At CEO (Boardroom Media) we track over 1,000,000 startups and over 5,000,000 people who hold key positions in these companies. We use this directory of startups to highlight top employees, founders and board members we think deserve more appreciation than they are currently getting.
This list showcases the top Chicago based CEO’ operating in the Digital Media space. If you think a CEO’ is missing from this list, feel free to contact our editor on [email protected].
The individuals on this list have been included because of exceptional performance in one of the following categories:
- Innovation – Operating as a key part in an extremely innovative business or startup.
- Growth – Operating as a key figure in the growth and upscale of a market leading business or startup.
- Management – Showing exceptional management skills.
- Societal impact – Putting their business on the map for their positive societal or environmental impact.
Our Data – We source our data from OSINT (open source intelligence) and public directories such as Crunchbase, SemRush and many more. The data from these sources should be treated with a degree of caution and verified yourself.

Aaron Frazin
Founder and CEO of Detective
Aaron Frazin is the Founder and CEO of Detective.io.
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About Detective: Detective is a digital adoption platform that automates the sales research process.
Anthos Chrysanthou
Founder & CEO of Emerge Media
Anthos Chrysanthou is Founder @ Emerge Media.
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About Emerge Media, HPA: Emerge Media is a media and Internet company focused on the core areas of search, communication, and online dating.

Don Russell
Chairmen, CEO of IndyBuild
Mr. Russell has more than 25 years of experience and a strong track record of success that includes streamlining operations and maximizing productivity. Prior to launching IndyBuild Corp, he served as President and CEO of Piracy Control Technology. Also, Mr. Russell served as Director of Marketing at Rockstar Beverage Corporation. There, Mr. Russell was responsible for researching and understanding product brand study demographics, producing promotions to target key areas, coordinating product breakouts to maximize productivity, and acting as a liaison between various departments. Mr. Russell gained additional experience by serving as the Creative Director of Expo Theatre Productions, where he prepared and presented client presentations and maintained responsibility for hiring independent contractors. He was also the President and Owner of PM Studios for more than five years, while serving as an A&R director at MCA/Universal Music Grou. Mr. Russell attended Columbia College in Chicago and the University of Phoenix – Chicago campus. He has extensive experience as a performer, producer, manager and director in the entertainment industry. He has performed in or directed several notable productions over the past 10 years. Some of his production credits include: • “Riverdance,” where he served as a principal artist • “Satin Suite,” where he performed as headliner on the Olive Garden Theater stage at Walt Disney World • “Broadway Soul Jam,” where he performed in Amsterdam as a headliner in the very popular and successful musical directed by Maurice Hines Mr. Russell’s innovation in the area of musical theater has captured the attention of many great icons such as: • Oprah Winfrey, on whose show Mr. Russell performed • Gregory Hines, with whom he has performed • President Bill Clinton, for whom Mr. Russell performed for at the opening ceremony for the 1996 Democratic National Convention As sole owner of one of California’s premier recording studios, Mr. Russell has had the opportunity to work with such talents as R. Kelly, Dr. Dre, Jamie Fox, Randy Jackson, Common, Kid Rock, Ludacris, Jermaine Dupri, Be Be Winans, Glenn Jones, Al B Sure, Faith Evans, Jon B, The Brat, Onyx, Ideal, 112, Savion Glover, LeVert, The Gap Band, Terrance Howard, Malik Yoba, Brian McKnight, The Nicolas Brothers, Sinbad, Bernie Mac, and Steve Harvey. Mr. Russell has also directed or produced industrials and tradeshows for such companies as Honda, Seagram’s, McDonalds, Coca-Cola, Fujitsu, Nupremis, AMD, Unisys, and IBM.
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About IndyBuild: IndyBuild is a free entertainment industry platform developed to fully showcase creative and performing artists

Greg Fenton
Co-Founder & Chief Executive Officer of RedShelf
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About RedShelf: RedShelf is a distributor of digital learning materials for the higher education community.

