Chicago Journal’s Top 10 Influential CEOs in 2021

Despite the rising number of aspiring and emerging entrepreneurs from virtually every part of the globe today, it’s still easy to recognize those who truly stand out from the rest of the crop. Entrepreneurs change the world. They lead with innovative ideas that make life better, pose solutions to problems, and add a little more life to society. CEOs also create opportunities for other people, creating jobs in both urban and rural areas; and their leadership helps professionals grow in their craft.

Just as wine gets better with time, these CEOs have also been seasoned with years of decision-making, problem-solving, challenging adversities, and continual changes in their respective industries. They have been tested by economic circumstances, political considerations, and unprecedented global conditions such as the COVID-19 pandemic. Still, they emerged as the strongest, recognized by world leaders worldwide as changemakers who have committed their knowledge and expertise to address what ordinary individuals are yet to see beyond the horizon.

  1. Dave Calhoun

David Calhoun is the renowned president and CEO of The Boeing Company, an American multinational corporation that designs, manufactures, and sells airplanes, rotorcraft, rockets, satellites, telecommunication equipment, and missiles to both public and private entities in more than 150 countries worldwide. Calhoun earned the position of the Chicago-based aerospace company in January 2020. Under his leadership, there are 140,000 employees across the globe. 

Now at 64, Calhoun leverages his expertise in business strategy and executive management to continually maintain Boeing’s position as the top exporter in the United States in the aerospace industry. Before becoming Boeing’s CEO, Calhoun served as the senior managing director and head of portfolio operations at The Blackstone Group, an investment firm. He also became the executive chairman of the board for Nielsen Holdings from 2014 to 2016, but he joined the company in 2006 as CEO. 

Calhoun is a Pennsylvania native and co-author of the book How Companies Win. He acquired his bachelor’s degree in accounting from Virginia Tech. 


  1. David Santiago

On his aptly named venture, Scalp Solutions®, David Santiago is recognized as the brilliant mind behind a revolutionary procedure: scalp micropigmentation. A procedure that creates hair follicle simulation, SMP is one of the most advanced sciences in the hair loss industry. Since founding Scalp Solutions® in 2017, David has been the premier provider. David also recently started a product line of after-care products and hair maintenance, which have proven more than effective in restoring scalp and hair health. This entrepreneur doesn’t stop there. He’s also the founder and CEO of Sanport Group, which provides trucking, logistics, and consulting services nationwide. 


  1. Nick Luciano

Nick Luciano is a 24-year-old cowboy from North Texas. Nick is a TikTok star, videographer, and entrepreneur. Over the course of 2020, he took himself from being a broke engineer to celebrity influencer and entrepreneur. He started his company, Luciano Media LLC, a year ago in hopes of positively impacting the world through content creation. 

Over the past year, he has amassed five million followers, accomplished well over six figures in sales and brand deals, and earned executive roles in various companies to scale their businesses and social media platforms. Nick was named TikTok’s Favorite Cowboy by New York Weekly and he plans to use the influence he has to become the world’s favorite cowboy entrepreneur.


  1. Willie J

Willie J of Belleville, Illinois, born in East Saint Louis is an internationally known CEO, artist, author, musician, and speaker. Willie is on the move with the global success of his company, Pure Mission Entertainment, creating hope through arts and entertainment. He and his company are continuing to thrive with massive success during these most trying times. 

He’s riding high off of the recent success of his new EP “Sunshine with the Rain” vol.1, which was released this past Valentine’s Day. The EP already has over 1.5 million streams on SoundCloud in 100 countries. This project features the hit records “Sunshine with the Rain” featuring (NAACP winner) Arthur Flash Johnson at 2 million streams, “We Love You Puerto Rico” featuring various artists, a musical dedication to Hurricane Maria Victims which is now at 3 Million Streams and hit number 2 on the European Top 200 Indie Charts. Another song “In the Morning,” dedicated to the COVID-19 victims, has more than 5 million streams globally!

Willie was most recently featured as a “NY Weekly Top 20 Musician of 2021.” His latest release entitled “Isabell” is already at 1 million streams and talks about teen suicide.


