They say timing is everything and it couldn’t have been more apropos that a $1 billion investment into Indiana innovation and entrepreneurship was announced the same morning John McDonald, CEO of CloudOne, gave the keynote speech at IBJ’s Fast 25 breakfast honoring an exclusive list of Indy’s fastest-growing private companies. With nearly a quarter of the list comprised of technology firms, the common thread distinguishing those honored was not only impressive revenue growth, but a strong entrepreneurial spirit.

With growth comes transformation and the evolution of almost everything in a business. John understands that all too well. After serving as a technical sales executive at IBM for over 20 years, John took a leap of faith in 2010 to serve as CEO of CloudOne. In the early days, the startup was the world’s first company to create IBM Software-as-a-Service (SaaS) and Virtual Private Cloud delivery of IBM software products.

Six years later, the company has evolved to become an enabler of IoT solutions, transforming the way enterprises are keeping pace in the age of digital disruption. Expanded services, growing employee headcount, $21.9 million in investment and new, cutting-edge headquarters in Fishers, Ind., have allowed John to learn a lot along the way as it relates to entrepreneurship and building a growth-stage business.

John McDonald’s 10 Lessons Learned About Entrepreneurship

Lesson #10 — Leadership is framed by inquiry.

Great leaders ask questions to clarify and give a frame of reference. Do you give directives or do you ask questions?

Lesson #9 — People believe either they do things to the world or the world does things to them.

Are you inspiring both kinds of people on your team who have different points of view?

Lesson #8 — Culture is a tribal survival knowledge, learned when reward is greater than effort.

Are you a culture victor or victim? Anytime someone new joins your company, it is like a full-scale assault. It is imperative that those joining adhere to the culture you have established for your company.

Lesson #7 — Passing up opportunity is the most difficult thing.

Do you make overconfident jumps? Many companies fail when they try to do something in another industry. It doesn’t always transfer. A key lesson in entrepreneurship is learn when it’s OK to hold back.

Lesson #6 — Creativity is seeing the extraordinary in the ordinary.

Do you tolerate ordinary? Make an effort to seek the extraordinary in the ordinary.

Lesson #5 — There is always another right answer.

Do you have the courage to reframe and seek it? Keep asking questions as there is always another right answer.

Lesson #4 — Leadership is not management. It is people following you.

Ask yourself who is following? Leadership is very different than management. They actually have very different meanings. If no one is following, then you are just a guy out for a walk.

Lesson #3 — Bad patterns become prisons.

Do you challenge bad patterns? When bad patterns occur with regularity, we actually stop being aware of them. Don’t get stuck inside that cage.

Lesson #2 — It is complete when nothing else can be removed. 

Do you make difficult things simple? Always be editing and remove what’s not necessary.

Lesson #1 — Success is separation.

Separation is often the sign of success. When a student graduates and leaves school it’s a success. When a child leaves home to go out on their own, it’s a success. You know a business you created is truly a success when they no longer need you.


In today’s fast-paced business world, it’s imperative to recognize and celebrate the accomplishments of Indiana’s tech ecosystem and their contributions to the overall business climate. As today’s tech leader’s generously share the lessons learned that have helped them thrive, they are also paving the way for the next generation of aspiring Hoosier entrepreneurs. As Greg Morris, publisher of IBJ, commented after John left the stage, “The best leaders always undersell themselves.” The complete IBJ Fast 25 list can be found at