Emily L Barr
President & Chief Executive Officer of Graham Media Group
Emily L. Barr is President & Chief Executive Officer of Graham Media Group, the television broadcasting division of Graham Holdings Company. She has held this position since July 2012. Prior to joining Graham Media Group, Barr served as President and General Manager of ABC 7 Chicago (WLS–TV), the ABC-owned station in Chicago, a position she held from April 1997 until July 2012. Under her leadership and throughout her tenure, ABC 7 strengthened its dominance in the market and remained the top-rated/most watched station in Chicago. In 2009, Barr helped create The Live Well Network, a digital broadcast, online and wireless network focused on home, health and lifestyle programming. A native of Haverhill, MA, Barr is a graduate of Phillips Exeter Academy and holds a BA in Film Studies from Carleton College in Northfield, MN. In 1986, she earned an MBA from George Washington University in Washington, DC.
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About Graham Media Group: Graham Media Group is a broadcast media company.
Jeff Guzzi
Founder and CEO of Visionary Financial (VF)
Jeff has acquired hands on experience in Portfolio Management, Venture Capital and Private Equity. Between Merrill Lynch / Edge and a mid-sized asset manager in Chicago, he earned a Series 7, Series 63 and Series 65. Jeff started investing, researching & mining cryptocurrency in 2013. He founded Visionary Financial because he strongly believes Crypto & Blockchain are going to change financial infrastructure.
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About Visionary Financial (VF): Global Crypto / Blockchain Media and PR Agency
Brian Duggan
Co-Founder & Co-CEO of Livly
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About Livly: Livly is a platform for activating new digital experiences and revenue streams for buildings.
Alex Samoylovich
Founder, Co-CEO of Livly
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About Livly: Livly is a platform for activating new digital experiences and revenue streams for buildings.

Terry Jimenez
CEO & Board Member of Tribune Publishing
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About Tribune Publishing: Tribune Publishing Company, is a diversified media and marketing-solutions company.

Ivy Walker
Founder & CEO of Helios Digital Learning
Ivy Walker is a start-up and growth executive whose background includes a wide range of entrepreneurial experiences in both for-profit and not-for-profit/social venture settings. She has previously held roles such as President of a venture-backed consumer health start-up that successfully launched a health gamification platform, CEO of a global social venture that brought diagnostic medical imaging to developing countries, and CEO of a business accelerator for start-up and high growth companies. Ivy holds an MBA from the Kellogg School of Management at Northwestern University and a Bachelor of Science degree from the University of Illinois at Urbana-Champaign. She was awarded Kellogg’s Alumni Entrepreneur Supporter of the Year Award and the Anti-Defamation League’s Rising Star Award. Her civic and professional activities include serving as Board Vice Chairman for Kaleidoscope Inc., a non-profit child welfare agency and serving on the board of Golden Apple Foundation, a nationally recognized non-profit that prepares teachers to be successful in schools of need in Illinois. She is also an active member of the Economic Club of Chicago and the Chicago Club. Ivy lives in Chicago’s Printers’ Row neighborhood with her daughter Faith-Christina. She is an avid traveler and is pursuing a lifelong goal of visiting 100 countries and all seven continents. She is also an aspiring Cessna Pilot.
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About Helios Digital Learning: Helios Digital combines immersive storytelling, EQ, behavioral economics and analytics to help employees make better ethical decisions.

