college—was written in an effort to improve upon the professor’s inadequate course book. He also wrote the primary resource today for beginner glass-blowers. Similarly, at LaunchCode, he is developing programmers through training and education to enhance the local talent market. These leadership pursuits exemplify Jim McKelvey’s belief in people.

The Square co-founder has impressed those who have worked for him.
Jim McKelvey’s bold leadership has made a lasting impression on those who have worked with him.

A Bold Leader who Strives to Make a Difference in the World

As the Square founder, Jim McKelvey provides a solution to help artists and small businesses excel. At LaunchCode, he aims to reduce poverty and unemployment by developing technology skills in the community. And at Invisibly, Jim McKelvey wants to enhance the published content society enjoys by ensuring content creators are appropriately rewarded. Underlying each of Jim McKelvey’s pursuits is a social agenda.

The drive to make the world a better place has always been a core piece of Jim McKelvey’s leadership. His father, a chemical engineering pioneer, and professor instilled these motivations within Jim McKelvey. His friends at Washington University in St. Louis also helped him appreciate humility, integrity and a down-to-earth perspective. This combination of influences is what molded Jim McKelvey’s passion for helping others. And it remains a key part of his bold leadership today.

Advice for Bold Leaders and Entrepreneurs of Tomorrow

McKelvey is a great example of a modern-day bold leader who serves as a role model for countless others. With this in mind, the Square founder encourages others to be real and authentic and to follow their passions. In addition, he emphasizes that cultivating relationships and investing in self-education is critical. But above all else, he heartens people to lead with integrity and to expect failure before certain success. As I wrote in a recent article featured in ProjectBoldLife, the path to success is rarely linear and requires course correction along the way. McKelvey is a master at understanding this is and persevering against the odds.

“Failure with a startup is really a question of the entrepreneur giving up. Now you can say. ‘Well if we don’t have funding, we have to let everybody go.’ But many times, I’ve had my company reduced to me. It doesn’t die until you quit, and I just never quit,” Jim McKelvey Founder of Invisibly, LaunchCode and Square.

Being bold requires courage, and bold leadership demands this and much more. But as Jim McKelvey demonstrates, this combination of pursuits can drive tremendous success and cultivate strong leadership potential along the way.

To learn more about Jim McKelvey’s newest venture, visit our exclusive story, video, and infographic on Invisibly.

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