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Gregory R. Raifman

The GRR Report was the brainchild of Gregory R. Raifman "["GRR] who has been an Internet industry veteran from the early days of the Web, with a specialty in Technology & Internet/Web Services & marketplaces, data analysis and software platforms, and possesses demonstrated proven leadership and partnership skills in fast paced startup environments as well as publicly traded growth companies.  Experienced in building companies from inception to scale, Greg has extensive direct experience working within and scaling large corporate enterprises in public company environments.

Most recently, Greg was the President of Nexstar Digital, LLC, a wholly owned subsidiary of Nexstar Media Group, Inc. [NASDAQ: “NXST”], publicly traded with over 15,000 employees and headquartered in Irving, Texas.  Nexstar Media Group is the second largest broadcast company in the United States with nearly $2B in annual revenues and about $2B in EBITDA. As President of Nexstar Digital, a wholly owned subsidiary of Nexstar, Mr. Raifman developed and implemented the digital strategy for the combined Nexstar company, as well as managed the day to day operations of the portfolio companies and product lines within Nexstar Digital.  Under Mr. Raifman’s leadership eight initial portfolio companies were combined into Nexstar Digital and one additional company was acquired.  Mr. Raifman is responsible for or supported all digital revenues and strategy for Nexstar’s 197 station sites as well as non-owned and operated digital revenues and data-driven revenues.  In four years, Greg grew the digital businesses from a loss of $15M to over $40M annually in EBITDA with an expected run rate of $50M in 2021.


From 2013 through March 2017, Greg was President and a member of the Board of Directors of Rubicon Project, Inc., [NYSE: “RUBI”], a publicly traded advertising technology company based in Los Angeles with over 680 team members worldwide in 26 offices.  Rubicon Project, now Magnite, is on a mission to automate the buying and selling of advertising and operates the largest independently marketplace worldwide for buying and selling advertising.  As President, Greg oversaw the day-to-day operations of Rubicon Project, including its revenue & business development, product & engineering, finance & legal, marketing & communications and  strategy & corporate development.  Under his watch, Rubicon Project completed a very successful IPO in 2014, grew by 4x to over $1b in ad spend in its marketplace, increased gross margin by 10 points, delivered EBITDA profitability each year, is routinely recognized globally for its inventory quality and at one point reached a market capitalization of over $1 billion.  While at Rubicon Project, Greg served on several Boards of Directors, including the Mobile Marketing Association, IAB’s Trustworthy Accountability Group and Advertising Women of New York. 

Before Rubicon, Greg acted as the Executive Chairman of LiveRail, Inc., a video ad exchange and real-time bidding company based in San Francisco and helped to develop the strategy to pivot LiveRail from a video serving company to a video exchange.  LiveRail was acquired by Facebook in July 2015 for $500 million.

Greg also founded Dragon Media Online, Inc., a performance-based online media company that owns “”, one of the leading career advancement sites. provides a highly targeted, lead generation platform and social community to match potential employees and students worldwide with prospective employers and schools through the use of very targeted and searchable user profiles.  

Prior to founding Dragon Media Online, Greg founded and served as the Chairman, CEO and President of Mediaplex, Inc. [NASDAQ: “MPLX”]. Under his watch, Mediaplex developed from inception to a publicly traded global advertising technology company valued at one point over $4 billion in less than four years.  Mediaplex ultimately merged with ValueClick, Inc. in October 2001. Mediaplex Inc. developed many of the initial ad serving technologies for the advertising space which are still used today, including adXML and mobile java objects (MOJO).

Prior to Mediaplex, Greg founded PointBreak Ventures, LLC, a venture capital firm that founded or invested in several internet pioneers, including GlobalCast, TimeShift, Internet Extra Corporation, MindSource, Sandpiper Networks, Good Technology, and The Internet Mall/SHOPNOW.  As an investor, advisor and/or operator, Mr. Raifman has worked or associated with many of the key venture capitalists or investment managers that target technology investing, including Pequot Capital, Bain Capital, Technology Crossover Ventures, New Enterprise Associates, Golden Gate Ventures, Rockridge Capital, Digital Ventures, Sequoia Capital, Accel Partners, Mohr Davidow Ventures, Greylock Partners, RedPoint Ventures, Pond Ventures, among others.  

Mr. Raifman, through his investment affiliate Gekko Holdings, LLC, recently invested in dba “Co-Promote”, YouNow,, LiveRail, Inc., Up Communications, Brightpath Capital Partners, LP, POPI Investments, and has acted as an advisor for to many emerging stage and growth companies, such as Conference Hound, Brushfire Media Group, and Ringz.TV.  

Being an avid cyclist, Greg also founded and was the Chairman and CEO of Momentum Sports Group, LLC, the owner and operator of professional cycling teams from 2003 to 2019, including the Health Net Pro Cycling Team Presented by Maxxis, the number one domestic-based professional cycling team in the United States for 2004-09.  In 2010, UnitedHealthcare assumed title sponsorship of the Team and through 2019, the team raced as the “UnitedHealthcare Pro Cycling Team” and was the best cycling US based cycling team for most of the years 2011-18 until the team ended its operations in 2019.

Greg has appeared on Fox Business, CBS, CNN, CNBC, FNN and ABC News, was featured on the cover of Fortune Magazine, The New York Times and The Wall Street Journal, and has presented before numerous leading Wall Street investment institutions.  Greg is also routinely interviewed in online publications and has lectured and written extensively about entrepreneurship, corporate finance, and technology for companies and educational institutions such Johnson & Johnson, The Wharton School, The Haas School of Business at the University of California, The University of Michigan, and the Georgetown University Law School.

Mr. Raifman received a J.D. from The Georgetown University Law Center where he was Executive Editor of the International Law Review and published an article entitled “The Effect of the US-Swiss Agreement on Swiss Banking Secrecy and Insider Trading” (1983) 15 L. & Pol. of Intl. Bus. 565.  After law school, Mr. Raifman clerked for the Honorable Anthony A. Alaimo, Chief Judge, United States District Court for the Southern District of Georgia, and then began his career working as an attorney, specializing in mergers and acquisitions and and corporate financings.  Mr. Raifman worked at Skadden, Arps, Meagher & Flom and Montgomery Securities.  

Mr. Raifman received his A.B. from the University of Michigan where he made the Dean’s List and was a double honors student in Economics and History.  Since 2000, Mr. Raifman has been a Member of the Georgetown University Law Center Board of Visitors.

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