Stopher Bartol
Founder & Chief Executive Officer of Legacy.com
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About FireStarter Fund, Legacy.com: Legacy.com is a commercial provider of online memorials that hosts online obituary sections for newspapers throughout the U.S.
Tony Hunter
Chairman and CEO of The McClatchy Company
Tony W. Hunter was appointed chief executive officer of Tribune Publishing in July 2011, assuming responsibility for the strategic priorities and day-to-day digital and print operations of seven Tribune newspaper companies including the Baltimore Sun in MD: Chicago Tribune in IL; Daily Press in VA; Hartford Courant in CT; the Morning Call in PA; Orlando Sentinel and Sun Sentinel in FL. He is currently leading the transformation of these traditional newspaper companies into media and business service companies. Hunter served as one of the four members of Tribune Company’s Executive Council, which exercised the responsibilities of the office of Chief Executive and President from October 2010 to May 2011. Since September 2008, Hunter has served as publisher and CEO of Chicago Tribune Company, overseeing a robust print and digital media portfolio including the Chicago Tribune, RedEye, Hoy, chicagotribune.com, TribLocal, and Chicago Magazine. During this time, Hunter helped lead the recent redesign and expansion of content at the Chicago Tribune; the establishment of the “Breaking News Center,” an around-the-clock digital operation leveraging capabilities of Chicago Tribune, WGN-TV, WGN-AM and CLTV; the signing of printing and distribution agreements Sun-Times News Group; numerous digital initiatives including 435digital; a redesigned Chicago Tribune website and several mobile products. Hunter previously was senior vice president/circulation and operations for Chicago Tribune, a position he assumed in 2007. In this capacity, he was responsible for production, technology and circulation, as well as marketing strategy, customer acquisition/retention, manufacturing and distribution. Hunter joined Chicago Tribune in 1994 as manager/circulation planning and analysis. During his tenure, he led the development of the pricing and distribution strategies for the launch of RedEye. Prior to joining Chicago Tribune, Hunter worked for the Audit Bureau of Circulations (ABC) as Director of Field Auditing-Newspapers and held a variety of auditing positions from 1984 to 1994. A native of Calumet City, Illinois, Hunter holds an MBA in leadership and organizational development from DePaul University and a BA in accounting, business administration and economics from Coe College in Cedar Rapids, Iowa. He is a CPA, the former president of Illinois Fatherhood Initiative, a current member of the Civic Committee, and board member of Metropolitan Family Services. Hunter and his wife Sue, live in Chicagoland.
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About The McClatchy Company: McClatchy is a publicly news publisher with 30 newsrooms including The Miami Herald, Charlotte Observer, Kansas City Star and Sacramento Bee
Michael Small
Co-Founder and CEO of K4 Mobility
Michael Small is a co-founder and CEO of K4 Mobility. He is a wireless industry veteran, most recently serving from 2010 to 2018 as President and CEO of Gogo Inc, an inflight wireless company that went public in 2013 at a valuation of $1.4 billion. Prior to that, Michael served as CEO of Centennial Communication Corp from 1999 until it was sold to AT&T for $3 billion in 2009. He has twice received the E&Y Entrepreneur of the Year Award in 2005 and 2012, and the Illinois Technology Association CEO of the year award in 2013.
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About Hyde Park Angels, K4 Mobility: K4 Mobility is a digital platform that harnesses the power of the Internet to provide services for maritime ships.

Tyler Mose
CEO of Indirap Productions
Tyler Mose is a CEO at Indirap Productions.
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About Indirap Productions: Indirap Productions is a full-service production and marketing agency that offers creative insight for the development of video content.

Rakesh Kumar
Founder and CEO of MarketEnomics
Founder at IIMnet.com and MarketEnomics. Currently working on launching marketEnomics : a digital media analytics and publishing platform which helps marketers to convert ‘social graph’ data into meaningful insights. The analytics engine provides visibility to key business levers such as ‘cost of customer acquisition’, ‘Campaign Effectiveness’,’Channel Effectiveness’ and others. Experience in designing and developing online marketing campaigns that drive organic traffic for client organizations. Develop success metrics and campaigns for inbound marketing and SEO initiatives. Act as a subject matter expert for SEO/SEM/Social Media and other digital marketing applications that enhance marketing initiatives. Specialties: Search Engine Marketing – SEM, Certified Google Adwords & Analytics Specialist, Digital Marketing, Online Marketing, Social Graph – Influencer Marketing, Social Media Marketing, Web Analytics, Inbound/Content Marketing, Email marketing.
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About IIMnet, MarketEnomics: MarketEnomics is an integrated digital media agency that provides its clients with analytics solutions.

David Schawk
CEO of Schawk
David Schawk is the CEO at Schawk
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About Schawk: Schawk is a global brand deployment company that produces brand assets and protects brand equities to make brands more profitable.

Odeh Tadros
CEO of Flickogram
Odeh Tadros is Founder at Flickogram
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About Flickogram: Flickogram is a mobile based photo and video sharing platform that enables its users to share photos and videos using stylized filters.
Elisa All
Founder, CEO of 30Seconds
Elisa is the founder and CEO of 30Seconds. She’s a Latina mother of three who previously founded iParenting, a “Best of the Web” dotcom that she sold to The Walt Disney Company, where she served as Director of the Disney Interactive Media Group. Elisa has been a newspaper columnist, magazine editor, radio and video host, and has created content and marketing programs for various Fortune 500 companies. She has a BA in Communications from the University of Wisconsin-Madison, which awarded her its Entrepreneurial Achievement Award, and an MSJ in Journalism from the Medill School of Journalism at Northwestern University, where she’s on the Board of NUvention Media Entrepreneurship program.
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About 30Seconds: 30Seconds is a digital media platform makes life better in 30 seconds through the power of content and community.