will interview
The Man Behind The Success At iWill Enterprise, Inc.

Written by Kristin Vaughn

iWill Enterprise Inc. is comprised of a team ready to succeed and take on any new challenge that is thrown their way. The main reason for this? The CEO behind iWill Enterprise, William Smith. Will comes from a very diverse background that led him to pursuing his own company to allow himself to help others accomplish their goals and succeed. I sat down with Will to learn more about his background and what has inspired him the last 3 years to accomplish the success that he has seen.

“Tell me about yourself?”

Will: Before the business, I was in the United States Navy for 7 years as an Electrical Engineer, a 2nd class petty officer. The military showed me what I wanted to do in life and also highlighted what I did not want to do when I was finished serving. I realized that I did not want to work for anyone anymore. So, I bought into some businesses in San Diego, and became the co-owner at a restaurant and co-owner of a barber shop/beauty salon. I was also very involved in the music industry as a producer and manager. I have been on American Idol twice and The Voice once as well. I have also had the opportunity to sing on stage with Stevie Wonder, which was an amazing, once in a lifetime experience. Before I left the music industry to pursue other passions, the company I worked with was nominated for a Grammy in 2015 for work we did with Beyoncé.

“With all your previous success, what prompted the change in careers?”

Will: I was very active in the community and enjoyed hiring local individuals for my restaurant and barber shop, as well as doing community service, but wanted to do things on a much bigger level. I wanted to give people an opportunity to also become an entrepreneur and change their family’s dynamic.

“How long have you been a CEO and ran iWill Enterprise?”

Will: I opened up iWill Enterprise in September of 2016.

“How many offices do you currently oversee?”

Will: I currently oversee 3 offices throughout the Midwest and East Coast.

“What is one of your favorite memories since establishing iWill Enterprise?”

Will: My favorite memory was promoting my first manager to oversee their own office. This was a great memory for me because I understood what I was able to do on a bigger scale in my career and what I had to offer others. I see people go through multiple challenges and now I am able to grant them same opportunity to become an entrepreneur that I received and overcome their struggles. One of my greatest pleasures in life is watching others succeed, and once I promoted my first employee into a management position, I was able to see this success first hand and know that I played a part in that. 

“What is a mistake you’ve made and advice you could give others to not make the same mistake?”

Will: There has been a lot of mistakes I have made in the last 3 years, and many of those were accompanied with good decisions in the future as I learned along the way. I would say my biggest mistake was being a bit hard-headed when I first joined the business. I was not as open-minded to new ideas and was set in the way I thought success would come. My training system was overthought and too long, and I gave way too much information on the forefront. This caused high turnover within my company because I didn’t teach hands on, I lectured and expected everyone to learn the same and learn quickly. I had to learn to adapt and change the way I taught with each new individual that joined the iWill team. I also didn’t teach people finances correctly. I could show people how to make money, but not manage it successfully.

“What are your goals for 2020?”

Will: I want to expand my organization to a total of 6 offices- doubling in size. I want to help develop individuals to become successful entrepreneurs and set the parameters for a strong organization. This will allow me to create the path for me to become a Senior Regional Manager within the next couple of years.

“What 3 things have contributed the most to your success?”

Will: The first thing is having an amazing partner in the business. My partner Brooke is my right hand who helps with delegation and running the organization. I can bounce ideas off her and always have another set of eyes and ears present. Finding the right partner is key. Second, taking risks and understanding that opportunities come and go, so you have to be ready to take on the next challenge and embrace it. Lastly, networking with other individuals who are doing a better job than I am and finding out what is working for them so I can implement it. Always being a student and focusing on what I can do to continue improving myself and my business.

“What is a piece of advice you could give an applicant applying for iWill Enterprise, Inc.?”

Will: Expect the unexpected and be ready for challenges and adaptation. The biggest obstacle at iWill Enterprise is being ready for change and what comes with it. We are in a world that is constantly evolving with new technology and processes to make daily tasks more efficient, so you must be adaptable, or you will fall behind the curve. 


If you feel you have what it takes to be a part of our winning team, take the opportunity to apply with us now. If we select your application, you will be contacted within 24 hours to set up your interview.

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