Win Big: How Being ‘Crazy and Fearless’ Can Lead to Millions

Arthur Wylie made his first million by the age of 26—not by playing it safe and following all rules, but by using a “crazy and fearless” plan of attack.

As a college student, he started his own wealth management company, taking on clients from his dorm room.  “At the time, the job market was shrinking, and I knew the best way to get a job was to create one,” Wylie says. “I wanted to look at a way to earn money, be good by myself and contribute to my family.”

With a father in the financial services industry and several mentors, Wylie was able to expand his brand into film and real estate.

Today, the founder and CEO of Arthur Wylie Enterprises shares his secrets to success in his latest book, Only the Crazy and Fearless Win BIG! The Surprising Secrets to Success in Business and in Life (BenBella Books; $24.95), exploring the inspiring stories and enterprising success models of innovators and entrepreneurs who took risks and reaped the benefits of thinking beyond limits.

BlackEnterprise.com caught up with Wylie to find out how being crazy and fearless can lead to career fulfillment and lucrative prosperity.

BlackEnterprise.com: What are some of the skills that “crazy and fearless” leaders use every day?

Arthur Wylie: In the book, I looked at common traits of successful businesspeople — Steve Jobs, Henry Ford, Mark Zuckerberg, Sean “Diddy” Combs, Sara Blakely. They all had a crazy vision and created things even when they did not already exist. For whatever they wanted to do, they thought big. It wasn’t just about that, they put together a fearless plan of attack. They had a vision and a power plan, knew how to execute, how to market themselves and how to deal with the unknown.

They were comfy with understanding that if they continued on their path, they wouldn’t have to worry about what would happen next because they did the right thing to prepare. They knew how to network with the right people and they were okay with dealing with that fear factor.

Speaking of the fear factor, many young people are taught to play it safe when it comes to life and their careers. How can young people tap into being crazy and fearless to achieve success?

Sometimes it’s a bigger risk not doing anything that goes above and beyond the norm. To say, ‘One day I’m just going to walk off my job’ is not what I’m talking about. You have to have a plan of attack—that crazy and fearless plan. You have to think beyond boundaries and execute.

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You’ve had mentors to help guide you in your path. How do mentors play into the “crazy and fearless” pursuit of success?

From Ray Kennedy [founder, president and CEO at American Product Distributors] to [businessman] Richard Griffin, who gave me the first office I could work out of for my business, to my father, who was in the insurance and investment game for over 30 years—their efforts were very instrumental. With mentors, you must look at what they do, understand how they do it, and move forward. It’s  essential to have them. Some you may know personally and some you may model after by example. You have to have these mentors to look at the steps they took toward their success and also learning from their failures.

When does crazy and fearless go too far in business?

When you go after a crazy idea with no plan of attack. It’s no good when you’re not looking at your vision and fleshing it out or you neglect to make sure you understand the process and create a business or life plan accordingly.

You need to analyze and look at things, from short-term to mid-term to long-term goals. If you’re not doing those things, I think it’s stupid. It doesn’t make any sense. It’s okay to say, “Hey I want to get to the moon.” Many people would say that’s ‘crazy,’ but if you have a game plan for getting there, that’s success.

How does one go about thinking outside of the box to achieve the “crazy and fearless” success?

First understand, I didn’t even know there WAS a box. There is no box, and you can’t think out of something that is not there. Don’t limit yourself. You must create and innovate, as many of the successful people mentioned in my book have done.

Check us out tomorrow Wylie’s six “crazy and fearless” steps to career success, and a chance to win Arthur Wylie’s book Only the Crazy and Fearless Win BIG! The Surprising Secrets to Success in Business and in Life.