  1. Dr. Velma Trayham

Meet Dr. Velma Trayham, who is considered as one of the Nation’s Top Business Experts and Influencers. With ten plus years of experience across a wide spectrum of companies, Dr. Trayham is an expert in building and scaling companies as Founder and CEO of Thinkzilla Consulting Group. Dr. Trayham is the mastermind behind creating programs that empower and educate underrepresented communities and minority businesses around the globe. She has grown several companies for clients by 40 in just three years, mentored more than 5,000 women entrepreneurs, and has served as marketing / PR consultant for several fortune 500 companies, small to midsize businesses, and start-ups.

Having been born into poverty, Dr. Trayham understands the realities associated with growing up poor. That’s why she has devoted her life to helping other women achieve success. Her best-selling book titled When God Says Go represents her philosophy on life and her commitment to being of service to others.


  1. April Custodio

House of Talent was created when April Custodio merged her love for the entertainment industry and helping talent make their dreams come true. April Custodio is credited for being one of the fastest growing and hands on casting companies the industry has to offer. 

“Visions change by the second so we must be sharp and on top of everything 24/7. My clients and talent have access to me at all times.” This creates an industry-leading organization focused on trust, service, and performance. Combining her corporate, entertainment, and philanthropic principles, April Custodio has been named as one of the Top 10 Entrepreneurs of 2021 along with Elon Musk, as well as one of the top 10 Instagrams to follow along with Matthew McConaughey.

Instagram: @tallapril


  1. Ari Evan Gold

Ari Evan Gold began his career in business as a snowboard shop owner (Trinity Board Supply) in beautiful Lake Tahoe in 2000 and has been running a charity, The Doogood Conservatory since he founded it in 2002. In 2016, he started working on a new type of wound care bandage. With Canndaid, he incorporated raw honey, organic tea tree oil, colloidal silver and organic hemp extract (cbd) on a latex free bandage. 

After doing beta research in the Ecuadorian jungle, he came back to the States and quickly won Top Ten Military Tech by and followed that up with winning Most Beneficial Product at the coveted CBD CUP in 2017. This year he and his team have successfully negotiated an exit with health care perennial powerhouse Johnson and Johnson. 

He has now started focusing on continuing the testing and scientific verification of his quantum grounding inventions. These include his 13-year-old skateboard brand, Paradox Grip; its technology, Paradox Formula; and the newest invention, Enduritek. 

Enduritek will extend the shelf of all liquids and has the potential to eliminate massive wastes, known as shrinkage, from occurring. Ari is very committed to cause oriented projects and welcomes any opportunity to serve.


  1. Brian Humphries

Photo courtesy: Brain Humphries

That there are no shortcuts to success is something Brian Humphries, the esteemed CEO of emerging digital corporation Cognizant, knows all too well. Although the Irish native did not have much exposure to multinational corporate behemoths until his early 20s, he was still able to establish a reputable standing in the industry. After graduating from the University of Ulster, he joined the computer company Digital Equipment Corporation, which would later be acquired by Compaq and then HP. After 18 years, he then transferred to Dell and Vodafone, respectively. His move into the position of CEO at Cognizant came in mid-2019. 


  1. Joe Ariel

Photo courtesy: Goldbelly 

Standing at the helm of Goldbelly, Joe Ariel holds a B.A. in Economics from Vanderbilt University & is an alumnus of Y Combinator. On top of that, he is a regular guest on CNBC, Bloomberg, and Fox Business and has been interviewed by Entrepreneur, Forbes, Fast Company, and Fortune Magazine. This luminary has always always been passionate about bringing comfort to people through food. Thus, he created Goldbelly, a platform that empowers small shops, chefs, and restaurants. It has been named one of Time Magazine’s “Top 50 Websites in America,” Fox News’ “Best New Food Companies,”  and Inc Magazine’s “5 Startups to Watch.” 


  1. Diishan Imira

Diishan Imira is the founder and CEO of Mayvenn, an Oakland, California-based hair extension company that partners with stylists who serve as the salesforce for the hair extensions their clients buy. On top of that, this technology company has also revolutionized how retail products are distributed. As a graduate from Georgia State’s business school in 2010, Diishan has acquired a vast background in international trade, logistics, and investment. Although he has lived and worked in several countries, including China, France, Brazil, and Ethiopia, this luminary specializes in China. His interests revolve around technology and how it relates to global commerce.Website: